match me up! with a place to go in the carribbean

so my dad and i are planning on going to cuba this summer but i am an american and he is a canadian so there is chance i might not be able to get in even though i am a minor and we will be flying out if canada. our plan is to fly through another carribbean island so that if i get kicked out of cuba we can just stay on that island. so now i want to know what island we should fly through.

we want peace. i dont want to go to a very touristy place. somewhere that is more down to earth and cultural (like cuba) but since we are going in the summer it cant be too far south or else it will be too close to the border and waaaaaay to hot. i also want to have rainforest. the more the better. so basically someplace not very touristy with some beautiful nature and beaches.

can you match me up with a carribbean island?

thanks a ton

I really think you'll have very little trouble with Cuban Immigration (it's the USA that you have to be careful with). As for a second island that's not too hot w/rainforest and "down to earthness" - that pares down the list quite a bit since an island needs to be pretty large to have a rainforest, and pretty poor to be down to earth (most islands these days are covered with golf courses and resorts). My best guess would be Jamaica or the Dominican Republic. (Puerto Rico is out since that's the USA!)

If you wait a few months, I think Obama wants to lift all travel restrictions in the not too distant future.
I'd like to see Cuba myself - I hear it's cheap with good food (my kind of environment!)

The southern coast of the Dominican Republic is scenic and not very "touristy". That's travelling west out of Santo Domingo towards the Haitian border. Spent a week there a couple of years ago, and enjoyed it. A few nights in Barahona, a little bit more than halfway to Haiti. Quite interesting and we hardly saw any tourists. A few national parks in the area as well, but no rainforests. I have never been to the island of Dominica, but I understand that island is fairly untouched and it does have Forest reserves (rainforests).

Like bgl mentioned already, I can seriously recommend Dominica. The interior is totally covered with rainforest and it's a great place for culture as well. The Carib Indians still live in a small part along the eastcoast, one of a few place where they still have their own community.
Dominica is not a favorite beach destination, but if you look carefully, you will find a few good ones, especially in the northeast, east of Calibishie.

Other islands to have peace certainly are Saba and Montserrat. Try and do a combination of the islands I've mentioned, you won't regret it, they are very pretty and lack a massive tourist industry!

Have fun!
Michael