Caribbean Sailing Vacations
4.5 stars on(7,218 reviews)- Choose from 35 Caribbean tours
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35 Caribbean sailing trips
Compiled by
MelissaCaribbean travel expert at TourRadar
- Discover the Yachting Islands of the Caribbean 2025 - 15 Days (22 destinations)
- Discover the Hidden Wonders of the Caribbean
- Discover the Grenadines & Windwards islands
- Discover Eastern Caribbean & Grenadines 2025-2026 - 15 Days (from Bridgetown to Marigot)
- Discover the yachting islands of the Caribbean 2026 - 15 Days
- Caribbean Yachting Hideaways 2026
- Discover Eastern Caribbean & Grenadines 2025-2026 - 15 Days (from Marigot to Bridgetown)
- Discover the hidden treasures of the Caribbean 2025-2026 - 22 Days (from Bridgetown to Marigot)
- Discover the yachting islands of the Caribbean 2025-2026 - 15 Days (including St John's)
- Caribbean Yachting Hideaways 2025-2026
- Embark on a luxury yacht cruise in the Caribbean
- Explore Barbuda's pink-sand beaches and bird sanctuary
- Discover Les Saintes' French-Caribbean culture fusion
Duration 15 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Puerto Rico, St Martin Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $61,680
44% Off- US$34,323You save $27,357
- Embark on a luxury yacht in Bridgetown
- Snorkel in the clear waters of Tobago Cays
- Explore historic Nelson’s Dockyard in Antigua
Duration 14 days Destinations Barbados, Saint Vincent and the Grenadines, Saint Lucia, Guadeloupe, Antigua and Barbuda, St Martin Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $14,780
58% Off- US$6,250You save $8,530
- Embark on a luxury yacht in Bridgetown
- Snorkel in the clear waters of Tobago Cays
- Explore the historic Nelson’s Dockyard
Duration 15 days Destinations Barbados, Saint Vincent and the Grenadines, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Anguilla, St Martin Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $15,180
58% Off- US$6,440You save $8,740
- Embark on a luxury yacht in St. John's
- Explore the pink sands of Barbuda
- Visit Fort Napoleon in Les Saintes
Duration 15 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Virgin Islands, U.S., Puerto Rico Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $16,780
28% Off- US$12,110You save $4,670
- Embark on a luxury yacht in St. Thomas
- Swim and play with marina toys in Culebra
- Explore the shops of Cruz Bay, St. John
Duration 8 days Destinations Virgin Islands, U.S., Puerto Rico, Virgin Island, British, Antigua and Barbuda Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $8,390
63% Off- US$3,145You save $5,245
- Explore Marigot and board a luxury yacht
- Snorkel in Anguilla's clear blue waters
- Shop in Gustavia's historic downtown
Duration 15 days Destinations St Martin, Anguilla, Guadeloupe, Saint Kitts and Nevis, Antigua and Barbuda, Saint Lucia, Barbados, Saint Vincent and the Grenadines Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $21,340
50% Off- US$10,650You save $10,690
- Embark on a luxury yacht cruise from St. John's
- Explore the pink sands of Barbuda's beaches
- Tour Fort Napoleon in Les Saintes
Duration 15 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Puerto Rico Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $15,980
28% Off- US$11,510You save $4,470
- Embark on a luxury yacht cruise from San Juan
- Explore Culebra's white-sand beaches and reefs
- Stroll through Cruz Bay's bustling streets
Duration 8 days Destinations Puerto Rico, Virgin Island, British, Antigua and Barbuda Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $7,990
63% Off- US$2,945You save $5,045
