I imagine that this is a difficult question
but where would you go with a 10 year? Big
Island of Hawaii or Anguilla/Malliouhana Hotel. Would there be enough to do in Anguilla?

Avoid Caribbean in hurricane season (Aug-Oct). Avoid Hawaii in winter (Nov-Mar). You can get cool rainy days in winter in Hawaii. Also Caribbean water temperatures in winter are as warm as peak Hawaiian water in late summer.

From US east coast I'd go to the Caribbean, and US west coast I go to Hawaii.

I have traveled to Hawaii in the winter five times. Never had a cool, rainy day. Passing showers a couple of days at most. It's a great winter destination.

I agree with suze ...Makes alot of sense!:-? Belle.

pdx - i was in Maui a couple of weeks ago and had three cool (like I could have used a sweatshirt), rainy, windy days in a row. I was told that it happens 3 or 4 times per year, mostly from Jan. to March. So, while unlikely, it is possible.

Which coast you live on impacts the decision greatly. If you live on the east coast, but only have a week off, go to the caribbean. Anguilla has some awesome beaches(I hear) but is a quiet place. St. Martin with tons of shopping is a ferry ride away. I believe you can see it from your beach in Anguilla. If you want rest and relaxation away from children or not, than Anguilla will be a nice quiet trip. If you like a vacation with sightseeing and being on the move, I recommend Hawaii. Have you ever been to Hawaii? Do you have kids or are planning to start a family soon? If you don't have children, than this may be a good time to take a big trip to Hawaii. If you have small ones at home, your wife may not want to travel so far...So many questions!!! Good luck and let us know where you choose!

Okay, I thought I was getting old, but I read your post as a 10 year anniversary. Than I read your post on the Caribbean board and a ten year old!Ha! I would go to Hawaii. I think that it would be a great experience for a 10 year old(I have one too) and she would love it. Anguilla is just sitting on a beach and relax. You can take her anytime for that. Hawaii is an experience with volcanoes and luau's and I think you can also sit by a great beach in Hawaii too! Go for Hawaii.

I, too, thought you meant a 10 year anniversary! We've been to both islands and I agree that a ten year old would get bored on Anguilla. I loved it there, but its' very laid back beachtime. The Big Island is fantastic for kids. How long will you stay? What month?

I think a 10 year old would enjoy STJ or Virgin Gorda as well! Belle

The only problem I see with Hawaii is that the surf is very rough at the beach and the water isn't particularly warm. Otherwise there is way more to do in Hawaii - my 7 year old really wants to go there.

I think it depends on what you want and what your ten year old enjoys. You are going to have a vast array of things to do on Hawaii, but a lot more activity (less of a secluded back to basics sort of feel) as well. On a more remote caribbean island you'll find more quiet unspoiled beauty, but you and your ten year old would need to enjoy outdoor activities if you want to stay busy (hiking, snorkeling, etc). Living in the midwest and having been to Maui and several caribbean island, I personally don't think I'll ever make the long trip to Hawaii again. DH and I totally enjoyed Hawaii, but really REALLY loved the quiet uspoiled island of St John in USVI. We plan to take our young children once they are old enough to snorkel.

With or without a 10yr old and wherever you live I'd go for Hawaii.

Anguilla has gorgeous beaches and top notch restaurants but Hawaii has these and so much more overall.

Hawaii, Hawaii, Hawaii.

I will add that we had a spectacular January on Maui. Wonderful weather, and we watched the whales from our hotel room every day.

Heavenly!

Happy 10 year!