Best Sailing Trips in the Caribbean: The Best Routes You Have to Know

By Anna

Need a holiday? Get a free and personalised offer from us!

For many people around the world, the best sailing trips in the Caribbean are exactly what a holiday in paradise would look like. The islands’ year-round sunny weather makes them constants in people’s holiday plans, especially as a perfect choice for winter sailing. But we think their ubiquitousness in the tourism industry can be attributed to more than just good weather. Here, we’ll outline a few of the best Caribbean sailing trips that outline the best that the Caribbean islands have to offer your sailing vacation.

When is the Best Time to Discover the Best Caribbean Sailing Destinations:

Optimal: December to June, when it is drier and cooler (relative to the intense temperature experienced in the thick of summer). Before the wet season brings about unpredictable showers and strong winds. In the Caribbean, the wet season generally coincides with the Atlantic hurricane season, officially running from 1 June to 30 November.

Popular time: when the western hemisphere experiences cold, aka starting December until March. If you’re the kind of person who enjoys the atmosphere of a social, and filled-in beach, then this might be the time you’ll want to go. Just beware that sometimes boats book out a year in advance during Christmas time.

When not to travel: during the hurricane season, when significant rainfall and thunderstorms put a literal damper on your days. Most of the time, the tropical storms won’t develop into full-fledged hurricanes, but the risk is always there and it’s best to consult your sales agent for the best advice. We advise that you check in advance on what specific Caribbean destinations might be safe for traveling during your selected dates.

When to go for the Best Sailing Trips in the Caribbean:

  • In terms of availability, people have the best shot at booking their sailing trips between dry season and wet season, in May or June. During this time the temperature will usually be around 29 Celsius. There will also be less tourists, less clouds, and more fruits in season. Since these months fall after high season, costs might be lower, too.
  • In terms of optimal pleasure, February might the best month. Most importantly, you’ll get to escape from the general wintry misery suffered by most of Europe and North America.

Advantages of enjoying a sailing trip in the Caribbean:

  • the experience of being on a boat is unmatched by any other modicum of travel.
  • on a boat, you can mix your penchant for exciting, athletic activities, with the relaxation of a boat cruising below clear skies.
  • traveling by boat also lets you explore more destinations in less time.
  • what would take you several days to explore. For example, can be done in a week through the convenience of a boat you can dock in and out of ports along the coast.

The best Caribbean sailing trips – top destinations:

  1. Dominica
  2. Aruba
  3. North and Middle Caicos
  4. Antigua
  5. Barbados
  6. Bahamas
  7. Jamaica

Sailing trips in Dominica

  • How to get there: Fly into nearby Douglas Charles Airport. You also have the option of taking a ferry from Rouseau to three nearby islands.
  • Where to dock: Roseau, Woodbridge Bay, Cabrits.
  • What to see: Black Sands Beach, Marceau Bay, Purple Beach.
  • What to do: If you love the outdoors, then this underrated Caribbean island might be right for you. Its sometimes called the Nature Isle, and its known for its several rainforests, natural hot springs, and scenic trails. Spend an afternoon tubing down a calm river, or challenge yourself by canyoning down Dominicas many waterfalls (just make sure you have a high level of fitness before embarking on the more intense water sports!). Sure, the Caribbean can be great for relaxing, but Dominica is the perfect vacation for people who want some thrills mixed into their travels as well.
The best sailing trips in the Caribbean include a trip to the Dominican Republic, which can be seen in this picture. The colourful boat surrounded by palm trees show how beautiful this place is

Sailing trips in Aruba

  • How to get there: Fly into Queen Beatrix International Airport.
  • Where to dock: Aruba Ports Authority.
  • What to see: Palm Beach, Arashi Beach, Hadicurari Beach.
  • What to do: As Aruba is one of the most easily accessed desert islands in the Caribbean, itll also be a bit more crowded than its neighboring isles. But not to worry most people are here for the beaches, and a relaxed atmosphere can be experienced across both ends of the island. The white-sand beaches offer a comfortable cool to walk on even at the height of the afternoon. In the evenings, venture into town for authentic Indonesian food and Dutch street fare.
This picture shows a palm tree at a beach in the best destinations in the Caribbean

Sailing trips in North and Middle Caicos

  • How to get there: Sail here or take a 25-minute ferry ride from Providenciales.
  • Where to dock: Sandy Point Marina.
  • What to see: Mudjin Harbor Beach, Bambarra Beach, Conch bar caves.
  • What to do: This island is perfect for sailing trips in the Caribbean, as its known as one of the unspoiled (and less traveled!) ones. Its even quieter than the rest of the Caribbean. Also, it is the perfect sailing vacation for people who want to replicate the peace of their boats, on land. Lounge on deserted strips of beach, or flex your muscles by exploring the renowned, and extensive, above-water cave system here.


  • How to get there: Fly into VC Bird International Airport.
  • Where to dock: English Harbour, Falmouth Harbour, Jolly Harbour and Parham Harbour.
  • What to see: Dickenson Bay, Darkwood Beach, Half Moon Bay.
  • What to do: While Antigua is known as the home of the sweetest pineapple in the world, the Antigua Black, to many others, its also known as the sailing capital of the Caribbean. That might be in part because theres such a diverse array of small beaches (365, to be exact!). You can choose from pink sand beaches and beaches ideal for snorkeling, to beaches accessible only by boat. The difference from beach-to-beach is just enough change to keep you from getting bored. Nevertheless, you will not stress yourself out trying to decide on your destinations.

One of the Best Sailing Trips in the Caribbean is Barbados

  • How to get there: Fly into Grantley Adams International Airport.
  • Where to dock: Deep Water Harbor.
  • What to see: Animal Flower Cave, Bottom Bay.
  • What to do: Barbados offers nonstop service from London, so you might hear some British accents in the air (its history as a former British colony might also play a part). But why do so many non-islanders like to flock to Barbados? The popular rum culture is one reason. Its also the pervasive island culture that you’ll experience through Caribbean food, lively music, or the beaches that invite hours-long naps. If you’re traveling by boat, even better: The shores here are dotted with groups on sailing vacations.
bridgetwon barbados

Sailing trips in the Bahamas

  • How to get there: Fly into Nassau International Airport or Grand Bahama Airport (the two largest airports in the area).
  • Where to dock: The Bahamas have tons of marinas, but Bay Street Marina or Nassau Yacht Marina are two of the most prominent in Nassau.
  • What to see: Bathsheba Beach, Barbados Boardwalk, Mount Gay Distillery.
  • What to do: The majority of holidayers here flock to the large casinos and glittering resorts this island is known for. The all-inclusive resorts are the embodiment of luxury, and offer tourists the benefits of low-stress (though high-cost!), fully-servied travel, spas, bungalows to lounge on, and fine-dining opportunities. When you want to incorporate some activity into your Caribbean sailing trip, you can head out to Pig Beach to swim with the pigs, walk along pink sands beaches, or snorkel along the Great Barrier Reef.


  • How to get there: Fly into Norman Manley International Airport in Kingston.
  • Where to dock: Kingston Harbour.
  • What to see: Montego Bay, Dunns River Falls, Mammee Bay Beach.
  • What to do: As the third largest of the Caribbean Islands (Cuba, and Haiti & Dominican Republic take the first two places), Jamaica is full of things to do. Take advantage of all the activity options by heading down to Reach Falls, a trek that climaxes with a waterfall cascading down a rock face. Go swimming with horses in Montego Bay, or even bamboo rafting. When you’re ready for a snack, go crazy on a plate of jerk chicken, the national dish of Jamaica.