Thanks to all.Really appreciate your time given. I think I can put an amazing itinerary together now. Merry Christmas to all!

My DH and I have been 'wintering' in Hawaii for thirty years. We've stayed Poipu, Kauai; Waikiki on Oahu; the Kohala Coast of the Big Island of Hawaii; and now we stay in South Maui. Winter brings cool, wet, windy weather and rough ocean conditions to the northern parts of Kauai and Oahu. (World surfing championships are held north shore Oahu in winter.) You can stay south and tour north, choosing a 'best weather' day. With just two weeks, though, I would regretfully leave Kauai off the list for this trip. Winter IS a good time to stay where the whales are most numerous: Off Maui, and to a lesser extent, off Big Island.

Plan some nights Honolulu/Waikiki. You can skip a rental car within the city, hiring one for a day to drive around the coast. Do 'historic' and 'city' here.

One way to allocate time is to think what you want to see and do on each island. They all have some of the same 'typically tropical' scenery and beaches, but each has some unique parts -- or 'best of' something. Get maps. Discover how long it will take to accomplish your 'wish list', then locate a convenient lodging on each island from which to tour.

Oahu is very developed. Maui is a bit less less developed. Big Island is relatively undeveloped -- and much, much larger than all the others put together. Visitors usually stay NW on Big Island plus a night or two SE (Volcano and Hilo). Fly KOA and ITO to avoid crossing the island twice.

A hotel/condo combination is nice -- more economical as well as more relaxing over 14 nights away from home. YOU will have to select your islands, but we can help with suggestions once we know your needs and lodging budget. You need flights to/from Hawaii, interisland flights, rental cars, and lodging.

This may seem 'far away', but people do book a year in advance for winter, and you have some research to do. I like "Hawaii For Dummies" as a quick read about each island's personality. I do NOT recommend the touring advice on the following site (dangerous, sometimes illegal tips), but the lodging portion is useful: www.hawaiirevealed.com

You can enjoy two or three islands in two weeks, but not each needs the same amount of time. Day One is largely adjusting to the time change. Each transit between islands eats 4 - 5 daylight hours, door to door. All the islands have *traffic* today. Condos are generally 'best buys' for minimum one-week stays. We've seen more problems with airbnb than VRBO, but neither outfit vets for legal lodgings. There are also good rental agencies local to each island.

Thanks so much, I’ve been looking at flights from home to Honolulu...will spend at least 4 nights there on Oahu. Found a hotel in Waikiki that I like, next to a car rental, close to shopping, restaurants and beach for some down time. Want to hike to Diamond head, visit Pearl Harbor, snorkeling , take in a Luau ( maybe keep that for Maui. Fly to Maui for a week, not sure what area yet. Big Island sounds interesting also. Still doing research. Appreciate your help.

Here's where 'best of' comes in. You can 'do it all' on almost any island, but you don't have months in the state. You need to budget your time and activities. Just comparing Oahu and Maui:

Oahu has beaches and good sea life, but it's more crowded, with more traffic. Maui has many easy-access beaches with good sea life where you can walk up or park free to swim or snorkel. It has raft and cat expeditions to Lanai and Molokini -- and along its own shores. Waikiki Beach is packed with tourists. Sand erodes badly. Rain runoff creates 'brown water (other islands, too, but this is a 'city' beach).

The Mormon's Polynesian Cultural Center on Oahu has an excellent theatrical production. The luau on Maui are lower key. Two highly rated stand-alone luau are in Lahaina Town, and two Wailea hotels host popular luau. There's less hassle getting TO places on Maui. (Well, Kaanapali is pretty buzzy.)

Honolulu has Pearl Harbor exhibits, the Iolani Palace, the Bishop Museum, iconic Waikiki, and a wide variety of ethnic cuisine. It has shops and nightlife. I'm content to view Diamond Head, but yes, you can walk or take the bus there and climb up! (Morning is cool.)

You can drive the pretty coast of Oahu easily in a day. You'd want several different days to see *some* of Maui's major sights: Road to Hana, Haleakala and Upcountry, West Maui, South Maui -- a week is too short for everything -- too much 'windshield time'. Maui does not have much nightlife or as wide a range of 'man-made'. (Kauai and Big Island are slower still.)

Ok thanks , so I think we will only do Oahu and Maui so I’ve map out our trip in Oahu 4,
or 5 days...Got that done. Now, Maui ...where should we fly into and where do you suggest we stay, seeming it’s February . Want to rent a two bedroom condo , on the beach for a week and we will rent a car to get around. Any ideas would be so appreciated, thanks.

This is the official state visitors' site: https://www.gohawaii.com/

There is also a site for each island: https://www.gohawaii.com/islands/maui

There's also printed guides but not sure if they're available outside US.

Have a great trip:)

Looks like ten nights for Maui.

South Maui is more convenient to the rest of the island. OGG is in Kahului, which is also where you start for Haleakala and Upcountry, Road to Hana, Iao Valley, Paia Town. We drive South Kihei - Kahului in 25 minutes mid-day. Lahaina is 45 minutes north -- unless there's a problem on West Maui's sole access, a 2-lane road between Maalaea and Lahaina Town. Lahaina - Kahului is close to an hour; another 20 minutes from Kapalua.

You could move, exploring West Maui from within it. JHM is in Kapalua. It's more expensive to rent a car at one airport and return it to the other.

I wouldn't plan an overnight in windward Hana in winter. You can drive it in 12 hours, making most stops; there are tours.

Some more affordable condos on Maui are in Kihei and Maalaea in South Maui, and in Kahana and Honokowai in West Maui. These are outside of the three 'tourist destination developments' of Kaanapali, Kapalua and Wailea.

All Hawaiian beaches are open to the public. With a car, you can sample more than 'the one out front'. True *beachfront* is expensive; not every place 'on sand' has good swimming or snorkeling. You will want air conditioning. Because condos are owned by individuals -- and there are few new complexes on Maui -- you need to be selective. Ask who will help you with any 'surprises'. I prefer low-rise, low-density condo complexes, but there is a case for taller buildings during whale season. Budget will determine some of where you stay.

Thanks again, now the more I research, the more I would like to do Kauai also... we will have 20 days in all. I know that I want to spend 4 nights in Oahu... we will fly home from there also so maybe two nights there before visiting other islands and 2 nights at end of our trip to relax a little before the long trip home. I see that Kauai is north of Oahu and Maui, south and then there’s the big island ...
dont want to be flying steady . Will I regret not visiting the big island?

It's your decision, you could spend 20 days split between two islands, or visit Oahu for 4 nights and the balance between Maui and Kauai. Save Big Island for another trip, lovely as it is.
My personal inclination, since Oahu and Maui are the two "busiest" and most visited, would be to spend time in one busier island and one more laid back and less visited. Have a great trip.

I wouldn't split Oahu. Because that takes time and hassle checking in and out of hotels twice. IF you need to fly thru Honolulu both directions, I'd try to make it so one of those times I just stayed at the airport and transferred to the next island directly. Just a thought.

Will I regret not visiting the big island?

I haven't yet had that regret, but I've only been to Hawaii a half-dozen times (once to Maui the rest on Oahu).

Don't worry about which island is north or south or whatever, since you're going to the airport anyway, that part really doesn't matter.

I personally think 20 days will seem very short if you try to go to every one of the islands! And it will feel like "flying steady".

Stay Oahu *either* first or last. Do not trek away from HNL and back twice. You may want to stay Oahu first to avoid a very long travel day at the end of your trip. It can be nice to do the buzzy city first, then gear down on a slower island. (Maui is slow-ER; not as slow as the very spread out Big Island or Kauai.)

We've discussed Kauai in winter. The gorgeous north will be wet and overcast, with rough oceans. Tours on the ocean and in the air often cancel or are unpleasantly rough. The entire northernmost portion of the island still has road closures today due to LAST winter's floods. Poipu may have sun, but is not the lush (RAINY) part of Kauai.

You have to decide how much time you're comfortable wasting in interisland travel. You lose 4 - 5 daylight hours, door to door, each time.

Have you made your list of see/do for each island under consideration?

You say you have made some choices regarding Oahu. You might want to run those past us for comment.

IF you want Big Island, and IF you want to stay both sides, give it a week-plus and fly via both KOA and ITO. You cold give Maui one week (in one location) then short Honolulu/Waikiki -- at ONE end of the trip. This limits interisland flights to three.

What are your best flight options round trip Home to HNL?

Just got back from 12 days in Kauai and Maui. If you are going to visit Kauai in the winter, you may get rain. Less likely in Poipu.
Our only rain occurred in Kauai. But we stayed in Poipu and avoided most of the showers on the rest of the island. You might be able to check the forecast and take day trips up north.
For Maui, I am also a fan of keeping a base in Kihei. We like the southern beaches -- there seems to be enough to go around and we've found good snorkeling there, too. We drive to Lahaina for dinner and the strolling down Front Street. You can also take a day trip upcountry and visit Haleakela with a bit less driving than staying in west Maui. It's really just up to you.

Our flight from Ontario, Canada to Honolulu is cheaper priced if we include return flights.
Starting in Oahu
Arrive late afternoon at our hotel, one block from Waikiki beach, so that day is gone.
What we want to do in Oahu...
1.Some nightlife
2.Beach time for first day
3.Pearl Harbor
4.Diamond head hike
5.Polynesian culture centre for luau
6.Halona blowhole lookout
7.Iolani Palace
8.Bishop museum
9.Drive the coast.
Anything else that is a “must see” on Oahu?
How many nights on Oahu to visit those spots.
Seeing waterfalls to photograph?
Snorkeling and kayaking?
We wait for this on another island?
Will buy a Go Oahu card, 3 day pass?
Also a Hop on, hop off, 3 or 4 day bus pass?
That will bring us to those places I mentioned, so won’t need a car except for one day to drive the coast.

Next Island, Kauai
I have a good list to do, for this island.
Haven’t found a place to stay yet.
But thinking central...closer to Lihue.
Checked out condos in Poipu ...
Still looking...

Found a 2 bedroom beachfront condo in Maui that we really like, close to Lahaina.
Have a list to do, for this island also.
We will rent a car on both Maui and Kauai.
Thinking of a week on each island.
We will fly from Kauai to Maui , then back to Oahu to catch our plane home .��

Sounds like you have your plans well under control. I just want to add that you mentioned you are going in the winter. I would personally not go around the Christmas or New Years holiday (unless that is when you prefer to go) as all accommodations will be at best doubled what you'd pay in November for example.

Since you will have a car I'd drive to the North Shore of Oahu (Pipeline, Waimea Bay, Sunset Beach) which have the iconic, world famous surfing beaches. It is more rural and old school Hawaiian surfing culture. You probably dont want to swim in the 15 to 20 foot waves, but it is fun to watch the surfers.

If you guys like snorkeling I would also recommend Hanauma Bay in Oahu. But you may need advance reservations and go as early as possible. It is (I believe) a state park.

Thanks to everyone for all the info. We will definitely check out Hanauma Bay and surrounding areas.

Not Lihue or Kapaa. (Congested, urban; no swimming beaches). Not northern Kauai in winter. Floods there are annual events. Last winter's was just worse. Constant rescues of dumb tourists from flash floods and muddy trails.

I only know of one *beachfront* condo complex in Poipu, Kiahuhna Plantations -- a few units are beachfront; most stretch back to a road. Old construction. Since all Hawaiian beaches are *public places*, beachfront has some drawbacks, too.

Snorkel Maui over congested Oahu. Free, lots of easy-access beaches w/good sea life -- not AS good as Big Island, but easier access.

The Marriott Waiohai two doors down is configured similarly - there are actual beachfront units, but the buildings are around in a horseshoe shape. The property is very nice (the units are typical Marriott Hawaii condos, the hallways are a little clinical, but the grounds are gorgeous and the location is great). All the units are two bedroom.

While the majority of the east shore beaches are not swimmable, there are a few exceptions such as part of Kealia, Lydgate, and Kalapaki Beach in front of the Marriott. I am not a fan but the condos there are a lot cheaper than many in Poipu.
You can also normally get into the water at Anini Beach and Hanalei Beach on the North Shore and contrary to Sue's repeated belief, it does not rain all day every day up there (although the odds are a bit higher).

Thanks, it so helps when we have names of places to check out��