First time in Hawaii - Need advice

[WalnutBaron]

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!

 

[Egret1986]

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.

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 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.

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.

 

[JIMinNC]

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!

 

[Luanne]

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.

 

[Judith Frye]

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!

 

[Kapolei]

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?

 

[linsj]

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.

 

[Mosescan]

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.

 

[Judith Frye]

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

 

[Judith Frye]

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!

 

[Mosescan]

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

 

[JIMinNC]

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.

 

[Egret1986]

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.

 

[taterhed]

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.

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!

 

[Kapolei]

......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.

 

[taterhed]

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......

 

[slip]

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.

 

[JIMinNC]

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.