My husband and I decided we are going to Hawaii in 2009 for our 25th Wedding Anniversary. We are able to travel at any time and will try to get frequent flyer tickets for the trip - thus starting to plan so early.

I have three questions for anyone who has been there:

What time of the year would you recommend going?

What island would be your first choice and not to be missed?

If you were able to stay anywhere, where would you stay?

It all depends on what type of activities you enjoy. Our first trip was to Kauai for our 30th anniversary and we've been back every year since. (it's a bit addictive) Next week we'll be making our 4th trip and they all have been great. So far we've done trips in November, May and June/July time frames and the weather has been perfect each time. This time we're trying Dec/Jan to hopefully see more whales. Most of our time is spent hiking, snorkeling and just hanging out on the incredible beaches during the days and then enjoy the dining in the evenings. Each trip we've stayed a few days on one of the other islands but always spend the majority of our time on the North Shore of Kauai. We prefer to stay in a condo in Princeville instead of a resort. Based on our experience I don't think you can go wrong whenever or wherever you decide.

Thanks dfarr for your response.

As far as activities, we will be pretty laid back. Since it is out first trip, we will be exploring the island(s), checking out the beaches, relaxing, and looking for fine dining restaurants in the evenings.

We have rented condos and houses on vacations, and I really like the idea of the extra space vs one room.
Something I will also check out.

You say you are returning in Dec/Jan to hopefully see more whales. Have you seen whales in the past from the beach or whale searching boats?

It's great that you like Kauai so much you have returned yearly after the first visit. I will start by researching that island and with any luck may also "catch" your addiction.

Have a great time.

Laid back is exactly what you'll get in Kauai, especially on the North Shore. Not a lot of what I'd consider "fine" dining but it is quite enjoyable although a bit expensive.

Lots of great condos to choose from. We use VRBO.com and rent directly from the owners. We've always stayed in Princeville but Hanalei and Haena have some places that really have island charm.

During our trip in May we saw whales every day right from our condo but May is at the very end of the whale season. It typically runs from late November through early May.

The commonly refered to "Blue Book" is a great starting point for whichever island you choose. They have books available specific to each of the islands. Check out wizardpub.com or you can pick one up at Amazon or Barnes & Noble.

Spend time browsing and asking questions here. I have a couple of trip reports here from our past trips that might help.

Good Luck!

Congratulations on your 25th anniversary! We celebrated our 25th on Hawaii last year. If you click on my name, you can eventually bring up my trip report. I will also try to bring it to the top of the messages for you.

We had previously been to Kauai, Maui and Oahu, and so for this trip (our 4th to Hawaii) we chose the Big Island. We stayed there for 10 nights.

We have been to Hawaii in June, July, August and October, and we've loved all the times. I think we were able to get good deals in October.

For a first trip, a lot of people recommend Maui. I love Maui, but my favorites are Kauai and the Big Island. It depends on what your interests are. We are not interested in nightlife, and we love outdoor activities, so Kauai and the Big Island are perfect for us.

On the Big Island, I would recommend staying in 2 or 3 places if you're able to stay over a week. In 10 nights, we stayed at 3 places at different areas of the island. The most luxurious place we stayed was the Fairmont Orchid. It was great.

On Kauai, the big decision is staying on the north or south side. Depending on the time of year you are there, people recommend different sides. I personally like the south side (Poipu area), and we loved staying at the Kauai Hyatt. It's a really nice resort.

Have fun planning!

Yes, first of all, congratulations on your 25th! What a wonderful occasion to celebrate in the islands.

In 2001, we celebrated our 25th by having a wonderful vow renewal ceremony on the beach in front of Kauai Marriott and it was just beautiful.

Through the years, we visited all of the major Hawaiian islands and each one of them is wonderful in its own right. Moreover, my not-to-be-missed may not at all comport with your idea of not-to-be-missed, so how could I comment?

We have been to Kauai way more than a dozen times, probably close to that many to Maui, twice to Oahu and once to the Big Island. I think I would like to explore the Big Island a little more and, of course, revisit my heart in Kauai where it rightfully belongs.

Any time of the year would be a great time to go, perhaps with the exception of July-August when there are lots of families with kids. Been there--done that and it is our time now. I would suggest that you go close to the anniversary and celebrate there to make it more meanigful.

As to where to stay, if you are planning to go for a week or less and can afford it, I would say stay in a great hotel and enjoy.

Anna Roz

More to see & do on Oahu than any other island.

Lots of info including sites with free brochures for all islands:

http://fodors.com/forums/threadselec...1&tid=34812564