Sailing Tours & Trips in Caribbean
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.
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10 best Sailing Caribbean tour packages
Compiled by

MelissaCaribbean travel expert at TourRadar
- Discover the Pearls of the Caribbean 2026
- Discover Eastern Caribbean & Grenadines 2026
- Discover the Best of the Caribbean
- Classic Caribbean 2026
- Splendours of the Caribbean 2027
- Discover the Hidden Wonders of the Caribbean
- Discover the Grenadines & Windwards islands
- Quintessential Caribbean 2027 - 8 Days (from Saint Thomas Island to San Juan)
- Eastern Caribbean with St. Barths 2026-2027
- Discover the Pearls of the Caribbean 2027 - 15 Days
Duration 15 days Destinations Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Anguilla, St Martin, Virgin Island, British Age Range Ages 12+ Operator Emerald Cruises From
- US$15,540
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 Ages 12+ Operator Emerald Cruises From
- US$15,440
The Emerald Azzurra glides through Caribbean harbors, from Marigot's French charm to Bridgetown's colonial heritage. Visit UNESCO-listed Nelson's Dockyard, swim with turtles in Tobago Cays, and savor Îles des Saintes' French-Caribbean fusion. The 16-night luxury sailing accommodates 100 guests.
Duration 17 days Destinations St Martin, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent and the Grenadines, Barbados Age Range Ages 12+ Operator Emerald Cruises From
- US$13,240
Duration 10 days Destinations St Martin, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent and the Grenadines, Barbados Age Range Ages 12+ Operator Emerald Cruises From $7,445
21% Off- US$5,907You save $1,538
Duration 7 days Destinations Virgin Islands, U.S., Saint Kitts and Nevis, Antigua and Barbuda, Virgin Island, British, Puerto Rico Age Range Ages 12+ Operator Emerald Cruises From $5,295
33% Off- US$3,566You save $1,729
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, Saint Kitts and Nevis, St Martin Age Range Ages 12+ Operator Emerald Cruises From
33% Off- US$15,765
What our customers ask about Sailing Tours & Trips in Caribbean
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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