A Guide to Island Hopping in the Caribbean

Many Caribbean islands are very close together– so why not visit more than one?

If you just can’t get enough of the Caribbean, perhaps island hopping is for you. It’s all about visiting more than one island during your Caribbean vacation.

The first thing you might think of when you hear the term “island hopping” is embarking on a Caribbean cruise. Many Caribbean cruises allow travelers to visit several islands over the course of a few days.

However, cruising has one huge disadvantage: you can’t create your own schedule. You’ll only be able to spend the allotted amount of time on each island, and you have to adhere to a strict schedule in order to avoid being left behind!

So how can a free-spirited, flexible traveler visit several Caribbean islands without being bunkered down in a luxury liner?

Simple: take a look through our quick guide to island hopping in the Caribbean. We’ll give you an idea as to which Caribbean countries are in close proximity to each other, allowing for easy travel between islands.

From St. Martin

The island of St. Martin is a great place to begin if you’re keen on visiting the eastern Caribbean islands. First of all, the landmass of St. Martin itself is divided into two countries: St. Martin and Sint Maarten. While St. Martin offers French elegance, Sint Maarten presents Dutch charm. After exploring both sides, you can visit the nearby Caribbean island countries of Anguilla, Saba, and St. Barthelemy.

Travel Information for St. Martin–Sint Maarten–Anguilla–Saba–St. Barthelemy

We suggest flying to St. Martin from your home country, since it has a larger airport than the smaller nearby eastern Caribbean countries. Princess Juliana International Airport in Simpson Bay offers direct flights to and from the US, Europe, South America and the Caribbean. As for entry and immigration requirements, citizens of France, Canada, the United States, and several other countries do not need a visa. Consult entry requirements by country here.

Once you have arrived in St. Martin, you can spend some time in one country, and then simply cross over to the other. Since there’s no physical border between the Saint Martin and Sint Maarten, people and goods can travel in and out freely. In fact, the border between these two nations is known for being one of the most peaceful borders in the entire world!

Next, you can travel to the neighboring island of Anguilla via ferry. Public ferries run daily, at 45-minute intervals. You can also book a private ferry boat for a higher price. In addition, you can take ferries to Saba and St. Barts from St. Martin.

Ferry routes from Saint Martin/ Sint Maarten to Saba. (Source: StMartinbookings.com)

See schedules and book ferries from St. Martin to Anguilla, Saba, or St. Barts here.

From Puerto Rico

Puerto Rico is a US commonwealth located in the northeast Caribbean Sea. It consists of one main island and several tiny islands on which several thousand people live.

Travel Information for Puerto Rico–Vieques–Culebra–Dominican Republic–Haiti

You can catch flights from many countries to Puerto Rico’s main airport in San Juan. From there, you can take inexpensive ferry rides to Culebra and Vieques, two gorgeous islands off the coast of this US territory. Then, you can either travel by ferry or by plane to the Dominican Republic. It’s a quick trip and often costs less than $100 for a plane ticket from San Juan to Santo Domingo. Once you’ve explored the Dominican Republic, you can cross the border to Haiti, since these two countries are both located on the island of Hispaniola. (Keep in mind that entry requirements may be different for each country).

Click here to see information about the ferry route from San Juan, Puerto Rico, to Santo Domingo, Dominican Republic.

Other short flights are available from Puerto Rico to many other islands in the Caribbean. Regional carriers like Cape Air and Seaborne make this possible. Some of the closest islands to Puerto Rico, besides the Dominican Republic, are the British Virgin Islands and the US Virgin Islands.

From the ABC Islands

Within the Leeward Antilles chain of islands in the Caribbean lie the ABC islands. Aruba, Bonaire, and Curacao are in close proximity to each other, making island hopping between them easy. Aruba is a laid-back, luxurious island belonging to the Kingdom of the Netherlands. Bonaire is well-known for its coral reefs and marine life, making it a fabulous island for snorkeling and scuba diving. Curacao is a charming Dutch island famous for its quaint European architecture and rich cultural history.

Travel information for the ABC islands

You can visit all three ABC islands in just one trip! To do so, however, you’ll need to charter a boat or buy a plane ticket. If that seems too impractical, don’t lose hope just yet– the minister of transport has announced plans for providing fast ferry service between Aruba, Bonaire, and Curacao in the near future.

Traditional multi colored town houses on waterfront at dusk in Willemstad, Curacao.

From Saint Lucia

Saint Lucia is a gorgeous island with some top-notch resorts, and easy access to various other Caribbean islands. Once you have arrived, you can easily take a ferry boat to Martinique, Guadeloupe, and Dominica!

Travel information for Saint Lucia–Martinique, Guadeloupe, and Dominica

If you’ve arrived in Saint Lucia by plane, head to the city of Castries and take a ferry boat to Fort-de-France, Martinique. Once you’ve explored this beautiful French overseas territory, take another ferry ride from Fort-de-France to Pointe a Pitre, Guadeloupe. Once you’re ready to leave Guadeloupe, you can either take one of various ferries to the smaller islands of Guadeloupe, or head to the country of Dominica.

Ferry Boats for Island Hopping in the Caribbean

Ferries make it incredibly easy and economical to island hop in the Caribbean. Click here to see all available ferries in the Caribbean islands.

Unfortunately, not all Caribbean islands are connected by ferry boat or flight, but as each year passes, more and more means of transportation are being added.