# First time in Hawaii - Need advice



## njny2000 (Oct 4, 2017)

Planning our first trip to Hawaii and would like some advice from you seasoned Tugg'ers. 
We are planning to use the winter break (Fri. 2/16 to Sun. 2/25) for our trip to Maui or Oahu.There will be 4 of us (DW and two daughters - 9 and 7). 

I would like to use my United miles for the airfare, unfortunately they only have award travel from Mon 2/19 so I can book say from Mon 2/19 to Tue 2/28.

But this poses a challenge with renting a TS for those dates. The best option I see on redweek is from 2/18 to 2/25 with no oceanfront (DW would really like oceanfront). I see oceanfront options for 2/17 to 2/24. So if I book a TS, I will waste at least 1-2 days of my stay and will still have to find a place to live for 1-2 day after the TS rental.

So here is my question: We really like renting TS and have rented them for our last 4 beach vacations. But in this case, do you think I am making it more complicated necessary or are there options? Are there comparable hotels I should look at? Advise? 

Thanks,
Sam


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## jnsywg (Oct 4, 2017)

You can stay at the Westin timeshare properties like a hotel guest by booking via www.spg.com. This includes bookings by the night.

On Maui you can also look at something like http://www.honuakai.com. 



njny2000 said:


> Planning our first trip to Hawaii and would like some advice from you seasoned Tugg'ers.
> We are planning to use the winter break (Fri. 2/16 to Sun. 2/25) for our trip to Maui or Oahu.There will be 4 of us (DW and two daughters - 9 and 7).
> 
> I would like to use my United miles for the airfare, unfortunately they only have award travel from Mon 2/19 so I can book say from Mon 2/19 to Tue 2/28.
> ...


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## njny2000 (Oct 4, 2017)

Thanks, I will check those two out, but I am under the impression that renting TS will be significant saving over comparable hotel/resort.


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## vacationtime1 (Oct 4, 2017)

njny2000 said:


> Thanks, I will check those two out, but I am under the impression that renting TS will be significant saving over comparable hotel/resort.



Your "impression" is quite correct.  It will also be cheaper than AirBnB, vrbo, etc.

And the problem you describe -- expensive airfares on Saturdays -- is similarly accurate.

If using frequent flyer miles is a necessity -- which airfares from the east coast makes likely -- your best bet may be renting a Sunday to Sunday timeshare, checking in a day late, and renting a hotel for the last two nights.  Not optimal, but probably cheaper than paying for flights.


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## WalnutBaron (Oct 4, 2017)

I agree with Robert's assessment. Ultimately, I think you're going to have to build a little spreadsheet to help you analyze the overall costs to determine which option gives you the highest cost savings. Here are your options: 1) United miles for airfare, but paying hotel room costs for a few nights until you can bridge to one of the timeshares' check-in dates; 2) Pay for airfare and have your desired check-in dates for timeshare, avoiding hotel room fares; 3) (if you have hotel points), using United miles, hotel points, and timeshare to achieve the lowest overall cost.

I suspect that since you'll be paying for four airline tickets, Option 1 will work best for you--unless you have hotel points that can be used for 2-3 free nights to bridge you to a timeshare check-in date.

In any case, you and your family will LOVE Hawaii. It will create many happy memories, and you'll start planning your return trip as soon as you get back home. Aloha!


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## taterhed (Oct 5, 2017)

Sounds like a great family trip.

A word of caution:  We're east-coasters and frequent travelers.  We go to Hawaii every year and are VERY familiar with dragging family on the 10 hour and 41 minute flight (if you're lucky enough to go direct) from EC to Hawaii.  Then comes the inter-island flight.  Spending less than 7 days in HI from the EC is brutal and not recommended.  Ok, so you're not doing that.  But, spending 7 days and moving resorts and locations really cuts into your beach/fun time.  It's hard to move groceries, clean toys/clothes etc and schlupp the gang across town/island.  Plus, that's peak week time.  I'd look at better airfare combos, companion tickets etc... and sticking with a timeshare that has availability for the whole start/stop days of travel.  Most timeshares are Fri, Sat, Sun check-ins.  That is very peak time, so reservations won't be plentiful and/or cheap I think. 

Suggest this:  How about using miles for NJ to SFO or LAX or SEA or SAC,  then using another means to get to Maui OGG or HNL?  There are many cheaper fares from West Coast to HI.  Also, I think you might be able to apply for Alaskan credit card (both you and wife could get one...) and get companion fares.  Not sure, but an option.  Also, check Hawaiian Air fares from non-peak airports (Sacramento or Phoenix) for bargains. I'd choose island based on cheaper air fare if there was a significant difference.

Maui vs Oahu. 
Depends on the famdamily. IMHO

If the family has been watching re-runs of Hawaii 5-0, they are in for a disappointment (old series).  But, if they expect the Waikiki vibe....well, you can only get that from Honolulu IMHO.  That particular vibe includes tons of asphalt, tons of cars, concrete, hi-rises, shopping, bars etc...  Lots of traffic during rush hours.  It's not bad, it's just Honolulu.   The monuments are great, the shopping, bars and hi-rise vibe is very cool.  It's not my favorite though.  The drive from the airport to downtown is about 45 mins at rush. 10 mins otherwise. The drive to KoOlina is about 45 mins.  If you are shoppers, restaurant goers, bar hoppers and fashionista's, then HNL is for you.

Maui has great beaches, snorkeling, awesome resorts and lots of island vibe to go with it.  The volcano looks like mars, the coastal drives are primitive and there is a good sampling of restaurants, some limited shopping and bars in the smaller cities (and at the resorts of course).  If you're going to Hawaii to sit on the beach, have a drink by the pool, make some meals in the timeshare, walk in the sand, stare at the ocean, see the volcanos, see rain forest, dessert, moonscape all in 30minutes drive....then Maui is for you.  I think Maui is our new favorite; Kauai being second.  The drive from the airport to Kaanapali is about 30-45 mins, less if no traffic.  The road from the airport to the resorts gets busy, but traffic in the resort areas is much less congested than HNL.

If I could do it....I thought it might just be a one time or long-time deal....I'd definitely do Maui.  All for one reason:  Whales.  The whale viewing in Maui is spectacular.  The ridged zodiac boat tour (I'll look it up) is fantastic.  Being close to a whale, on the water is a once in a lifetime must do for me.  Others may correct me, but I think the whale viewing on Oahu is much less thrilling and I can't imagine the whale watching tours to be as good as 'whale soup' at Maui.

If there's anything else you need to know, just ask. Make a good TS week reservation, book the best airfare possible for those dates and enjoy your vaca.


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## WinniWoman (Oct 5, 2017)

Since you are going so far you might want to think of going to two islands instead of one. Maybe Maui and Kauai, or Kauai and the Big Island or whatever. No matter what, you will have to land in Oahu first- so depending on how you plan your connecting island flights- either coming or going- you might be able to get a bit of Honolulu in and Pearl Harbor.

Our last trip there we stayed in an exchange timeshare on Kauai- rented a couple of extra nights at that resort- to make it coincide with our second exchange timeshare week- which was on the Big lsland. Then, on the way home we took a red eye back to NY, so we had some down time on Oahu and went to Pearl Harbor and had dinner in Honolulu..


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## taterhed (Oct 5, 2017)

mpumilia said:


> Since you are going so far you might want to think of going to two islands instead of one. Maybe Maui and Kauai, or Kauai and the Big Island or whatever. No matter what, you will have to land in Oahu first- so depending on how you plan your connecting island flights- either coming or going- you might be able to get a bit of Honolulu in and Pearl Harbor.
> 
> Our last trip there we stayed in an exchange timeshare on Kauai- rented a couple of extra nights at that resort- to make it coincide with our second exchange timeshare week- which was on the Big lsland. Then, on the way home we took a red eye back to NY, so we had some down time on Oahu and went to Pearl Harbor and had dinner in Honolulu..



Actually, there are many airlines that fly direct to  OGG, LIH, KOA (and of course HNL) from the west coast.  LAX, SFO and SEA all have direct flights to all the islands..
Breaking a westcoast trip (EWR, JFK or LGA) up into two equal legs (EWR to SFO, SFO to OGG) doesn't add much time to the over all itinerary, but certainly makes the 12 hours more bearable.
Also, NOT having to drag your bags in HNL to change airplanes is HUGE.  You should get automatic bag transfer in any mainland airport.  That connecting bag drag/ag inspection is the bane of my existence sometimes.

Also, I think there are some better fares available (points too) by looking at alternate routes between 'joisey and the islands other than HNL direct. 

Just my2c, but lots of experience with this.  Just scanning the fares right now, I see a $300 dollar difference EWR-HNL vs the SFO connection.  YMMV


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## DeniseM (Oct 5, 2017)

There is only one way I would try to do 2 islands on a short 9 night trip:

1)  Fly into Oahu and spend 2 nights in a hotel to see the historical and cultural sights.
2)  Fly to your 2nd destination, and spend 7 night, and fly home from that island (if possible.)


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## taterhed (Oct 5, 2017)

Um...the vacation is actually 7 days (barely).   It's just that he can't get airfare via points from when vacation starts--Friday to Sunday (or Sat-Sat, Sun-Sun etc...), but only Mon-Mon or Mon-Tue etc.....  No timeshare check-ins on Mon or Tue apparently .

In fact, if you leave EWR on Friday, you'll be lucky to make 4pm check-in on Saturday in Hawaii due to travel time.  Same going home only worse.
Leave Hawaii at noon on Sunday.......you'll be back late on Monday and useless on Tuesday morning for school or work.

So, think carefully:  Leave on Fri or Sat and plan for the brutal return to east coast time from Hawaii (6 hours on the time zone, 12 hours on the airplane plus)

I agree with Denise: I would not do two islands in 7 days.


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## DeniseM (Oct 5, 2017)

From the first post:


> We are planning to use the winter break (*Fri. 2/16 to Sun. 2/25*) for our trip to Maui or Oahu



I belive this is 9 nights, and as I said, the only way I would do 2 islands (as suggested in post #7) is 2 days on Oahu and 7 on Maui.  

If they are only going to go for 7 nights - they should just do one island.


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## taterhed (Oct 5, 2017)

You are correct, but (perhaps the OP can respond)

I'm guessing that the first practical day for departure would be Friday (16)....arrive late Friday or early Saturday (17)
I'm also guessing that the crew needs to be back in school on Monday (26)...that means leave Saturday (24) arrive Sunday (25)
Probably only 7 or 8 nights

So....I'm thinking the 9 days thing was only to accommodate the available booking dates for reward miles. In any case, you loose 1 or 2 nights depending on the departure date time and the lost day on the way home.  I'm pretty sure the family doesn't want to land at midnight and send the kids back to school at 6am.  Or maybe they really do!!!    So mom and dad can get some sleep.

I mean yeah, if you've got 8 or 9 full nights to see two islands, then maybe.  But, if the real issue here is price sensitivity on airline tickets and rooms....then island hopping with a family of (4?) is probably not the best use of vacation dollars.  Especially for east-coasters who spend 12 hours in the plane/airport on both ends of the trip as well.

One note/thought:  The first night arriving from the mainland is ideal for a hotel at the airport stay.  By staying in a (cheaper) hotel by the airport, you get some quick rest after the long flight and save the cost of a rental car day (in some cases).  Now you are able to be ready to check-in as soon as possible the next day and not waste a valuable day of expensive resort time.  Checking into a $300 a night timeshare at midnight local to sleep (and sleep in the next day) is not the best use of the resort IMHO. 

Alternatively, if you use the NJ-San Fran-Hawaii type of routing, you could grab an airport hotel room at SFO (especially if you leave late out of NJ) and eat/sleep the night on the west coast.  The next day, you can grab the earliest flight from the west coast location to Hawaii.  These flights tend to be cheaper than later connecting flights, get you into Hawaii ahead of some of the crowd and again, avoid wasting an expensive night in HI when you're just dead tired.

Just some stuff to consider.  Hope it helps.  Sorry Denise, I can usually count, but not always!


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## WinniWoman (Oct 5, 2017)

taterhed said:


> Actually, there are many airlines that fly direct to  OGG, LIH, KOA (and of course HNL) from the west coast.  LAX, SFO and SEA all have direct flights to all the islands..
> Breaking a westcoast trip (EWR, JFK or LGA) up into two equal legs (EWR to SFO, SFO to OGG) doesn't add much time to the over all itinerary, but certainly makes the 12 hours more bearable.
> Also, NOT having to drag your bags in HNL to change airplanes is HUGE.  You should get automatic bag transfer in any mainland airport.  That connecting bag drag/ag inspection is the bane of my existence sometimes.
> 
> ...




I am only familiar with flights that stopped on the West Coast (from NY) and then again in Honolulu and then flew from there to the islands. I don't remember what happened with our luggage but it might have been forwarded to the next flight by the airline? I honestly can't remember but I know we did not lug our suitcases around with us.

When we did the two islands we did a 19 day trip- 2: 8 days/7 nights timeshare weeks and 3 days in between rental. We were a family of 3. Our son was about 14 years old.

Then again, we did 4 islands for our honeymoon 40 years ago in 14 days. Hotels.

Honestly, because the OP is coming from the East coast, I would not even consider going to Hawaii for less than 2 weeks.


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## geist1223 (Oct 5, 2017)

While doing Ohau and Honolulu if you have never been there is a good idea. If your family has never done a long flight vacation I would suggest you hold off on the 2 Island deal to a 2nd and 3rd trip. Just go to Maui or Kauai for this first trip. There will be so many things for you to do on either of these Islands that you will stay busy. Once you make up your mind as to Island or Islands pickup a copy (ies) of Maui Revealed or Kauai Revealed.


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## njny2000 (Oct 5, 2017)

Wow, thanks for all the detailed suggestions. very helpful! Oh, I wish I was able to do more days, but 9 days/ 8 nights is most we can do. 

Anyhow, finally decided (and pulled the trigger) to use my United miles to book the airfare with the following Itinerary:

Mon 2/19: NJ to Ohau. Booking a Oceanfront Marriott TS listed at the TUG Marketplace (I will lose one night but no regrets..I think it is worth it)
Sun 2/25: Checkout and morning flight to Honolulu. Now need to find 2 nights stay in Honolulu. Any recommendation on the area / hotel to make the most out of our 2 days in Honolulu?
Tues 2/27: direct flight back to NJ

Once again, I greatly appreciate you all taking the time to respond to my post.


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## geist1223 (Oct 6, 2017)

I am confused. NJ to Ohau on 2/19 then on 2/25 checkout and morning flight to Honolulu. Ohau and Honolulu are one and the same. I assume that on 2/19 after arriving on Ohau you take a flight to another Island and then fly back to Ohau/Honolulu on 2/25.


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## njny2000 (Oct 6, 2017)

Sorry, 2/19 to Maui and then 2/25 to ohau.


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## taterhed (Oct 6, 2017)

Cool.. 
I hope you're landing OGG at 5pm and not one of the 10 or 11pm flights.
I also hope both the primary and connecting flight are on the same itinerary (booking reference).
I also hope that it's UAL and Hawaiian Air.
I'm not certain of the current status of affairs, but at one point, you could not check you luggage all the way thru to OGG unless both flights were booked on the same itinerary and were compatible carriers (UAL and HA are, I think).  There is also a minimum connection time.  Otherwise, the luggage will make the next flight.  Not a long delay, but it can catch you.
I'd confirm the above issues ahead of time. Perhaps others can help.

Be aware, the drive from Maui Airport to Kaanapali Beach (MOC) is a 28 mile drive that takes at least 45 mins.  You'll be leaving the airport at rush hour, but the traffic will dissipate by the time you get the car and groceries.  The drive is mixed:  city traffic, highway traffic, 2 lane road with steep drop-offs and two lane plane old country road.  The locals in Hawaii (in general) drive a bit more aggressive than the tourists.  The tourists drive, well...., like tourists.  Be very careful, you'll be driving at 6 or 7pm local, but it will be well after midnight on your home (circadian) east coast time. Lots of speed changes and stop/go traffic.

Right by the airport is a fabulous Costco.  Get the car and roll into the parking lot of Costco. Stock up, one stop shop for food, drinks, toys, booze and vaca supplies.  The Costco beach gear can be as cheap as 1 or 2 rentals from the beachside rental vendor. Food, groceries and beverages will NOT be cheaper anywhere else...at least for what we eat/drink.  The Pineapple Marg's (pre-mix) are worth a look.   Behind the Costco (town side) is a Krispy Kreme donut factory.  My advice?  Plug mom and dad full of hot coffee to make the drive and unpack and first night tolerable and awake.  Plug the kids full of hot steaming fresh Krispy crème donuts and a big ice-cold milk.  That should put the kids to sleep and make the drive smoother. 

Near the MOC: happy hour at Maui brewery is good for some good cheap eats and some cold bevs.  Trolley service from MOC to brewpub I think. Capt Steve's rafting (zodiac whale tour) leaves from dock in Lahaina and is an amazing tour.  Not for the faint of heart though.  If you don't like powering through waves and being 'close to the water' then try one of the big catamaran tours...book early though...they fill up quick.  The big steel boats are fine, but the experience is more 'Staten Island Ferry with whales' than an exciting adventure--my opinion.
Pretty decent snorkeling right in front of the MOC (and to the right) and turtles often beach in front of the resorts.  Keep at least 6' away from turtles, the conservation folks will come running to rope them off or shew you away.

For downtime in the resort (if there is such a thing) consider bringing a ROKU or Fire stick.  Good for rainy days or sunburn or just a quick movie night. Work great on the MOC TV's.

Have a great time!  Report back.



Waikiki
Not sure if you have any military affiliations....there is a good military hotel in HNL.  Otherwise, there are many, many hotels. The outriggers are nice. 
IF you have affiliations with travel industry, Costco, military, fire, police, unions etc... there are a number of sights that have nightly rentals for a discount, some at timeshares, hotels, condos etc...  Worth a look.

The Outrigger, Hyatt, Westin beachfront hotels (not OF rooms) look to be around $250-300 night.  All nice.
The off-beach hotels, Hilton Garden Inn and similar are around $200. 
I don't have any experience with the <$200 a night hotels.


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## njny2000 (Oct 6, 2017)

I hope you're landing OGG at 5pm and not one of the 10 or 11pm flights. - _*Check, flight lands at 6:10 PM*_
I also hope both the primary and connecting flight are on the same itinerary (booking reference). *Check, everything on same booking with UAL*
I also hope that it's UAL and Hawaiian Air. *Check, UAL and Hawaiian*
I'm not certain of the current status of affairs, but at one point, you could not check you luggage all the way thru to OGG unless both flights were booked on the same itinerary and were compatible carriers (UAL and HA are, I think). There is also a minimum connection time. Otherwise, the luggage will make the next flight. Not a long delay, but it can catch you.
I'd confirm the above issues ahead of time. Perhaps others can help. *UAL flight get in at HNL at 2:40 PM with flight to HNL to OGG at 5:30 PM, so hopefully we should be fine*

 Great suggestion with the Costco ( I am a member), I will absolutely purchase everything needed before heading to the resort. 

Question: Do you advise booking a car for the approx. two days we are in Honolulu or is the public transportation (or Uber) systems good enough for us to do some sightseeing (WWII memorial etc.)?
*
*


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## taterhed (Oct 6, 2017)

The bus and uber in HNL is fine.  The bus people get really upset if you drag too much luggage on the bus.  So, don't try the 5 suitcase thing.  Ask me how I know...
Car parking, rental fees will set you back a bunch. Traffic is not good.  skip the car. Take a bus to Diamond head if you want.

The uber isn't cheap (check estimated pricing) but there are shuttles as well.  If you're planning on doing pearl, read the reviews, get the tour information and book ahead.  They fill up.  Make sure your kid's (age unknown) are aware of the keen sense of respect and honor around the memorial.  They take it seriously (as they should).

The market and other sites in HNL are fun.  Lots of tourist stuff.  Dukes, Rumfire, Kona Brewery, Moana, are all great beach front bar/restaurants.  Very nice beachy feel. 
The best souvenirs (IMHO) have got to be the Crazy Shirts.  Look it up.  They run $30-35 bucks, but they are quality, last a long time and come very nicely wrapped in cellophane bags with a nice packaging.  You can get them customized with a loc/date stamp.  Toys and knick-knacks break, but the shirts live on and on.  The wine/beer/chocolate/curacao dyed shirts are fun to talk about.  my closet is littered with them.

He who wears the Maui Brewery Crazy Shirt to Maui Brewery on Weds drinks $4 pints.  Cheap flatbreads on happy hour (I think)


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## Kapolei (Oct 6, 2017)

If you decide to do several days on Oahu and renting a car, avoiding traffic will be the most important part of your trip planning.

I would look at the new Embassy Suites in Kapolei as an option for someone who is spending a couple of days on Oahu and then going to a neighbor island resort for a week.  You will need to plan around rush hour traffic if you are doing things town side.  However, you will have a brand new hotel.  It will not be next to the beach.  However, you can visit nearby Koolina or White Plains Beach while you are there.

http://embassysuites3.hilton.com/en...tes-by-hilton-oahu-kapolei-JRFOKES/index.html


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## geist1223 (Oct 6, 2017)

Good plan. For adults Patti and my favorite drink is POG (Passion Fruit Juice, Orange Juice, and Gauva Juice) and Dark Koloa Rum (from Kauai) with ice. You can buy both at Costco. If you enjoy zip lining try Piiholo Ranch. They offer two courses. One is a Tree Top Tour. The other is basically a 5 zip back and forth across a canyon. Each segment is longer than segments on the Tree Top Tour and the final zip is over a half mile long. This is a side by side zip line. Patti and I have done both over the past 5 years. We are currently 63.

Can't give you advice about Kaanapali area as we stay in the Kihei area. You will want to fine a place for good Loco Moco in Kaanapali. Some of the best coffee we have ever had is Maui Mokka Estate. You can find them at 277 Lahainaluna Road, Lahaina, next to the Pioneer Mill Smokestack. We enjoyed the Alexander & Baldwin Sugar Museum. Have a great time.


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## dsmrp (Oct 15, 2017)

Kapolei said:


> If you decide to do several days on Oahu and renting a car, avoiding traffic will be the most important part of your trip planning.
> 
> I would look at the new Embassy Suites in Kapolei as an option for someone who is spending a couple of days on Oahu and then going to a neighbor island resort for a week.  You will need to plan around rush hour traffic if you are doing things town side.  However, you will have a brand new hotel.  It will not be next to the beach.  However, you can visit nearby Koolina or White Plains Beach while you are there.
> http://embassysuites3.hilton.com/en...tes-by-hilton-oahu-kapolei-JRFOKES/index.html



+1 for staying in Kapolei, as it's also closer to the Arizona Memorial (need reservations). And for cheaper souvenirs you can also hit the Aloha Stadium swap meet   Also can go to the touristy Dole plantation by Wahiawa (their pineapple whip drink is tasty).  
Just gotta remember to plan your trips cross-flow to local rush hour.  In the morning, traffic is going eastbound into Honolulu, and in afternoon (3-6) westbound back to Kapolei, Waipahu, Pearl City etc.
Can also take scenic  H3 from Aiea to Kaneohe; scenic for passengers, not for driver .



taterhed said:


> The best souvenirs (IMHO) have got to be the Crazy Shirts.  Look it up.  They run $30-35 bucks, but they are quality, last a long time and come very nicely wrapped in cellophane bags with a nice packaging.  You can get them customized with a loc/date stamp.  Toys and knick-knacks break, but the shirts live on and on.  The wine/beer/chocolate/curacao dyed shirts are fun to talk about.  my closet is littered with them.



The Ward center Crazy Shirt location is their outlet store.  I usually hit them up when I'm in Honolulu.
Somehow I thought they were closing, but think I mixed them up with the next door Ward Warehouse mall which is closing to make way for (i think) condos. Prime real estate, across the street from Fisherman's wharf, so ocean views... and prime prices   Anyway I think the Crazy Shirt Ward store is still open.  I'll check when I'm there again around Thanksgiving.


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## easyrider (Oct 16, 2017)

njny2000 said:


> Wow, thanks for all the detailed suggestions. very helpful! Oh, I wish I was able to do more days, but 9 days/ 8 nights is most we can do.
> 
> Anyhow, finally decided (and pulled the trigger) to use my United miles to book the airfare with the following Itinerary:
> 
> ...




The Courtyard by Marriott on the North Shore is really close to Polynesian Cultural Center, Banzai Pipeline and Sunset Beach and Turtle Bay and includes a decent continental breakfast.

Bill


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## Caligirlfrtx (Feb 16, 2018)

taterhed said:


> Actually, there are many airlines that fly direct to  OGG, LIH, KOA (and of course HNL) from the west coast.  LAX, SFO and SEA all have direct flights to all the islands..
> Breaking a westcoast trip (EWR, JFK or LGA) up into two equal legs (EWR to SFO, SFO to OGG) doesn't add much time to the over all itinerary, but certainly makes the 12 hours more bearable.
> Also, NOT having to drag your bags in HNL to change airplanes is HUGE.  You should get automatic bag transfer in any mainland airport.  That connecting bag drag/ag inspection is the bane of my existence sometimes.
> 
> ...





DeniseM said:


> There is only one way I would try to do 2 islands on a short 9 night trip:
> 
> 1)  Fly into Oahu and spend 2 nights in a hotel to see the historical and cultural sights.
> 2)  Fly to your 2nd destination, and spend 7 night, and fly home from that island (if possible.)


This may have just solved my delima. Great idea! I'm trying to plan Hawaii from the east coast, stopping in Ca for cheaper fares then to Hawaii for two weeks. Must see the historical sites but don't necessarily need to spend too long there, final destination would be Hiltons on the BI for two weeks.


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## WalnutBaron (Feb 17, 2018)

Caligirlfrtx said:


> This may have just solved my delima. Great idea! I'm trying to plan Hawaii from the east coast, stopping in Ca for cheaper fares then to Hawaii for two weeks. Must see the historical sites but don't necessarily need to spend too long there, final destination would be Hiltons on the BI for two weeks.


If you're headed to the Big Island Hilton resorts, be sure to book your last leg of your trip to KOA (Kona side of the island), not ITO (Hilo side). I've made that mistake, and had to drive across the island to get to Kona during our first visit to the Big Island many years ago. All of the Hilton resorts are in or near Waikoloa on the Kona side. Aloha!


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## Egret1986 (Mar 21, 2018)

taterhed said:


> We're east-coasters and frequent travelers.  We go to Hawaii every year and are VERY familiar with dragging family on the 10 hour and 41 minute flight (if you're lucky enough to go direct) from EC to Hawaii.  Then comes the inter-island flight.
> 
> It's hard to move groceries, clean toys/clothes etc and schlupp the gang across town/island.  Plus, that's peak week time.  I'd look at better airfare combos, companion tickets etc... and sticking with a timeshare that has availability for the whole start/stop days of travel.
> 
> ...



Researching a potential 2-week vacation next year during whale season.  This will be our second trip to Hawaii.  The first was in June 2015 to Kauaii (Poipu/Princeville) and Kona, BI.  It was a great vacation.

We are East Coasters and I just realized that you are also from Virginia.  Since you've actually done a 10 hr 41 min direct flight  to the Islands, I will assume you live nearer an International airport than I do.  The best that I've seen is more than 13 hours.  I still can't wrap my head around being on a plane for that many hours.  When we did our 2015 trip, we stopped on the West Coast for the night and flew to Kauai the next morning.  Curious if you are able to fly First Class.  I'm not sure that I could fly through to the Islands even in First Class.  Maybe.  I will be attempting to utilize my AA Miles and the timing is now or pretty soon to ensure good routes.

Maui is the island that we plan to visit this time, though going back to Kauai for the second week or visiting Oahu for a few days after our Mauai stay has potential.  We're definitely open to staying on Maui for the two weeks.  Stay at the same resort for the two weeks or do a move and spend time in another area?  I am leaning towards the Kihei area.  We prefer smaller resorts with a more casual vibe.  

The whales will be a spectacular bonus.


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## JIMinNC (Mar 21, 2018)

My 2-cents...we're not in Virginia like taterhed, but are nearby in North Carolina, so we have the same flight time issues as you do. We did the west coast overnight stopover once - on our honeymoon in 1992 - and vowed never to do it again (unless there was some reason we wanted to visit for a few days on the west coast). In our eight subsequent trips, we've flown straight through from Charlotte to/from the islands, with a single flight connection in either Phoenix, Dallas, Atlanta, Denver, Los Angeles, or San Francisco. 

In a nutshell, if you try to break it into two legs with an overnight stopover on the west coast, the five-hour flight from the east coast to the west coast basically ruins one entire day with the time getting to the airport/check-in, the flight, and then baggage claim, ground transport to overnight hotel. Then the five-hour flight from the west coast to Hawaii, plus the front-end check-in and back-end baggage claim ruins yet another day. Same thing on the way back home. IMHO, better to get it all over with in one day. In reality a flight to Hawaii is not that much longer than an 8-10 hour flight to/from Europe, and people do that all the time without considering doing a stopover in Greenland or the Azores!


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## Luanne (Mar 21, 2018)

We break the trip up with two nights in San Francisco each way.  We are retired so have no time constraints.  It also gives us a chance to see our older dd who lives in the area.


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## Judith Frye (Mar 22, 2018)

Hello Tug friends! I don't know if I should start a new thread for this or tag onto the existing one.  My husband and I have been to many Caribbean islands (including our home timeshare in St. Maarten) over 20+ years but we're thinking of trying Hawaii this May.  We live in Chicago. I wanted to go to Maui because we love beaches (never go into pools) but for 24 hours I have on hold via SFX getaways a 1-bedroom May 26-June 6 at the King's Land Hilton Grand Vacation Club on the Big Island. It seems we could visit Hapuna beach, Maniniowali, 69 beach, 49 beach etc.  So - if we wanted to spend about 2 weeks in Hawaii, where should we consider for May 19-26? We can get Maui Sunset Condos May 14-21 (2-day overlap) or rent a week from someone in the TUG Marketplace.  We need to figure out our flights of course - we have frequent flyer options (an Alaska companion fare, Alaska miles, United miles, lots of Avios for American, etc.).  It seems there are no nonstops from Chicago to Kona so we'd have to change planes in Honlulu, is that right?  All advice is welcome for first-timers to Hawaii who love beaches and space of at least a one-bedroom unit size, for this May.  Thanks!


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## Kapolei (Mar 22, 2018)

Judith Frye said:


> Hello Tug friends! I don't know if I should start a new thread for this or tag onto the existing one.  My husband and I have been to many Caribbean islands (including our home timeshare in St. Maarten) over 20+ years but we're thinking of trying Hawaii this May.  We live in Chicago. I wanted to go to Maui because we love beaches (never go into pools) but for 24 hours I have on hold via SFX getaways a 1-bedroom May 26-June 6 at the King's Land Hilton Grand Vacation Club on the Big Island. It seems we could visit Hapuna beach, Maniniowali, 69 beach, 49 beach etc.  So - if we wanted to spend about 2 weeks in Hawaii, where should we consider for May 19-26? We can get Maui Sunset Condos May 14-21 (2-day overlap) or rent a week from someone in the TUG Marketplace.  We need to figure out our flights of course - we have frequent flyer options (an Alaska companion fare, Alaska miles, United miles, lots of Avios for American, etc.).  It seems there are no nonstops from Chicago to Kona so we'd have to change planes in Honlulu, is that right?  All advice is welcome for first-timers to Hawaii who love beaches and space of at least a one-bedroom unit size, for this May.  Thanks!



You will get many different opinions.  Mine is that all first timers should spend at least a few days on Oahu.  Then Big Island and/or Kauai.  I would skip Maui on a first trip.  But, some people love Maui.  And would only go Maui.  So your question is not much different than I am going to California, what would you suggest?


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## linsj (Mar 22, 2018)

Judith Frye said:


> It seems there are no nonstops from Chicago to Kona so we'd have to change planes in Honlulu, is that right?



I only know United, which doesn't have a nonstop ORD-KOA. The plane change is in LAX or SFO or Honolulu that puts you on another airline.


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## Mosescan (Mar 22, 2018)

I can’t speak to the other islands as we’ve only been to Oahu. We’re at kingsland in a few weeks. 

The pointer I will suggest is for flights. From where I live in Canada we could fly directly to Kona but it lands late and wastes the first day so we are flying to Honolulu first and then inter island to get in much earlier. That way we get some beach/pool time the first day.


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## Judith Frye (Mar 22, 2018)

I do understand that there are judgment calls involved of course. (I advise people on differences among the Caribbean islands, for example.) In this case I'm trying to understand about the places with the best beaches for swimming and snorkeling (not surfing) where I can pay less than $3000/week on a rental; and the easiest flight options (what's the best airline strategy in terms of price or miles/points to get to some other island nonstop on 3/19, then fly to Kona 3/26, then get home the shortest time possible 6/6). I see in resort reviews that some people fly in a day early and stay somewhere for one night to avoid a late night arrival to their timeshare week, or use a free hotel night for the 12 hours between 10 am checkout time and redeye flight departure on their last day, so that kind of advice would be welcome too.  Thanks! Judith


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## Judith Frye (Mar 22, 2018)

Mosescan said:


> I can’t speak to the other islands as we’ve only been to Oahu. We’re at kingsland in a few weeks.
> 
> The pointer I will suggest is for flights. From where I live in Canada we could fly directly to Kona but it lands late and wastes the first day so we are flying to Honolulu first and then inter island to get in much earlier. That way we get some beach/pool time the first day.


This is what I was posting about as you were writing, thank you!


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## Mosescan (Mar 22, 2018)

IIRC we left 2-2:30 hrs between flights as we’ll have to collect luggage and re check in.


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## JIMinNC (Mar 22, 2018)

American Airlines flies nonstop from Phoenix and Los Angeles to all four main islands - Oahu/Honolulu, Kauai, Maui, and Big Island/Kona, so you could fly Chicago to either LA or Phoenix and connect to the island of your choice and avoid having to deal with the inter-island terminal change and bag claim/re-check at Honolulu. From Chicago, you can only fly nonstop to Honolulu.


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## Egret1986 (Mar 23, 2018)

Kapolei said:


> You will get many different opinions.  Mine is that all first timers should spend at least a few days on Oahu.  Then Big Island and/or Kauai.  I would skip Maui on a first trip.  But, some people love Maui.  And would only go Maui.  So your question is not much different than I am going to California, what would you suggest?



Our first trip in 2015, we went to Kauai, then the Big Island.  Only two weeks, only two islands.  There is little availability for Maui when exchanging, and those two islands offered availability.  A trip is being considered for early 2019 to check out Maui.  We're considering either two weeks in Maui or a shorter trip on Maui and spending about three days on Oahu.  

I am interested as to your reasons for not being a Maui lover.  You are correct, some people love Maui and would only go to Maui.  It's hard not to be influenced to head to Maui.  We loved both the Big Island and Kauai.  We are wondering if we should do Kauai again for the second week.

Please share your reasons for preferring other islands to Maui.


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## taterhed (Mar 23, 2018)

Egret1986 said:


> Researching a potential 2-week vacation next year during whale season.  This will be our second trip to Hawaii.  The first was in June 2015 to Kauaii (Poipu/Princeville) and Kona, BI.  It was a great vacation.
> 
> We are East Coasters and I just realized that you are also from Virginia.  Since you've actually done a 10 hr 41 min direct flight  to the Islands, I will assume you live nearer an International airport than I do.  The best that I've seen is more than 13 hours.  I still can't wrap my head around being on a plane for that many hours.  When we did our 2015 trip, we stopped on the West Coast for the night and flew to Kauai the next morning.  Curious if you are able to fly First Class.  I'm not sure that I could fly through to the Islands even in First Class.  Maybe.  I will be attempting to utilize my AA Miles and the timing is now or pretty soon to ensure good routes.
> 
> ...



Well, decided to wait to reply....and let the others make some comments first.

We have spent a great deal of time in Hawaii for work and pleasure over the years.  Most 'work' was on Oahu.  I understand why people would want to spend a (full) day in Pearl, to see the sights and absorb some of the Hollywood image of Hawaii,  but I could never personally recommend Honolulu for more than just a day or two.  It's far too much like every other big city you've ever seen.  But, to each his own.

We have made the annual pilgrimage to HI for vacation the last 4 (5?) years using a number of strategies and routes.  This last year (Jan/Feb), I think we got it right.

Long-haul, _*No*_:Traveling from the East Coast (EC) to HI, non-stop, is brutal. We've tried sleeping it off (including sleeping pills), staying awake, drinks-movies-food (not necessarily in that order)....it's still painful.  Then, unless you're staying on Oahu, you probably have an overnight hotel stay or an inter-island flight.  Ugh.  Nothing makes Jack a dull boy like 10:41 of flying, 3 hours of waiting, 20 mins of cab ride or another flight etc... etc...  I *do not* recommend this. 
Med-haul, *Yes*: Traveling from EC to HI with one stop  Now you're talking.  By making a stop in IAH, ORD, DEN, SEA or SFO/LAX, you open-up lots of options to fly direct to Maui or Kawai etc.... and give yourself a much need break.  I planned flights with 3-4 hour layovers.  Perfect for a break, freshen, meal, drinks--whatever.  Great time to use that Priority/Airline lounge pass. By breaking-up the flights, they seem much shorter IMO.  Plus, you can choose to do a leg in first class (for me, wide-body only, not on the 737).
Arrival:  We like to avoid HNL airport.  Sorry, but the luggage drag (inter-terminal) and traffic etc... is not for us. YMMV.  Flying direct to OGG or LIH etc... yields much better results for us.
Arrival:  We always plan to arrive a day early.  We stay in a hotel (or Worldmark) and generally don't rent a car the first day.  Why?  this allows us to hit Costco early, get the rental car on our own time-line and then arrive at the resort early on check-in day.  We got a horrible room assignment one year because our flight was delayed.  Then we had to go back to town to hit Costco the next day.  We lost a full day this way.
Inter-island: Fly early.  This fits with the rental car strategy (early first day, early last day) and will allow for 1-2 delays due to weather.  It happens.
Departure:  Leave late.  No matter how early you leave on your last day....you'll still get back late (East Coast).  Plus, after two weeks in HI, you'll never sleep on the plane during daylight hours....you'll just be exhausted when you get home.   IF you leave late (even red-eye) you can stay at the resort all day or go into town.  You can shop, eat, drink and be ready to leave.  Jump on the plane, sleep.  Change planes...eat breakfast, freshen up....and head home.  Circadian should be good enough to get you home without falling asleep. By the time you start to unpack.....you'll be sleepy again.
We were very 'suspicious' of Maui before we went.  So many rumors of crowds, congestion and 'overdeveloped.'  After hitting Maui for the last 2 years, I can definitely say that Maui is tied with Kauai as my favorite island.  Beaches are amazing, volcano is spectacular, jungle is....well, jungle.  There are just as many wild and wonderful areas as you have time to explore.  You could easily fill two weeks of vaca in Maui and still just be scratching the surface.  The whale-watching in Maui is definitely amazing.

Kauai was our first love--from many years ago--and is still our first love.  We call it a 'tie' with Maui to avoid hurting anyone's feelings. I'm not sure that there is anywhere more beautiful on Earth (IMNSHO) than the Napali coastline.  Kauai definitely seems more 'natural' than Maui (to me) and there is more to do than you can shake a stick at. 

My first instinct was to recommend staying in Maui for two weeks.  But, if you're going to stay in Kihei and smaller more 'intimate' resorts, I might consider 1 week Maui and 1 week Kauai.  There really are a lot of nice smaller resorts to choose.  Or, maybe a week in Kihei and a week in Kaanapali?  Keep in mind, the northshore of Kauai can have some weather in the Jan/Feb months.

What ever you do, have a great time and take pics!


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## Kapolei (Mar 23, 2018)

Egret1986 said:


> ......Please share your reasons for preferring other islands to Maui.



My preference might be a bit esoteric.  It is not the sights and the scenery.  Or the quality of the hotels.   I live on Oahu.  I just personally would find myself more “at home” on Kauai, Molokai, or the Big Island.  That doesn’t mean I wouldn’t prefer Maui over some other places on the mainland.

As my screen name indicates my bias is towards west Oahu.  No better place. But again, just my preference.  And we have our problems like anywhere else.


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## taterhed (Mar 23, 2018)

Kapolei said:


> My preference might be a bit esoteric.  It is not the sights and the scenery.  Or the quality of the hotels.   I live on Oahu.  I just personally would find myself more “at home” on Kauai, Molokai, or the Big Island.  That doesn’t mean I wouldn’t prefer Maui over some other places on the mainland.
> 
> As my screen name indicates my bias is towards west Oahu.  No better place. But again, just my preference.  And we have our problems like anywhere else.



For the record....I've never stayed at Ko'Olina (yet) but I do like Oahu just fine....once you get east/north or west of HNL.   Just not a fan of the city etc......


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## slip (Mar 23, 2018)

I like Kauai first and Maui second but the Big Island is a close third.  We stayed three weeks once and did two weeks on Maui followed by one week on Kauai. My wife always says she wished it was the other way around but it worked great. We stayed one week in Kihei and one week in Kahana. Maui is a beautiful island and only second to Kauai in my opinion but the one thing I don’t like about it is a lot of the island is only accessible though that road to Hana or that north shore road that’s just as bad. Too many turns and very slow going. And even after traveling on those roads there really wasn’t much to return to again anyway. Of course, just my opinion.


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## JIMinNC (Mar 23, 2018)

We've always been drawn more to Maui for a few reasons - 1) As others have noted, it has some of the same natural beauty as Kauai. Kauai is still more naturally scenic and more unspoiled, but Maui is a close second in that category. 2) We have always loved the Kaanapali Resort area and the little town of Lahaina is one of our favorite places on the planet - think sunsets over the island of Lanai from Cheeseburger in Paradise or Kimos! 3) Maui combines the scenery and great upscale resorts with outstanding restaurants in the west Maui area - Lahaina/Kaanapali/Kapalua. We have our favorites that we always have to visit. We never plan to eat dinner in the room on Maui - too many great restaurants, and that's one of the things we like best about traveling is eating great food in nice restaurants. Those three factors cause Maui to rise to the top of our list, but we also love Kauai and the Big Island. We'll be spending a week on each next Feb/Mar.

Since the OP says they prefer simpler, smaller timeshares, then Kihei may be a better match for them than West Maui - although there are a few smaller, older independent resorts in the Kahana area between Kaanapali and Kapalua. Can't offer much help on Kihei or Kahana since we usually just pass through Kihei on our way to Makena Beach or to play golf at the Wailea Resort, and rarely need to drive through Kahana, since there is a by-pass on the Honopiilani Highway.


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