Island Hopping Tours & Trips in Caribbean
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10 best Island Hopping Caribbean tour packages
Compiled by
MelissaCaribbean travel expert at TourRadar
- Discover the yachting islands of the Caribbean 2025-2026 - 15 Days (including St John's)
- Caribbean Yachting Hideaways 2025-2026
- Discover the yachting islands of the Caribbean 2026 - 15 Days (from San Juan to Saint Thomas Island)
- Caribbean Yachting Discovery 2026
- Caribbean Yachting Discovery 2025-2026
- Work+Travel Barbados, Grenada and Trinidad and Tobago (3 months)
- Caribbean Yachting Hideaways 2025 - 8 Days (16 destinations)
- Discover the yachting islands of the Caribbean 2026 - 15 Days
- Caribbean Yachting Hideaways 2026
- Splendours of the Caribbean 2027
- 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
52% Off- US$3,820You save $4,170
Discover the yachting islands of the Caribbean 2026 - 15 Days (from San Juan to Saint Thomas Island)
- Embark on a luxury yacht cruise from San Juan
- Explore the pristine beaches of Culebra
- Stroll through the vibrant streets of Philipsburg
Duration 15 days Destinations Puerto Rico, Virgin Island, British, St Martin, Guadeloupe, Virgin Islands, U.S. 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 cruise in St. John's
- Explore the Pink Sandy Beach in Barbuda
- Visit Fort Napoleon in Les Saintes
Duration 8 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Virgin Islands, U.S. Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $8,390
51% Off- US$4,115You save $4,275
- Embark on a luxury yacht cruise from St. John's
- Explore the pink sands of Barbuda's beaches
- Tour Fort Napoleon in the Les Saintes archipelago
Duration 8 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 $7,990
52% Off- US$3,820You save $4,170
- Explore Barbados, the birthplace of rum
- Enjoy surf and turf activities in Barbados
- Discover Grenada's organic chocolate and spices
No departure dates availableDuration 90 days Destinations Barbados, Grenada, Trinidad and Tobago Age Range 18 to 50 year olds Operated in English Operator SOCA ISLANDS 
- Embark on a luxury yacht cruise from San Juan
- Explore the white sands of Flamenco Beach
- Tour the historic Annaberg Plantation Ruins
Duration 8 days Destinations Puerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $30,840
50% Off- US$15,327You save $15,513
- 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
51% Off- US$4,115You save $4,275
- Embark on a luxury yacht cruise from Saint Thomas
- Explore Cruz Bay's vibrant town and architecture
- Relax on Nevis's tranquil beaches and lush landscapes
Duration 7 days Destinations Virgin Islands, U.S., Antigua and Barbuda, Guadeloupe, Virgin Island, British, Puerto Rico Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $7,190
53% Off- US$3,405You save $3,785
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