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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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  • 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. 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

    58% Off
    US$6,105
    You save $8,385
    View tour
  2. 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 $11,990

    59% Off
    US$4,970
    You save $7,020
    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 $15,490

    50% Off
    US$7,745
    You save $7,745
    View tour
  4. Discover the Yachting Islands of the Caribbean 2027-2028 - 15 DaysMap of Discover the Yachting Islands of the Caribbean 2027-2028 - 15 Days
    Sailing
    Duration 15 days
    DestinationsPuerto Rico, Virgin Island, British, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $23,980

    50% Off
    US$11,985
    You save $11,995
    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 $9,990

    62% Off
    US$3,810
    You save $6,180
    View tour
  6. 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 $12,990

    58% Off
    US$5,445
    You save $7,545
    View tour
  7. 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 $13,490

    50% Off
    US$6,720
    You save $6,770
    View tour
  8. Caribbean escapade 2026 - 8 Days (from San Juan to Miami)Map of Caribbean escapade 2026 - 8 Days (from San Juan to Miami)
    Sailing

    Exclusive ports beckon aboard Emerald Sakara from San Juan to Miami. Gordon's Beach's white sands, Grand Turk's colonial charm, and Nassau's offshore reefs await, complemented by an infinity pool and upscale dining.

    Duration 8 days
    DestinationsPuerto Rico, Bahamas, USA
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $12,490

    50% Off
    US$6,210
    You save $6,280
    View tour
  9. Caribbean Yachting Discovery 2025-2026Map of Caribbean Yachting Discovery 2025-2026
    Sailing

    The Emerald Azzurra glides through Caribbean waters, stopping at exclusive ports from Antigua to Puerto Rico. Barbuda's Pink Sandy Beach, Virgin Gorda's The Baths, and Norman Island's legendary pirate caves await. Luxury amenities and gourmet dining enhance this 8-day adventure.

    Duration 8 days
    DestinationsAntigua and Barbuda, Guadeloupe, Virgin Island, British, Puerto Rico
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $11,640

    51% Off
    US$5,745
    You save $5,895
    View tour
  10. Caribbean Yachting Hideaways 2025-2026Map of Caribbean Yachting Hideaways 2025-2026
    Sailing

    The finest harbors of the Caribbean welcome Emerald Azzurra, sailing from San Juan to Cruz Bay's vibrant waterfront. White Bay Beach on Jost Van Dyke and Philipsburg's Dutch colonial charm lead to Saint Barthélemy on this luxury sailing with 72 crew members.

    Duration 8 days
    DestinationsPuerto Rico, Virgin Island, British, Antigua and Barbuda
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $12,040

    51% Off
    US$5,945
    You save $6,095
    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
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