Since the Cuban revolution traveling to Cuba from the United States has always been tricky. Until recently direct commercial flights were illegal so most travelers arrived via expensive charter flight from Miami. Thousands of travelers didn’t follow the rules at all; they entered through the Cayman Islands, Mexico, The Bahamas or they fly from Canada, then requested the Cuban immigration officials didn’t stamp their passports. Those who were caught face serious penalties. Lately the laws have changed and flights can go, but travel opportunities to Cuba are still somewhat few and far between.
However you get there — we won’t ask — you can use Lonely Planet’s entry on Cuba as a backpacker’s guide to visiting one of the world’s most welcoming countries. For example, Cuba is one of the only countries where hitchhiking is one of the recommended forms of travel. From the Cuba Hitchhiking Guide: “Government vehicles traveling with empty passenger seats are obliged by law to stop and pick up hitchhikers. If [government vehicles] are seen failing to pick up hitchhikers they can be reported to the authorities and fined.” A bit different from the U.S.
If you plan to bring the kids, check out TravelForKids.com’s Cuba page. Cuba has beaches, caves and cigars…kids love all those things!