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Boat rental in the Lesser Antilles is the ideal way to explore the Caribbean – authentic, free, and in close contact with nature. The eastern Caribbean offers steady trade winds, warm temperatures, and stunning islands strung like pearls. Each island has its own charm – shaped by French, British, Dutch, or Creole influence.
Popular departure bases include Martinique, Guadeloupe, St. Lucia, Grenada, St. Martin, and the British Virgin Islands. From there, exciting sailing itineraries are easily put together – with short distances, sheltered anchorages, and tropical highlights.
The best time to sail the Lesser Antilles is between December and May, when the dry season brings sunny skies, steady northeast trade winds, and pleasantly warm temperatures. This period offers ideal sailing conditions, especially for those who enjoy consistent wind and reliable weather. From November onward, conditions begin to improve, and by December, the full sailing season is in swing. The sea is generally calm, visibility excellent, and rain is rare. Daytime temperatures range between 25 and 30 °C, while the sea stays invitingly warm at 26 to 28 °C.
From June to October, the rainy season begins. Though many days remain warm and sunny, there’s an increased risk of showers and storms, particularly in August and September when the Atlantic hurricane season peaks. While some sailors still explore the region during these months, it's best suited to those with experience and flexibility. For most charter guests, the dry season is the most comfortable and predictable time to enjoy the area.
Thanks to these seasonal patterns, the Lesser Antilles have become one of the most attractive winter sailing destinations in the world. Whether you're looking for consistent wind for active passages or calm anchorages for swimming and snorkeling, the months between December and May deliver some of the Caribbean’s most enjoyable and reliable sailing experiences.
Sailing in the Caribbean is a unique experience that sets itself apart from typical Mediterranean cruising. The steady northeast trade winds provide reliable propulsion nearly year-round, averaging between 15 and 25 knots, which creates dynamic but manageable sailing conditions for most crews. Unlike in European waters, tidal differences in the Caribbean are minimal, making anchoring, dinghy landings, and maneuvering far less complicated – ideal for those seeking a smoother, more relaxed cruising style. Navigation is often visual, with many islands lying within sight of each other, which helps simplify route planning and adds to the scenic value of each leg.
However, open Atlantic swell is a notable factor, especially when crossing between island groups. On passages like St. Lucia to Bequia or Dominica to Les Saintes, the sea state can be more challenging, requiring some experience and preparation, particularly on longer legs. While these crossings are rarely extreme, they do add an element of offshore sailing that distinguishes the region from more sheltered Mediterranean waters.
For those new to sailing or looking for an easier introduction to Caribbean cruising, the British Virgin Islands are a top choice. With short distances, calm anchorages, and excellent marinas and provisioning services, the BVI offer a welcoming and well-equipped environment. This combination of consistent winds, warm weather, clear navigation, and diverse islands makes the Lesser Antilles a dream destination for sailors at all levels.
Itinerary from Antigua: Jolly Harbour – Green Island – Barbuda – Great Bird Island – Dickenson Bay – back to Antigua
Antigua offers 365 beaches, good infrastructure, and varied sailing – ideal for both beginners and seasoned crews.
Itinerary from St. Vincent: Blue Lagoon – Bequia – Mustique – Tobago Cays – Union Island – return via Canouan
This route explores the dreamy Grenadines with crystal-clear waters, coral reefs, and Caribbean charm.
Itinerary from British Virgin Islands: Road Town (Tortola) – Norman Island – Peter Island – Cooper Island – Virgin Gorda – Jost Van Dyke – return to Tortola
The British Virgin Islands are known for their sailor-friendly layout: short distances, sheltered anchorages, and perfect facilities. Ideal for families and first-timers.
Itinerary from Martinique: Le Marin – St. Lucia – Soufrière – Bequia – Tobago Cays – Union Island – return via St. Vincent
Itinerary from Guadeloupe: Pointe-à-Pitre – Marie-Galante – Les Saintes – Dominica – return via Îles des Saintes
Itinerary from Grenada: St. George’s – Carriacou – Union Island – Tobago Cays – Mayreau – back via Petit Martinique
These routes can be adjusted to suit weather, crew experience, and personal preferences.
The Lesser Antilles offer a cultural richness as diverse as their island landscapes. This string of islands reflects a layered history shaped by Creole traditions, African roots, and centuries of French, British, and Dutch colonial presence. As you sail into harbors lined with colorful boats and market stalls, you're met with the beat of reggae, the scent of spiced meats and tropical fruit, and the warm welcome of communities proud of their heritage. Colonial towns like Fort-de-France in Martinique or St. George’s in Grenada blend European architecture with Caribbean rhythm, telling tales of plantation economies, resistance, and renewal. Plantation houses, old forts, and local museums preserve the island histories, while everyday life unfolds in market squares, rum shops, and festivals filled with music and dance.
Food is central to this cultural expression. Far beyond sustenance, Caribbean cuisine speaks of migrations, trade, and survival. On a yacht charter through the Lesser Antilles, every anchorage offers a new taste. Freshly grilled fish and lobster are staples, as are plantains, rice dishes, and thick curries with local spices. In Martinique, don’t miss Colombo – a unique blend of Indian curry with French technique. On Grenada, known as the “Spice Island,” nutmeg flavors stews and desserts. St. Lucia offers grilled snapper and zesty lime sauces. In the British Virgin Islands, communal feasts celebrate the sea’s bounty. Rum, whether sipped neat or mixed in punch, is more than a drink – it’s part of island storytelling.
Sailing the Lesser Antilles means discovering not only stunning island scenery but also one of the world’s most fascinating underwater landscapes. The warm, crystal-clear waters of the Caribbean are a true paradise for snorkelers and divers alike, home to vibrant coral reefs, graceful rays, curious sea turtles, and an incredible variety of tropical fish. One of the top spots is the Tobago Cays, a postcard-perfect marine park where you can swim with turtles in their natural habitat. The waters around Les Saintes are equally impressive, with excellent visibility, small caves, and dense forests of gorgonians. For dramatic rock formations and colorful anemone reefs, Virgin Gorda in the British Virgin Islands is a must.
Many yachts offered by Master Yachting come equipped with snorkeling gear, making it easy to explore the underwater world whenever the opportunity arises. For those who want to go deeper, numerous marinas along the route offer guided diving excursions. These tours are also suitable for beginners and offer safe, professionally led adventures that turn your sailing holiday into a truly unforgettable experience
A yacht charter in the Lesser Antilles with Sailogy offers:
All available with or without skipper, depending on your qualifications.
Additional costs:
Yes – especially around Martinique, Guadeloupe, and the Grenadines. The islands are manageable, distances short, and anchorages well protected. Catamarans offer great space and stability. Tropical nature, friendly locals, and vibrant marine life make this region a hit with kids.
To rent a boat in the Lesser Antilles, you'll need a recognized boating license (e.g., ICC or RYA Day Skipper). In some countries, a VHF certificate may be required. No license? No problem – book a yacht with skipper for a relaxed charter experience.
Sun protection (clothing, sunglasses, sunscreen)
Swimwear, light clothing
Windbreaker for crossings
Mosquito net, insect spray
Water bottle, snacks, personal medication
Pack soft bags only – hard-shell suitcases don’t work well on a yacht.
The region is as linguistically diverse as it is culturally:
English is widely understood. French helps on the French islands.
You can reach the Lesser Antilles via direct flights or connections through major Caribbean hubs like Barbados, St. Maarten, or Antigua. Main charter airports include:
Transfers to the marina are often available by taxi or shuttle. Sailogy is happy to assist with arrangements.
Because here, you feel the real Caribbean – warm, colorful, and relaxed. A yacht charter in the Lesser Antilles with Sailogy combines freedom, nature, culture, and cuisine. Whether island hopping or relaxing in a secluded bay – this is sailing at its tropical best.