Caribbean

Stayinto · Boat charter· Caribbean

Caribbean

849 boats to choose fromDeparting from 32 ports

The Caribbean Islands span one of the world's most celebrated sailing regions, encompassing the British Virgin Islands alongside neighbouring territories including Antigua and Barbuda, Anguilla, Barbados, Belize, Bermuda, the Bahamas, Colombia, and beyond. This expansive area of…

The Caribbean Islands span one of the world's most celebrated sailing regions, encompassing the British Virgin Islands alongside neighbouring territories including Antigua and Barbuda, Anguilla, Barbados, Belize, Bermuda, the Bahamas, Colombia, and beyond. This expansive area offers consistent trade winds, sheltered anchorages, and a rich tapestry of island cultures, each with distinct character and appeal.

The sailing infrastructure here is substantial and well-established. A fleet of 812 charter yachts provides options across all vessel types and experience levels, from bareboat to fully crewed expeditions. With 32 marinas distributed throughout the region, cruising yachts benefit from reliable provisioning, repair facilities, and secure mooring across multiple islands. This density of support makes extended passages and island-hopping both practical and pleasurable.

Beyond the sailing itself, 43 day-charter and activity experiences allow you to explore beyond your vessel—whether diving pristine reefs, visiting colonial settlements, or engaging with local communities. The combination of accessible anchorages, established hospitality infrastructure, and diverse cultural encounters makes the Caribbean Islands a destination where both seasoned sailors and those new to cruising find genuine reward.

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The fleet

The boats

849 boats available · 24 of 849 shown

Be Hang LooseCatamaran

Be Hang Loose

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4 cabins8 guestsBocas del Toro

From 8,173 € / week

Champs-ElyseesCatamaran

Champs-Elysees

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5 cabins10 guestsFort Burt Marina

From 5,226 € / week

Sol GrisoCatamaran

Sol Griso

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6 cabins10 guestsMarlin Marina Cienfuegos

From 7,630 € / week

Soleil RaeCatamaran

Soleil Rae

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5 cabins10 guestsFort Burt Marina

From 6,942 € / week

Parrot IceCatamaran

Parrot Ice

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5 cabins10 guestsFort Burt Marina

From 5,425 € / week

Maya UluCatamaran

Maya Ulu

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6 cabins12 guestsSan Blas

From 14,385 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsWickhams Cay II Marina

From 4,926 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsWickhams Cay II Marina

From 4,926 € / week

Moorings 44.3 Exclusive PlusSailboat

Moorings 44.3 Exclusive Plus

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3 cabins7 guestsWickhams Cay II Marina

From 5,444 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsWickhams Cay II Marina

From 4,926 € / week

Moorings 44.3 Exclusive PlusSailboat

Moorings 44.3 Exclusive Plus

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3 cabins7 guestsWickhams Cay II Marina

From 5,444 € / week

Fountaine Pajot Astrea 42 - 4 + 1 cab. - Pleasant Arbour - 2020Catamaran

Fountaine Pajot Astrea 42 - 4 + 1 cab. - Pleasant Arbour - 2020

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4 cabins9 guestsRitter House Marina

From 3,817 € / week

Fountaine Pajot Astrea 42 - 4 + 1 cab. - Fortunata - 2023Catamaran

Fountaine Pajot Astrea 42 - 4 + 1 cab. - Fortunata - 2023

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4 cabins9 guestsRitter House Marina

From 4,365 € / week

Bali 4.2 - Hard Deck - 2023Catamaran

Bali 4.2 - Hard Deck - 2023

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4 cabins8 guestsHodge's Creek Marina

From 4,685 € / week

Moorings 44.3 Exclusive PlusSailboat

Moorings 44.3 Exclusive Plus

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3 cabins7 guestsPort Louis Marina

From 5,639 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsMarina Fort Louis

From 5,185 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsMarina Fort Louis

From 5,185 € / week

Moorings 44.3 ExclusiveSailboat

Moorings 44.3 Exclusive

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3 cabins7 guestsMarina Fort Louis

From 5,185 € / week

Fountaine Pajot Aura 51 - Mer Sea - 2025Catamaran

Fountaine Pajot Aura 51 - Mer Sea - 2025

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5 cabins10 guestsFrenchtown Harbour Marina

From 12,500 € / week

Lagoon 51 OW - 4 + 1 cab. - Moondance - 2024Catamaran

Lagoon 51 OW - 4 + 1 cab. - Moondance - 2024

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4 cabins9 guestsNanny Cay

From 12,513 € / week

Dufour 530 - 4 cab. - Pura Vida - 2022Sailboat

Dufour 530 - 4 cab. - Pura Vida - 2022

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4 cabins8 guestsRitter House Marina

From 3,321 € / week

Fountaine Pajot Elba 45 - 4 + 2 cab. - Two Phish - 2023Catamaran

Fountaine Pajot Elba 45 - 4 + 2 cab. - Two Phish - 2023

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4 cabins10 guestsRitter House Marina

From 10,500 € / week

Fountaine Pajot FP 44 Maestro - 3 cab. - Serenus - 2026Catamaran

Fountaine Pajot FP 44 Maestro - 3 cab. - Serenus - 2026

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3 cabins7 guestsNanny Cay

From 6,912 € / week

Fountaine Pajot FP 44 Quatuor - 4 cab. - Emma Rose - 2026Catamaran

Fountaine Pajot FP 44 Quatuor - 4 cab. - Emma Rose - 2026

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4 cabins8 guestsHodge's Creek Marina

From 8,590 € / week

Ready to board in Caribbean?

Set your dates and sailing style. Stayinto Concierge is available 7 days a week to confirm your charter.

Destination guide

Everything about Caribbean

Overview

The Caribbean Islands span one of the world's most celebrated sailing regions, encompassing the British Virgin Islands alongside neighbouring territories including Antigua and Barbuda, Anguilla, Barbados, Belize, Bermuda, the Bahamas, Colombia, and beyond. This expansive area offers consistent trade winds, sheltered anchorages, and a rich tapestry of island cultures, each with distinct character and appeal.

The sailing infrastructure here is substantial and well-established. A fleet of 812 charter yachts provides options across all vessel types and experience levels, from bareboat to fully crewed expeditions. With 32 marinas distributed throughout the region, cruising yachts benefit from reliable provisioning, repair facilities, and secure mooring across multiple islands. This density of support makes extended passages and island-hopping both practical and pleasurable.

Beyond the sailing itself, 43 day-charter and activity experiences allow you to explore beyond your vessel—whether diving pristine reefs, visiting colonial settlements, or engaging with local communities. The combination of accessible anchorages, established hospitality infrastructure, and diverse cultural encounters makes the Caribbean Islands a destination where both seasoned sailors and those new to cruising find genuine reward.

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