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Planning a Hawaii timeshare trip for 2022. Any advice accepted.

Luanne

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Because of the historical things that most people want to see on a first visit, there's a lot more than just Pearl Harbour.
I understand there is more to see on Oahu than just Pearl Harbor. And maybe you're just trying to give the OP more ideas. But when someone has expressed an interest in what they want to see and do, I'm not sure why we need to give them more options.
 

Dean

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I understand there is more to see on Oahu than just Pearl Harbor. And maybe you're just trying to give the OP more ideas. But when someone has expressed an interest in what they want to see and do, I'm not sure why we need to give them more options.
First we'll have to agree to disagree here if you think it's inappropriate to make the recommendations I made, you don't know what you don't know. Second, in reading the OP the choices were very broad. They can then decide for themselves.
 

zentraveler

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Because of the historical things that most people want to see on a first visit, there's a lot more than just Pearl Harbour.

There really is. The north shore is great and the drive from HNL is beautiful (and stop for lunch at the shrimp trucks). Doris Dukes home if one wants history and culture, Chinatown, and more depending on desires. Only uselful to the OP as a way of broadening horizons if the other islands don't work out.
 

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Hnl also has the most air connections. We have been to all islands and are adding a week after BI on Oahu (3 for day trips around island and 3 to veg at dvc aulani). No desire to do anything on Waikiki. Easy/cheap air back to mainland.
 

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If you are retired military (from Active Duty or Reserves) you can Book a Cabin at KMC (Kilauea Military Camp), which is located within the Volcano National Park. The cost depends on size of Cabin and your military rank at time of retirement.
 

slip

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The first thing the OP has to decide on is there list of must sees. Sounds like they know the more islands, the more difficult it is. The, without killing ourself, comment shows they know the dangers with that type of planning. But it sounds like they are still open to that type of trip.

I don’t vacation that way. I have to avoid rushing around and hurrying to the next thing I need to see. When I was coming here often, I only made one two island trip. It was three weeks with two on Maui and one on Kauai. Since then I have done Maui and Molokai but that was after years coming to the islands.

I would do both weeks on the Big Island, especially since the volcano is active again. Otherwise, I would do the Big Island and then a week on Maui.

That’s my 2 cents.
 

DaveNV

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This is a pretty ambitious trip idea. Step back and think "big picture."

I think it needs to be mentioned that OP is expecting to make exchanges through II for accommodations. Presuming the Mexico timeshare will have the trade power to pull it off, there are considerations:

Island hopping will need to be curtailed, unless exchange days are sacrificed to meet the island hopping schedule. To see the volcano, Maui, and Kauai is going to require three exchanges, unless hotel time is to be booked somehow. It would also require three rental cars, which can quickly add a lot to the cost. Staying for less than a week anywhere seems like a waste of money, since the exchanges will probably be seven nights each. Trying to see everything at once is do-able, but the added expense and logistics also make it rather impractical.

My advice to the OP is to decide on a max of two islands, and stay one week at each. If airfare is booked multi-city, into one island, and out of the other, then all that's needed is one inter island flight, and two rental cars.

I do not agree the cruise around the islands is a good idea for a first visit to Hawaii, unless you want to give yourself over to the tour companies. In-port hours will be limited, and OP would have to book a tour to see anything - which will also add to the cost, especially if there are four people in the group. Better to have the time to see what they want to see, on their terms.

To the OP: Going in, accept that there is no way you can see everything in one trip, and have it mean anything. So don't even try. Slow down, take your time to enjoy where you are, and what you're seeing. Then figure you'll need to make another trip in the future, to see other things. Each island has its own appeal, and you could spend your entire vacation on just one island, and still not see it all.

There are many people on Tug (myself included) who have been to Hawaii dozens of times, and who keep returning, because once it gets under your skin, there is no way to get over it. Don't force the issue, and give yourself space to enjoy your vacation. It could be the start of something wonderful in your life.

Get started on those exchanges. It will not be easy to get them in prime season like that, and may be nearly impossible to get them during back to back weeks. Where you can get an exchange may decide which island(s) you'll be able to visit.

Dave
 
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alwysonvac

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Yes, thank you. I would view the NCL ship as a means of transportation with some inexpensive meals. We would not expect our usual ship experience. But you can’t beat the itinerary. I’m just not willing to spend 4-6 days at sea getting to the islands and back. Not in the middle of the Pacific anyway.

Sent from my iPhone using Tapatalk

JMHO...I won’t rule out cruising. It really depends on what you want. Cruising will give you the opportunity to briefly explore each port and it also helps you to determine which places you want to come back to visit in the future ;).

During my first visit to Hawaii, it was an extended family trip (4 couples). We also decided to view the cruise as a means of transportation. We had a ten night cruise from Honolulu in 2000 which included a non-US port. For that initial trip, we did a few nights in Oahu before and after the cruise. We had a great time exploring the various islands. Each island is unique, offering a different experience and personality. Cruising the various islands made me want to return and stay longer. I’ve also been back many times over the last 20 years with various friends and family members. I even bought a few Hawaii weeks along the way. There’s a link to my photo album below that covers some of our Hawaii trips through the years.

NCL’s Pride of America does offer a very nice itinerary. I like that it stays overnight on two islands.
- 2 days in Maui
- 1.5 days in Kauai
- 1 day each in Hilo
- 1 day in Kona

If you decide to take the Pride of America cruise, definitely checkout the tips and reviews on the Cruise Critic boards (especially tips on rental cars and private tours) - https://boards.cruisecritic.com/

Here are a few threads:

Whatever you decide you‘ll have a great time. Everyone has their favorite island but honestly all of the Hawaiian islands are wonderful and offer lots to see & do.
 

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I agree with the post that Maui is sort of the image of Hawaii. The Big Island is different. Oahu is different. Kauai, seems to depend on where you are. When I arrive on the Big Island, which I do enjoy, I also could be in LOTS of places. When I arrive in Maui there is no doubt about where I am — Hawaii.

I disagree with those that say don’t go to Oahu, and don’t understand those that have been to Hawaii multiple times and have never been to Oahu. There’s so much to see and do there. Waikiki is a world destination. You don’t have to spend a week there, but a couple days to experience it is like spending a few days in Vegas, or Manhattan, or San Francisco. That aside, and Pearl Harbor aside, the drive around the island, the North Shore, Turtle Bay, the pineapple plantations (Dole) etc., are beautiful. Why would anyone never want to see that part of Hawaii, I don’t get.

But for me the place I always want to go back to is Maui.
 

zentraveler

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I agree with the post that Maui is sort of the image of Hawaii. The Big Island is different. Oahu is different. Kauai, seems to depend on where you are. When I arrive on the Big Island, which I do enjoy, I also could be in LOTS of places. When I arrive in Maui there is no doubt about where I am — Hawaii.

I disagree with those that say don’t go to Oahu, and don’t understand those that have been to Hawaii multiple times and have never been to Oahu. There’s so much to see and do there. Waikiki is a world destination. You don’t have to spend a week there, but a couple days to experience it is like spending a few days in Vegas, or Manhattan, or San Francisco. That aside, and Pearl Harbor aside, the drive around the island, the North Shore, Turtle Bay, the pineapple plantations (Dole) etc., are beautiful. Why would anyone never want to see that part of Hawaii, I don’t get.

But for me the place I always want to go back to is Maui.

I feel exactly that way on all of the islands; like I have landed in Hawaii. Probably the most is landing in KOA since you walk straight off the plane into the Hawaiian air (so few airports like that anymore), and LIH because it has an open air airport and baggage claim. Every one of these islands has so much charm and so many things to do and so many rural aspects that for me the place I always go back to is any one of the islands that works for a given trip. I truly don't have a favorite (although Princeville may come close).
 

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Who knows where things will be Covid in 2022, but right now if you spend 72hrs and then get a test you skip quarantine even for Kauai. So might want to plan to spend at least 72 hours on a Island before you go to next.
For me this is the Advice I give folks:
Oahu - If you want the Brady Bunch/TV Special going to Hawaii/Tourist Hawaii this is it. For me it always feels too much like any other resort Island. Nice but not really as special. Felt more like this is what you think Hawaii will be like. But, Pearl Harbor, Diamond Head, Waikiki Beach, North Shore etc... Are Iconic so. And flight to HNL are easy and cheap.
Maui - I bought a Go Pro and want to show it off Island. Lots of good adventure stuff to do. Road to Hana, Haleakala etc.. If Whale season, must do.
Big Island - If Volcano can be seen, cool. When we last went drove forever from resort to see dirt in the bottom of a hole and a small glow way off in the ocean, so YMMV. If you are a coffee or chocolate fan, can see farms. Not of fan of the distances for driving but cool Island.
Kauai - I love Jurassic Park Island or we just want to chill and enjoy our Honeymoon. If you go, spend the bucks and do a Helicopter ride. It is Amazing and gives you those views of waterfalls you see on video. Very laid back feel. I prefer this Island as my return Island but if first trip, I would not just do Kauai.
 

LisaRex

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I've been to Hawaii 7 times and my personal favorite island is Maui. My advice is to stick to 2 islands, esp if you're trying to get timeshare exchanges, which are often weekly. Which 2 islands you pick is entirely up to you. Generally speaking, Oahu is the most crowded with tons to do and tons of people, Maui and BI are like the suburbs, and Kauai is more rural, with not as much touristy things to do.

Anyway, here's my advice:

1) Decide on what is most important to you: Airfare OR lodging:

If you absolutely must rely on timeshare exchanges, then clearly securing II lodging is the most important. That will probably dictate what islands you visit, in what order you visit them, and what weeks you travel. If that's the case, then put in your searches as early as possible to try and get that nailed down, because you can't book airfare or activities or rental cars until you do. Note that Jan-Apr is high season on the islands, and probably the most difficult to exchange into unless you pick the 1st/2nd week of January. If you can switch to the fall, you'll find a lot more availability.

If renting lodging is an option, then that really opens up your options, and you can be more in control of where and when you go. A few years I divested my timeshares in lieu of RENTING timeshares, and I found that much less stressful when planning vacations. I cut down significantly on my budget by being able to shop airfares and/or securing flights with my travel points. I've also found that traveling on a Tuesday or Wednesday can often cut airfare by a few hundred bucks/points per person, which usually means 3 or 4 extra nights for no additional money.

Once I get my travel dates locked down, then I secure my lodging via Tug Marketplace or Redweek. Booking a unit with a kitchen and washer/dryer allows me to save a few hundred bucks on luggage fees as I'm able to pack much more lightly. With a reasonable budget of $3500 per week for a 2 bdrm, I can usually find exactly what I want.

Once I get my main timeshare/condo booked, then I work on filling in any extra days. For instance, if I'm flying in on a Wednesday, and can't check into my timeshare until Saturday, I book "side" adventures, away from the resort to fill in the extra nights. For instance, on Big Island, I'd book a B&B in Hilo for 3 nights. On Maui, I'd book 3 nights in Hana. On Oahu, I'd book 3 nights on the North Shore. Etc.

Tips:
When booking airfare, note that you can fly into one island and home from another on the same itinerary. No need to return to the island you landed in, though the most CONVENIENT itineraries are most often through Oahu. If the most convenient/cheapest flight is via Oahu, then consider adding 2 nights to see the Pearl Harbor exhibits, which IMO are incredibly worthwhile. PREFERABLY do this at the beginning of your trip so that you begin your trip on a busy note and end it on a relaxing note.

If you want to see the volcano on BI, which is a 2-3 hour drive from the resort area of Kona, don't try to do a day trip. Instead, do yourself a favor and book a B&B for at least 2 nights to give yourself plenty of time. This requires packing warmer clothes (e.g. long pants and rain jackets), but worth it. Also note that there are 2 airports on BI, so take advantage of that by beginning your trip on one side and ending on the other, which means renting your car with pick up from one and drop off in the other. The Hilo side only accommodates intraisland flights, so if BI is your 1st island, fly into Kona and to the next island via Hilo. If it's your 2nd island, then fly into Hilo and home from Kona.
 

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Once I get my main timeshare/condo booked, then I work on filling in any extra days. For instance, if I'm flying in on a Wednesday, and can't check into my timeshare until Saturday, I book "side" adventures, away from the resort to fill in the extra nights. For instance, on Big Island, I'd book a B&B in Hilo for 3 nights. On Maui, I'd book 3 nights in Hana. On Oahu, I'd book 3 nights on the North Shore. Etc.
This is something often missed by people. I've found on many occasions by going a couple days early or staying a day or two longer the airfare savings pays for the extra days. Since TS are often Sat-Sat affairs, and those can be the most expensive for airfare, I always look at Thursday and Monday/Tuesday air and then book something for those "gap" days, adding several days to a Hawaii trip with no added cost.
 

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I have a different take on Hawaii. I have been to all the islands several times over approximately 7 trips over the years. I like Maui the least of the islands. I love Oahu, believe it or not. As long as you are not in Waikiki, Oahu feels more Hawaiian and real that Maui. I like Kauai and the Big Island a lot. To me, the ocean in Oahu, Kauai and the Big Island is much nicer than Maui. Maui is a deep blue ocean whereas the other islands have more variety in the ocean colors depending on where you are. Kauai has such variety on one island from the ultra lush Princeville to the gorgeous ocean and beaches in Poipu. Big Island has a beautiful ocean in the Mauna Lani area. That is my favorite part of the Big Island. You definitely need more than a day to see the Big Island. Oahu has so much variety from the calm bays in by Marriott Ko Olina and Aulani, to the surfing hot spot on the North Shore, to the beautiful ocean on the east side. Plus Oahu has so many tourist attractions, probably more than all the other islands. Maui is nice but it’s the Bora Bora of Hawaii, IMHO.
 

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First we'll have to agree to disagree here if you think it's inappropriate to make the recommendations I made, you don't know what you don't know. Second, in reading the OP the choices were very broad. They can then decide for themselves.

I also suggested Oahu as having the most to see, the most variety, the most tourist attractions and some of the most beautiful ocean. I do not see anything wrong with suggesting other options since he is asking about Hawaii.
 

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I also suggested Oahu as having the most to see, the most variety, the most tourist attractions and some of the most beautiful ocean. I do not see anything wrong with suggesting other options since he is asking about Hawaii.
I think the point is, you’d be hard pressed to find a place in Hawaii where you would not be able to enjoy yourself. I’ve personally not been anywhere in Hawaii where afterward I said, I wish I had not gone there.
 

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I would spend a week on 1 island ,then do a cruise that hits them all. We did that one yr and loved that we never spent a full day at sea, traveling at night and waking up in a new place to explore. Flying to 3 islands uses up too much of your 2 weeks.
 

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Many years ago, we did three weeks, three islands - Maui, Kauai and the Big Island. The advice above to choose two islands if you are only staying two weeks is spot on. It's time consuming to fly from island to island and navigate the rental car hassles. Coming from the eastern US, we also needed a few days to recover from jet lag. We were two adults with two teens and two younger kids. It was a great adventure.

I went back later with just my husband and youngest son to spend two weeks on Maui. The adult kids are lobbying for another trip to Hawaii after COVID calms down.

Sheila
 

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I would spend a week on 1 island ,then do a cruise that hits them all. We did that one yr and loved that we never spent a full day at sea, traveling at night and waking up in a new place to explore. Flying to 3 islands uses up too much of your 2 weeks.

How did you sightsee on the islands? I've never cruised, but I've read about organized tours you can sign up for. Is that what you did or were rental cars readily available?

Sheila
 

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I think the point is, you’d be hard pressed to find a place in Hawaii where you would not be able to enjoy yourself. I’ve personally not been anywhere in Hawaii where afterward I said, I wish I had not gone there.


Yes I agree. I resisted visiting Oahu for 30 years. When I finally visited a couple years ago, I was pleasantly surprised and it might be my favorite island.
 

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How did you sightsee on the islands? I've never cruised, but I've read about organized tours you can sign up for. Is that what you did or were rental cars readily available?

Sheila
We were let off near rental car centers at each location. There was also the option of excursions. We needed to be back on the ship by 6 pm . We did dinner and a show each night and woke up to a new island or side of an island. There were 2 days on the big island, 2 on Kaui etc. We passed the volcano at night while it was erupting. I believe it was Norwegian. We aren't typically cruise people but this was perfect for us. You will want to come back and spend more time in your favorite islands.
 

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Do you have the ability to extend your stay longer? I would spend one week each on Maui and Kauai via II exchange and then 3-4 days on BI to see the volcano, either a cash stay, or a II getaway If available. To me personally, BI while pretty, has limited stuff that I am interested in.
 

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The first time I went to Hawaii, we started on the Island of Maui and it was great but I felt I still had not seen Hawaii as I had seen it in pictures. We then spent 2 nights in Waikiki and on Waikiki beach, wow, then I had seen Hawaii as I had been presented. I recommend two nights in Waikiki, take in Pearl Harbor and Waikiki beach area.
 

Luanne

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The first time I went to Hawaii, we started on the Island of Maui and it was great but I felt I still had not seen Hawaii as I had seen it in pictures. We then spent 2 nights in Waikiki and on Waikiki beach, wow, then I had seen Hawaii as I had been presented. I recommend two nights in Waikiki, take in Pearl Harbor and Waikiki beach area.
Personally I was very disappointed in Waikiki beach.

We own on Maui and spent many summers going there. The first trip we took to Oahu with our dds was so that we could go to Pearl Harbor. As we flew into Honolulu their comment was "THIS is Hawaii???".
 
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