Sailing Tours from San Juan
4.5 stars on(7,181 reviews)- Choose from 6 San Juan tours
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6 best Sailing tour packages from San Juan
Compiled by
MelissaSan Juan travel expert at TourRadar
- Puerto Rico Experience 4Days/3Nights
- Discover the yachting islands of the Caribbean 2025-2026 - 15 Days (including St. John)
- Caribbean escapade 2026 - 8 Days (from San Juan to Miami)
- Caribbean Yachting Hideaways 2025 - 8 Days (7 destinations)
- Discover the yachting islands of the Caribbean 2026 - 15 Days (from San Juan to Saint Thomas Island)
- Caribbean Yachting Hideaways 2025-2026
- Explore the vibrant Isla Verde beach
- Zip through Toro Verde's adventure park
- Tour the historic Old San Juan
Duration 4 days Destinations San Juan Age Range 1 to 99 year olds Operated in English, Italian, French, Spanish Operator Across Caribbean Excursions From $1,626
10% Off- US$1,463You save $162
- Embark on a luxury yacht cruise from San Juan
- Explore the vibrant marine life of Culebra
- Relax on the stunning beaches of Jost Van Dyke
Duration 15 days Destinations Puerto Rico, Virgin Island, British, Guadeloupe Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $16,380
51% Off- US$8,040You save $8,340
- Start your cruise in historic San Juan
- Unwind at sea with luxury yacht amenities
- Explore Grand Turk's beaches and history
Duration 8 days Destinations Puerto Rico, Bahamas, USA Age Range up to 90 year olds Operated in English Operator Emerald Cruises From $7,590
65% Off- US$2,660You save $4,930
- 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
56% Off- US$13,457You save $17,383
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 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
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