2 wks in Hawaii 9/12
 

My husband & I would like to travel from Boston to Hawaii this September to celebrate our 35th anniversary. We have two weeks available & would like to plan a balance of sight seeing, adventure & relaxation. We have visited areas such as St. John U.S.V.I., Bermuda, Grand Cayman Island and the Bahamas and can only imagine how amazing a visit to Hawaii would be. First of all, do you recommend a night or two in California or some where along the way in either direction to break up the travel time? Which islands are a must see & what do you recommend for an itinary. We are fortunate to be able to fly using sky miles & have sufficient Starwood points to stay in several of their properties.

With two full weeks, I'd recommend visiting 3 islands - picking from among Oahu, Kauai, Maui and Hawaii. I haven't been to the Big Island in 30 years, so I can't comment on that, but Oahu has Waikiki, beautiful beaches, Diamond Head, gorgeous drives, Pearl Harbor and other sightseeing (although we don't "sightsee" in Hawaii, as in museums, there are some museums and such that might interest you), Hanauma Bay. Maui has great resorts, the drive to Hana, sunrise at Haleakala, Kauai has gorgeous nature/views, hiking, Waimea Canyon, the NaPali coast.

I find one week per island is optimal. In that way you can really know each island. It's hard to recommend any one island. Everybody has their own favorites. The more populated islands are Maui and Oahu. Those islands have more "culture" in the broadest sense. They have many fine restaurants, good entertainment and great shopping. There are many fun things to do on those two islands. They also have more people, congestion and other drawbacks.

Hawaii and Kauai are less populated and I find them more beautiful. However, beauty is in the eye of the beholder. Snorkeling is best on the Big Island. It also has many fine National Parks. Kauai has the most incredible hikes. It's Hawaii the way you dream about it. Where to go really depends on what you want to do.

Definitely take a two day stop in the LA area to avoid the burnout from cross country travel... make it a mini vacation... we stayed in Santa Monica on our trip and it was perfect for location, dining and fun... you will make better use of your time than dragging around Hawaii for two days...

We did a similar trip and followed this path:

Day one: East coast to Santa Monica 1 night (Shutters on the Beach)

Day two : fly to Oahu 3 nights at Waikiki

day 5: fly to Big Island 3nights

day 8: fly to Kauai 2 nights

day 10: fly to Maui 3 nights

Day 13 connecting flight through Oahu to LAX hotel

Day 14 return home...

It seems on Paper to be a hectic run of travel, but the inter island flights are less than an hour and the airports are not crazy like the mainland... we never felt shorted, saw everything we wanted to and looked forward to each island...

We now know that we liked Maui best and will return there for more time....

good luck planning...

just to clarify.. one LA day at each end of the trip...

Why waste a day in LA if you are going to Paradise. And if you needed to stop - I would recommend San Diego. :)

As for the Islands, I think starting in Oahu is the best way -say 3 or 4 days - and it's a good intro and a place to start to wind down - and do snorkel in Hanamau Bay, drive around the Island, etc.

From there - it's your choice. Our favorite is Kauai - for the beauty - and we love the north shore - Princeville/Hanalei area. See the old classic Rogers and Hammestein movie - South Pacific - 1957? - and one of our favorite beaches if Lumahai - where Mitzi Rodgers "washes that man right out of her hair". :)

We also really like Big Island (the most diverse - and yes, it's the biggest - take all of the others islands put together and it's still bigger), but having said that - Maui is also beautiful with great beaches and the most nightlife outside of Waikiki if that's your thing.

I would fly from Oahu to one of the other islands, spend maybe 4 days - and then spend six or seven days really kicking back on a 3rd/last island. The inter-island flights are short - only 20 minutes to Kauai - and we can leave our hotel, get to the airport, check in pretty quickly at the Inter Island terminal - and be at the next island - while one of us waits for luggage and the other goes to get the rental car - in about 2 hours - maybe a little more :) An hour later you can be checked into your new place and then get out and explore.

long flight from Boston to Hawaii but just like we Californians flying to Europe, I like to just get there. I for one do not wind down in Oahu unless it is on the other side of the Island and not Waikiki. Waikiki is very crowded and noisy. We wind down on Kauai and it starts instantly. 2 weeks I would not do more than 2 islands but since it is so long, some people take in 3 just because it is such a long trip. Kauai and Big Island are my favorites (heading back to BI in Feb) both are much more laid back but if you want more excitement then Oahu is a definite. Kauai...Poipu more populated than Princeville area but more hotels to choose from. Drive from airport to Poipu is shorter than all the way to North Shore. There are some very funky little towns and great beaches on Kauai. Big Island is very volcanic but has a beauty all its own. Kona-Kailua on Big Island is low key, whereas Kohala Coast more upscale. Hilo is on the opposite side of island. Great drive over to Hilo and all the wonderful ranch country in between. Can't go wrong. Aloha....enjoy your trip

I personally would fly directly to Hawaii from the east coast. It's no more than for me going from Seattle to Europe. Just get it out of the way and be there!

For two weeks, I would pick only one or two islands myself. Check out a few guidebooks from the library and look at the pictures and read about the islands. For a first trip I'd go with Oahu/Maui, but nothing wrong with Big Island/Oahu, or Maui/Kauai, or any other combination!