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Cruises to Caribbean leaving San Juan, Puerto Rico cruise port 249 Caribbean Cruises Found

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Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. John's, Antigua
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - St. John's, Antigua - Castries, St. Lucia - Bridgetown, Barbados - Roseau, Dominica - View more ports

Celebrity Summit M

4.1
(2233 Reviews)

2024 sail dates: Dec 14,

$549*
$78/night*
Inside
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$549* directlinecruises.com $549* luxurycruiseconnections.com $549* americandiscountcruises.com $549* americandiscountvacations.com $549* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Basseterre, St. Kitts
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • Charlotte Amalie, St. Thomas
View more ports

Ports

San Juan, Puerto Rico - Tortola, British Virgin Islands - Basseterre, St. Kitts - Castries, St. Lucia - Bridgetown, Barbados - Roseau, Dominica - St. John's, Antigua - Philipsburg, St. Maarten - Charlotte Amalie, St. Thomas - View more ports

Viking Sea S

4.4
(87 Reviews)

2024 sail dates:

2025 sail dates: Dec 29,

$3299*
$330/night*
Balcony
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$3299* luxurycruiseconnections.com $3299* luxuryonly.com $3299* dreamvacations.com $3299* directlinecruises.com
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Ports

  • San Juan, Puerto Rico
  • Frederiksted, St. Croix, U.S.V.I.
  • Charlotte Amalie, St. Thomas
  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - Frederiksted, St. Croix, U.S.V.I. - Charlotte Amalie, St. Thomas - Philipsburg, St. Maarten - Basseterre, St. Kitts - Bridgetown, Barbados - View more ports

Rhapsody of the Seas L

4.1
(1333 Reviews)

2024 sail dates: Dec 08, Dec 22,

2025 sail dates: Jan 05, Jan 19, Feb 02, Mar 16, More

$1055*
$151/night*
Inside
View Deal
$1055* directlinecruises.com $1048* cruises.com $1048* cheapcruises.com $1040* cruisehub.com $1048* dreamvacations.com $1048* cruisesonly.com $643* americandiscountcruises.com $643* americandiscountvacations.com $751* gotosea.com
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$759*

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$759*

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$744*

$1471*

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$759*

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$1608*

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$1595*

$1646*

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$3364*

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$1588*

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$3342*

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$1645*

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$1580*

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$3348*

 

$1588*

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$1596*

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$959*

$1146*

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$2159*

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$958*

$1138*

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$2158*

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$958*

$1138*

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$943*

$1130*

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$2143*

 

$958*

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$958*

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$930*

$1117*

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$2130*

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$959*

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$2159*

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$1539*

$1626*

$2449*

$3184*

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$1538*

$1626*

$3076*

$3183*

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$1538*

$1626*

$3076*

$3183*

 

$1523*

$1611*

$2433*

$3168*

 

$1538*

$1626*

$3076*

$3183*

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$1538*

$1626*

$3076*

$3183*

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$1510*

$1597*

$2420*

$3155*

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$1510*

$1597*

$2420*

$3155*

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$1539*

$1626*

$2449*

$3184*

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$1044*

$1121*

$1584*

$2574*

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$1043*

$1121*

$2371*

$2574*

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$1043*

$1121*

$2371*

$2574*

 

$1028*

$1106*

$1569*

$2559*

 

$1043*

$1121*

$2371*

$2574*

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$1043*

$1121*

$2371*

$2574*

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$785*

$849*

$1555*

$2545*

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$785*

$849*

$1555*

$2545*

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$1044*

$1000*

$1584*

$2574*

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$1055*

$1116*

$1809*

$2051*

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$1048*

$1115*

$2396*

$2033*

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$1048*

$1115*

$2396*

$2033*

 

$1040*

$1100*

$1793*

$2036*

 

$1048*

$1115*

$2396*

$2033*

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$1048*

$1115*

$2396*

$2033*

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$643*

$816*

$1781*

$2024*

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$643*

$816*

$1781*

$2024*

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$751*

$1116*

$1809*

$2051*

Ports

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • St. John's, Antigua
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Philipsburg, St. Maarten
  • Charlotte Amalie, St. Thomas
View more ports

Ports

San Juan, Puerto Rico - Tortola, British Virgin Islands - St. John's, Antigua - Bridgetown, Barbados - Castries, St. Lucia - Philipsburg, St. Maarten - Charlotte Amalie, St. Thomas - View more ports

Norwegian Viva XL

4.3
(85 Reviews)

2024 sail dates: Dec 29

2025 sail dates: Feb 09, Mar 02,

$1951*
$279/night*
Inside
View Deal
$1951* cruises.com $1951* dreamvacations.com $2201* directlinecruises.com $1951* cruisesonly.com $2201* americandiscountcruises.com $1951* cheapcruises.com $2201* americandiscountvacations.com $2201* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. John's, Antigua
  • Castries, St. Lucia
  • Bridgetown, Barbados
  • Roseau, Dominica
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - St. John's, Antigua - Castries, St. Lucia - Bridgetown, Barbados - Roseau, Dominica - View more ports

Celebrity Summit M

4.1
(2233 Reviews)

2024 sail dates: Dec 28

$862*
$123/night*
Inside
View Deal
$862* directlinecruises.com $862* luxurycruiseconnections.com $1012* cruisesonly.com $1012* dreamvacations.com $1012* cruises.com
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Ports

  • San Juan, Puerto Rico
  • Frederiksted, St. Croix, U.S.V.I.
  • Charlotte Amalie, St. Thomas
  • Philipsburg, St. Maarten
  • Castries, St. Lucia
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - Frederiksted, St. Croix, U.S.V.I. - Charlotte Amalie, St. Thomas - Philipsburg, St. Maarten - Castries, St. Lucia - Bridgetown, Barbados - View more ports

Rhapsody of the Seas L

4.1
(1333 Reviews)

2024 sail dates:

2025 sail dates: Jan 12, Feb 09,

$912*
$130/night*
Inside
View Deal
$912* directlinecruises.com $911* cruises.com $911* cheapcruises.com $896* cruisehub.com $911* dreamvacations.com $911* cruisesonly.com $737* americandiscountcruises.com $737* americandiscountvacations.com $912* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC
  • Oranjestad, Aruba
  • Willemstad, Curacao
  • Castries, St. Lucia
  • Basseterre, St. Kitts
View more ports

Ports

San Juan, Puerto Rico - PUNTA CANA (LA ROMANA), DOMINICAN REPUBLIC - Oranjestad, Aruba - Willemstad, Curacao - Castries, St. Lucia - Basseterre, St. Kitts - View more ports

Norwegian Viva XL

4.3
(85 Reviews)

2024 sail dates:

2025 sail dates: Jan 05, Jan 12, Jan 26, Feb 02, Feb 16, Feb 23, Mar 09, Mar 16, Mar 30, Apr 06 More

$1047*
$150/night*
Inside
View Deal
$1047* ncl.com $1047* cruises.com $1047* dreamvacations.com $1047* directlinecruises.com $1047* cruisesonly.com $1047* americandiscountcruises.com $1047* cheapcruises.com $1047* americandiscountvacations.com $1047* gotosea.com
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$1596*

$1946*

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$3746*

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$2426*

 

$1276*

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$2346*

$3096*

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$1596*

$1996*

$2476*

$4596*

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$1596*

$1996*

$2476*

$2596*

 

$1596*

$1996*

$2476*

$2596*

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$1596*

$1996*

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$2596*

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$1996*

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$1996*

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$1996*

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$1996*

$2476*

$2596*

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$1996*

$2476*

$2596*

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$1996*

$2096*

$2146*

$4826*

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$1996*

$2096*

$2146*

$2596*

 

$1996*

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$2146*

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$1996*

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$2146*

$2596*

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$1996*

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$1996*

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$1996*

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$2146*

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$1996*

$2096*

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$2596*

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$1996*

$2096*

$2146*

$2596*

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$1996*

$2096*

$2146*

$5296*

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$1996*

$2096*

$2146*

$2796*

 

$1996*

$2096*

$2146*

$2796*

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$1946*

$2096*

$2146*

$2796*

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$1996*

$2096*

$2146*

$2796*

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$1946*

$2096*

$2146*

$2796*

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$1996*

$2096*

$2146*

$2796*

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$1946*

$2096*

$2146*

$2796*

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$1946*

$2096*

$2146*

$2796*

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$1796*

$1936*

$2196*

$5046*

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$1796*

$1936*

$2196*

$2646*

 

$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$1796*

$1936*

$2196*

$2646*

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$2096*

$2146*

$2196*

$5096*

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$1977*

$2146*

$2196*

$2796*

 

$1977*

$2146*

$2196*

$2796*

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$2096*

$2146*

$2196*

$2796*

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$1977*

$2146*

$2196*

$2796*

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$2096*

$2146*

$2196*

$2796*

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$1977*

$2146*

$2196*

$2796*

See Offers

$2096*

$2146*

$2196*

$2796*

See Offers

$2096*

$2146*

$2196*

$2796*

Ports

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • St. John's, Antigua
  • Philipsburg, St. Maarten
View more ports

Ports

San Juan, Puerto Rico - Tortola, British Virgin Islands - Bridgetown, Barbados - Castries, St. Lucia - St. John's, Antigua - Philipsburg, St. Maarten - View more ports

Valiant Lady L

4.3
(96 Reviews)

2025 sail dates:

2026 sail dates: Mar 21

$973*
$139/night*
Inside
View Deal
$973* luxurycruiseconnections.com $973* cruisesonly.com $973* dreamvacations.com $973* cruises.com $973* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Fort-De-France, Martinique
  • Basseterre, St. Kitts
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Bridgetown, Barbados - Castries, St. Lucia - Fort-De-France, Martinique - Basseterre, St. Kitts - View more ports

Valiant Lady L

4.3
(96 Reviews)

2025 sail dates:

2026 sail dates: Feb 28

$974*
$139/night*
Inside
View Deal
$974* luxurycruiseconnections.com $974* cruisesonly.com $974* dreamvacations.com $974* cruises.com $974* gotosea.com
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Read all 96 Valiant Lady reviews

Ports

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Philipsburg, St. Maarten
  • Frederiksted, St. Croix, U.S.V.I.
  • Roseau, Dominica
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - Charlotte Amalie, St. Thomas - Philipsburg, St. Maarten - Frederiksted, St. Croix, U.S.V.I. - Roseau, Dominica - Bridgetown, Barbados - View more ports

Jewel of the Seas L

4.0
(2167 Reviews)

2025 sail dates: Dec 27

$954*
$136/night*
Inside
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All prices are per person based on double occupancy and do not include port/government fees and gratuities.

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