Why is the Caribbean good for sailing? Where are the best places for sailing? Sailing in the Caribbean is a dream of many sailors. The beautiful sea, the trade wind and the pleasant waters are ideal for a sailing vacation, not to mention the fact that navigating amongst the many islands here is quite exciting. The ports and islands in the Caribbean are ideal for those who love adventures, beautiful sights, and hotness. This article will be the most useful read for those who want a comprehensive but friendly guide to the weather, routes, ports and attractions in Caribbean.

• What is the best month to sail the Caribbean?
• Where are the best sailing in the Caribbean?
• Sail in the Caribbean! Caribbean sailing trips – itineraries
• Caribbean sailing vacation in the BVI
• Sailing the caribbean islands – Martinique
• Caribbean sailboat excursions in Antigua
• Sailing vacations in the Caribbean: The Bahamas – for experienced sailors
• Caribbean sailing holidays in US Virgin Islands

What is the best month to sail the Caribbean?

The best time to sail is the dry season, from December to April, when the skies are clear and rainfall is minimal. Caribbean sailing offers pleasant weather for most of the year, with warm average temperatures of 25°C to 30°C. The northeast trade winds provide a steady breeze, which allows for smooth sailing. The winter-spring high season is stable, but the strength of the trade winds varies by region: BVI/USVI is mostly beginner-friendly, while between the southern islands (e.g. St. Lucia–St. Vincent) there are more open passages and larger waves.

When not to sail in the Caribbean?

The period to avoid sailing in the Caribbean typically falls during hurricane season, which runs from June to November. The best time to avoid sailing in the Caribbean is during hurricane season, which runs from June to November. Tropical storms are more common during this time, so it is recommended to only go sailing with a flexible plan, daily weather advice, and adequate insurance. The highest risk is usually from late August to October. The highest chance of a hurricane is from late August to mid-October, depending on the location of the area. The southern Caribbean generally has a lower hurricane risk, but tropical disturbances can occur there during the season – always base your decision on the daily forecast.

Is sailing in the Caribbean easy or hard?

Sailing in the Caribbean is generally accessible to all levels of sailors, but the difficulty depends on the season and location. The region offers steady trade winds and mostly calm seas, making it ideal for beginner and intermediate sailors. However, certain areas can be challenging due to coral reefs, unpredictable weather patterns, and hurricane season. For more experienced sailors, navigating the open waters between the islands can be an exciting challenge. Choosing the right season and route significantly affects the ease of navigation.

Is the Caribbean a rough sea?

The Caribbean is generally known for its calm waters, especially during the dry season (December to April), thanks to constant trade winds and minimal storms. However, the sea gets rougher during hurricane season (June to November), when tropical storms and strong winds can create challenging sailing conditions. Some areas, such as inter-island channels, experience stronger currents or rough seas. In general, the seas are manageable for most sailors, but conditions vary by season and location.

Where are the best sailing in the Caribbean?

British Virgin Islands (BVI)

The BVI is the sailing capital of the Caribbean, known for its steady winds, calm waters, and short distances between islands. Top attractions include The Baths on Virgin Gorda, the hidden caves of Norman Island, and the beach bars of Jost Van Dyke. The archipelago offers world-class sailing and easy navigation, making it ideal for both novice and experienced sailors.

Road Town Harbor (Tortola)

Road Town is Tortola’s main harbor, a full-service marina that’s a great base for embarking on a BVI island-hopping adventure.

Soper’s Hole Marina

Located on the western tip of Tortola, Soper’s Hole is a picturesque and well-equipped marina perfect for exploring Jost Van Dyke or Norman Island. yacht rental BVI

St. Martin / St. Maarten

St. Martin sailing in , half French, half Dutch, offers a unique blend of European charm and Caribbean beauty. The island is a premier sailing destination with excellent marinas, a vibrant nightlife and nearby destinations such as Anguilla and St. Barts. Its sheltered lagoons and steady winds make it an excellent base for island hopping.

Simpson Bay Marina (Dutch side)

One of the largest and most modern marinas in the Caribbean, offering top-notch facilities

Marigot Bay Marina (French side of St. Martin)

A quieter and more picturesque marina, located near charming French cafes, markets and duty-free shopping. St.Martin yacht charter

Antigua and Barbuda

Antigua is famous for its 365 beaches and a long sailing history, while Barbuda offers secluded pink sand beaches and clear blue waters. Antigua sailing is a favorite for yachting and regattas with its steady trade winds and sheltered harbors.

English Harbour & Nelson’s Dockyard

A historic and world-famous sailing hub, home to superyachts, regattas and a bustling maritime scene. The well-preserved 18th-century shipyard is a UNESCO World Heritage Site.

Jolly Harbour

A modern marina with full-service facilities, a relaxed atmosphere and restaurants. boat rental Antigua

St. Barts

St. Barts is a luxurious Caribbean island, popular for its upscale resorts, French cuisine and exclusive sailing events. Its beautiful coastline, crystal-clear waters and elegant marinas attract elite sailors.

Gustavia Marina

A small but upscale marina offering yacht moorings, high-end shops and excellent French restaurants. A must-see for those looking for a mix of sailing and luxury.

Grenada and the Grenadines

Known as the “Spice Isles,” Grenada is a lush and welcoming sailing destination. The Grenadines, a chain of small islands south of St. Vincent, offer some of the best sailing in the Caribbean, with pristine anchorages and turquoise lagoons. Grenada sailing

Port Louis Marina (Grenada)

A modern and well-protected marina with full-service facilities and a great departure point for the Grenadines.

Bequia Marina (Grenadines)

A quiet but charming marina close to some of the Grenadines’ most beautiful beaches. Grenadines yacht charter

The Bahamas

With over 700 islands and countless islets, the Bahamas is a sailor’s paradise with turquoise waters, coral reefs and white sandy beaches. The Exumas and Abacos are among the best sailing regions.

Nassau Harbour

The capital’s main port with great facilities, duty-free shopping and nightlife. Ideal for starting a Bahamas sailing adventure.

Marsh Harbour (Abacos)

A sheltered harbour and excellent promenade, providing easy access to the best coves and reefs in the Abacos. yacht rental Bahamas

St. Lucia

St. Lucia is a stunning island known for its dramatic Pitons, lush rainforests and excellent sailing conditions. It is a great stop for sailors sailing north or south in the Caribbean. sailing in St. Lucia

Rodney Bay Marina

One of the best marinas in the Caribbean, offering full service and restaurants.

Soufrière Bay

A scenic anchorage near the famous Pitons with stunning views and nearby natural hot springs. St.Lucia yacht charter

Puerto Rico and Culebra

Puerto Rico offers a blend of Spanish colonial charm with lush landscapes close to the Spanish Virgin Islands. Culebra is a quiet, natural paradise perfect for anchoring.

San Juan Marina

A large, full-service marina near the historic Old Town of San Juan.

Ensenada Honda (Culebra)

A sheltered, tranquil anchorage in Culebra, with crystal-clear waters and access to the famous Flamenco Beach.

USVI Islands (USVI)

The USVI consists of three main islands: St. Thomas, St. John, and St. Croix, as well as several smaller islands. It’s a sailing paradise with crystal-clear waters, abundant marine life, and excellent anchorages. St. Thomas is the busiest of the three islands, offering luxury marinas, shopping, and a vibrant nightlife. St. John is mostly protected as a national park, with pristine beaches and secluded anchorages like Maho Bay and Caneel Bay. St. Croix is ​​further south and offers a laid-back atmosphere, historic sites, and excellent diving.

Charlotte Amalie Harbor (St. Thomas)

One of the largest natural harbors in the Caribbean, offering full-service and shopping options.

Cruz Bay (St. John)

A charming harbor with a small-town feel, moorings near the Virgin Islands National Park, and beautiful snorkelling spots. US Virgin Islands sailing, USVI yacht charter

The Dominican Republic

The DR is an emerging sailing destination with a rich culture, beautiful beaches, and affordable marinas. The island is a great stopover between the Caribbean and the United States.

Ocean World Marina (Puerto Plata)

A modern and safe harbor with excellent facilities.

Samana Bay

A stunning bay with lush scenery and whale watching opportunities.

Martinique

Sailing in Martinique is a French-Caribbean island that offers the perfect blend of tropical beauty and European sophistication. It is a great sailing hub with excellent marinas and anchorages.

Le Marin Marina

One of the largest and best-equipped marinas in the Caribbean, offering easy access to Martinique’s best beaches and sailing routes.

Fort-de-France Bay

A large, picturesque port offering a mix of French-Caribbean culture, dining and shopping. yacht charter Martinique

Guadeloupe

Guadeloupe, an overseas region of France, is an idyllic Caribbean sailing destination with its butterfly-shaped islands, vibrant Creole culture and diverse landscapes. The archipelago consists of Basse-Terre, Grande-Terre, Marie-Galante, Les Saintes and La Désirade, offering pristine beaches, volcanic peaks and excellent sailing conditions. The sailing in Guadeloupe offers sheltered waters, offshore sailing and short island hopping routes, making it ideal for all skill levels.

Pointe-à-Pitre

Pointe-à-Pitre is the main port and capital of Guadeloupe, offering modern marinas, catering and cultural attractions. The city is a great base for sailing adventures, with easy access to the lush mountains of Basse-Terre and the white sandy beaches of Grande-Terre.

Les Saintes

Les Saintes is a charming archipelago south of Guadeloupe, known for its turquoise waters, historic forts and French-Caribbean charm. Terre-de-Haut is the main island, home to a picturesque bay and excellent snorkeling spots. The anchorage at Bourg des Saintes is well-protected, with mooring buoys and local restaurants. yacht charter Guadeloupe. Rent a boat in Caribbean and experience what it feels like when everything is perfectly timed – the sunset, the sea, and freedom.

Sail in the Caribbean! Caribbean sailing trips – itineraries

Caribbean sailing vacation in the BVI

This itinerary offers a classic island-hopping Caribbean experience with short day trips and well-protected waters. Watch out for coral reefs and buoys, but in return you’ll get stress-free, family- and beginner-friendly sailing with excellent infrastructure.

Careful navigation is required due to coral reefs, as buoys are common. Recommended level: Beginner, intermediate Open sea sections: no (mostly sheltered between islands)

Day 1. Parham Town – Peter Island

9.43 km (5.86 nm)
The port of Peter Island is fairly small, which makes it one of the most expensive port of the Virgin Islands. Despite the price, it’s still worth docking here, as the beach is fabulous. The classic Caribbean atmosphere is guaranteed in the Dead Man’s bay, where you can enjoy the beach with palm trees and cocktails.

Day 2. Peter Island – Salt Island

4.87 km (3.03 nm)
On the second day, our destination is Salt Island. The island got its name from the salt distillers in the middle region. You can anchor on the northwestern side of the island. Here you will find a charming little beach where you can relax. The island is popular amongst scuba divers. In 1867, a steamer called Rhone sank at Dead Chest island while trying to escape a hurricane. The wreck is lying 9-24 meters deep in the sea today.

Day 3. Salt Island – Cooper Island

2.38 km (1.48 nm)
There is an opportunity to dock more than three dozens of yachts at Manchionel Bay at Cooper Island. Get yourself a buoy, and head to the beach! The coral-coloured sand and the palm trees are a great sight. Hobby photographers will love the place due to the beautiful landscape.
There are awesome restaurants and bars on the beach. You should try them before going to bed on your boat.

Day 4. Cooper Island – Virgin Gorda (Spanish Town)

11.33 km (7.04 nm)
The island called Virgin Gorda is 10 kilometres long and 1-4 meters wide, and it can be found only 5miles from Cooper Island. The Bath National Park, which is the most beautiful shore segment on the island, is located in the southwestern region. Its uniqueness comes from the fact that there are giant round-shaped granite rocks on the beach, forming exciting little caves. We can only dock here temporarily during the day, but it’s worth going on a short trip on these weird shores as well.

Day 5. Virgin Gorda – Beef Island

10.21 km (6.34 nm)
The last day of our trip is Beef Island, the shape of which reminds us of a lying bull. Marina Cay is located opposite Scrub Island; 30 buoys are available for sailors here. Tourists love the red English phone booth at the port. Since this is the last day of your trip, you should spend it on the beach swimming and doing watersports.

Day 6. Beef Island – Jost van Dyke, Great Harbour

24.25 km (15.07 nm)
As the name suggests, Great Harbour is the largest harbour on Jost van Dyke. The area is well-protected thanks to the high mountains. The depth of water is between 5 and 9 metres. We can anchor or use the mooring balls. There are many bars, restaurants, churches and shops ashore, and we can go scuba-diving at an amazing reef nearby.

Day 7. Jost van Dyke, Great Harbour – Road Town – Parham Town

30.9 km (19.2 nm)
Road Town is the capital of Tortola and the sailing centre of the British Virgin Islands. We can enter the port through the Sir Francis Drake Channel. Road Harbour has several yacht marinas providing full service and accommodation. We can find Road Reef Marina, Fort Burt and Wickham’s Cay I and II here; Road Reef Marina and Fort Burt are on the western side, while Wickham’s Cay is on the north. There are over 120 berths and downtown Road Town can be found nearby.

After you have docked at Parham Town, it’s worth making a short trip to one of the national parks on the island, Mount Healthy, where you can admire a mill used to process sugar. Read more about what to do in Tortola, Tortola sailing, or Tortola boat rental
More BVI sailing itineraries

Grenada sailing route

This route offers one of the most spectacular and authentic sailing experiences in the Caribbean, with lush green islands, pristine anchorages and crystal clear waters. Watch for trade winds picking up in the straits and more open crossings, but expect less crowded ports, excellent snorkeling and a true “classic Caribbean” feel. Recommended level: Beginner, intermediate-advanced Open sea sections: no.

Day 1. Grenada – Ronde Island 34,36 km (21,35 nm), Day 2. Ronde Island – Sandy Island 21,88 km (13,60 nm), Day 3. Sandy Island – Union Island 13,47 km (8,37 nm), Day 4. Union Island – Palm Island 3,34 km (2,08 nm), Day 5. Palm Island – Petite Martinique 6,98 km (4,34 nm), Day 6. Petite Martinique – Bedford Point 41,14 km (25,56 nm), Day 7. Bedford Point – Dragon Bay – Grenada 32,33 km (20,09 nm)

Caribbean sailboat excursions in Antigua

Nice, rhythmic sailing awaits around Antigua, while a more open sea crossing towards Barbuda adds a touch of adventure. Watch out for wind and wave conditions on longer trips, but in return you get less crowded, spectacular beaches and clean anchorages. Early departure and stable weather conditions are recommended. Recommended level: Intermediate. Open sea sections: yes (more open crossings towards Barbuda).

Day 1. English Harbour – Nonsuch Bay 18, 24 km (11, 33 nm), Day 2. Nonsuch Bay – Low Bay (Barbuda) 55, 26 km (34, 34 nm), Day 3. Low Bay – Coco Point (Barbuda)18, 41 km (11, 44 nm), Day 4. Coco Point – Dickenson Bay 52, 91 km (32, 88 nm), Day 5. Dickenson Bay – St.John’s 6, 34 km (3, 94 nm), Day 6. St.John’s – Jolly Harbour 13, 56 km (8, 42 nm), Day 7. Jolly Harbour – Carlisle Bay – English Harbour 20, 13 km (12, 51 nm).

More Antigua sailing holidays

Sailing vacations in the Bahamas Caribbean – for experienced sailors

Shallow, clear water, sandbars and coral reefs, where navigation requires precision rather than strong winds. Pay close attention to currents and water depth, but you can expect unique colors, swimming pigs and unique experiences. Recommended level: Advanced. Open sea sections: yes.

Day 1. Nassau (Palm Cay / ONE Marina) – Highbourne Cay (Highbourne Cay Marina) 57, 29 km (35, 60 nm), Day 2. Highbourne Cay – Bells Cay and its surrounding – Compass Cay 59, 28 km (36, 84 nm), Day 3. Compass Cay – Staniel Cay – Great Guana Cay – Safe Harbor Marina 48, 04 km (29, 85 nm), Day 4. Safe Harbor Marina – Emerald Bay Marina 49, 73 km (30, 90 nm), Day 5. Emerald Bay Marina – Farmer’s Cay (Little Farmer’s Cay Yacht Club) 58, 66 km (36, 45 nm), Day 6. Farmer’s Cay – Warderick Wells Cay – Shroud Cay (dock at Highbourne Cay) 97, 99 km (60, 89 nm), Day 7. Highbourne Cay – The wonderful Atlantis – Nassau 72, 59 km (45, 10 nm)

More Bahamas sailing tours

Caribbean sailing holidays on US Virgin Island

This itinerary includes longer daily stages and open sea sections, so it’s more for experienced sailors. Timing and daily weather decisions are key, but in return you get a true “open sea” Caribbean sailing experience. Recommended level: Advanced. Open sea sections: yes.

Day 1. Saint Thomas – Red Hook 8,06 km (5,01 nm), Day 2. Red Hook – Hull bay 14,49 km (9,00 nm), Day 3. Hull bay – Culebra 39,51 km (24,55 nm), Day 4. Culebra – San Juan 94,54 km (58,74 nm), Day 5. San Juan – Loiza 27,47 km (17,07 nm), Day 6. Loiza – Fajardo 30,80 km (19,14 nm), Day 7. Fajardo – Brewers Bay – Saint Thomas 81,00 km (50,33 nm)

bareboat charter USVI

How to choose?

• If you are just starting out, going with family, and want a relaxed, “island-hopping” week: BVI (Tortola circuit) Why? Short daily distances, more sheltered waters, easy-to-manage logistics.
• If you already have a routine, but don’t want an extreme open-water challenge: Antigua–Barbuda or Puerto Rico–USVI shortened version. Why? More varied rides, sometimes more open sections, but still good infrastructure.
• If you are specifically looking for a challenge (long stages, tactics, weather window): Bahamas (advanced route) or USVI–Puerto Rico with long rides. Why? The key to success here is timing: when do you start, where do you wait, how much do you undertake.

Sailing in the Caribbean FAQ

• When is the best time to sail in the Caribbean? The most stable period is usually from December to April, when there is less rainfall and more consistent trade winds.
• When is it not recommended to plan a Caribbean sailing trip? Hurricane season runs from June to November; tropical storms are more common during this time, so it is worth setting off with a flexible plan and daily meteorological decisions.
• Which Caribbean region is best for beginners? The British Virgin Islands (BVI) are one of the most beginner-friendly: the distances are short and there are many protected sections.
• How much should a beginner sail in a day? The ideal daily distance for beginners is usually 10–25 nautical miles (nm), which means 3–5 hours of comfortable sailing. Days above 40 nm require an advanced level and a stable weather window.
• What does “open sea section: yes” mean? That there are some courses where the waves can build up faster and the weather window plays a greater role.
• Catamaran or monohull is better for the Caribbean? For beginners and families, a catamaran is often more comfortable (more stable, more space), while for more experienced people, a monohull gives a more “sailing” experience.
• What should I watch out for with coral reefs?Keep to designated channels, use a current chart/plotter, and slow down near buoys/shallow water, especially around the BVI.
• How far in advance should I book?Good boats sell out quickly during peak season (Dec–Apr) – book well in advance to ensure a good selection.
• What do I need for a quick quote? Date + number of people + boat type + do I need a skipper + preferred region

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