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Caribbean Sailing Vacations
Caribbean Sailing Vacations

Caribbean Sailing Vacations

4.6 stars on(9,296 reviews)
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
  • Choose from 48 Caribbean tours
  • 46 verified reviews from TourRadar travelers
  • 24/7 customer support
  1. Island Paradises of the BahamasMap of Island Paradises of the Bahamas
    Sailing
    Duration 8 days
    DestinationsMarsh Harbour, Great Guana Cay, Green Turtle Cay, Elbow Cay, Abaco
    Age Range Ages 6+
    OperatorDERTOUR

    From

    NZ$4,070
    View tour
  2. Discover Island Rhythms & Coastal DreamsMap of Discover Island Rhythms & Coastal Dreams
    Sailing
    Duration 15 days
    DestinationsPuerto Rico, Virgin Island, British, Bahamas, USA
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $45,316

    50% Off
    NZ$22,640
    You save $22,676
    View tour
  3. 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 $28,746

    50% Off
    NZ$14,373
    You save $14,373
    View tour
  4. Colours of the Caribbean: Antigua to San JuanMap of Colours of the Caribbean: Antigua to San Juan
    Sailing
    Duration 10 days
    DestinationsAntigua and Barbuda, Guadeloupe, Dominica, Virgin Island, British, Puerto Rico
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $25,570

    50% Off
    NZ$12,750
    You save $12,820
    View tour
  5. 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 $17,629

    50% Off
    NZ$8,753
    You save $8,876
    View tour
  6. Caribbean Yachting Hideaways 2027-2028Map of Caribbean Yachting Hideaways 2027-2028
    Sailing
    Duration 8 days
    DestinationsPuerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $21,158

    50% Off
    NZ$10,535
    You save $10,623
    View tour
  7. 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 $27,334

    50% Off
    NZ$13,667
    You save $13,667
    View tour
  8. West Indies Island Hopping 2027 - 8 Days (7 destinations)Map of West Indies Island Hopping 2027 - 8 Days (7 destinations)
    Sailing
    Duration 8 days
    DestinationsPuerto Rico, Virgin Island, British, Virgin Islands, U.S., Guadeloupe
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $22,923

    50% Off
    NZ$11,461
    You save $11,461
    View tour
  9. Tropical Charms of the CaribbeanMap of Tropical Charms of the Caribbean
    Sailing
    Duration 10 days
    DestinationsVirgin Island, British, Guadeloupe, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $23,805

    50% Off
    NZ$11,858
    You save $11,947
    View tour
  10. Caribbean escapade 2026 - 8 Days (from Miami to San Juan)Map of Caribbean escapade 2026 - 8 Days (from Miami to San Juan)
    Sailing

    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
    DestinationsUSA, Bahamas, Puerto Rico
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $17,629

    50% Off
    NZ$8,753
    You save $8,876
    View tour
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2025

Jan
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Apr
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2026

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2027

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