how much $$ does it cost to travel around Caribbean?

If you are living/staying on one of the islands, how much time & money does it take to do a tour of the various islands (Cuba, DR, Jamaica, Trinidad, Curacao)? Could a person do a grand tour for less than $1000 travelling money? I would be willing to go by boat or plane. Gracias.

The fuel cost from the DR to Cuba is probably more than $US 1,000 if you travel by boat. If you want to enjoy yourself bring 10k.

There's no way you can travel through the Caribbean with 1,000. Maybe 1 island but not all the islands that you wanna visit. I live in P.R. and every year I go to Domican R. and it cost me $300 or $400. Is not cheap to travel along the caribbean. The only thing you could do is go to Dom Rep or P.R. take a cruise and it takes you to different island and is a week of fun and the food is included. A cheap cruise is Desnity from Carnival. You'll stop in 4 island and have a lot of fun. It will be like $300 is you go alone. If you get a cabinet for 4 people is $800.