Since January Americans traveling for one of 12 purposes have been able to do so without needing a license, including visiting relatives, academic programs, cultural programs, professional research and person to person exchanges. The new rules allow family members of people traveling for an approved reason to travel with them, in essence really anyone can then travel to Cuba. Still, ordinary tourism remains off limits, travelers have to complete a form denoting the purpose of the trip and are required to keep receipts for five years after traveling, generally you are also required to have a schedule of activities with you related to your purpose of travel. In other words you can’t legally just head down to chill at the beach.
The most popular way to travel to Cuba is a person to person trip, which are organized trips that anyone can go on with a full organized schedule of events and cultural exchanges which can be pricey running between $2500 and $4000 a week including hotel and flights. Cuba suffers from a shortage of high end hotels, tour operators are already booking blocks of rooms through next year, which makes going through a tour operator almost required to stay in a high end hotel. Bed and breakfasts are an alternative but hard to book online.
Other issues are how do you get there and using credit cards on the island. There are currently no commercial flights to Cuba and all flights are chartered, however the FAA is currently in talks with Cuba to set up commercial flights, though no timeline on when that would happen. Under the new rules cruise ships and ferries can sail to Cuba so long as those travelers are licensed, Carnival is going to begin sailing to Havana in April. The Treasury Department did loosen regulations to allow travelers to use American credit cards on the island, but ATMs are far and few between on the island and many establishments can’t process credit cards, cash is still king.
And one last important new rule of you decide to go to Cuba, you can now bring back $400 in souvenirs including $100 in cigars.