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Sailing Holidays Caribbean & Yacht Vacation

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Caribbean

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What do guests say about yacht holidays in Caribbean?

Read verified reviews from travelers who booked yacht holidays in Caribbean, covering service quality, onboard experience and overall trip satisfaction.

AI summary of verified sailing holiday reviews
The destinations visited are often a highlight, along with skippers’ guidance on sailing routes and places to snorkel. Professional, friendly service from charter companies is another recurring highlight in guests’ experiences.
How is this summary generated?This summary is generated by AI analyzing verified guest reviews from bookings completed through viravira.co. The AI identifies and summarizes recurring experiences and notable themes across the reviews; it does not create new guest reviews.

Verified

Gerold P.19 Jan 2025

Captain Rudy was very professional in his performance, he used the sails, he helped us know good routes and good places to sail and snorkel, it was a fantastic trip that I would recommend.

SSabine

Listing owner: SabineRoad Town / British Virgin Islands

274 yachts are available for overnight charter in Caribbean.

DISCOUNT
INSTANT BOOKING
St. George's Sailboat 4 cabin 10 berths 10 guests 13.13 m Listing Number: #1389
  • Beneteau, Oceanis 43
  • 2009
  • St. George's 
4.38(2)
Without skipper
  • 10 berths
  • 4 cabin
  • 13.1 m
  • 2 WC

Lowest339 € / night

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INSTANT BOOKING
St. George's Catamaran 4 cabin 10 berths 12 guests 13.99 m Listing Number: #22771
  • Lagoon, 46
  • 2023
  • St. George's 
4.38(79)
Without skipper
  • 10 berths
  • 4 cabin
  • 14 m
  • 4 WC

Lowest3,098 € / night

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INSTANT BOOKING
St. George's Catamaran 5 cabin 10 berths 10 guests 16.9 m Listing Number: #21147
  • Lagoon, 55
  • 2024
  • St. George's 
4.38(79)
Skipper mandatory
  • 10 berths
  • 5 cabin
  • 16.9 m
  • 5 WC

Lowest7,789 € / night

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INSTANT BOOKING
Martinique Catamaran 5 cabin 10 berths 10 guests 16.9 m Listing Number: #21146
  • Lagoon, 55
  • 2024
  • Martinique 
4.38(79)
Skipper mandatory
  • 10 berths
  • 5 cabin
  • 16.9 m
  • 5 WC

Lowest7,789 € / night

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INSTANT BOOKING
Antigua Catamaran 5 cabin 10 berths 10 guests 16.9 m Listing Number: #21145
  • Lagoon, 55
  • 2024
  • Antigua 
4.38(79)
Skipper mandatory
  • 10 berths
  • 5 cabin
  • 16.9 m
  • 5 WC

Lowest7,789 € / night

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INSTANT BOOKING
Pointe a Pitre Catamaran 5 cabin 10 berths 10 guests 16.9 m Listing Number: #21144
  • Lagoon, 55
  • 2024
  • Pointe a Pitre 
4.38(79)
Skipper mandatory
  • 10 berths
  • 5 cabin
  • 16.9 m
  • 5 WC

Lowest7,789 € / night

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INSTANT BOOKING
St. George's Catamaran 4 cabin 10 berths 12 guests 13.99 m Listing Number: #16355
  • Lagoon, 46
  • 2020
  • St. George's 
4.38(79)
Without skipper
  • 10 berths
  • 4 cabin
  • 14 m
  • 4 WC

Lowest3,435 € / night

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INSTANT BOOKING
St. George's Catamaran 4 cabin 10 berths 10 guests 12.8 m Listing Number: #16060
  • Lagoon, 42
  • 2020
  • St. George's 
4.38(79)
Without skipper
  • 10 berths
  • 4 cabin
  • 12.8 m
  • 4 WC

Lowest2,975 € / night

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INSTANT BOOKING
Pointe a Pitre Catamaran 4 cabin 10 berths 10 guests 12.8 m Listing Number: #28375
  • Lagoon, 42
  • 2024
  • Pointe a Pitre 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 12.8 m
  • 4 WC

Lowest3,208 € / night

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St Vincent Catamaran 4 cabin 10 berths 10 guests 12.8 m Listing Number: #28373
  • Lagoon, 42
  • 2020
  • St Vincent 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 12.8 m
  • 4 WC

Lowest2,975 € / night

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INSTANT BOOKING
Castries Catamaran 4 cabin 10 berths 10 guests 12.8 m Listing Number: #28370
  • Lagoon, 42
  • 2020
  • Castries 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 12.8 m
  • 4 WC

Lowest2,975 € / night

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INSTANT BOOKING
Martinique Catamaran 4 cabin 10 berths 10 guests 12.8 m Listing Number: #24025
  • Lagoon, 42
  • 2020
  • Martinique 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 12.8 m
  • 4 WC

Lowest2,975 € / night

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INSTANT BOOKING
Martinique Catamaran 4 cabin 10 berths 12 guests 13.99 m Listing Number: #23987
  • Lagoon, 46
  • 2020
  • Martinique 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 14 m
  • 4 WC

Lowest3,435 € / night

DISCOUNT
INSTANT BOOKING
Martinique Catamaran 4 cabin 10 berths 12 guests 13.99 m Listing Number: #23986
  • Lagoon, 46
  • 2023
  • Martinique 
New
Without skipper
  • 10 berths
  • 4 cabin
  • 14 m
  • 4 WC

Lowest3,098 € / night

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INSTANT BOOKING
Cienfuegos Catamaran 5 cabin 9 berths 9 guests 12.37 m Listing Number: #6532
  • Lagoon, 410
  • 2004
  • Cienfuegos 
4.60(6)
Skipper optional
  • 9 berths
  • 5 cabin
  • 12.4 m
  • 4 WC

Lowest371 € / night

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Cienfuegos Catamaran 4 cabin 8 berths 8 guests 11.55 m Listing Number: #6527
  • Lagoon, 380
  • 2005
  • Cienfuegos 
4.60(6)
Skipper optional
  • 8 berths
  • 4 cabin
  • 11.6 m
  • 2 WC

Lowest314 € / night

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INSTANT BOOKING
Cienfuegos Catamaran 6 cabin 8 berths 8 guests 11.9 m Listing Number: #6512
  • Lavezzi, 40
  • 2005
  • Cienfuegos 
4.60(6)
Skipper optional
  • 8 berths
  • 6 cabin
  • 11.9 m
  • 2 WC

Lowest286 € / night

DISCOUNT
INSTANT BOOKING
Pointe a Pitre Catamaran 6 cabin 8 berths 10 guests 13.99 m Listing Number: #25543
  • Lagoon, 46
  • 2023
  • Pointe a Pitre 
New
Skipper optional
  • 8 berths
  • 6 cabin
  • 14 m
  • 4 WC

Lowest2,922 € / night

DISCOUNT
INSTANT BOOKING
Pointe a Pitre Catamaran 6 cabin 10 berths 10 guests 11.55 m Listing Number: #25542
  • Lagoon, 380
  • 2016
  • Pointe a Pitre 
New
Skipper optional
  • 10 berths
  • 6 cabin
  • 11.6 m
  • 2 WC

Lowest1,753 € / night

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INSTANT BOOKING
Road Town Catamaran 4 cabin 10 berths 11 guests 13.72 m Listing Number: #19737
  • Leopard, 45
  • 2023
  • Road Town 
5.00(1)
Skipper optional
Super Boat Owner
  • 10 berths
  • 4 cabin
  • 13.7 m
  • 4 WC

Lowest693 € / night

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INSTANT BOOKING
Pointe a Pitre Catamaran 6 cabin 10 berths 10 guests 13.85 m Listing Number: #27133
  • Lagoon, 43
  • 2025
  • Pointe a Pitre 
New
Skipper optional
  • 10 berths
  • 6 cabin
  • 13.8 m
  • 4 WC

Lowest2,922 € / night

Yacht charter options for sailing holidays in Caribbean

Compare bareboat, skippered and crewed charters for your yacht vacation, and choose the option that suits your experience and travel style.

Skippered yacht charter in Caribbean

Skippered Charter

A professional skipper handles the sailing on a skippered yacht charter, while you relax and enjoy. No sailing experience required.

Bareboat yacht charter in Caribbean

Bareboat Charter

Captain the yacht yourself for total freedom on a bareboat yacht charter. A valid sailing license is required.

Crewed yacht charter in Caribbean

Crewed Charter

Enjoy ultimate comfort with a private captain and crew on a crewed yacht charter.

Best value yachts for sailing holiday trips in Caribbean

Find yachts in Caribbean offering the best balance of price, amenities and guest ratings for a multi-day yacht holiday.
How is this calculated?
Yachts ranked by price-to-value ratio, considering guest ratings, amenities and charter prices.

Why choose viravira.co for sailing holidays in Caribbean?

Plan your yacht vacation with a wide choice of yachts, AI-assisted messaging and verified guest reviews.

Yacht types for a sailing holiday in Caribbean

Explore yacht types for sailing holidays in Caribbean, including catamaran, sailboat, and motor yacht.

208 catamarans
Catamaran for charter in Caribbean

Catamaran

Ideal for those seeking stability and spacious comfort

64 sailboats
Sailboat for charter in Caribbean

Sailboat

Wind-powered, natural and more active sailing experience

2 motor yachts
Motor yacht for charter in Caribbean

Motor Yacht

A perfect combination of speed and luxury at sea

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Sailing holiday prices in Caribbean

Average nightly rental prices for a yacht vacation in Caribbean start from €286.
YACHT TYPE
AVERAGE PRICE
BOAT COUNT
Sailboat
LOWEST
AVERAGE PRICE
€765

/ night

LOWEST
BOAT COUNT
64

sailboats available

€339

€2,007

Catamaran
AVERAGE PRICE
€1,380

/ night

BOAT COUNT
199

catamarans available

€286

€20,900

Motor yacht
HIGHEST
AVERAGE PRICE
€5,960

/ night

HIGHEST
BOAT COUNT
2

motor yachts available

€4,001

€7,918

Prices vary by yacht type, size, season and charter type. Additional costs such as fuel, skipper fees and security deposit may apply.

Last updated at October 18, 2026

Frequently asked questions about sailing holidays in Caribbean

Learn what to know before planning a sailing holiday in Caribbean, including destinations, costs, season, trip length, inclusions and sailing requirements.

How much does a sailing holiday in Caribbean cost?

Sailing holiday prices in Caribbean start from €286 per night. The average charter price is €1,123 per night.
Starting prices by yacht type:
- Sailboat: from €339 per night / €2,373 per week.
- Motor Yacht: from €4,001 per night / €28,007 per week.
- Catamaran: from €286 per night / €2,002 per week.
Prices vary by yacht size, travel dates, departure location and trip length.

What are the most popular destinations for sailing holidays in Caribbean?

is the most popular destination for sailing holidays in Caribbean. Other popular destinations include .

When is the best time for a sailing holiday in Caribbean?

The seasonal guide for sailing holidays in Caribbean is:
- Recommended months — sweet spot: .
- High season: .
- Shoulder season: .
- Low season: .
During the sweet-spot months, air temperatures average °C and sea temperatures average °C, with sunny days per month and winds averaging knots.

How long is a yacht holiday in Caribbean?

The average yacht holiday in Caribbean lasts 6 nights. Minimum stays vary by yacht: 1-7 nights.

What is included in a yacht holiday in Caribbean?

Skipper services for a yacht holiday in Caribbean cost an average of €198 per day. Depending on the yacht, this fee may be included in the charter price or charged separately. Fuel, meals, marina fees, cleaning and transfers may also carry additional charges. Included services, the exact skipper fee and payment terms are shown on each yacht’s detail page.

Can I book a bareboat, skippered or crewed sailing holiday in Caribbean?

Sailing holiday options in Caribbean include:
- Bareboat: 260 yachts available without a skipper
- Skippered: 231 yachts available with a professional skipper
- Crewed: 4 yachts available with a captain and crew
Bareboat charters may require a valid boating licence and relevant experience. Confirm the requirements with the boat owner before booking. For skippered or crewed yacht holidays, guests generally do not need a boating licence or sailing experience.

All sailing holidays locations in Caribbean

British Virgin Islands

150 yachts

Martinique

31 yachts

Saint Lucia

16 yachts

Guadeloupe

14 yachts

Bahamas

13 yachts

Grenada

13 yachts

Belize

11 yachts

Saint Vincent and Grenadines

10 yachts

Cuba

10 yachts

Antigua and Barbuda

4 yachts

Puerto Rico

2 yachts

Catamaran

208 yachts

Sailboat

64 yachts

Motor Yacht

2 yachts

Luxury

2 yachts

Bareboat

260 yachts

Skippered

231 yachts

Crewed

4 yachts