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Explore 415 cruise vacations
Showing Loading cruise vacations: All Destinations, September 2025 - April 2027
Departs San Juan, Puerto Rico
Showing 45 cruise vacations that match your search
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UP TO $600 OFF
Saint (Isles) & Seas of the Caribbean
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,226$3,166
per Cabin
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UP TO $600 OFF
Sunny Miles of Tropical Isles
- 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
70% off second Sailor
Insider cabins from
$1,666$2,414
per Cabin
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UP TO $600 OFF
Thanksgiving in the Lesser Antilles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,666$2,400
per Cabin
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San Juan to Barbados & the St. Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Roseau, Dominica
- Bridgetown, Barbados
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,428$2,066
per Cabin
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UP TO $600 OFF
Nicky Jam x Virgin Voyages
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Roseau, Dominica
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,904$2,766
per Cabin
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UP TO $600 OFF
St. Lucia, St. Maarten, Barbados & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Roseau, Dominica
- Bridgetown, Barbados
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,666$2,416
per Cabin
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UP TO $600 OFF
Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,508$3,698
per Cabin
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UP TO $600 OFF
Valiant New Year’s Ahoy!
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$3,768$5,658
per Cabin
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UP TO $600 OFF
Aruban Sights & Antiguan Nights
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,946$2,850
per Cabin
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UP TO $600 OFF
Virgin Island Views & Saint Isle Blues
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Kingstown, St. Vincent
- Basseterre, St. Kitts and Nevis
- St. Croix, U.S. Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,086$3,078
per Cabin
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UP TO $600 OFF
St. Kitts, Barbados, Martinique & More
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,086$3,066
per Cabin
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UP TO $600 OFF
Barbados, Antigua, BVI & More
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,088$3,062
per Cabin
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UP TO $600 OFF
Antigua & the St. Isles
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,260
per Cabin
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UP TO $600 OFF
St. Lucia, Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Bridgetown, Barbados
- Charlotte Amalie, St. Thomas
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,262
per Cabin
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Valiant Valentine's Voyage
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- St. Croix, U.S. Virgin Islands
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,226$3,284
per Cabin
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UP TO $600 OFF
Antigua, Martinique, & Barbados & More
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,228$3,278
per Cabin
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UP TO $600 OFF
Quaint Castries to Elegant Antigua
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Castries, St. Lucia
- Fort-de-France, Martinique
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Sea View cabins from
$2,086$3,070
per Cabin
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UP TO $600 OFF
Sunsets in the Lesser Antilles
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,226$3,274
per Cabin
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Tortola, Charleston, Newport & More
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Puerto Plata, Dominican Republic
- Charleston, South Carolina
- Newport, Rhode Island
- New York City, New York
70% off second Sailor
Insider cabins from
$1,964$2,800
per Cabin
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Valiant's Haunted Halloween Soirée
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,366$3,490
per Cabin
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Caribbean East: Virgin & Saint Isles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Basseterre, St. Kitts and Nevis
- St. John's, Antigua
- Castries, St. Lucia
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$1,908$2,618
per Cabin
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Thanksgiving: St. Isles, Aruba & Curaçao
- San Juan, Puerto Rico
- Charlotte Amalie, St. Thomas
- Willemstad, Curaçao
- Oranjestad, Aruba
- Basseterre, St. Kitts and Nevis
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,864$4,226
per Cabin
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Antiguan Elegance & Sunny St. Isles
- 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
70% off second Sailor
Insider cabins from
$2,366$3,422
per Cabin
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Valiant Caribbean Holidays
- San Juan, Puerto Rico
- Basseterre, St. Kitts and Nevis
- Fort-de-France, Martinique
- Oranjestad, Aruba
- Willemstad, Curaçao
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,786$4,136
per Cabin
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Valiant New Year's Ahoy!
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Fort-de-France, Martinique
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$4,186$6,274
per Cabin
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Puerto Rico to Aruba, Bonaire & More
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Kralendijk, Bonaire
- Fort-de-France, Martinique
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,704$3,894
per Cabin
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Lesser Antilles: Valentine's Day
- San Juan, Puerto Rico
- Oranjestad, Aruba
- Willemstad, Curaçao
- Fort-de-France, Martinique
- Basseterre, St. Kitts and Nevis
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,506$3,620
per Cabin
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Saint Isles & The Greater Antilles
- San Juan, Puerto Rico
- Tortola, British Virgin Islands
- Castries, St. Lucia
- Bridgetown, Barbados
- Roseau, Dominica
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,366$3,392
per Cabin
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UP TO $600 OFF
Saint (Isles) & Seas of the Caribbean
- San Juan, Puerto Rico
- Philipsburg, St. Maarten
- Bridgetown, Barbados
- Castries, St. Lucia
- St. John's, Antigua
- Tortola, British Virgin Islands
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,366$3,380
per Cabin
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Barbados, Dominica & St. Isle Spring
- San Juan, Puerto Rico
- Charlotte Amalie, St. Thomas
- Bridgetown, Barbados
- Kingstown, St. Vincent
- Roseau, Dominica
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Insider cabins from
$2,864$4,156
per Cabin
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Colorful Curaçao, Aruba & Antigua
- San Juan, Puerto Rico
- Willemstad, Curaçao
- Oranjestad, Aruba
- St. John's, Antigua
- Philipsburg, St. Maarten
- San Juan, Puerto Rico
70% off second Sailor
Sea Terrace cabins from
$4,480$6,644
per Cabin
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San Juan to Miami: Dominican Daze
- San Juan, Puerto Rico
- Puerto Plata, Dominican Republic
- The Beach Club at Bimini, Bahamas
- Miami, Florida
70% off second Sailor
Insider cabins from
$1,490$2,052
per Cabin
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