Caribbean Sailing Vacations
4.5 stars on(7,695 reviews)- Choose from 34 Caribbean tours
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34 Caribbean sailing trips
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- Vibes of the Virgin Islands
- Caribbean Yachting Discovery 2025-2026
- Caribbean Yachting Discovery 2026
- Caribbean Yachting Hideaways 2025-2026
- 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 escapade 2026 - 8 Days (from Miami to San Juan)
- Discover the Grenadines & Windwards islands
- Discover the Hidden Wonders of the Caribbean
- Discover Eastern Caribbean & Grenadines 2025-2026 - 15 Days (from Bridgetown to Marigot)
The Caribbean's most exclusive ports await aboard Emerald Sakara, sailing from Saint Thomas to Gustavia. The famous Baths of Virgin Gorda, crystal waters of Norman Island for snorkeling, and pristine beaches of Anguilla highlight this luxury voyage with all-inclusive fine dining.
Duration 8 days Destinations Virgin Islands, U.S., Virgin Island, British, Anguilla, Dominican Republic, Guadeloupe Age Range up to 90 year olds Operator Emerald Cruises From $7,590
50% Off- US$3,760You save $3,830
The Emerald Azzurra glides through Caribbean waters, stopping at exclusive ports from Antigua to Puerto Rico. Barbuda's Pink Sandy Beach, Virgin Gorda's The Baths, and Norman Island's legendary pirate caves await. Luxury amenities and gourmet dining enhance this 8-day adventure.
Duration 8 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Puerto Rico Age Range up to 90 year olds Operator Emerald Cruises From $7,990
51% Off- US$3,920You save $4,070
Secluded bays and pristine beaches unfold aboard Emerald Azzurra. The route winds from St. John's past Pink Sandy Beach in Barbuda to Norman Island's pirate caves. Virgin Gorda's famous Baths and French-Caribbean culture in Deshaies complement premium beverages throughout.
Duration 8 days Destinations Antigua and Barbuda, Guadeloupe, Virgin Island, British, Virgin Islands, U.S. Age Range up to 90 year olds Operator Emerald Cruises From $8,390
51% Off- US$4,120You save $4,270
The finest harbors of the Caribbean welcome Emerald Azzurra, sailing from San Juan to Cruz Bay's vibrant waterfront. White Bay Beach on Jost Van Dyke and Philipsburg's Dutch colonial charm lead to Saint Barthélemy on this luxury sailing with 72 crew members.
Duration 8 days Destinations Puerto Rico, Virgin Island, British, Antigua and Barbuda Age Range up to 90 year olds Operator Emerald Cruises From $8,390
51% Off- US$4,120You save $4,270
Pink-sand beaches of Barbuda and Les Saintes' French-Caribbean fusion ports highlight this sophisticated Emerald Azzurra yacht journey. The route from San Juan through the Virgin Islands to Guadeloupe's Deshaies offers exclusive access to pristine bays and colonial towns.
Duration 15 days Destinations Puerto Rico, Virgin Island, British, Guadeloupe Age Range up to 90 year olds Operator Emerald Cruises From $21,580
51% Off- US$10,640You save $10,940
Exclusive ports beckon aboard Emerald Sakara from San Juan to Miami. Gordon's Beach's white sands, Grand Turk's colonial charm, and Nassau's offshore reefs await, complemented by an infinity pool and upscale dining.
Duration 8 days Destinations Puerto Rico, Bahamas, USA Age Range up to 90 year olds Operator Emerald Cruises From $7,590
50% Off- US$3,760You save $3,830
Bahamian waters sparkle aboard Emerald Sakara, showcasing Nassau's Queen's Staircase and Cable Beach. Grand Turk's historic lighthouse and San Salvador's coral reefs highlight this 8-day journey with luxurious Yacht Suites.
Duration 8 days Destinations USA, Bahamas, Puerto Rico Age Range up to 90 year olds Operator Emerald Cruises From $10,890
50% Off- US$5,410You save $5,480
Exclusive ports from Bridgetown to Marigot shine aboard luxurious Emerald Azzurra. Intimate harbors like Port St. Charles and Falmouth Harbour provide gateways to Tobago Cays' turtle-rich waters and Bequia's secluded beaches, with yacht-based activities at each stop.
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 Operator Emerald Cruises From $14,780
50% Off- US$7,350You save $7,430
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 Operator Emerald Cruises From $21,340
50% Off- US$10,650You save $10,690
What our customers ask about Caribbean Sailing Vacations
Which Caribbean sailing routes are best for exploring hidden gems and less touristy spots?
The Caribbean's quieter corners reveal themselves along select sailing routes that venture beyond the typical tourist paths. The journey from Martinique to St. Vincent winds through the Grenadines taking sailors to the peaceful Mayreau Island and the protected waters of Tobago Cays Marine Park. Those sailing from Tortola can explore the British Virgin Islands' lesser-known attractions like the water-carved caves of Norman Island and Anegada's remote reefs. Small properties like Saba Rock Resort in the BVIs provide close access to these routes while Palm Cay Yacht Club in Nassau serves as an excellent starting point for Bahamas exploration. A recent traveler described their experience: "Discovering Nunjack Cay was incredible - probably the most remote and untouched atoll in the Bahamas with amazing snorkeling spots only accessible by boat."
What types of boats are used for Caribbean sailing tours?
Caribbean waters welcome vessels ranging from intimate yachts to spacious catamarans. Notable examples include the 110-meter Emerald Azzurra and Emerald Sakara which carry up to 100 guests with a crew of 72. These ships offer accommodation options from expansive Owner's Suites with private terraces to well-appointed Deluxe Balcony Suites and comfortable Staterooms. Standard features include infinity pools observation decks and varied dining venues. Guest feedback often points to the balanced experience as noted by one sailor: "The Emerald Azzurra provided the perfect blend of luxury and intimate sailing experience."
What are the most popular sailing routes in the Caribbean?
Established Caribbean routes draw sailors to well-tested paths through crystal waters. The British Virgin Islands circuit connects Norman Island Virgin Gorda and Jost Van Dyke. Sailors departing from St. Martin navigate the Leeward Islands touching St. Barths Antigua and Barbuda. The Grenadines passage from Carriacou to Bequia includes stops at Tobago Cays and Mayreau. A seasoned traveler shares: "The route through the British Virgin Islands offered the perfect mix of secluded beaches vibrant ports and incredible snorkeling spots at The Baths in Virgin Gorda."
What activities are typically included during Caribbean sailing tours?
Days at sea blend water activities with cultural exploration. Travelers can snorkel Tobago Cays' reefs trek Virgin Gorda's trails or delve into history at Fort Napoleon in Les Saintes. Beach time splits between Barbuda's Pink Sandy Beach and Jost Van Dyke's White Bay. Port stops in Gustavia and Philipsburg introduce local markets and regional cooking. As one traveler notes: "The variety of activities was incredible - from swimming with sea turtles at The Baths to exploring the colonial architecture in St. John's Antigua."
What types of marine life can you expect to see while sailing in the Caribbean?
Caribbean waters host an array of sea life across different habitats. Tobago Cays Marine Park offers close encounters with sea turtles and coral gardens while Norman Island and The Indians in the BVIs attract manta rays and tropical fish. The clear waters around White Bay Beach teem with colorful species and Warderick Wells Cay in the Bahamas presents thriving coral ecosystems. One sailor reports: "The marine life at Horseshoe Reef in Anegada was incredible - we saw countless species of fish spotted eagle rays and even a nurse shark!"
What are the best local dishes to try when sailing Caribbean?
Each port presents distinct flavors reflecting local culinary traditions. Philipsburg Sint Maarten serves Dutch-Caribbean fusion while Gustavia Saint Barthélemy specializes in French-Caribbean cuisine at spots like Le Select. Fresh seafood dominates menus from Cruz Bay to Esperanza where waterfront restaurants showcase daily catches. Beach barbecues on Norman Island add local music to the mix. A recent guest notes: "The local cuisine was a highlight especially the fresh fish at the waterfront restaurants in Port Elizabeth Bequia."