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How to Caribbean-Island Hop and Experience 13 Countries

Bahamas? Check. St. Lucia? Check. With careful planning and a few plane rides or cruises, you can visit them all.

Are you keen on visiting all 13 countries in the Caribbean? There’s an easy way to make that happen. By taking as few as four or five cruises throughout the Caribbean, you’ll be able to check off nearly all the countries.

Some of these island nations are part of the U.S. Virgin Islands (such as St. Thomas) and British Islands (the Cayman Islands and Turks & Caicos are the most popular). Others are in the French Caribbean (like Martinique or Guadeloupe) or governed by the Netherlands (like St. Maarten). If you want to geek out, try to visit as many territories as possible. For example, there are four major U.S. Virgin Islands, including St. Croix, St. John, and St. Thomas. Curious about the list of 13 Caribbean countries? It consists of: Antigua and Barbuda, Bahamas, Barbados, Cuba, Dominica, Dominican Republic, Grenada, Haiti, Jamaica, St. Kitts and Nevis, St. Lucia, St. Vincent and the Grenadines, and Trinidad and Tobago.

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Here are some tips on how to work this Caribbean-island-hop strategy, from the booking stage to how you’ll maximize your time in each port.

Opt for More Than a Weekend Cruise

This probably goes without saying, but the more nights you are on a ship, the more miles you’ll sail and the more port stops you’ll make. In the Caribbean, this translates to even more countries you can visit. While it might be tempting to choose a long weekend with the girls and not use up too many vacation days, that probably means you are only visiting the Bahamas. Even with a five-night sailing, you can hit up at least three Caribbean countries.

Book a Port-Intensive Itinerary

When booking a cruise, you’ve got many choices for port stops. If you select a sailing with several sea days, that means you’ll be able to visit fewer islands. Ask yourself: did you board this cruise to chill on the Lido deck or to see the world? While you might find yourself exhausted at the end of a multi-day sail, you can also disembark knowing you visited a handful of different Caribbean islands. Believe it or not, this is possible given that the miles between the islands are few. Basically, the captain steers the ship while you’re eating dinner and falling asleep each night. Imagine waking up each day in a different Caribbean country!

Plan Cruises in Segments

Unless you want to spend 14 nights on the ship, it’s going to be challenging to visit the entire Southern Caribbean and part of the Eastern or Western Caribbean in a week if you’re departing from South Florida (Miami or Fort Lauderdale). By departing from San Juan, Puerto Rico, you’re nearly halfway there into the Southern Caribbean segment, and your itinerary may include one or two ports outside of the region. Think of a sailing itinerary in different segments. For one cruise, you might experience the Western Caribbean; another one could focus on the Eastern Caribbean, and a third might highlight the Southern Caribbean countries. This is the best way to start checking off all 13 Caribbean countries.

Choose Shore Excursions off Island

Some Caribbean islands, such as St. Barth’s and Anguilla, lack commercial airports, but you can enter via ferries from neighboring islands. Look for a ship-sponsored shore excursion (or book one on your own) on a ferry from St. Maarten to either St. Barth’s or Anguilla, for example. Another option is traveling to St. John from St. Thomas via these two ferry routes, either 20 minutes or 40 minutes each way. As the St. Maarten to Barth’s route on The Edge is only 45 minutes (departing at 9 a.m. from Simpson Bay Resort to Gustavia and returning at 4 p.m., Mondays and Thursdays only), you’ll be back to St. Maarten by dinner. Or, The Voyager offers five daily one-hour ferry rides from Marigot Bay to Gustavia. The only catch here is that you have to consult the ferry schedules closely, so they match up with the hours and days you’re in port.

Tack on a Night or Two Before Embarkation

Say you are taking this 13-day Viking Cruises “Amazon & Caribbean Adventure” sailing departing from San Juan to Manaus. What if you flew into San Juan a day early to experience Vieques and Cataño? Puerto Rico Ferry offers a ferry route from San Juan to Cataño and Ceiba to Vieques. To get from San Juan to Ceiba, you would need to rent a car for the 72-km trip. And if your sailing’s itinerary does not visit the Bahamas but leaves out of South Florida, there’s a 2.5-hour ferry ride you can take with Balearia between Fort Lauderdale and Bimini or Freeport in the Bahamas, either as a day trip or overnight. Now you’ve added even more islands to your itinerary.