For the maximum relaxation, kick back and enjoy the aloha experience (and with no consideration of the logistics of flying between the islands) I would do the islands in this order Oahu, Hawaii, Kauai. Honolulu is a high energy place, though the north shore is pretty laid back. Then the island of Hawaii-which requires more driving to experience all its facets) and lastly the quintessential green, dreamy tropical island of Kauai.

It may be possible to get a non-stop to Honolulu from one of the NY area airports (there are a few at least in the winter). Then a non stop on Hawaiiin to either Kona or Hilo on Hawaii. Then a one-stop (in Honolulu) to Lihue on Kauai. Then a one-stop from Lihue back to the NY area. From looking at Hawaiian Air's website it appears that all flights between the islands have a stop in Honolulu.

We had a car when we were in Honolulu for 4 nights since our time there was limited and we didn't want to have to wait for the bus to get where we wanted to go--Pearl Harbor, north shore, Bishop Museum, the tour to Doris Duke's Shangri-la, dinner at Alan Wong's. Parking around Waikiki is pricy--but when considered in the context of the cost of the entire vacation--it is worth it, IMHO, for the flexibility it gives you.

I don't know about flying from NY but I just booked round trip from Cleveland to Honolulu. Round trip to Honololu, flying on a Mon,Tues,Wed or Thru was the cheapest way for me to go. We are doing three islands also and plan to fly Hawaiian Air for those. It is $86.00pp one way. I would suggest for you to go to Kayak and begin checking all your possibilies. You can check price and amount of hrs in the trip. Some of the trips are quite long if you have 3-4hr layovers somewhere. For me the actual hrs from home to Honolulu and price were my determining factors.

New Otani is a beautiful hotel. I've not stayed there but have been to their lovely bar, seen the restaurant and common areas. It sits slightly off a bit by itself at the quieter Kapiolani Park end of Waikiki. One thing to note (since you mention swimming) the hotel does NOT have a pool.

As far as car rental or not, depends what you want to see and do. I'm most often there solo, and don't get a car myself and get around on The Bus (an award winning public transportation system) and walking everywhere. But I can see how it might be worth the expense for the convenience for some people.

For your plane tickets I'd just get out on a general website like Expedia and look around to see the various options, routes, pricing offered. When you narrow down a few possible itineraries go to the airlines' own website to book. Sometimes it's cheaper to fly in and out of Oahu, and do your other island 'hops' from there. Sometimes you can find an "open jaw" arriving one island leaving a different one, which is worth looking for too.

I agree with Martym. Do Oahu first- there's plenty to do and see, but unless you get away from Waikiki, you arent' going to find the idylic calm tropical vibe. I do quite well without a car in Honolulu for 4 nights, then I need to move on. Either to the north shore (where I do want a rental car) or on to another island.

You will need rental cars on any island other than Oahu.

May is a beautiful time to visit Kauai, at that time of year Id look into staying at a condo on the North Shore, just gorgeous. I have used this site for good car rental prices:

discounthawaiicarrentals.com

I agree about the order of seeing the islands. I would stay in Oahu 4 nights, fly to Hilo and stay there 3 nights (to explore the volcano area), drive to the Kapalua coast and stay 6 nights (for swimming, snorkeling, boat trips), and then fly to Kauai for 7 nights.

We have used Discount Hawaii Car Rentals several times; they have always had the best prices.

The Big Island and Kauai are our favorites of the 4 major islands. Kauai is stunningly beautiful. I could stay there for weeks. A couple of months ago we spent 8 nights on Oahu and loved it, but since you are going to 2 other islands, I think just a few nights on Oahu would be plenty.

We fly from Atlanta to Hawaii and prefer non-stop flights.

I think Samsaf means "Kohala Coast" ?? that's where the best beaches (and resorts) are located on the Big Island.

My DH and I stayed two to four weeks on each of the four major islands for about 30 years before buying in South Maui. We go to escape Midwest winter and for Whale Season (Jan. - Mar.). I'd love to go in May sometime. It's good weather pretty much everywhere in Hawaii, and families with school-age children aren't yet vacationing.

We like to fly one long leg nonstop into HNL. Look for 767's or 330's. I avoid 757's and west coast connections. We fly ORD-HNL and hop to Maui without leaving airport security; baggage is through-checked. We use miles to upgrade to first, but otherwise we'd book "Coach Plus" for more room, especially appreciated on the redeye flights home. It will be easier to through-check baggage if you have everything on a single ticket. (You don't want to have to claim baggage and re-check it, then wade through the TSA nonsense again.)

For what amounts to a first visit, I'd suggest you do three islands. If it's the three small ones, stay a week on each -- adjusting time depending on what is most important to you on each island. If one of the three will be Big Island of Hawaii, give that more time. You'll stay in two locations: Kohala area (NW); and Volcano (SE). Fly into one side and out of the other so that you needn't drive back around the island. Big Island and Kauai are nice contrasts, and Honolulu/Waikiki is completely different.

If beaches, swimming and snorkeling are important -- Maui has the most easy-access beaches and a wide choice of condos and hotels ON beaches; the other islands, not so much. Big Island has the best sealife, but few easy-access beaches. Sealife quality diminishes as you go north in the chain.

Interisland flights are best on Hawaiian Airlines. Realize that each 'hop' will eat at least four hours of your vacation time -- longer if you have to make connections.

Better to get on Island Time and enjoy what is special about Hawaii than to try to cram in too many things. I would stay Waikiki first, then decompress. Honolulu may seem 'too much' after other islands. You can float through HNL from your last island.

New Otani on San Souci beach would be a very nice choice. My NY cousin (who could stay anywhere) chooses it. It has wonderful views, and is quieter than the heart of Waikiki. The cottages at Turtle Bay are a nice change from the city buzz if you have enough time to split a stay on Oahu.

I hope you'll have a wonderful time -- and not wait 20 years to return! LOL

Yes, sorry. I meant Kohala Coast. We like the Fairmont Orchid. There are dozens of sea turtles on the beach there, and you can snorkel from their beach.

Thanks so much for all the informative responses. I will read up and return with further questions...

New Otani is a super choice for your stay in Oahu - which I too would suggest to be 3 or 4 days. Do get to Hanamau Bay to snorkel - but go early to avoid the crowds and get the best visibility, and then drive on around at least the south end of the island on that day- to Kailua - if not continuing on up the east side - to Turtle Bay - and past the fabled north shore surfing beaches - Sunset and Pipeline among them (although it will probably be flat) - and then back down through Haliewa, where you should be sure to stop for a shave ice.

Would also second next flying into Hilo and staying a couple nights up at the Volcano - and there are some nice places in Volcano Village - and the Volcano Village Lodge is our favorite, but our friends sold it recently. http://www.emmaspencerliving.com/volcano-village-lodge/

From there - enjoy the drive over to the Kona side - and there are a number of nice resorts up the Kohala Coast - but none has a better beach than the Mauna Kea, and that's why Rockerfeller picked it to first develop way back when, 60's was it? http://www.princeresortshawaii.com/mauna-kea-beach-hotel/index.php

From there - over to the Garden Isle of Kauai - and the north shore/Bali Hai - is our favorite place in all of Paradise. The St. Regis is the top rated hotel, but if you can get a home/condo right on the beach along Hanalei bay - or even further out toward our favorite beach - Ke'e - that's hard to beat. Waking up every morning on the beach - having some great Hawaii coffee and fresh fruit - and other local treats. Doesn't get any better.

Hey - we even make sushi and have been known to enjoy it for breakfast, or perhaps make some Macadamia Nut or Banana pancakes, and try various syrups.