I usually travel to Italy or Spain during the months between September and November.
But my partner has some difficulty walking more than 2-3 blocks, so it's getting more and more difficult to travel to many destinations. Hawaii might be a good option for us: A relaxing trip where we could visit some of the natural wonders without undue physical exertion. I know there are some sites that do require walking, but we could skip those, or I could go alone.

So, not in this order, focus would be: Natural beauty, food, swimming in pools or in flat, warm seas. Snorkeling??

I've been to Hawaii once, many years ago on an invited trip, but most of my time was spent on a ship stopping at a few ports on different islands, so I'm a total novice.
Partner has never been.

I'e done some reading but would like to know of either a good guidebook(S) and online sites for planning help.

We could take 2-3 weeks, and most likely have to fly into Honolulu. Should I plan any time for that city? (I've been to Pearl Harbor on that first trip but might like to return; not essential; would like to visit Bishop Museum). I'm laser- focused on food and would like to find some interesting places; not interested in fancy, with tasting menus; hole-in-the-wall and food courts are good.
I thought we might want to spend a few nights there to recover from jet lag and wander around. (Or, better to stop there on the way home (??) )

After that: Two islands other than Oahu, I think, and from what I've read, the Big Island and Kauai seem to be the most tempting. is this true for most of you?

On Kauai, should I be looking around the Princeville area? One base should be good on that island, right?

For Big Island: Two bases? I want to stay in the VNP. Are there any recommended hotels around there?
Someone close to me just returned from Mauna Kea Hotel; he was the one that got me interested in taking this trip he just raved about the hotel and the island. We try to avoid large hotels but since we want luxury with a great pool, this might not be possible--the luxury hotels I've seen online seem to all be very large.
One thing is non-negotiable: I need a great swimming pool. Calm water for sea swimming would be a. huge plus. I'd also like to snorkel.

We'd be happy to rent a car, unless it's better to get out by UBER or taxis (??).

Looking for upscale hotels, but not those in the $2,000 per night category.

We fly from NYC and would prefer a direct flight, of course. But I've never been to Vancouver and would love to stop there if that's part of an airline's route.
Never been to Seattle, either, so a stopover would be okay, if I can fly to Hawaii direct from there.....

What other info should I offer here in order for the "experts" to guide me in planning?
Ideally, I'd like to be there anytime from late September until Thanksgiving--up to three weeks is good..

Thanks a million for any help!!

A perfect option would be this particular hotel in St. Lucia - https://www.viceroyhotelsandresorts.com/sugar-beach/

It is gorgeous. Nestled on the beach, between the two Pitons, it's hard to find a prettier spot. It's also harder to find a better snorkeling spot, because you can just wade in from the beach and snorkel at the base of one of the Pitons. If you want to snorkel elsewhere, you can also take a boat out and they will take you to other snorkel sites. The roads can be rough on the island, but you can take one of the boats to anywhere else you want to go on the island - the market, Rodney Bay for lunch, wherever. There are cottages with plunge pools and continuous van service to the beach available but there are new(er) lodging options near the pool. Check recent reviews but it was paradise when we used to go. One particular boat taxi driver recognized us from previous years and we were able to see his son grow up. On the other side of the Piton is the black sand beach of Anse Chastenet but it has lots of steps and I don't think it is airconditioned. We went there for a beach day (via the boat) but I would not recommend that for a day trip with mobility issues.

Note - the water taxi drivers were off the beach of the resort. We'd arrange a day trip and they would take us anywhere we wanted to go. One day we'd go to the market. Another day to Rodney Bay and then you could add a snorkel stop. We also took a jeep tour around the island and stopped at waterfalls and took a hike in the jungle to a natural hot springs, but that would not work for your situation. Other than that, there's not much "city" or a lot of things to do off resort. Maybe things have changed since we would go though.

For a change of scenery, you could move up the hill to the Ladera resort -
https://www.ladera.com/
It's on the ridge, again between the Pitons. The original rooms (I think they've added new options too) were three walled rooms with private plunge pools. The 4th wall is open - as in open to the sky and the view. The 4 poster beds have mosquito netting but for whatever reason we didn't had no problem with bugs when we were there. We did weather through a tropical storm and that was an adventure. We were given the option to move into the main building for the night. Your months does bring the risk of hurricanes so that may not be an option at all for you. The restaurant there is fantastic (or was) and everything is easy walking via sidewalks. The infinity pool is gorgeous (pools at both places are beautiful). They do sent a van down to the beach a few times a day but we would get our beach time in and then move up to the ridge.
https://www.ladera.com/dining
Dasheene is their fine dining restaurant.

Back to Hawaii - on the Big Island we spent a week at the Wailkoloa resort and without checking out took a 2 day driving trip around the island and spent the night near Volcano. That was a good way to see the Big Island. We also spent five days at the Four Seasons Hualalai but didn't go off resort for that trip. That was a company retreat trip and it was fabulous. The place I loved in Maui is no longer there. We also stayed at the Waimea Plantation Cottages at Kauai and I really liked that but it's not for everyone.

The snorkeling at St Lucia was the best snorkeling I've done - and for 10 years my partner and I planned trips around snorkeling. For a snorkel trip, you can't beat just wading into the snorkel areas from the beach at the resort linked about. (It used to be the Hilton Jalousie and I still think of it as that, but that was many moons ago)l

I’ve been to Hawaii four times but always for business/conventions. The first time was to Oahu and stayed at the Hilton Hawaiian Village which was a large hotel but designed beautifully and has a large beach with a view of Diamond Head. Yes to visiting Pearl Harbor as it is so interesting and very moving. The second and third times were both to the Big Island and both to the Hilton Waikoloa which is an outstanding hotel but there are also many condominiums in the Waikoloa complex and finally the fourth time was to Maui to the Hyatt Regency. Neither the Hilton Waikoloa or the Hyatt in Maui have real beaches but they do have beautiful pools.

We always had a rental car on all these trips and I think a car is pretty essential in Hawaii. The Big Island is really big as it is an Island the size of Connecticut and to me it is the most interesting because of the varying tops of environment- snow covered mountains to tropical rainforest to cowboy country with longhorn cattle to fields of lava.

Coming from NY we always changed planes On the West Coast in either LA or SF. Since then Hawaiian Airlines offered service direct from NY to Honolulu. It is a long haul getting from the East Coast to Hawaii and back.

I've been to Hawaii, six times to Oahu staying in Waikiki, once on a family trip to Maui. You don't need a rental car on Oahu. You do need it on every other island. 14 days is very different from 21 days as far as picking islands. Big Island - they don't call it that for nothing is large and with a very different landscape than most people think of when picturing Hawaii.

Which guidebook doesn't matter just get a couple from the library for the history, photos, and highlights (don't use it for hotels, restaurants or current pricing). Get that online, here and on Trip Advisor and others.

We've chatted over other tropical destinations before. Oahu is what I know second best to Puerto Vallarta.

Personally I think you could do 2-3 weeks there only, flying in and out of HNL and barely scratch the surface. Oahu has the natural beauty of the other islands, but it also is packed with history and cultural options... Bishop Museum, Iolani Palace, ShangriLa Estate, Honolulu Academy of the Arts, Byodo-In Temple, Foster Botanical Garden, Ho'omaluhia botanical Garden, Nuk'uanu Pali Lookout, Chinatown, and we haven't even mentioned all the various beaches, free shows of Hawaiian music and dance...

My hotels are more in the $200 not $2000/night category -lol!

aloha suze

Living in California all my life, Hawaii has always been our quick (7-10 days) vacation destination. I can't count the number of times I have visited. Been to all the islands multiple times.

Oahu has the most historic sites, but is very crowded and staying in Honolulu can result in a lot of walking. We always got a car so we could visit all over the island. If you or your partner are retired military, Hale Koa Resort is wonderful and next to the Hilton Hawaiian Village. Hilton Hawaiian Village is a wonderful hotel also. HHV has fireworks every Friday night, which are great to watch from the beach. Loads of sightseeing all over the island.

Kauai is beautiful. I have stayed in the Princeville, Kapaa, Poipu and Lihue areas. I like the southern end of the island. My least enjoyable stay was in Princeville. We ended up driving south everyday for a week it was cloudy and cold in Princeville (mostly cliff hugging resorts), but beach weather in Poipu. The Sheraton Kauai is fantastic (I have stayed there) and has nice snorkeling. Kauai also has the fern Grotto (you get to via a river cruise),Waimea Canyon, Hanalei Valley Lookout (near Princeville), Koloa Rum Company Tasting room near Lihue, Lydgate Farm Chocolate Tour (near Kapaa), plus many more small but nice beaches. Due note that the north and east facing beaches on Kauai can have choppy waters.

The island of Hawaii (Big Island) is not known for it's beaches. Much of it is rocky or cliffs. Some of the best snorkeling places (Champagne Pond, the Waiopae Tidepools) where east of Pahoa, but got covered up by the volcano flow. That said, I love the island. While there are many hotels in the Kailua-Kona area, none are known for their beaches. Most are on rocky cliffs or have rocky shores. The one hotel that has a fabulous pool and has a great beach is the Waikoloa Beach Marriott. The beach is Anaehoomulu Beach. Known to locals as A Beach. There is good snorkeling off the Captain Cook Monument, but is from a boat. Also, the snorkel boat (you really don't snorkel, just hold a floating rail) to see the Manta Rays opposite the Kona Airport is a must do. The manta rays swim all around you. It is at night and the bright lights attached to the floating rails attract the rays. Sooooo cool! Volcano only has one hotel (most lodging is B&Bs, small inns, etc). It is the Volcano House. It sits in the National Park, very close to the Visitor's Center. It was refurbished a few years ago and has a restaurant. You can also visit Puuhonua O Honaunau National Historical Park. If you are over 65 and have a Senior National Park Pass, you can get into the parks for free.

Maui holds a special place in my heart. My brother used to live there, so I would visit frequently. Kaanapali Beach area is very nice. The best snorkeling is at Black Rock Beach on the north end of the Sheraton Maui Resort. Napili Bay area is nice also. South of Kehei (my brother lived there, so I would stay in a condo on the beach) is the Grand Wailea Resort. It is very, very nice (reflected in the price!!) Beautiful pool , nice beach and shopping next door. The condo complex I always stay at is next to a beach with an ancient "fishpond". Native Hawaiians used it to "catch" fish. It has long stone walls that are submerged during high tide. Fish get caught in it during low tides. During low tides it is a shallow "swimming pool" with fish and turtles. You can even snorkel in the waters. I usually get a condo with an ocean view and can see the "fishpond" down below. In February and March I can watch the whales from the balcony.

With 2-3 weeks, I would stay on more than one island. Many airlines have nonstop service from Maui (Kahalui), Big Island (Kona) and Kauai (Lihue) to Seattle, Denver, San Francisco and points east. You do not have to go back to Honolulu unless you want get a nonstop to New York.

Hope this helps.

I did a 3 week 3 island vacation in January. Some comments:

Flights: most Americans away from the West Coast fly the nonstops to and from Honolulu then take the Hawaiian Airlines hoppers between islands. We flew Alaska Airlines to Seattle then easy connections to any island. We wanted to put Oahu in the middle as the more urban island for variety. If I had to do it again I would start with the Big Island since I found it the least attractive and frankly unappealing so it was a downer to end with this island.

Snorkeling is good across Maui with easy walking in off sandy beaches. Snorkeling on the Big Island requires launching from rocky shores, only for more adventurous people. Oahu is quite beautiful with much history but lots of people.

I'm overwhelmed by all of the help you all offered! Thank you!!

Suze: I hoped you'd answer; you were so helpful to me with all of the PV info. I had to nix that idea but might go alone one of these years in near future..

Starrs: I've always wanted to go to St. Lucia and will look at that island for the future. That's much easier for us, coming from NY, but I want to go next fall and I think weather is still iffy in the Caribbean then

Tom: Could you let me know a lititle more what yo found so unappealing on the Big Island? I certainly will not be diving off any rocks to snorkel, that's for certain. I was down to what Madam wrote, the various landscapes..

Barb: I thought Princeville was the prettiest area on the BI but as you know, I know very little about Hawaii. There was a poster here who moved there, Songdoc, and I remember how much he loved that area.... Does it make sense to stay I two locations on Kauai?

I need to read more so I can ask more informed questions; right now I'm all over the place.
I will take out a couple of library books; I'm trying to get a sense of the whole place.

I'm assuming that Molokai (except for possible day trip) and Lanai are best left for future visits, right?

I read about many people booking with Costco for packages to the islands. Would I pay so much more if I just booked all hotels through their websites? I would not want any meals other than breakfast at the hotels. Do you all book packages when you go to Hawaii?

I have never booked a package. I travel solo and don't rent a car. So I just buy a plane ticket and book a hotel room.

*I'm trying to get a sense of the whole place.*

That is impossible It's even tough to get a sense of each of the islands individually. There is no "whole place" that is the Hawaiian islands. Each has some common but some unique history, traits, geography, etc. I honestly found the first few trips planning Hawaii as a newbie to be harder than figuring out where to go in Europe or Mexico!

For Kauai, Maui or Oahu I would pick only one location to stay as the islands aren't that big. Only for the Big Island might I pick two (although for a first trip I'd skip Big Island entirely myself. It just doesn't appeal to me like the other more 'tropical' ones do).

suze

Maui and Oahu are strikingly beautiful, the Big Island is usually stark, pretty in its own way but lots of exposed lava flows and grasslands which are interesting but not beautiful. Every beach we visited on the BI was basically unswimmable due to submerged rocks. There is definitely variety in landscapes and many pretty vistas, especially in the north coast, but the drive to the vistas is likely plain. Kona is almost dumpy in the center but there are gorgeous sea coasts just south and houses and condos have a nice view here. Snorkeled twice, once from a rocky ledge (hard exit, timed to wave peaks) or carefully picking over rocks. Missed the easy Maui snorkeling effortlessly from sandy beaches. Traffic is pretty bad in Kona, similar to Maui. Hilo has many homeless and an edgy (depressing) vibe.

Seeing the volcano errupt made my Big Island visit, but not going back.

Probably worth mentioning that Hawaii has a perfect climate, the Caribbean does not, too muggy and hot.

I loved the Big Island.
For snorkeling, check into Captain Cook. I recommend going on a smaller boat. Not sure your husband would enjoy the excursion though. I tried snuba there for the first time.

No need to stay two places on Kauai. Yes, Princeville/Hanalei area is very pretty and lush. Lushness comes with more rain, less sun and cooler weather. Also, it is farther from all the other sights on Kauai. Depends on what you really want to do on the island, whether you want to stay on a beach, etc. I have a friend who loves the Hanalei area. Everyone is different.

I, too, love the Big Island. Madam397 is correct, the BI has all types of environment. Waimea with the Parker Cattle Ranch and it's Paniolo (Hawaiian Cowboy) heritage; lush green of the areas north of Hilo plus Volcano (Akatsuka Orchid Gardens is there) and moon scape caused by the volcanic flows. Hilo is what I call "rough around the edges", but retains it's Hawaiian charm.

Molokai is very lush, laid back and very interesting. I took a long day trip there and really enjoyed it. Too much walking for your partner if it is a day trip.

All beautiful descriptions. Which is exactly why I say at least one hard-copy guidebook with tons of photos and maps are where you need to start.

That's how I first nixed Big Island -for me- just not the landscape I seek when there are lush tropical options more than freerange cowboys. Just kidding. I have no volanco desire. So any of that would mean... go there.

Then working out your timeline and how much you want to move around place to place. And taking into consideration mobility and accomodations each new island.

aloha suze

eks, there's a dynamic and quite diverse food scene on Honolulu, fairly easy to put together an interesting dining itinerary, although I remember your partner saying no Asian when you came to Oakland, so that could be a little challenging. Over the past few years I've visited a few times (after a pause of a decade+) because my niece is attending university there.

For guidebooks, I've always found the Lonely Planet guides have the most detail, great maps and they cover things in-depth. The more recent publications might be different, after the company being sold a few times.

If you have secondhand bookshops near you, or thrift shops, library, try them for a few different books, they all have different styles. DK have lots of coloured photos, great at home but not good to take travelling as their books are heavy.

We visited Oahu, Maui, Kauai and the Big Island, some multiple times. On the Big island, we stayed in Hilo and also Kona. It was my least favourite island.

I got a pile of guidebooks from the library at the beginning of planning my first trip. Things like nature photos, maps, history don't change. But I'd stick to the internet for information about prices, hotels, restaurants, because those (not just Hawaii, anywhere) change more quickly.

I'll buy a guidebook soon. Frommer's has a new one out but no idea how good that one would be. For sure I will get LP.

Leely, Asian food will be great....we avoided it in California (except for one meal) because of the friends we dined with....I've been reading about the food scene in Honolulu: So many things new to me! I just wonder how much time to plan in that city before flying out to (I think) Kauai and the Big Island.

Last night I read the book, MOLOKAI, and I am now reading the sequel, DAUGHTER OF MOLOKAI.

Just fyi, in case you haven’t seen the new generation of LP books. The company was sold & the new owners have rendered their new editions useless, stripping out all the information many of us found most useful. Hotels, restaurants, addresses, prices, etc, etc, . . . the nuts & bolts information that made them so valuable. Intending to buy a new “Mexico” I checked the new edition out of my library first & glad I did. So what I bought was a copy of the last edition published by the real L.P. Consider having a look before you buy.

reading about the food scene in Honolulu: So many things new to me! I just wonder how much time to plan in that city before flying out
I've spend 7-10 days on Oahu in Waikiki on various trips. Feel like I have barely scratched the surface, and I'm not even into the food scene. I'd definitely recommend more than "a few nights" especially since you have 2-3 weeks for the trip.

Frommer's has a new one out but no idea how good that one would be.
Just looked at that on Amazon, and see it's a 2026 edition covering all the islands. That seemed decent for an overview since you're starting from scratch. I couldn't find a new publication date for any of the Lonely Planet guides that covered all the islands? Seemed like mostly used paperbacks and/or one island per each book.

Just reading this now as I would love to visit Hawaii some day. I agree with MmePerdu about the new LP guidebooks. I am so disappointed in the new versions. They used to be my "go to" guidebooks but not any more.

Suze, that's what I saw with the LP books. No one overview, just books on a few of the islands. Maybe I will take out an older LP book from the library, just to get the lay of the land, but not pay attention to the hotels listed since the older books will be out of date. And buy the Frommer's since it's new.

I'm getting excited about this; from what I read on this thread, and online, I am pretty sure we will fly into Honolulu and spend time there before or after visiting two other islands.
We have three weeks and might even be able to push it to a few more days.


Is the city/town of Hilo interesting?

I'd like to sample the various local foods and go to one of the Farmer's Markets...or at least one.

What about those luaus? Are they so touristy that they are cringy? I do want to try Kalua pork. Maybe a taste of poi. I'll read up about the luaus.. But maybe Ii should just ask where I can find great kalua pork. Is this a dish that would be common on menus in local restaurants?

The truth is that Hawaii seems much more foreign to me than Italy, or Spain....so may islands, so many places to see.....and me without a clue!!