
Stayinto · Boat charter· Caribbean
Caribbean
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.
Pick your week
The fleet
The boats
849 boats available · 24 of 849 shown
Be Hang Loose
From 8,173 € / week
Champs-Elysees
From 5,226 € / week
Sol Griso
From 7,630 € / week
Soleil Rae
From 6,942 € / week
Parrot Ice
From 5,425 € / week
Maya Ulu
From 14,385 € / week
Moorings 44.3 Exclusive
From 4,926 € / week
Moorings 44.3 Exclusive
From 4,926 € / week
SailboatMoorings 44.3 Exclusive Plus
From 5,444 € / week
Moorings 44.3 Exclusive
From 4,926 € / week
Moorings 44.3 Exclusive Plus
From 5,444 € / week
Fountaine Pajot Astrea 42 - 4 + 1 cab. - Pleasant Arbour - 2020
From 3,817 € / week
Fountaine Pajot Astrea 42 - 4 + 1 cab. - Fortunata - 2023
From 4,365 € / week
Bali 4.2 - Hard Deck - 2023
From 4,685 € / week
Moorings 44.3 Exclusive Plus
From 5,639 € / week
Moorings 44.3 Exclusive
From 5,185 € / week
Moorings 44.3 Exclusive
From 5,185 € / week
Moorings 44.3 Exclusive
From 5,185 € / week
Fountaine Pajot Aura 51 - Mer Sea - 2025
From 12,500 € / week
Lagoon 51 OW - 4 + 1 cab. - Moondance - 2024
From 12,513 € / week
Dufour 530 - 4 cab. - Pura Vida - 2022
From 3,321 € / week
Fountaine Pajot Elba 45 - 4 + 2 cab. - Two Phish - 2023
From 10,500 € / week
Fountaine Pajot FP 44 Maestro - 3 cab. - Serenus - 2026
From 6,912 € / week
Fountaine Pajot FP 44 Quatuor - 4 cab. - Emma Rose - 2026
From 8,590 € / week
Ports map
32 departure ports in this area
Each marker is a marina where your charter can start.
- Wickhams Cay II Marina — 205 boats
- Hodge's Creek Marina — 96 boats
- Ritter House Marina — 78 boats
- Le Marin — 70 boats
- Nanny Cay — 68 boats
- Fort Burt Marina — 38 boats
- Beach Resort Marina — 37 boats
- Marina Fort Louis — 31 boats
- Blue Lagoon — 29 boats
- Marina Bas-du-Fort — 27 boats
- Palm Cay One Marina — 23 boats
- Rodney Bay Marina — 23 boats
- TradeWinds Yacht Club — 23 boats
- Frenchtown Harbour Marina — 22 boats
- Port Louis Marina — 14 boats
- Nelson's Dockyard — 9 boats
- Placencia — 9 boats
- Marlin Marina Cienfuegos — 7 boats
- Grenada Yacht Club — 6 boats
- Robert's Grove Marina — 6 boats
- San Blas — 6 boats
- Bequia Marina — 4 boats
- San Blas, Corazon de Jesus — 4 boats
- Soper`s Hole Marina — 3 boats
- Bocas del Toro — 2 boats
- Isla Aguja Cabins San Blas — 2 boats
- Marsh Harbour Marina — 2 boats
- Bobby's Marina — 1 boat
- Linton Bay Marina — 1 boat
- Marina de L'Anse Marcel — 1 boat
- Panama, Bocas del Toro, IGY Red Frog Beach Island Marina — 1 boat
- Rue de Sandy Ground — 1 boat
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.