Sailing in the Caribbean – A Perfect Getaway

You will keep coming back after you start a Caribbean vacation. The Caribbean provides everything that distinguishes sailing. Many paths, continuous breeze, countless beaches with white, black, even pink sand, a rich undersea world and mouthwatering cuisine. The Caribbean consists in hundreds of amazing and intriguing locations.

You are in the right place if you want the best sailing advice for the Caribbean. Keep reading to cover the following:
- Why would one cruise the Caribbean?
- The Caribbean’s greatest sailing season falls when?
- Here, are the sailing conditions?
- Like what is marine infrastructure?
- Caribbean sailing is really expensive. How much?
- The most ideal sailing locations
- Suggested Caribbean paths
Why sail in the Caribbean?
Comprising more than 700 islands, the Caribbean is The Caribbean islands are unique since every one of them has particular traits. This is a large territory never likely to cause boredom.
Based on sailor popularity, the Caribbean is considered as a chain of Antillean islands run from north to south from the Bahamas archipelago (including the Turks and Caicos Islands). The most well-known ones are the British Virgin Islands, Antigua and Barbuda, Saint Martin, Guadeloupe, Dominica, Martinique, Saint Lucia, Saint Vincent and the Grenadines and Grenada. Geographically speaking, the Caribbean islands comprise small Dutch islands above South America (the so-called ABC islands – Aruba, Bonaire, Curacao) and Trinidad & Tobago as well as big islands with nations including Cuba, the Dominican Republic, Haiti and Puerto Rico.

Depending on the mood, time and degree of sailing expertise, you can enjoy the quiet sea around the leeward islands (e.g., British Virgin Islands, Guadeloupe, St. Martin, Dominica) or sail abundantly in the trade winds around the windward islands (e.g., Grenada, Martinique, St. Lucia, Barbados).

One will much value the Caribbean by:
- On islands like the British Virgin Islands, Barbuda and Antigua, recreational sailors who like a gentler wind and small waves will discover their bit of heaven.
- Around the windward islands, sporty sailors will have great fun. Long and difficult crossings to sail against the wind abound (e.g., the 120 nautical mile length from Martinique to Barbados or a route from Martinique to Guadeloupe).
- Underwater beauty of the Grenadines and Grenada archipelago will delight divers and coral reef seekers.
- Fans of dance, flowers, rum, rich fauna and vegetation will remain happy anyplace in the Caribbean.
The Caribbean’s greatest sailing season falls when?
From December to May is the sailing season; the peak falls from February to May. June to October spans the time most likely to see storms and devastating hurricanes.
Since Martinique is easily reachable by air, most sailors leaving Europe choose this French colony. The British Virgin Islands are another often used starting place. A few courageous folks “conquer” the Caribbean using a popular transatlantic ship from the Canary Islands.


What are the sailing conditions?
The northeastern (NE) trade winds blow throughout the Caribbean sailing season. They travel in a straight line, hence a sudden change in the wind will not catch you. On the Atlantic side of the Antilles, in the northern portion of the Caribbean, the Antilles Current (NW direction) will be felt merging with the strong Gulf Stream above the Bahamas.
Many shallows, or underwater coral reefs, might surprise you. The guidebooks so stress on seeing the situation from the bow using your own eyes. Not all shallows and obstacles show up on maps or in programs.
Given its low draft and better comfort in the tropical heat, a catamaran is clearly the most appropriate kind of watercraft in Caribbean seas. Considered as one of the world’s warmest seas is the Caribbean one.
Between lesser Caribbean islands, night sailing excursions are not advised. At night, the visibility of coral reefs and shallows is virtually nil.
You have to consider customs formalities and navigate the boat to the “port of entry” of the nation in issue, where you will register, when traveling between islands with different countries. This operation could last anywhere from a few minutes to half a day. You have to consider it while you map your path. Moreover, random and regular Coast Guard inspections shouldn’t surprise you.
What is maritime infrastructure like?
There are many of well-protected bays and marinas in the Caribbean. Plan your arrival at the anchorage as early as possible to avoid peak season.
Every Caribbean island boasts good and sheltered anchorages.


Among the most sought-after bays and islands below are a few:
- British Virgin Islands (BVI) – White Bay, Diamond Bay, Cane Garden
- American Virgin Islands – Francis Bay, Hawksnest Bay
- Anguilla – Road Bay, Crocus Bay
- St. Martin – Baie de Grand Case, Friar’s Bay
- St. Kitts and Nevis – White House Bay
- Antigua and Barbuda – Nonsuch Bay, Palmetto Point
- Guadeloupe – Baie Mahault, Deshaies, Point a Pitre
- Dominica – Prince Rupert Bay
- Martinique – Sainte Anne, Saint-Pierre, Anse Noire
- St. Lucia – Marigot Harbour, Anse des Pitons
- St. Vincent and Grenadines – island Mayreau (Windward Bay, Saline Bay) and island Carriacou (Tyrell Bay)
- Grenada – Mangrove
Caribbean sailing: how much does it cost?
Not only do sailors find the Caribbean appealing, but also visitors and celebrities. Though fortunately not all islands are costly, this area is not cheap by any possibility.
Two weeks of renting a new catamaran will cost about 1077 USD per person.
Dinner will be cheap since you may just catch one by yourself straight from the water. Summertime restaurant costs on the French islands reflect those of other European nations.


The top sailing spots in the Caribbean
Every single Caribbean island presents unique opportunities, not confined to beaches only.
The Bahamas and Abacos archipelago will most definitely become your favourite place if you wish to enjoy undemanding sailing mixed with bathing on pristine sandy beaches. Popular stop in this northern part of the Caribbean are the northern Turks and Caicos with their opulent beach. The island’s other half is somewhat run-down whereas one side looks like a lovely postcard. Several Caribbean islands have such dualism.
The British Virgin Islands (or BVI) will surely mesmerize you if you find swinging in the surf unacceptable. One excursion will let you discover several brilliant bays thanks to the rocky coastline of four large coral islands and scores of smaller islands near by. Particularly delighting snorkelers will be the large coral lagoon of the BVI.
Every single Caribbean island presents unique opportunities, not confined to beaches only.
The Bahamas and Abacos archipelago will most definitely become your favourite place if you wish to enjoy undemanding sailing mixed with bathing on pristine sandy beaches. Popular stop in this northern part of the Caribbean are the northern Turks and Caicos with their opulent beach. The island’s other half is somewhat run-down whereas one side looks like a lovely postcard. Several Caribbean islands have such dualism.
The British Virgin Islands (or BVI) will surely mesmerize you if you find swinging in the surf unacceptable. One excursion will let you discover several brilliant bays thanks to the rocky coastline of four large coral islands and scores of smaller islands near by. Particularly delighting snorkelers will be the large coral lagoon of the BVI.
On the island of St. Martin, extroverts will have great time. This area boasts great cuisine, lots of bars and discos. Hurricane Irma severely damaged the island in 2017; now, you can still clearly observe the effects of this calamity. Maho Beach, from where daring visitors snap pictures of jets perilously near above their heads, makes St. Martin also world-famous.
The island of Antigua boasts exactly 365 beaches if you were to spend an entire year in the Caribbean. The only place with a native Indian population from the Carib tribe, the picturesque island of Dominica shapes the Caribbean as it is known. Here was filming Pirates of the Caribbean. Though it lacks spectacular beaches, Dominica is a volcanic island with a real Caribbean vibe that the flood of visitors has not yet ruined. The island of lovely beaches is the French one Guadeloupe. Still, the climb to the volcanic top—the highest mountain in the Lesser Antilles—adds to the special appeal.
On the island of Martinique, you can combine French glitz with Caribbean passion. This island has advantages in terms of air accessibility, euros as currency, and low sailing distances to nearby islands. Some people may find great disadvantage in big waves and heavier wind. Martinique is where you will find the most unique and mouthwatering Caribbean rum available. Stuck out of the sea to the south of the island, the magnificent and iconic Diamond Rock stands Black sand beaches including Anse Couleuvre also abound in Martinique.
St. Lucia is a volcanic island, hence the wild environment including waterfalls and rainforests seems unaltered here. Rising out of the sea, the iconic jagged rocky peaks of Pitons are so exquisite and distinctive that they qualify as UNESCO legacy. Saint Lucia’s rich trees and birdlife make one think of Seychelles. Here you may also find the national emblem of the island, the Amazon parrot. Picturesque villages and harbours will let you savor great cocoa and locally produced chocolate. Also, on this island, you will find black sand beaches.
The Grenadines and Grenada are an amazing place for more seasoned sailors. Dolphins and perhaps even whales could accompany you on your trip in the Grenadines. Worth a visit are the islands of St. Vincent, Bequia, and Mayreau with their protected turtles and magnificent Whistle Bay and Tobago Cays. The common nutmeg gives Grenada its nickname, the spice island. Chocolate aficionados won’t walk off this island empty-handed. Divers will too have unforgettable encounters. Underwater parks featuring life-sized sculptures and shipwrecks are among the most well-known diving destinations worldwide.
Recommended sailing routes in the Caribbean
We believe you will have to come back for another season; even the two weeks of sailing are insufficient to see the Caribbean. :)
The most often used sailing paths follow from the north of Martinique towards Dominica, from the south of Martinique towards the Grenadines, and in the primary sailing area around the BVI.

- Martinique St. Lucia St. Vincent and the Grenadines Grenada
Great sailing in the vicinity of windward direction.
The route has the drawback of the windier sailing conditions and the check-in in the Grenadines on every island. - Martinique (EU) – Dominica’s visa-free travel European Guadeloupe (EU)
Given the strong waves on this section, resistant stomachs might find it more appropriate.
The route has the benefit in that you avoid dealing with custom bureaucracy. - BVI (Tortola, Norman island, Beef island, Virgin Gorda, Leverick Bay, Anegada, Cane Garden Bay, Jost Van Dyke, Peter island)
The benefit is a peaceful and safe sailing experience as well as lovely coves reminiscent of a paradise you come upon at every “corner”.