Caribbean
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Page 4 - Charter a sailboat in Caribbean with or without a captain

345 boats available in Caribbean
Jeanneau Sun Odyssey 45
4.7 (37 reviews)
Golfo de San Blas
Imagine waking up aboard a private sailboat, surrounded only by the Caribbean Sea, turquoise waters, and small tropical islands. Welcome to Guna Yala (San Blas), one of the most authentic and least crowded corners of the Caribbean. Aboard Mama Isi, you will enjoy a private experience exclusively for your group: sailing among paradisiacal islands, discovering hidden beaches, snorkeling in crystal clear waters, practicing paddle surfing, and enjoying incredible sunsets from the deck. It's not a sh...
Sailboat
Captain mandatory
6 pers.
4 cabins
2007
44 ft
Top owner
from $976,65
Dufour 37
Le Marin
Embark on board the Spicy Rum, an amazing Dufour 37 to discover the region of Le Marin. This sailboat was built in 2024 to ensure complete comfort and performance at sea. The boat has 3 fully-equipped cabins and a capacity of 6 people. With an overall length of 11 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Le Marin For your comfort, Spicy Rum has 1 toilet with a shower This boat is equipped with a Full batten mainsail and a Fu...
Sailboat
Captain optional
6 pers.
3 cabins
2024
35 ft
from $513,60
Poncin Yachts Harmony 42 Elegance
5.0 (8 reviews)
Fort-de-France
I am a professional skipper and I am waiting for you on board my sailboat Harmony 42, a good sailer and equipped for cruising (outdoor shower, dinghy, paddle, barbecue, and fishing equipment. I only welcome 2 people so we can choose the route together according to your desires. This is not a cruise but a sailing course where you will participate in all maneuvers
Sailboat
Captain mandatory
2 pers.
3 cabins
2011
42 ft
Top owner
from $754,89
Bénéteau First 38 S
4.7 (7 reviews)
Bas du Fort
Looking to discover Dominica without worrying about transportation and accommodation? I offer the rental of my sailboat moored in Portsmouth, Dominica on a buoy. How does it work? Pick up in Guadeloupe. Crossing to Dominica done together to familiarize you with the boat and life on board. Stay independently on board on a mooring buoy in Portsmouth. Return crossing to Guadeloupe done together at the end of the rental. This formula is ideal to enjoy life on board and visit the island without ha...
Sailboat
Owner on board
6 pers.
3 cabins
1984
39 ft
Top owner
Instant booking
from $155,12
Bénéteau Oceanis 46.1
Ribishi
We offer for rent a Oceanis 46.1 of 2025 departing from Ribishi. Bieckert is a sailboat perfectly adapted for all rentals. This sailboat is very pleasant to handle for a week cruise or more. The boat has 5 fully-equipped cabins and a capacity of 10 people. With an overall length of 15 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Ribishi For your comfort, Bieckert has 3 toilets with a shower This boat is equipped with a Full batt...
Sailboat
Captain optional
10 pers.
5 cabins
2025
48 ft
from $689,40
Bénéteau Oceanis 40.1 - Beneteau - First Line
Ribishi
Incredible sailboat for rent in Ribishi. This Oceanis 40.1 - Beneteau - First Line from 2024 is an ideal boat for a vacation with family or friends. The boat has 4 fully-equipped cabin(s) and a capacity of 8 people. With an overall length of 13 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Ribishi This Oceanis 40.1 - Beneteau - First Line is equipped with 2 heads with a shower. This boat is equipped with a Full batten mainsail and a Furl...
Sailboat
Captain optional
8 pers.
4 cabins
2024
42 ft
from $507,86
Jeanneau Sun Odyssey 440
Playa Sardinera
Incredible sailboat for rent in Playa Sardinera. This Sun Odyssey 440 from 2022 is an ideal boat for a vacation with family or friends. The boat has 3 fully-equipped cabin(s) and a capacity of 6 people. With an overall length of 12 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Playa Sardinera For your comfort, COUNTING STARS has 2 toilets with a shower Booking requests and quotes are handled directly by SamBoat. You will get the best pric...
Sailboat
Bareboat
6 pers.
3 cabins
2022
40 ft
from $781
-20%
Jeanneau Sun Odyssey 410
Rodney Bay
SEA DROP is an extremely well kept 2021 Sun Odyssey 410. We cater for families or small groups of friends (we accommodate a maximum of four persons in two cabins) looking for quiet, calm holidays under the guidance of a 66 y. o. ex-Merchant Navy officer, with a vast experience of both sailing and the islands, good pedagogue and patient with children (he's a grandfather). Luis is fluent in English, French, Spanish and Portuguese, his mother tongue.
Sailboat
Captain mandatory
4 pers.
2 cabins
2021
39 ft
from $620,46
-20%
RM 1260
Fort-de-France
Sailing Day in Martinique – Sailing, Snorkeling, Fishing & Paradise Anchorages Would you like to discover Martinique from the sea and enjoy a truly different day on the water? As a qualified sailing instructor, I welcome you aboard Namaste, my twin-keel RM 12.60, a fast and comfortable cruising yacht… and one you definitely won’t miss! A genuine work of art has been painted directly onto the boat, giving her a unique personality that certainly stands out at anchor. A day at sea, at your ow...
Sailboat
Owner on board
8 pers.
2 cabins
2013
41 ft
from $838,77
Dufour 365 Grand Large
4.8 (5 reviews)
Pointe-à-Pitre
Sailboat in very good condition with rigorous maintenance. Engine inboard from 2022 with less than 1000 hours. Electric rechargeable auxiliary engine in 12volt or 220volt. Recent Raymarine electronics, latest model, interior and exterior GPS. Sails in good condition revised sailmaker in November 2024. Staysail on furler (useful with the trade winds). Inflatable paddle provided. Bedding and towels on board
Sailboat
Bareboat
6 pers.
3 cabins
2005
34 ft
from $236,69
Dufour 37
5.0 (1 reviews)
Calliaqua Bay
Superb Dufour 37, fully equipped. Ultra easy to navigate. It is available in the West Indies all year round (St. Vincent and the Grenadines)
Sailboat
Bareboat
6 pers.
3 cabins
2024
37 ft
from $426,28
Jeanneau Sun Odyssey 54 DS
5.0 (1 reviews)
Calliaqua Bay
Charter the beautiful Grenadines, with a professional skipper and hostess. We embark guest at Blue Lagoon Marina and sail around the Grenadines for the whole weeks. You only see the best islands...
Sailboat
Captain mandatory
8 pers.
4 cabins
2003
55 ft
from $984,69
Fountaine Pajot Lavezzi 40
5.0 (2 reviews)
Cartagena
ontaine Pajot Lavezzi 41 “Sirenas” – Key Features • Fontaine Pajot Lavezzi 41 catamaran in excellent condition. • 4 double cabins, spacious and well-ventilated. • 2 full bathrooms. • Air conditioning on board. • Interior dining area + exterior cockpit dining space. • Large forward net/sundeck for relaxation and sunbathing. • Two new 40 HP Yanmar engines (high efficiency and safety). • Impeccable sail set for stable, comfortable sailing. • Ideal for groups, families, and premium experien...
Sailboat
Captain mandatory
25 pers.
4 cabins
2020
41 ft
Top owner
from $1 500
Bénéteau Oceanis 41.1
4.7 (7 reviews)
Le Marin
Hello everyone, Notes: - Departures and returns are from Saturday to Saturday from Guadeloupe. For Martinique, St. Vincent, Antigua, or St. Martin, a €1,500 premium will be charged for the delivery of the boat. - Rentals include the boat, its equipment, and services excluding fuel and gas. Mandatory Options: - Return cleaning: €180 / rental Options: - Skipper: €200 / day + Meals - Dinghy + outboard motor: Included. We are renting this sublime sailboat, an Océanis 41.1 (2020). This dream sai...
Sailboat
Captain optional
8 pers.
3 cabins
2020
41 ft
Top owner
from $410,19
Dufour Atoll 50
Le Marin
"Welcome aboard BAILA! Are you dreaming of an escape to the Caribbean but find purchasing a boat too cumbersome? Opt for long-term leasing aboard BAILA! A hassle-free turnkey solution, focusing solely on the goal of enjoying yourself! BAILA, an Atoll50 from the DUFOUR shipyards, is available to fulfill your desires and needs for a cruise lasting from a few days to several months in the turquoise waters of the Caribbean. This Monohull, a perfect blend between a monohull sailboat and a catamara...
Sailboat
Captain optional
6 pers.
4 cabins
1999
49 ft
from $328,61
-10%
Bénéteau Oceanis 41
5.0 (1 reviews)
Gros-Islet
Incredible sailboat for rent in Rodney Bay. This Oceanis 41 from 2022 is an ideal boat for a vacation with family or friends. The boat has 3 fully-equipped cabin(s) and a capacity of 7 people. With an overall length of 13 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Rodney Bay This Oceanis 41 is equipped with 2 heads with a shower. Booking requests and quotes are handled directly by SamBoat. You will get the best prices through the platf...
Sailboat
Captain optional
7 pers.
3 cabins
2023
42 ft
from $505,56
-10%
Dufour 44
4.6 (40 reviews)
Gros-Islet
Incredible sailboat for rent in Rodney Bay. This Dufour 44 from 2025 is an ideal boat for a vacation with family or friends. The boat has 3 fully-equipped cabins and a capacity of 6 people. With an overall length of 14 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Rodney Bay For your comfort, has 3 toilets with a shower This boat is equipped with a Full batten mainsail and a Furling genoa. It has the following equipment: Auto-pilot,...
Sailboat
Captain optional
6 pers.
3 cabins
2025
45 ft
from $545,78
-10%
Bénéteau Oceanis 41.1
4.6 (40 reviews)
Gros-Islet
Sailboat for rent in Rodney Bay. This Sunsail 42 built in 2024 offers an excellent quality for its price for a cruise of a few days or even a few weeks. The boat has 3 fully-equipped cabins and a capacity of 6 people. With an overall length of 13 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Rodney Bay For your comfort, has 2 toilets with a shower This boat is equipped with a Full batte...
Sailboat
Captain optional
6 pers.
3 cabins
2024
42 ft
from $471,09
-10%
Dufour 44
4.8 (22 reviews)
Gros-Islet
Meet , an incredible sailboat dedicated for charters. Made in 2025, the Dufour 44 will take you to the most beautiful anchorages in Rodney Bay. The boat has 3 fully-equipped cabins and a capacity of 7 people. With an overall length of 14 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Rodney Bay For your comfort, has 3 toilets with a shower This boat is equipped with a Full batten mainsail and a Furling genoa. It has the following equ...
Sailboat
Captain optional
7 pers.
3 cabins
2025
46 ft
from $620,46

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