Showing cruise vacations: Caribbean, All Dates

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Departs San Juan, Puerto Rico

Summer 2027: Up to $400 onboard credit ends in

Showing 46 cruise vacations that match your search

Southern Caribbean Halloween Cruise

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$903~~$1,313~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,313~~

per Sailor

Departing on:

Sat, Oct 31 - Sat, Nov 07

Southern Caribbean Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$903~~$1,307~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,307~~

per Sailor

Departing on:

Sat, Dec 12 - Sat, Dec 19

Sat, Nov 07 - Sat, Nov 14

from (US$)$1,113

Sat, Jan 16 - Sat, Jan 23

ALASKA OR EUROPE? YES.

UP TO $1,000 SAVINGS + $400 ONBOARD CREDIT

Book select Summer 2027 sailings early.

Southern Caribbean Cruise

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
San Juan, Puerto Rico

Insider cabins from

$834~~$1,210~~

per Sailor

6 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$834~~$1,210~~

per Sailor

Departing on:

Sat, Jan 23 - Fri, Jan 29

Sat, Nov 14 - Fri, Nov 20

Sat, Mar 13 - Fri, Mar 19

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Willemstad, Curaçao
Oranjestad, Aruba
Basseterre, St. Kitts and Nevis
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$1,112~~$1,621~~

per Sailor

8 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,112~~$1,621~~

per Sailor

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$1,112

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$763~~$1,087~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,087~~

per Sailor

Departing on:

Sat, Nov 28 - Sat, Dec 05

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$763~~$1,098~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,098~~

per Sailor

Departing on:

Sat, Dec 05 - Sat, Dec 12

Sat, Jan 09 - Sat, Jan 16

Sat, Feb 27 - Sat, Mar 06

from (US$)$1,113

Southern Caribbean Holiday Cruise

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Fort-de-France, Martinique
Oranjestad, Aruba
Willemstad, Curaçao
San Juan, Puerto Rico

Insider cabins from

$973~~$1,421~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$973~~$1,421~~

per Sailor

Departing on:

Sat, Dec 19 - Sat, Dec 26

Southern Caribbean New Year's Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Fort-de-France, Martinique
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
San Juan, Puerto Rico

Insider cabins from

$1,603~~$2,382~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,603~~$2,382~~

per Sailor

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$1,603

Southern Caribbean Cruise

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

Insider cabins from

$1,043~~$1,520~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,043~~$1,520~~

per Sailor

Departing on:

Sat, Jan 02 - Sat, Jan 09

from (US$)$1,043

Sat, Mar 06 - Sat, Mar 13

from (US$)$1,043

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Kralendijk, Bonaire
Fort-de-France, Martinique
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$1,352~~$1,996~~

per Sailor

8 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,352~~$1,996~~

per Sailor

Departing on:

Fri, Jan 29 - Sat, Feb 06

from (US$)$1,352

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$763~~$1,058~~

per Sailor

7 nights

Valiant Lady & Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,058~~

per Sailor

Departing on:

Sat, Jan 08 - Sat, Jan 15

Sat, Feb 06 - Sat, Feb 13

from (US$)$1,043

Sat, Nov 20 - Sat, Nov 27

Sisters at Sea: Valiant Lady

San Juan, Puerto Rico
Samaná, Dominican Republic
Grand Turk, Turks and Caicos
Cabo Rojo, Dominican Republic
San Juan, Puerto Rico

Sea Terrace cabins from

$1,393~~$2,070~~

per Sailor

7 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Sea Terrace cabins from

$1,393~~$2,070~~

per Sailor

Departing on:

Sat, Feb 13 - Sat, Feb 20

from (US$)$1,393

Southern Caribbean Cruise

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Castries, St. Lucia
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$903~~$1,301~~

per Sailor

7 nights

Valiant Lady & Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,301~~

per Sailor

Departing on:

Sat, Nov 27 - Sat, Dec 04

Sat, Feb 20 - Sat, Feb 27

from (US$)$1,043

Sat, Apr 08 - Sat, Apr 15

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Kingstown, St. Vincent
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$952~~$1,388~~

per Sailor

8 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$952~~$1,388~~

per Sailor

Departing on:

Fri, Mar 19 - Sat, Mar 27

San Juan to Miami: Grand Turk & Bimini

San Juan, Puerto Rico
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$795~~$1,134~~

per Sailor

5 nights

Valiant Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$795~~$1,134~~

per Sailor

Departing on:

Sat, Apr 10 - Thu, Apr 15

Southern Caribbean Cruise

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
Bridgetown, Barbados
Castries, St. Lucia
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$1,112~~$1,616~~

per Sailor

8 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,112~~$1,616~~

per Sailor

Departing on:

Fri, Nov 12 - Sat, Nov 20

from (US$)$1,112

Southern Caribbean & Aruban Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Castries, St. Lucia
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$763~~$1,060~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,060~~

per Sailor

Departing on:

Sat, Jan 22 - Sat, Jan 29

Sat, Dec 11 - Sat, Dec 18

Sat, Mar 18 - Sat, Mar 25

Southern Caribbean & Aruban Holidays

San Juan, Puerto Rico
Philipsburg, St. Maarten
St. John's, Antigua
Roseau, Dominica
Oranjestad, Aruba
Willemstad, Curaçao
San Juan, Puerto Rico

Insider cabins from

$1,112~~$1,618~~

per Sailor

8 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,112~~$1,618~~

per Sailor

Departing on:

Sat, Dec 18 - Sun, Dec 26

from (US$)$1,112

Southern Caribbean Cruise New Year’s

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

$1,673~~$2,483~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$1,673~~$2,483~~

per Sailor

Departing on:

Sun, Dec 26 - Sun, Jan 02

from (US$)$1,673

Southern Caribbean Cruise

San Juan, Puerto Rico
Kingstown, St. Vincent
Bridgetown, Barbados
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$654~~$907~~

per Sailor

6 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$654~~$907~~

per Sailor

Departing on:

Sun, Jan 02 - Sat, Jan 08

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Kingstown, St. Vincent
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$763~~$1,057~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,057~~

per Sailor

Departing on:

Sat, Jan 15 - Sat, Jan 22

Southern Caribbean Cruise

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

$763~~$1,057~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$763~~$1,057~~

per Sailor

Departing on:

Sat, Jan 29 - Sat, Feb 05

Sat, Feb 26 - Sat, Mar 04

Sat, Mar 25 - Sat, Apr 01

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$833~~$1,160~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$833~~$1,160~~

per Sailor

Departing on:

Sat, Feb 12 - Sat, Feb 19

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Fort-de-France, Martinique
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$903~~$1,268~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$903~~$1,268~~

per Sailor

Departing on:

Sat, Mar 11 - Sat, Mar 18

Southern Caribbean Cruise

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$973~~$1,380~~

per Sailor

7 nights

Scarlet Lady

70% off 2nd Sailor

Up to $1,000 Instant Savings

Insider cabins from

$973~~$1,380~~

per Sailor

Departing on:

Sat, Apr 15 - Sat, Apr 22

Average starting price per Sailor (incl. taxes & fees)