For the first time in decades, U.S. citizens can (legally) vacation in Cuba. JetBlue just announced that it will be offering weekly roundtrip service to the island nation from New York's JFK beginning in July -- perfect timing for a summer getaway, in our opinion. And Obama also approved ferry service between Florida and Havana this week, although when this will start is yet to be determined.

Tell us, would you book a flight or ferry to Cuba? If you'd rather ease into it, first start with a trip to Key West (which is only 90 miles from the island) or visit the Dominican Republic, which many feel has a similar vibe and culture.