I meant "newbies". My less than nimble fingers typed two e's instead of w.

Three weeks? Septemeber is great! Lucky!!! I think you'd be able to see 3 islands plus a few days on Oahu. 5 on Kauai, 5 on BI 7 on Maui and 3 or 4 on Oahu unless you want to transfer some of those nights to another island. Or do 6 nights each island and just 3 on Oahu.

Fly into Oahu, spend a few days there.

There will be those who say you lose a whole day flying between islands. I don't agree with that. You may lose a few hours of sightseeing but the flights are short and changing islands is worth it in my opinion.

Totally agree with (both posts).

Briefly, Oahu is the most developed, that's where Honolulu is. But lots of the island is less developed and very tropical. You should see Waikiki and Pearl Harbor, snorkel at Hanauma Bay, climb Diamind Head for the view, kayak at Kailua and Lanikai beach area, drive across the island for the spectacular highways (simply breathtaking) and tAke in the little town of Haleiwa and the north shore beaches (beautiful) - Sunset, Waimea. This is where the famous Banzai Pipeline is, although the high surf is in winter. there are also other "cultural activities" (museums and the like), but we go to Hawaii for the weather, the beach and the outdoors, so I haven't been to those despite many trips.

Maui is beautiful, with some developed resort areas such as Kaanapali Beach(Hyatt Regency, Westin, etc) , but many other choices of areas to stay too - upscale Wailea (Marriott, Four Seasons), downscale Kihei and Napili. Maui has the drive to Hana, going up Haleakala (and biking down if you so choose). Many people take a catamaran cruise from Maui to either Molokii for snorkeling or to Lanai to see the island.

Kauai is not called the Garden Isle for nothing! It is lush and beautiful, with stunning cliffs, and the "grand canyon of the Pacific". Look for posts by Songdoc, who has been many times, and in fact is there until tomorrow, for descriptions. Kauai has great hiking and fantastic beaches. Many people like the north shore best - while I love going to the north shore (for the beaches, the incredibly lush scenery, the small town of Hanalei, the one-lane bridges, etc, I prefer to stay on the south shore mainly because the resorts are on, rather than above, the beach. If that weren't impt to me, I'd stay on the north shore.

I haven't been on the Big Island since the late 70s, so can't comment!

Hope that helps!

There is so much to see and do on each island. I would recommend getting a travel guide book.

Try Costco travel for deals. remember that you will need a car and their deals include cars. You save a few hundred dollars by using them. they might have something for airfare and hotels or try VRBO ifyou want condo's. For that much time, I like condo living - more room and option of eating in or out. Lanai is a must and ocean view is fabulous if you can get it and afford it. KAUAI is beautiful and lush...Northshore Kauai try Sealodge for excellent prices or Lawai Beach resort in Poipu area for another reasonable condo. 3 weeks gives you a nice amount of time on 3 islands. I'd skip Maui and head for BI instead ..BI is very different..beauty in its own way. GREAT beaches in the Kohala area especially. Hilo side is wetter and greener. but I know that many people love Maui but to me it is just a bunch of TShirt shops and high rises. Oahu has much to offer between Waikiki and Northshore - a few days in Honolulu (USS Arizona, the Missouri Shangri La), few on north shore, then Kauai and BI. we fly from SF to Hawaii and you are not tired or feel you have lost a day as you actually gain a few hours (Diferent time zone). Leave here at 9:00 and arrive at noon in time for lunch or massage. hope you find what you are looking for. september is great! good luck....Aloha

It's do-able, in part because September is a 'shoulder season' with fewer visitors. It's also Hawaii's hottest month; make sure you have A/C wherever you book.

Do you want hotels or condos? IMO a combination works well. What's the lodging buget?

You'll need air to Hawaii and between the islands, rental cars everywhere outside of Honolulu, and lodgings.

You have enough time to stay on four islands, but do you want to move that much? Every 'hop' will mean at least four hours 'in transit', and they are not cheap. If you book a condo somewhere, you'll get a better rate for a week or more, and it makes more sense to provision for more than a few days. Some condos have minimum stays too.

Another possibility is the NCL cruise that departs Honolulu every Saturday afternoon. You'd glimpse the highlights of three islands: Kauai, Maui and Big Island without 'doing time' in airports. It's not a deluxe cruise, but if you book a plain cabin and rent a car at some ports instead of taking ship's tours, it can be a good buy. You could stay on Oahu before the cruise and on another island after it.

"Hawaii For Dummies" is a quick read to get a feel for each island. There are individual travel guides for each island too.

Those of us who do not live on the coast envy your 'short' flights to the islands, but you will still need a day to get completely on "Island Time", which is one of the pleasures of visiting Hawaii. Don't rush around TOO much or you'll miss the Aloha!

I need 5 minutes to get on island time

I agree that you should spend a few days on Oahu, just to see the 'major' sights and enjoy Waikiki. I would spend more time on the big island if it were me. You could spend a week there, easily, dividing your time between Kona, Hilo, and the volcano area.

Sounds like a nice first trip to Hawaii!!! Lucky you!!!

I just wanted to say thank you to everyone who has given their advice and opinions! That is why I love this site so much. By all means, keep 'em coming!
Redd

agree with sf307...takes 5 minuttes to get on Island Time especially if you are on the west coast. It is one of the only places where we can instantly unwind. Must be the palm trees and ocean air!

Shar, I swear, I get it the minute the airplane door opens!

sf7307: What is your favorite South Shore hotel on Kauai? Thanks!

Have been to Maui, Big Island, Oahu and Kauai. Would definitely recommend the Big Island for the volcano. It is one of most memorable views of nature we have ever seen. Grand Canyon, Niagara Falls, and the Volcano the top three, not in that order. .

We have stayed at Kiahuna Plantation (condos), the Marriott Waiohai (timeshare) and the Grand Hyatt. We have not stayed at either the Sheraton or Koa Kea. I can't say one is my favorite (we liked all of them), but I can tell you what we liked and didn't about each.

Kiahuna - the grounds are fabulous, as is the beach. Not so great is that the pool is across the road at the tennis club, and the units don't have A/C.

Marriott - the units are fully outfitted apartments. Some buildings are better than others (you can see my full review on TripAdvisor under the same trade name). The grounds are really lovely, and the pool is very nice and located at the beach. The common corridors are institutional-looking, and the units' decor is standard-issue Marriott timeshare, which is very nice, but not at all "Hawaiian".

Grand Hyatt - this is a mega-resort. Huge lobby open to great ocean views. Fantastic pools. Downsides are the beach in front f the hotel is not swimmable (not really a negative for me because I don't swim in the ocean). There's a man-made lagoon right in front of the pool. I understand the spa is great, but although I used the fitness center, I'm not a "spa person", so I really have no idea. A lot of people really like the restaurants at the hotel, but that's another thing I never do - eat at hotel restaurants.

The Sheraton has recently been renovated, but I'd say it's still the most "low key" of the resorts - not glitzy at all. It shares the same beach as Kiahuna.

Koa Kea is boutiquey. The property is between Kiahuna and the Marriott. Although the hotel isn't technically on the beach, it's about 20' away!

If I were going with young kids, it would be Kiahuna, hands down. Without kids, you need to decide which hotel fits your style. I don't think you can go wrong!

Years ago, we went to Maui in September and two of the best hotel pools were renovating. We lucked out, but September seemed to be the time to do housekeeping. If you're going for a grand resort, I would inquire of their maintenance schedule and if anything will be closed in September.

Great information, sf. Thanks. Where would you stay if you wanted to splurge on a great hotel in Oahu?

Kauai's most gorgeous part is its' north. I'd stay there in September (but not in winter). Hanalei Bay Resort is more my style than the St. Regis. Since we do come in winter, we've enjoyed Poipu Kapili condos.

I still like the Royal Hawaiian, right in the heart of Waikiki. Two top hotels are the Halekulani (on Waikiki), and the Kahala Resort (east of the 'strip'). On the beautiful north shore, Turtle Bay is the only hotel choice AFAIK.

If I had three weeks.
One week on BI at the Mauna Kea
One week on Maui at the Makena Surf condo or a rental in Makena.
One week at home rental in Hanalei, Kauai.

Great information. Thanks!

3 weeks - excellent!
You WILL waste some time at airports and picking up cars and settling in to accomodation on each island but with 3 weeks to work with you should be able to see 4 islands easily.
I envy you - we only have 2 weeks for our upcoming vacation there - so I opted for the cruise + some Oahu time.

You could opt for the POA cruise and then concentrate on 2 islands BUT my gut feeling is with 3 weeks - do the air/land version because you will get 4-5 days on each island.

I recommend:
the Big island (Hawaii) - at least 5 days - it is BIG
Kauai - at least 4 days
Maui - at least 4 days
Oahu - 5 days - LOTS to do
You can decide where to "spend" with the extra days based on what appeals to you.

Kauai and Big island are my favorites.
Kauai has a pleasant relaxed country feel to it and is utterly gorgeous. Big Island gave me the strongest "YES I am IN HAWAII" feeling and hey it has a "real" active volcano.

Personally I am NOT a fan of big resorts but you know if you prefer them or not. I like B&Bs or condos or small hotels because I like feeling more in contact with the local scene and I find big resorts somewhat isolating but that's just me - do what you enjoy!

some accomodation recomendations (strictly based on what I liked on our last trip):

Oahu - we will be staying at the Ilima Hotel on our upcoming trip because:
1. it has a full kitchen
2. it is cheaper than the beachfront hotels but is just a short walk from the beach
3. it is very near Kuhio St. (lots of restaurants, etc)
4. We intend to use the Oahu bus system (The Bus) to get around so nearness to transit was critical (buses run along Kuhio)
IF you intend to rent a car in Oahu I would be seriously tempted to look for something like a B&B (maybe with a kitchen) on the Windward shore (say Kailua area) or the North Shore BUT I generally prefer to be away from "busy" places like Waikiki (if you like a lot of action - stay on the Waikiki area).

Kauai:
On our last trip we stayed at one of the smaller resort-hotels on the East coast because we got a VERY good deal and it had a kitchenette. We liked the East coast because it was "central" to the North and South shore BUT the best swimming and snorkeling are on the North and South shores - so you may want something on either of those 2 - if I was picking between those 2 I would probably go North shore.

Big island:
We stayed at a B&B - Macadamia Meadows and I HIGHLY recommend it. The accommodation was private and well-priced and Charlena was a great hostess - very helpful. We also found the local people in Nalehu and the Kau in general were very friendly.
BUT it is a little out of the way - so it was a long drive to Kilauea and in the opposite direction to Kona. We never made it as far as Hilo. However Nalehu is close to a Black sand beach with lots of sea turtles and to South Point (DO NOT SWIM there unless it is dead calm - we saw someone nearly get swept away)

Mauai - we stayed at a B&B near Lahaina but frankly were not impressed.
I would look for a condo there. Maybe in the Makena area

Have a great time