With international rules constantly changing, it is hard to know exactly what kinds of Caribbean travel documents you need when leaving on vacation. Ever country has specific rules and regulations, so you should check ahead by calling the airport, but in general, as of 2007, you need a passport no matter where your flight’s destination from the United States if you are flying out of country.  If you need to travel very soon and do not have a passport, you may not be able to get on your plane.

First and foremost, no matter what documentation you have, travel to Cuba is illegal for most United States citizens. Cuba is under a strict communist dictatorship rule, and United States citizens risk their lives by going there. The only people allowed to travel to Cuba are special government officials with certain clearances. Traveling to Cuba by going to another country, like Canada, is also illegal. You can be caught quite easily doing this because the U.S. customs officials will see the Cuban stamp in your passport. It is smarter and safer just to avoid traveling to Cuba, because you will be less likely to get hurt while in the Caribbean and less likely to face charges when entering the United States to get home.

For most Caribbean countries, you will need a passport to travel from the United States into the country. The Caribbean is not a country on its own—the region is actually made up for number of small island countries and European territories. Therefore, every time you enter a new country, you will need to present your passport to be stamped. Regardless of if you need a passport by the island’s law or not, you will need a passport to reenter the United States. If you lose your passport or otherwise find yourself without a passport in a foreign country, contact the airlines immediately to find out what to do.

In some Caribbean countries, you will also need to present your airplane ticket showing that you have a ticket to return home or a ticket to fly on to another country. Immigration is a problem, and if you have not figured out when you’re going to leave, some countries will not let you leave the airport at all. Make sure you have a return or forward flight, regardless of where you go.

You can go to Puerto Rico, which is a commonwealth of the United States without a passport. Even though it is a Caribbean island and you’ll have to fly or take a boat there, travel to Puerto Rico is really no different than travel to another state. A passport is not required, and you don’t have to go through customs at the airport either.

Along those same lines, you can also visit the U.S. Virgin Islands without a passport if you want to travel to the Caribbean. Again, these islands are a commonwealth of the United States, meaning that a passport and trip through customs is not necessary. St. Croix is the largest of the U.S. Virgin Islands, so many people fly there first, and other popular islands spots are the town of Charlotte Amalie on St. Thomas, which is the most popular cruise port in the Caribbean, and the rainforests of St. John.

When traveling, keep your documentation, tickets, and identification in a safe place that is quickly accessible. Remember that your luggage may arrive long after you actually get to the Caribbean, so keep everything on your person instead. It is a good idea to use a small outside pocket to carry this or to have one person from the family in charge of all of the information in order to prevent it from getting lost.