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Cruises to Caribbean - Southern leaving San Juan, Puerto Rico cruise port 134 Caribbean - Southern Cruises Found

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Ports

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curacao
  • Kralendijk, Bonaire
  • Fort-De-France, Martinique
  • Roseau, Dominica
  • Little Bay, Montserrat
  • SOUTH FRIARS BAY, ST. KITTS
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • Soper's Hole, Tortola, B.V.I.
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Port Elizabeth, Bequia, Grenadines
  • St. George's, Grenada
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - Oranjestad, Aruba - Willemstad, Curacao - Kralendijk, Bonaire - Fort-De-France, Martinique - Roseau, Dominica - Little Bay, Montserrat - SOUTH FRIARS BAY, ST. KITTS - St. John's, Antigua - Tortola, British Virgin Islands - Soper's Hole, Tortola, B.V.I. - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Port Elizabeth, Bequia, Grenadines - St. George's, Grenada - Bridgetown, Barbados - View more ports

Seabourn Ovation S

4.4
(27 Reviews)

2025 sail dates:

$9594*
$480/night*
Suite
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$9594* seabourn.com $9434* luxurycruiseconnections.com $9434* luxuryonly.com $9434* dreamvacations.com $9434* gotosea.com
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$9434*

 

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$9434*

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N/A

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$9434*

Ports

  • San Juan, Puerto Rico
  • Cartagena, Colombia
  • Willemstad, Curacao
  • Oranjestad, Aruba
  • Fort-De-France, Martinique
  • St. John's, Antigua
  • Philipsburg, St. Maarten
View more ports

Ports

San Juan, Puerto Rico - Cartagena, Colombia - Willemstad, Curacao - Oranjestad, Aruba - Fort-De-France, Martinique - St. John's, Antigua - Philipsburg, St. Maarten - View more ports

Valiant Lady L

4.3
(100 Reviews)

2025 sail dates:

$1530*
$139/night*
Inside
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$1530* luxurycruiseconnections.com $1530* cruisesonly.com $1530* cruises.com $1530* dreamvacations.com $1530* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Soper's Hole, Tortola, B.V.I.
  • SOUTH FRIARS BAY, ST. KITTS
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Fort-De-France, Martinique
  • Port Elizabeth, Bequia, Grenadines
  • St. George's, Grenada
  • Bridgetown, Barbados
  • Rodney Bay, St. Lucia
  • Little Bay, Montserrat
  • Willemstad, Curacao
  • Oranjestad, Aruba
  • Kralendijk, Bonaire
View more ports

Ports

San Juan, Puerto Rico - Soper's Hole, Tortola, B.V.I. - SOUTH FRIARS BAY, ST. KITTS - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Fort-De-France, Martinique - Port Elizabeth, Bequia, Grenadines - St. George's, Grenada - Bridgetown, Barbados - Rodney Bay, St. Lucia - Little Bay, Montserrat - Willemstad, Curacao - Oranjestad, Aruba - Kralendijk, Bonaire - View more ports

Seabourn Ovation S

4.4
(27 Reviews)

2025 sail dates:

$11034*
$552/night*
Suite
View Deal
$11034* seabourn.com $10879* luxurycruiseconnections.com $10879* luxuryonly.com $10879* dreamvacations.com $10879* gotosea.com
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$11034*

 

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$10879*

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N/A

$10879*

 

N/A

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$10879*

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N/A

N/A

N/A

$10879*

Ports

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curacao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
View more ports

Ports

San Juan, Puerto Rico - Oranjestad, Aruba - Willemstad, Curacao - St. John's, Antigua - Philipsburg, St. Maarten - View more ports

Valiant Lady L

4.3
(100 Reviews)

2026 sail dates:

$1043*
$149/night*
Inside
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$1043* luxurycruiseconnections.com $1043* cruisesonly.com $1043* cruises.com $1043* dreamvacations.com $1043* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Cartagena, Colombia
  • Willemstad, Curacao
  • Oranjestad, Aruba
  • St. John's, Antigua
  • Frederiksted, St. Croix, U.S.V.I.
  • Philipsburg, St. Maarten
View more ports

Ports

San Juan, Puerto Rico - Cartagena, Colombia - Willemstad, Curacao - Oranjestad, Aruba - St. John's, Antigua - Frederiksted, St. Croix, U.S.V.I. - Philipsburg, St. Maarten - View more ports

Valiant Lady L

4.3
(100 Reviews)

2026 sail dates:

$1529*
$139/night*
Inside
View Deal
$1529* luxurycruiseconnections.com $1529* cruisesonly.com $1529* cruises.com $1529* dreamvacations.com $1529* gotosea.com
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Ports

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curacao
  • Fort-De-France, Martinique
  • Basseterre, St. Kitts
View more ports

Ports

San Juan, Puerto Rico - Oranjestad, Aruba - Willemstad, Curacao - Fort-De-France, Martinique - Basseterre, St. Kitts - View more ports

Valiant Lady L

4.3
(100 Reviews)

2026 sail dates:

$1113*
$159/night*
Inside
View Deal
$1113* luxurycruiseconnections.com $1113* cruisesonly.com $1113* cruises.com $1113* dreamvacations.com
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Ports

  • San Juan, Puerto Rico
  • Tortola, British Virgin Islands
  • Philipsburg, St. Maarten
  • St. John's, Antigua
  • Basseterre, St. Kitts
  • Frederiksted, St. Croix, U.S.V.I.
View more ports

Ports

San Juan, Puerto Rico - Tortola, British Virgin Islands - Philipsburg, St. Maarten - St. John's, Antigua - Basseterre, St. Kitts - Frederiksted, St. Croix, U.S.V.I. - View more ports

Radiance of the Seas L

4.2
(1273 Reviews)

2026 sail dates: Apr 25, May 09, May 23, Jun 06, Jun 20, Jul 04, Jul 18, Aug 01, Aug 15, Aug 29, Sep 12, Sep 26, Oct 10, Oct 24, Nov 28, More

2027 sail dates: Jan 09, Jan 23, Feb 06, Feb 20, Mar 06, Mar 20, Apr 03, Apr 17 More

$751*
$107/night*
Inside
View Deal
$751* cruises.com $751* cruisesonly.com $640* americandiscountcruises.com $764* cruisehub.com $751* cheapcruises.com $751* dreamvacations.com $752* gotosea.com $640* americandiscountvacations.com $764* directlinecruises.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
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$969*

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$1455*

$2377*

 

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$1095*

$1195*

$1534*

$2427*

 

$1094*

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$1150*

$1300*

$1580*

$2525*

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$1300*

$1580*

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$1164*

$1314*

$1594*

$2526*

 

$1163*

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$1114*

$1214*

$1533*

$2426*

 

$1113*

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$1532*

$2425*

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$1100*

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$1520*

$2425*

 

$1100*

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$1113*

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$1533*

$2426*

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$1114*

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$1113*

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$1533*

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$987*

$1087*

$1329*

$2122*

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$987*

$1087*

$1329*

$2122*

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$988*

$1088*

$1330*

$2123*

 

$987*

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$987*

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$987*

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$987*

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$902*

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$1997*

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$916*

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$1998*

 

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$802*

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$1152*

$1857*

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$816*

$916*

$1166*

$1858*

 

$815*

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$1165*

$1857*

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$802*

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$1152*

$1857*

 

$802*

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$816*

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$1165*

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$816*

$916*

$1166*

$1858*

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$776*

$876*

$1126*

$1841*

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$776*

$876*

$1126*

$1841*

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$790*

$877*

$1140*

$1842*

 

$789*

$889*

$1139*

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$776*

$876*

$1126*

$1841*

 

$776*

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$790*

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$1139*

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$746*

$846*

$1096*

$1831*

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$747*

$847*

$1110*

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$759*

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$724*

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$824*

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$837*

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$704*

$804*

$1074*

$1778*

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$704*

$804*

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$717*

$804*

$1086*

$1779*

 

$717*

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$1778*

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$704*

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$1074*

$1778*

 

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$1903*

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$1053*

$1785*

 

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$761*

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$1148*

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$848*

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$749*

$849*

$1149*

$1894*

 

$761*

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$1161*

$1893*

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$748*

$848*

$1148*

$1893*

 

$748*

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$1148*

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$749*

$849*

$1149*

$1894*

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$749*

$849*

$1149*

$1894*

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$761*

$861*

$1161*

$1894*

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$748*

$848*

$1148*

$1993*

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$748*

$848*

$1148*

$1993*

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$749*

$849*

$1162*

$1994*

 

$761*

$860*

$1161*

$1993*

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$748*

$848*

$1148*

$1993*

 

$748*

$848*

$1148*

$1993*

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$749*

$849*

$1161*

$1994*

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$749*

$849*

$1162*

$1994*

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$761*

$861*

$1161*

$1994*

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$748*

$848*

$1148*

$2093*

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$748*

$848*

$1148*

$2093*

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$749*

$849*

$1162*

$2094*

 

$761*

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$1161*

$2093*

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$748*

$848*

$1148*

$2093*

 

$748*

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$1148*

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$761*

$849*

$1161*

$2094*

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$749*

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$748*

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$1148*

$1993*

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$748*

$848*

$1148*

$1993*

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$749*

$849*

$1149*

$1994*

 

$761*

$860*

$1161*

$1993*

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$748*

$848*

$1148*

$1993*

 

$748*

$848*

$1148*

$1993*

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$749*

$849*

$1149*

$1994*

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$749*

$849*

$1149*

$1994*

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$761*

$861*

$1161*

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$748*

$848*

$1148*

$1993*

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$748*

$848*

$1148*

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$749*

$849*

$1149*

$1994*

 

$761*

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$1161*

$1993*

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$748*

$848*

$1148*

$1993*

 

$748*

$848*

$1148*

$1993*

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$749*

$849*

$1149*

$1994*

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$749*

$849*

$1149*

$1994*

See Offers

$761*

$861*

$1161*

$1994*

Ports

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

Ports

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

Radiance of the Seas L

4.2
(1273 Reviews)

2026 sail dates:

$838*
$120/night*
Inside
View Deal
$838* cruises.com $838* cruisesonly.com $859* americandiscountcruises.com $865* cruisehub.com $838* cheapcruises.com $838* dreamvacations.com $858* gotosea.com $859* americandiscountvacations.com $858* directlinecruises.com
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Ports

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

Ports

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

Radiance of the Seas L

4.2
(1273 Reviews)

2026 sail dates: May 16, May 30, Jun 13, Jun 27, Jul 11, Jul 25, Aug 08, Aug 22, Sep 05, Sep 19, Oct 03, Oct 17, Oct 31, Nov 21, Dec 05 More

2027 sail dates: Jan 02, Jan 16, Feb 27, Mar 13, Apr 10 More

$697*
$100/night*
Inside
View Deal
$697* cruises.com $697* cruisesonly.com $698* americandiscountcruises.com $697* cruisehub.com $697* cheapcruises.com $697* dreamvacations.com $698* gotosea.com $698* americandiscountvacations.com $698* directlinecruises.com
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$771*

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$783*

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$771*

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Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. John's, Antigua
  • Roseau, Dominica
  • Basseterre, St. Kitts
  • Frederiksted, St. Croix, U.S.V.I.
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - St. John's, Antigua - Roseau, Dominica - Basseterre, St. Kitts - Frederiksted, St. Croix, U.S.V.I. - View more ports

Radiance of the Seas L

4.2
(1273 Reviews)

2026 sail dates:

$742*
$106/night*
Inside
View Deal
$742* cruises.com $742* cruisesonly.com $743* americandiscountcruises.com $755* cruisehub.com $742* cheapcruises.com $742* dreamvacations.com $743* gotosea.com $743* americandiscountvacations.com $755* directlinecruises.com
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121 - 130 of 134

All prices are per person based on double occupancy and do not include port/government fees and gratuities.

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