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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
  • Gustavia, St. Barthelemy
  • St. John's, Antigua
  • Tortola, British Virgin Islands
  • ROAD BAY, ANGUILLA
  • Miami, Florida
View more ports

Ports

San Juan, Puerto Rico - Gustavia, St. Barthelemy - St. John's, Antigua - Tortola, British Virgin Islands - ROAD BAY, ANGUILLA - Miami, Florida - View more ports

Explora I M

4.5
(7 Reviews)

2026 sail dates:

$3075*
$439/night*
Suite
View Deal
$3075* luxurycruiseconnections.com $4100* luxuryonly.com $4100* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$3075*

See Offers

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$4100*

 

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$4100*

Ports

  • San Juan, Puerto Rico
  • LOVANGO CAY, ST. JOHN, U.S.V.I.
  • Prickly Pear Island, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Charlestown, Nevis
  • SOUTH FRIARS BAY, ST. KITTS
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Port Elizabeth, Bequia, Grenadines
  • Tobago Cays, Grenadines
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - LOVANGO CAY, ST. JOHN, U.S.V.I. - Prickly Pear Island, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Charlestown, Nevis - SOUTH FRIARS BAY, ST. KITTS - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Port Elizabeth, Bequia, Grenadines - Tobago Cays, Grenadines - Bridgetown, Barbados - View more ports

SeaDream I S

4.9
(3 Reviews)

2026 sail dates:

$6599*
$660/night*
Oceanview
View Deal
$6599* luxurycruiseconnections.com $5699* luxuryonly.com $5699* dreamvacations.com
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Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6599*

N/A

$12599*

 

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$5699*

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$11399*

 

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$5699*

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$11399*

Ports

  • San Juan, Puerto Rico
  • Soufriere, St. Lucia
  • Canouan, Grenadines
  • Cabrits, Dominica
  • Gustavia, St. Barthelemy
  • St. John, U.S. Virgin Islands
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Ports

San Juan, Puerto Rico - Soufriere, St. Lucia - Canouan, Grenadines - Cabrits, Dominica - Gustavia, St. Barthelemy - St. John, U.S. Virgin Islands - View more ports

Ilma S

2026 sail dates:

$6200*
$886/night*
Suite
View Deal
$6200* luxurycruiseconnections.com $6200* dreamvacations.com $6200* luxuryonly.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$6200*

 

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$6200*

 

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$6200*

Ports

  • San Juan, Puerto Rico
  • Bridgetown, Barbados
  • Fort-De-France, Martinique
  • St. John's, Antigua
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
View more ports

Ports

San Juan, Puerto Rico - Bridgetown, Barbados - Fort-De-France, Martinique - St. John's, Antigua - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - View more ports

Ilma S

2026 sail dates: Feb 01, Feb 15

$6200*
$886/night*
Suite
View Deal
$6200* luxurycruiseconnections.com $6200* dreamvacations.com $6200* luxuryonly.com
Loading itinerary...
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Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$6200*

 

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$6200*

 

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$6200*

Ports

  • San Juan, Puerto Rico
  • Gustavia, St. Barthelemy
  • Tortola, British Virgin Islands
  • St. John's, Antigua
  • ROAD BAY, ANGUILLA
  • Miami, Florida
View more ports

Ports

San Juan, Puerto Rico - Gustavia, St. Barthelemy - Tortola, British Virgin Islands - St. John's, Antigua - ROAD BAY, ANGUILLA - Miami, Florida - View more ports

Explora I M

4.5
(7 Reviews)

2026 sail dates:

$3075*
$439/night*
Suite
View Deal
$3075* luxurycruiseconnections.com $4100* luxuryonly.com $4100* dreamvacations.com
Loading itinerary...
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Top positive review

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Read all 7 Explora I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3075*

See Offers

N/A

N/A

N/A

$4100*

 

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$4100*

Ports

  • San Juan, Puerto Rico
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • Soufriere, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Marigot, Saint Martin
View more ports

Ports

San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - View more ports

Star Seeker S

2026 sail dates: Jan 23,

$5390*
$385/night*
Suite
View Deal
$5390* luxurycruiseconnections.com $5390* luxuryonly.com $5390* dreamvacations.com
Loading itinerary...
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Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$5690*

See Offers

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$5690*

 

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$5690*

 

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$5390*

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$5390*

 

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$5390*

Ports

  • San Juan, Puerto Rico
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports

Star Seeker S

2026 sail dates: Jan 23, Mar 06

$3062*
$437/night*
Suite
View Deal
$3062* luxurycruiseconnections.com $3090* luxuryonly.com $3090* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

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$3362*

See Offers

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$3390*

 

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$3390*

 

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$3062*

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$3090*

 

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$3090*

 

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$3762*

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$3896*

 

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$3896*

Ports

  • San Juan, Puerto Rico
  • WHITE BAY, JOST VAN DYKE, B.V.I.
  • Gustavia, St. Barthelemy
  • St. Eustatius, Netherlands Special Municipality
  • Falmouth Harbour,Antigua
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Fort-De-France, Martinique
  • Bridgetown, Barbados
View more ports

Ports

San Juan, Puerto Rico - WHITE BAY, JOST VAN DYKE, B.V.I. - Gustavia, St. Barthelemy - St. Eustatius, Netherlands Special Municipality - Falmouth Harbour,Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Fort-De-France, Martinique - Bridgetown, Barbados - View more ports

SeaDream I S

4.9
(3 Reviews)

2026 sail dates:

$3999*
$571/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 3 SeaDream I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3999*

N/A

$7999*

 

N/A

$3999*

N/A

$7999*

Ports

  • San Juan, Puerto Rico
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • Soufriere, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Marigot, Saint Martin
View more ports

Ports

San Juan, Puerto Rico - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - View more ports

Star Seeker S

2026 sail dates: Feb 13

$3327*
$475/night*
Suite
View Deal
$3327* luxurycruiseconnections.com $3390* luxuryonly.com $3390* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3327*

See Offers

N/A

N/A

N/A

$3390*

 

N/A

N/A

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$3390*

 

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N/A

N/A

$3327*

See Offers

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N/A

$3390*

 

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$3390*

Ports

  • San Juan, Puerto Rico
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • Soufriere, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Marigot, Saint Martin
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports

Star Seeker S

2026 sail dates:

$5390*
$385/night*
Suite
View Deal
$5390* luxurycruiseconnections.com $5390* luxuryonly.com $5390* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$5390*

See Offers

N/A

N/A

N/A

$5390*

 

N/A

N/A

N/A

$5390*

211 - 220 of 249

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

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