British Virgin Islands

Yacht charter in Caribbean Islands

279 yachts available in Caribbean Islands. Departing from 2 marinas. Prices from €2,751 per week.

Browse 279 yachts See sample routes

279

Yachts available
€2,751

From / week
2

Marinas & bases

Practical info

Chartering from Caribbean Islands: the basics

Charter week: Saturday to Saturday
Departure marinas: 2
Licence needed?: Not always

On the water

Sailing conditions in Caribbean Islands

Prevailing wind: Easterly trades, firmest December – April
Hurricane season: June – November, peaking August – September
Typical boat: Catamaran — 430 of 538
Qualification: A sailing resume, not a certificate
Borders: Usually one per island
Changeover day: Saturday

Worth the detour

Where to drop anchor in Caribbean Islands

1

The British Virgin Islands

253 boats, nearly half the regional fleet. The islands ring a single sheltered channel about twenty miles long, so you navigate by eye and the next anchorage is usually in view. The most forgiving week in the Caribbean, and the most expensive.
2

Martinique and Guadeloupe

72 and 20 boats. French overseas departments, which means euros, EU rules and — in Guadeloupe's case — an archipelago you can cruise without clearing customs once.
3

The Grenadines

Saint Vincent and the Grenadines holds 19 boats and the chain's best argument: one country covering roughly sixty miles of islands, so you clear in once. The Tobago Cays sit inside a horseshoe reef with the Atlantic breaking on the far side.
4

Grenada and the southern end

21 boats, the cheapest Caribbean entry in our catalogue, and Carriacou and Petite Martinique as domestic water. Also where the hurricane-latitude question gets its most careful answer.
5

Antigua

11 boats, all of them berthed inside a working Georgian naval dockyard that is a UNESCO World Heritage Site. Nowhere else does handover happen on an 18th-century quay.
6

The Bahamas

37 boats, and a different kind of water entirely — vast shallow banks rather than deep channels between high islands. Eyeball navigation and tides matter here in a way they do not further south.
7

Belize and Panama

16 and 12 boats on the western side. Belize has the northern hemisphere's largest barrier reef and the strictest rulebook in the region; Panama's San Blas is an autonomous indigenous territory with its own permit system.
8

Cuba

14 boats and 300 miles of almost uncruised southern cays. It also has the region's most consequential paperwork, including restrictions that apply specifically to US persons.

Suggested routes

A week out of Caribbean Islands

How a Caribbean week is shaped

7 days

Rather than one route — these thirteen countries are spread across two thousand miles — this is the pattern a week here almost always follows. The country pages carry the actual itineraries.

1

Handover, late afternoon

Briefing, provisioning and clearance paperwork. Move one short leg rather than committing to a passage on day one.
2

The first anchorage

Usually a mooring buoy rather than your own anchor — the norm across much of the region to protect coral.
3

Working to windward

Go east or upwind early in the week while the crew is fresh. The trades make the return the easy half.
4

The far point

Often a border, which means clearing out and in. Build the office hours into the day, not just the mileage.
5

A reef or park day

Most countries here have at least one managed marine area with buoys, fees collected on the water, and a reason to be there early.
6

The downwind run back

Faster than the way out. This is the day most crews actually enjoy the sailing rather than managing it.
7

Back to base

Short final leg for the Saturday handover. Clear in if you have been out of the country.

Find a boat for this route

Before you book

Local rules and paperwork in Caribbean Islands

Sailing resume, not a licence — usually: Most countries here have no certificate requirement. Operators judge recent experience on comparable boats instead. Send the resume when you enquire rather than at handover; a thin one is normally met with an offer of a skipper for the first days rather than a refusal.
The real exceptions: Some countries require government paperwork, with lead times. Belize issues a temporary Certificate of Competency through its Port Authority and wants the application at least two weeks before arrival. Antigua and Anguilla both issue cruising permits on clearing in, Panama's San Blas has a Guna Congress fee system of its own, and Cuba requires an approved itinerary for every leg. Check the country page before booking flights.
Hurricane season terms: Read the storm clauses. From June to November availability, pricing and insurance all change. Latitude reduces the statistical risk toward the southern end of the chain; it does not remove it.
Mooring buoys are the norm: Often mandatory, not optional. Across much of the region anchoring is restricted to protect coral and buoys are laid instead, with park fees collected on the water. Carry cash — rangers frequently do not take cards.
Budget for clearance: Fees at both ends of every border. Separate from the charter price, and they add up on an island-hopping week. Passports travel with you on day trips, not just on the flight.
Check the cruising-area limit: Many agreements restrict which countries you may visit. A neighbouring island being eight miles away does not mean your charter permits it. Confirm the allowed area in writing before planning a route across a border.

Checked October 2026. Rules change — confirm the detail that matters for your trip when you book.

What is here

The Caribbean Islands fleet at a glance

The fleet in Caribbean Islands is made up of 209 catamarans and 70 sailing yachts.

Most boats here are catamarans, averaging 13.9 metres.

Weekly prices start in the €1,500 – €3,000 range, where 1 boats are listed.

Boats sleep between 4 and 12 guests, with cabins up to 6.

The most common size band is 13 – 16 m, with 169 boats.

74 boats can be chartered with a skipper; 210 are available bareboat.

The fullest month on the calendar right now is Nov 2026: 96% of the fleet already has at least one booking, while 10 boats are still completely open.

Budget

Charter prices in Caribbean Islands

Weekly rate, set by the operator. No booking fee.

Space on board

Boat sizes

Sleeping 4–12 guests

10 – 13 m 104
13 – 16 m 169
16 – 20 m 6

Availability

How full is the calendar in Caribbean Islands?

Share of the Caribbean Islands fleet that already holds at least one reservation, for each of the next twelve months. Taken from the operators' own calendars and refreshed daily — a boat with one week booked can still be chartered in the others.

Months further out look emptier simply because they are further away — most charters are booked a few months ahead, not a year.

Most booked month

Nov 2026

96% of the fleet already booked

Most still open

Sep 2027

213 boats with no booking yet

Pick a month to see what is still open that week.

Quiet
Picking up
Busy
Peak

Most common models in Caribbean Islands

Counted from our live catalogue.

Leopard Catamarans Leopard 50

38 available · from €8.976

Leopard Catamarans Leopard 42

34 available · from €4.582

Leopard Catamarans Leopard 46PC

32 available · from €7.507

Leopard Catamarans Leopard 45

29 available · from €6.258

Dufour Yachts Dufour 41

17 available · from €3.431

Leopard Catamarans Leopard 46

16 available · from €7.176

Yachts in Caribbean Islands

View all

2026

Har Bar

Road Town

12.8 m 3 cabins 6 guests

From €1.179 / day €8.250 / week

2026

Moorings 403 PC Exclusive Plus

Road Town

12.19 m 3 cabins 6 guests

From €863 / day €6.042 / week

2026

Moorings 4600 - 4 Exclusive Plus

Road Town

13.9 m 4 cabins 10 guests

From €1.379 / day €9.651 / week

2025

Sunsail 424/4/4 Premium Plus

Road Town

12.8 m 4 cabins 10 guests

From €607 / day €4.251 / week

2025

Sunsail 41.3 Premium Plus

Road Town

11.95 m 3 cabins 6 guests

From €490 / day €3.431 / week

About the destination

Why charter from Caribbean Islands

Across the thirteen countries that share this water we list 538 boats, and 430 of them are catamarans. No other cruising ground in this guide is so decisively multihull — eighty per cent, against 106 monohulls and two trimarans. The reason is what a Caribbean week actually consists of: anchoring in shallow water close to a beach, swimming, and sailing short legs between islands in a warm steady breeze. Shallow draught and deck space matter more than windward performance.

Four things are true almost everywhere here, and they are what this page is for.

The trade winds. The easterlies blow year-round and firm up from December to April, which is why the season concentrates there. They are the most reliable wind in this guide: you can plan a week around a direction rather than a forecast.

The hurricane season, June to November, peaking in August and September. Most operators restrict or reprice bareboat charter in that window and insurance terms change. Latitude matters — the southern end of the chain is statistically safer and some insurers draw a named-storm line around 12°40'N — but 2024 showed that a line on a chart is not immunity.

Every island is a country. This is the practical fact that shapes itineraries more than wind does. The next island in sight usually has its own immigration, its own fees and its own office hours, and clearing in and out takes time at both ends of a leg. A few jurisdictions are the exception and cover a whole chain in one clearance, which is a genuine advantage worth seeking out.

And no licence, but a resume. Unlike Europe, most of the Caribbean has no formal skipper certificate requirement. Instead operators ask for your sailing experience in writing — boats skippered, sizes, types and waters — and want recent time on something comparable. There are real exceptions with government paperwork and lead times.

The specifics differ sharply between these thirteen countries, so the country pages carry them. The fleet averages 13.7 metres and 4 cabins with a 2022 build year, 113 of the 538 boats are crewed, and weekly rates run from about €2,090.