Boat Rental Lesser Antilles: Caribbean Diversity Under Sail

432 boats in this area

Bareboat or skippered boat?

Still don't know if you need him? WIth sailing license you can rent a yacht without a skipper, in case you don't have it the skipper is an obligatory member of your crew.

484 boats
  • Catamaran
  • 2020
  • 42 ft

Lagoon 42

Pointe à Pitre, Guadeloupe

  • 12 berths
  • 4+2 cabins
  • 4 WC
  • Included Outboard Engine
  • GPS Plotter in cockpit
Up to-53%
Starting from€1,961

Price of the whole boat

  • Catamaran
  • 2024
  • 37 ft

Excess 11

Pointe à Pitre, Guadeloupe

  • 10 berths
  • 4+2 cabins
  • 2 WC
  • New boat
Up to-20%
Starting from€2,306

Price of the whole boat

  • Catamaran
  • 2020
  • 42 ft

Lagoon 42

From Le Marin, Martinique

To Pointe à Pitre, Guadeloupe

  • 12 berths
  • 4+2 cabins
  • 4 WC
  • Included Outboard Engine
  • GPS Plotter in cockpit
Up to-11%
Starting from€4,265

Price of the whole boat

  • Catamaran
  • 2023
  • 46 ft

Lagoon 46

Le Marin, Martinique

  • 12 berths
  • 4+2 cabins
  • 4 WC
  • Air conditioning
  • Watermaker
  • GPS Plotter in cockpit
Up to-20%
Starting from€4,234

Price of the whole boat

  • Sailing boat
  • 2022
  • 48 ft

Beneteau Oceanis 46.1

Le Marin, Martinique

  • 8 berths
  • 3 cabins
  • 2 WC
    Up to-18%
    Starting from€2,440

    Price of the whole boat

    • Catamaran
    • 2024
    • 54 ft

    Lagoon 55

    Marigot, Saint Martin (French)

    • Skipper on board
    • 10 berths
    • 5+2 cabins
    • 5 WC
    • New boat
    • No security deposit
    • Included Outboard Engine
    • Included SUP
    Up to-20%
    Starting from€11,847

    Boat price + skipper cost

    • Catamaran
    • 2024
    • 54 ft

    Lagoon 55

    Pointe à Pitre, Guadeloupe

    • Skipper on board
    • 10 berths
    • 5+2 cabins
    • 5 WC
    • New boat
    • No security deposit
    • Included Outboard Engine
    • Included SUP
    Up to-20%
    Starting from€11,847

    Boat price + skipper cost

    • Catamaran
    • 2024
    • 54 ft

    Lagoon 55

    Le Marin, Martinique

    • Skipper on board
    • 10 berths
    • 5+2 cabins
    • 5 WC
    • New boat
    • No security deposit
    • Included Outboard Engine
    • Included SUP
    Up to-20%
    Starting from€11,847

    Boat price + skipper cost

    • Catamaran
    • 2024
    • 54 ft

    Lagoon 55

    Antigua and Barbuda, Leeward Islands

    • Skipper on board
    • 10 berths
    • 5+2 cabins
    • 5 WC
    • New boat
    • No security deposit
    • Included Outboard Engine
    • Included SUP
    Up to-20%
    Starting from€11,847

    Boat price + skipper cost

    • Catamaran
    • 2024
    • 54 ft

    Lagoon 55

    Grenada, Windward Islands

    • Skipper on board
    • 10 berths
    • 5+2 cabins
    • 5 WC
    • New boat
    • No security deposit
    • Included Outboard Engine
    • Included SUP
    Up to-20%
    Starting from€11,847

    Boat price + skipper cost

    • Catamaran
    • 2022-2023
    • 45 ft

    Moorings 4500L

    Le Marin, Martinique

    • 10 berths
    • 4+1 cabins
    • 4 WC
    • Air conditioning
    • Watermaker
    • Generator
    • GPS Plotter in cockpit
    Up to-10%
    Starting from€5,849

    Price of the whole boat

    • Catamaran
    • 2022-2023
    • 45 ft

    Moorings 4500L

    St. Lucia, Windward Islands

    • 10 berths
    • 4+1 cabins
    • 4 WC
    • Air conditioning
    • Watermaker
    • Generator
    • GPS Plotter in cockpit
    Up to-10%
    Starting from€6,299

    Price of the whole boat

    • Catamaran
    • 2022-2023
    • 45 ft

    Moorings 4500L

    St. George, Grenada

    • 10 berths
    • 4+1 cabins
    • 4 WC
    • Air conditioning
    • Watermaker
    • Generator
    • GPS Plotter in cockpit
    Up to-10%
    Starting from€2,969

    Price of the whole boat

    • Sailing boat
    • 2024
    • 41 ft

    Beneteau Oceanis 40.1

    Le Marin, Martinique

    • 8 berths
    • 3+1 cabins
    • 2 WC
    • New boat
    • Included Outboard Engine
    • Watermaker
    Up to-3%
    Starting from€4,499

    Price of the whole boat

    • Sailing boat
    • 2024
    • 41 ft

    Beneteau Oceanis 40.1

    Saint Vincent and the Grenadine, Windward Islands

    • 8 berths
    • 3+1 cabins
    • 2 WC
    • New boat
    • Included Outboard Engine
    • Watermaker
    Up to-8%
    Starting from€2,881

    Price of the whole boat

    • Catamaran
    • 2023
    • 46 ft

    Lagoon 46

    Grenada, Windward Islands

    • 12 berths
    • 4 cabins
    • 4 WC
    • Included Outboard Engine
    • Included SUP
    • Air conditioning
    • Watermaker
    Up to-15%
    Starting from€7,195

    Price of the whole boat

    • Catamaran
    • 2017
    • 46 ft

    Lagoon 450

    Pointe à Pitre, Guadeloupe

    • 12 berths
    • 4+2 cabins
    • 4 WC
    • Included Outboard Engine
    • Watermaker
    • GPS Plotter in cockpit
    Up to-53%
    Starting from€2,331

    Price of the whole boat

    • Sailing boat
    • 2017
    • 32 ft

    Beneteau Oceanis 31

    Le Marin, Martinique

    • 6 berths
    • 2 cabins
    • 1 WC
    • Included Outboard Engine
    • GPS Plotter in cockpit
    Up to-18%
    Starting from€1,468

    Price of the whole boat

    • Catamaran
    • 2015 (refit 2019)
    • 52 ft

    Lagoon 52 F

    Le Marin, Martinique

    • Skipper on board
    • 10 berths
    • 5+3 cabins
    • 6 WC
    • Included Outboard Engine
    • Bow thruster
    • Air conditioning
    • Watermaker
    Up to-28%
    Starting from€10,318

    Boat price + skipper cost

    • Catamaran
    • 2020
    • 42 ft

    Lagoon 42

    Grenada, Windward Islands

    • 12 berths
    • 4 cabins
    • 4 WC
    • Included Outboard Engine
    • Air conditioning
    • Watermaker
    • Generator
    Up to-24%
    Starting from€3,262

    Price of the whole boat

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    Different boat types in Lesser Antilles

    Boat Rental Lesser Antilles: Caribbean Diversity Under Sail

    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.

    When Is the Best Time to Sail the Lesser Antilles?

    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.

    What Makes Sailing in the Caribbean Unique?

    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.

    Popular Sailing Itineraries in the Lesser Antilles

    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.

    Culinary & Cultural Discoveries – Caribbean with All Senses

    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.

    Snorkeling & Diving – Underwater Dreams in the Caribbean

    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

    What Boats Can You Rent in the Lesser Antilles?

    A yacht charter in the Lesser Antilles with Sailogy offers:

    • Sailboats: classic and sporty – perfect for couples or small groups
    • Catamarans: spacious and stable – ideal for families and larger crews
    • Motor yachts: for day trips or high-comfort cruising

    All available with or without skipper, depending on your qualifications.

    How Much Does It Cost to Rent a Boat in the Lesser Antilles?

    Additional costs:

    • Skipper: €150–200/day
    • Hostess/Cook: €120–150/day
    • Final cleaning, fuel, moorings: €200–600/week

    Is the Region Family-Friendly?

    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.

    What Licenses Do You Need?

    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.

    What Should You Bring On Board?

    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.

    What Languages Are Spoken in the Lesser Antilles?

    The region is as linguistically diverse as it is culturally:

    • Martinique & Guadeloupe: French and Creole
    • St. Lucia, Grenada, BVI, Antigua: English (with local dialects)
    • St. Martin: French (north), Dutch (south)
    • St. Vincent & the Grenadines: English

    English is widely understood. French helps on the French islands.

    How to Get to the Lesser Antilles

    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:

    • Fort-de-France (FDF) – Martinique
    • Pointe-à-Pitre (PTP) – Guadeloupe
    • Hewanorra (UVF) – St. Lucia
    • Tortola (EIS) – British Virgin Islands
    • St. George’s (GND) – Grenada

    Transfers to the marina are often available by taxi or shuttle. Sailogy is happy to assist with arrangements.

    Why Rent a Boat in the Lesser Antilles?

    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.