Caribbean Sailing Vacations
Ah, the Caribbean! Explore historic San Juan's forts, that have defended Puerto Rico for centuries. White Bay Beach on Jost Van Dyke has genuinely white sand, while natural pools form in coastal rocks. Caribbean sailing means island rhythms slowing everything properly. Each island maintains distinct accent, food, music, while turquoise water connects everything. The Caribbean is waiting. Come explore these tropical waters.
- Choose from 39 Caribbean tours
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39 Caribbean sailing trips with 5 reviews
Compiled by

MelissaCaribbean travel expert at TourRadar
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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 Ages 12+ Operator Emerald Cruises From $5,545
23% Off- US$4,278You save $1,267
Duration 10 days Destinations Puerto Rico, Virgin Islands, U.S., Turks and Caicos Islands, Bahamas, USA Age Range Ages 12+ Operator Emerald Cruises From $9,295
14% Off- US$7,972You save $1,323
Duration 8 days Destinations Puerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda Age Range Ages 12+ Operator Emerald Cruises From $6,845
16% Off- US$5,736You save $1,109
Sail through eight Caribbean island-nations aboard luxury yacht Emerald Kaia, stopping at Mosquito Bay on Vieques Island where bioluminescent waters glow at night and The Baths on Virgin Gorda Island where huge granite boulders create natural pools. Visit Gustavia's French-Creole streets on Saint Barthélemy and walk around old Fort Napoleon on Îles des Saintes.
Duration 15 days Destinations Puerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis Age Range Ages 12+ Operator Emerald Cruises From
16% Off- US$13,590
Duration 8 days Destinations St Martin, Anguilla, Virgin Island, British, Dominican Republic Age Range Ages 12+ Operator Emerald Cruises From $6,195
22% Off- US$4,840You save $1,355
Duration 6 days Destinations Puerto Rico, Virgin Islands, U.S., Virgin Island, British Age Range Ages 12+ Operator Emerald Cruises From $5,095
19% Off- US$4,138You save $957
Set sail on luxury yacht Emerald Kaia through British and U.S. Virgin Islands for 8 days. Check out Norman Island's hidden coves and snorkeling spots, then head to White Bay Beach on Jost van Dyke and historic Charlotte Amalie on St. Thomas. Try French-Creole food in Gustavia, Saint Barthélemy, and see Cruz Bay's Caribbean architecture on St. John.
Duration 8 days Destinations Puerto Rico, Virgin Islands, U.S., Virgin Island, British Age Range Ages 12+ Operator Emerald Cruises From $6,795
16% Off- US$5,686You save $1,109
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."
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