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Caribbean Sailing Vacations
Caribbean Sailing Vacations

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.

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2026

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1 Adult2 Adults, 1 Child2 Children

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AdultsAges 18 or above

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ChildrenUnder 18

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9,958 reviews on
  • Choose from 40 Caribbean tours
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  • J

    Jessie traveled in April

    5.0
    I loved this tour. It’s not a luxury cruise, you live aboard the boat and cook together. It’s managed by a German company, being non-German speaking I had no issues, the skipper and other crew members could speak English well. This is the best way to see the remote islands of St Lucia/St Vincent and learn the basics of sailing.
    Sailing through the marvellous Caribbean
  1. Caribbean Enchantment: roundtrip AntiguaMap of Caribbean Enchantment: roundtrip Antigua
    Sailing
    Duration 11 days
    DestinationsAntigua and Barbuda, Guadeloupe, Saint Lucia, Barbados, Saint Vincent and the Grenadines
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $10,045

    9% Off
    US$9,131
    You save $914
    View tour
  2. Vibes of the Virgin IslandsMap of Vibes of the Virgin Islands
    Sailing

    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
    DestinationsVirgin Islands, U.S., Virgin Island, British, Anguilla, Dominican Republic, Guadeloupe
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $5,545

    14% Off
    US$4,778
    You save $767
    View tour
  3. Paradise beaches from the U.S. Virgin Islands to The BahamasMap of Paradise beaches from the U.S. Virgin Islands to The Bahamas
    Sailing
    Duration 10 days
    DestinationsPuerto Rico, Virgin Island, British, Turks and Caicos Islands, Bahamas, USA
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $9,295

    9% Off
    US$8,472
    You save $823
    View tour
  4. Caribbean Yachting HideawaysMap of Caribbean Yachting Hideaways
    Sailing
    Duration 8 days
    DestinationsPuerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $6,845

    9% Off
    US$6,236
    You save $609
    View tour
  5. Discover the Yachting Islands of the Caribbean 2027-2028Map of Discover the Yachting Islands of the Caribbean 2027-2028
    Sailing

    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
    DestinationsPuerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis
    Age Range Ages 12+
    OperatorEmerald Cruises

    From

    9% Off
    US$13,590
    View tour
  6. West Indies Island Hopping 2027 - 8 Days (7 destinations)Map of West Indies Island Hopping 2027 - 8 Days (7 destinations)
    Sailing

    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
    DestinationsPuerto Rico, Virgin Island, British, Virgin Islands, U.S., Guadeloupe
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $6,795

    9% Off
    US$6,186
    You save $609
    View tour
  7. Tropical Charms of the CaribbeanMap of Tropical Charms of the Caribbean
    Sailing

    Sail aboard 110-meter Emerald Sakara with max 100 guests and 72 crew, checking out hidden Caribbean coves and beautiful coastlines. The yacht's Aqua Pool, spacious decks, and Owner's Suites provide luxury while anchoring at Norman Island's secluded bays, Virgin Gorda's towering rock formations, and Îles des Saintes' beaches.

    Duration 10 days
    DestinationsVirgin Island, British, Guadeloupe, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $8,095

    9% Off
    US$7,351
    You save $744
    View tour
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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2027

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Feb
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Nov
Dec

2028

Jan
Feb
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Apr
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