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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

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

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9,872 reviews on
  • Choose from 48 Caribbean tours
  • 5 verified reviews from TourRadar travelers
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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. Discover the yachting islands of the CaribbeanMap of Discover the yachting islands of the Caribbean
    Sailing

    Luxury awaits aboard Emerald Azzurra from San Juan to Saint Thomas. The yacht drops anchor at exclusive ports like Gustavia in St. Barth and White Bay Beach on Jost Van Dyke, with water sports available from the marina platform in multiple locations.

    Duration 15 days
    DestinationsPuerto Rico, Virgin Island, British, St Martin, Guadeloupe, Virgin Islands, U.S.
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $23,280

    34% Off
    US$15,360
    You save $7,920
    View tour
  2. 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 $16,290

    56% Off
    US$7,145
    You save $9,145
    View tour
  3. 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 $14,490

    57% Off
    US$6,225
    You save $8,265
    View tour
  4. 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 $9,990

    60% Off
    US$3,960
    You save $6,030
    View tour
  5. Caribbean Yachting Hideaways 2026 - 8 Days (from San Juan to St John's)Map of Caribbean Yachting Hideaways 2026 - 8 Days (from San Juan to St John's)
    Sailing
    Duration 8 days
    DestinationsPuerto Rico, Virgin Island, British, St Martin, Guadeloupe, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $12,040

    59% Off
    US$4,945
    You save $7,095
    View tour
  6. 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 $15,490

    56% Off
    US$6,745
    You save $8,745
    View tour
  7. 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 $12,990

    58% Off
    US$5,495
    You save $7,495
    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
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec