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Sailboat charter and rental in Caribbean Islands

111 boats available in Caribbean Islands

From €2,120 per week, departing from Road Town, Marigot and Castries.

Recommended Price: low to high Price: high to low Top rated Newest
sailboat Region: Caribbean Islands Clear all
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AI advisor’s picks

Three good places to start

Best value, best balance and most comfortable among these results — our AI advisor starts from the same three.

Best value
−10% Early booking New
6
Sailing yacht

Moorings 41.3 Exclusive Plus

St. George's, Grenada

3 cabins 7 guests 12.75 m 2025
Bathing platform Air conditioning
From €437 / day €3.059 / week campaign week €4.949
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Best balance
−15% Special offer New
6
Sailing yacht

Moorings 41.3 Exclusive Plus

Road Town, British Virgin Islands

3 cabins 7 guests 12.75 m 2025
Bathing platform Air conditioning
From €575 / day €4.026 / week campaign week €3.824 + extras €1,862
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Most comfortable
−15% Special offer New
5
Sailing yacht

Moorings 44.3 Exclusive Plus

Road Town, British Virgin Islands

3 cabins 7 guests 13.91 m 2025
Bathing platform Air conditioning Electric toilets
From €599 / day €4.196 / week campaign week €4.164 + extras €1,862
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Sailing yacht

Blue Bird

Admiralty Bay, St. Vincent and the Grenadines

4 cabins 8 guests 13.6 m 2010
Bathing platform
From €600 / day €4.197 / week + extras €556
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Sailing yacht

The Pink Pearl

Admiralty Bay, St. Vincent and the Grenadines

3 cabins 6 guests 14.98 m 2007
From €725 / day €5.077 / week + extras €563
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−19% Early booking
6
Sailing yacht

Silly Shark (GND)

St. George's, Grenada

4 cabins 10 guests 13.13 m 2009
From €303 / day €2.120 / week campaign week €2.004 + extras €310
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6
Sailing yacht

LITTLE WING

Martinique, Martinique

3 cabins 6 guests 10.86 m 2023
From €540 / day €3.780 / week + extras €280
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3
Sailing yacht

CARIBBEAN DANDY

Martinique, Martinique

3 cabins 6 guests 11.8 m 2019
Electric toilets
From €703 / day €4.920 / week + extras €320
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New
6
Sailing yacht

TOSTAKY

Martinique, Martinique

4 cabins 8 guests 13.55 m 2024
From €756 / day €5.290 / week + extras €340
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6
Sailing yacht

Windward Spirit

St Vincent, St. Vincent and the Grenadines

4 cabins 8 guests 16.75 m 2003
Air conditioning
From €929 / day €6.500 / week + extras €500
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New
4
Sailing yacht

Spicy Rum

St Vincent, St. Vincent and the Grenadines

3 cabins 6 guests 10.77 m 2024
From €471 / day €3.299 / week + extras €500
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New
5
Sailing yacht

Spicy Rum

St Vincent, St. Vincent and the Grenadines

3 cabins 6 guests 10.77 m 2024
From €572 / day €4.006 / week + extras €7,170
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6
Sailing yacht

Sailing Freedom

Puerto Lindo, Portobelo, Panama

4 cabins 8 guests 19.2 m 2008
Bathing platform Air conditioning
Price on request
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−15% Special offer New
6
Sailing yacht

Moorings 42.3 Exclusive

Marigot, St. Martin (French)

3 cabins 7 guests 12.87 m 2024
From €473 / day €3.314 / week campaign week €3.229
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6
Sailing yacht

Moorings 46.3 Club

Road Town, British Virgin Islands

3 cabins 8 guests 14.6 m 2022
From €880 / day €6.157 / week + extras €1,862
View
−15% Special offer New
6
Sailing yacht

Moorings 41.3 Exclusive

Road Town, British Virgin Islands

3 cabins 7 guests 12.75 m 2024
Bathing platform Air conditioning
From €575 / day €4.026 / week campaign week €3.824 + extras €1,862
View
−15% Special offer New
6
Sailing yacht

Moorings 41.3 Exclusive Plus

Road Town, British Virgin Islands

3 cabins 7 guests 12.75 m 2025
Bathing platform Air conditioning
From €575 / day €4.026 / week campaign week €3.824 + extras €1,862
View
−15% Special offer New
6
Sailing yacht

Moorings 41.3 Exclusive

Road Town, British Virgin Islands

3 cabins 7 guests 12.75 m 2025
Bathing platform Air conditioning
From €575 / day €4.026 / week campaign week €3.824 + extras €1,862
View
−15% Special offer
6
Sailing yacht

Moorings 46.3 Exclusive

Road Town, British Virgin Islands

3 cabins 8 guests 14.6 m 2023
From €539 / day €3.771 / week campaign week €4.164 + extras €1,862
View
−15% Special offer New
5
Sailing yacht

Moorings 44.3 Exclusive

Road Town, British Virgin Islands

3 cabins 7 guests 13.91 m 2024
Bathing platform Air conditioning Electric toilets
From €599 / day €4.196 / week campaign week €3.994 + extras €1,862
View
−15% Special offer
6
Sailing yacht

Moorings 42.3 Club

Road Town, British Virgin Islands

3 cabins 7 guests 12.87 m 2022
From €527 / day €3.686 / week campaign week €3.484 + extras €1,862
View
−15% Special offer New
6
Sailing yacht

Moorings 41.3 Exclusive

Road Town, British Virgin Islands

3 cabins 7 guests 12.75 m 2025
Bathing platform Air conditioning
From €575 / day €4.026 / week campaign week €3.824 + extras €1,862
View
−15% Special offer
6
Sailing yacht

Moorings 42.3 Club

Road Town, British Virgin Islands

3 cabins 7 guests 12.87 m 2022
From €527 / day €3.686 / week campaign week €3.399 + extras €1,862
View
−10% Special offer
6
Sailing yacht

Moorings 46.3 Club

Road Town, British Virgin Islands

3 cabins 8 guests 14.6 m 2022
From €859 / day €6.010 / week campaign week €5.395 + extras €1,862
View
−15% Special offer New
5
Sailing yacht

Moorings 42.3 Exclusive

Road Town, British Virgin Islands

3 cabins 8 guests 12.43 m 2024
From €728 / day €5.094 / week campaign week €3.569 + extras €1,862
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−15% Special offer
6
Sailing yacht

Moorings 52.4 Club

Road Town, British Virgin Islands

4 cabins 10 guests 15.94 m 2022
From €710 / day €4.970 / week campaign week €7.008 + extras €1,862
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−15% Special offer New
5
Sailing yacht

Moorings 46.3 Exclusive

Road Town, British Virgin Islands

3 cabins 8 guests 14.6 m 2024
From €846 / day €5.923 / week campaign week €3.399 + extras €1,862
View
Blue Bird
Sailing yacht

Blue Bird

Admiralty Bay, St. Vincent and the Grenadines

13.6 m (44.6 ft) 4 cab 8 guests 2010
Bathing platform
From €600 / day €4.197 / week
+ extras €556 Deposit €1,833
View
The Pink Pearl
Sailing yacht

The Pink Pearl

Admiralty Bay, St. Vincent and the Grenadines

14.98 m (49.1 ft) 3 cab 6 guests 2007
From €725 / day €5.077 / week
+ extras €563 Deposit €2,750
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LITTLE WING
Sailing yacht

LITTLE WING

Martinique, Martinique

10.86 m (35.6 ft) 3 cab 6 guests 2023
From €540 / day €3.780 / week
+ extras €280 Deposit €4,000
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CARIBBEAN DANDY
Sailing yacht

CARIBBEAN DANDY

Martinique, Martinique

11.8 m (38.7 ft) 3 cab 6 guests 2019
Electric toilets
From €703 / day €4.920 / week
+ extras €320 Deposit €5,000
View
TOSTAKY
New
Sailing yacht

TOSTAKY

Martinique, Martinique

13.55 m (44.5 ft) 4 cab 8 guests 2024
From €756 / day €5.290 / week
+ extras €340 Deposit €6,000
View
Windward Spirit
Sailing yacht

Windward Spirit

St Vincent, St. Vincent and the Grenadines

16.75 m (55.0 ft) 4 cab 8 guests 2003
Air conditioning
From €929 / day €6.500 / week
+ extras €500 Deposit €5,000
View
Spicy Rum
New
Sailing yacht

Spicy Rum

St Vincent, St. Vincent and the Grenadines

10.77 m (35.3 ft) 3 cab 6 guests 2024
From €471 / day €3.299 / week
+ extras €500 Deposit €5,000
View
Spicy Rum
New
Sailing yacht

Spicy Rum

St Vincent, St. Vincent and the Grenadines

10.77 m (35.3 ft) 3 cab 6 guests 2024
From €572 / day €4.006 / week
+ extras €7,170 Deposit €5,237
View
Sailing Freedom
Sailing yacht

Sailing Freedom

Puerto Lindo, Portobelo, Panama

19.2 m (63.0 ft) 4 cab 8 guests 2008
Bathing platform Air conditioning
Price on request
Deposit €2,000
View
Moorings 46.3 Club
Sailing yacht

Moorings 46.3 Club

Road Town, British Virgin Islands

14.6 m (47.9 ft) 3 cab 8 guests 2022
From €880 / day €6.157 / week
+ extras €1,862 Deposit €5,865
View
Moorings 44.3 Exclusive
−15% Special offer New
Sailing yacht

Moorings 44.3 Exclusive

Road Town, British Virgin Islands

13.91 m (45.6 ft) 3 cab 7 guests 2024
Bathing platform Air conditioning Electric toilets
From €599 / day €4.196 / week campaign week €3.994
+ extras €1,862 Deposit €5,865
View

About the fleet in Caribbean Islands

The fleet in Caribbean Islands is made up of 111 sailing yachts.

Most boats here are sailing yachts, averaging 13.4 metres.

Weekly prices start in the €1,500 – €3,000 range, where 5 boats are listed.

Boats sleep between 2 and 10 guests, with cabins up to 5.

The most common size band is 13 – 16 m, with 57 boats.

5 boats can be chartered with a skipper; 106 are available bareboat.

The fullest month on the calendar right now is Dec 2026: 91% of the fleet already has at least one booking, while 10 boats are still completely open.

Fleet breakdown

Sailing yachts
111 boats
avg 13.4 m · from €2,120

Weekly price ranges

€1,500 – €3,000
5 boats
€3,000 – €6,000
97 boats
€6,000 – €12,000
7 boats

Boat sizes

10 – 13 m
49 boats
13 – 16 m
57 boats
16 – 20 m
2 boats

Most common models here

  • Dufour Yachts Dufour 41 19 boats · from €3,059
  • Dufour Yachts Dufour 44 18 boats · from €3,059
  • Beneteau Oceanis 46.1 14 boats · from €3,144
  • Beneteau Oceanis 40.1 13 boats · from €2,609
  • Beneteau Oceanis 461 6 boats · from €3,345
  • Jeanneau Sun Odyssey 440 4 boats · from €2,634
  • Moorings 42.3 4 boats · from €3,685
  • Jeanneau Sun Odyssey 410 3 boats · from €2,750

Availability by month

Nov
88%
13 free
Dec
91%
10 free
Jan
88%
13 free
Feb
75%
28 free
Mar
69%
34 free
Apr
61%
43 free
May
42%
64 free
Jun
32%
76 free
Jul
30%
78 free
Aug
31%
77 free
Sep
27%
81 free
Oct
24%
84 free

Share of the fleet that already holds at least one booking that month.

Frequently asked questions

How many boats are available in Caribbean Islands?

111 boats are listed in Caribbean Islands: 111 sailing yachts.

How much does it cost to charter a boat in Caribbean Islands?

Weekly rates start in the €1,500 – €3,000 range. Most boats fall between €1,500 – €3,000 (5), €3,000 – €6,000 (97) and €6,000 – €12,000 (7).

How many people can these boats accommodate?

Boats in Caribbean Islands sleep between 1 and 10 guests, with up to 5 cabins.

When is the best time to book for Caribbean Islands?

As things stand, Dec 2026 is the month with most of the fleet already committed: 91% of boats hold at least one booking and 10 are still completely open. Months further out look emptier mainly because they are further away, so the earlier you look at a given month, the wider the choice.

Do I need a licence to charter in Caribbean Islands?

106 boats can be chartered bareboat, which requires a valid licence. 5 can be booked with a professional skipper, so no licence is needed.

Other boat types in Caribbean Islands

Catamaran 459 Trimaran 2 Motoryacht 1

Sailboat charter in other destinations

Road Town 70