I have 35K miles while is enough for Hawaii or the Carribean. I won't get me to Mexico, South America or Europe. Those require more mileage. (I think Europe is 50 or 60)

i've been to the caribbean and hawaii - and would add my vote to hawaii too.

If you can already fly to the Carribean for free, then it sounds like Hawaii is the way to go. It is a LONG trip for you, though. Any chance of adding on a few days?

I stand corrected.....

Apparently I can go to the following:
Canada
Mexico
Carribean
Hawaii
Central America
Ecuador
Peru
Venezuela
Colombia

I need 5K more miles for Europe.

I believe Mexico requires the same amount of miles as the Caribbean on AA. Also, AA has awards to Europe that are 40K miles. If you do decide on Hawaii, however, I would stick to one island since your time is limited. Why waste an extra day traveling between islands?

Wow, now you've made it even harder to decide! Lucky you that you have so many choices. We've been to Costa Rica also and loved it. It has a lot of the same things Hawaii has to offer - volcanoes, waterfalls, beaches, but it also has amazing wildlife, and your travel time would be shorter, and you wouldn't have the time difference that you'd experience with Hawaii. A combo of Arenal and Manuel Antonio is a nice first trip. Costa Rica requires a bit of an adventurous spirit, but we loved it. Let us know what you decide.

Everyone keeps mentioning hurricane season, and I was on Bermuda when it was hit by one; we had some nasty weather and were unable to fly out. Unlikely to happen, but still something to think about.

I'd absolutely say Hawaii. We went for our honeymoon and there is just so much culture and history there - and it is a part of the United States that is just so different from "the lower 48" - it's definitely worth going at some point. And you can actually make the jet lag work in your favor if you try: first, when you get there, if you plan on visiting Maui or the big island, you can do a day trip that takes you to the top of the volcano where you can watch the most beautiful sunrise! Since you'll be on Eastern time, being up at such an awful hour to get to the top of the volcano on time isn't so bad (it'll be more like 10-11am to you!). Also remember that you can try and schedule your flight back to NY so that you get as much sleep as possible!

Hawaii

It's probably just getting repetitive now, but...HAWAII! I hate flying, and I would get on a plane tomorrow and fly the thirteen hours (with layover) that it take to get there from Philly -- anything to go back!