Currency, current value
$USD

Explore 399 cruise vacations

Showing Loading cruise vacations: Caribbean, July 2025 - October 2026
Departs San Juan, Puerto Rico
Showing 21 cruise vacations that match your search
Showing 21 cruise vacations that match your search
Sort price type, current value Price per cabin
Sort options, current value Sails first
DEAL

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
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:

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
Insider cabins from
per Cabin
Loading
6 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
8 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

Aruban Sights & Antiguan Nights

  • San Juan, Puerto Rico
  • Oranjestad, Aruba
  • Willemstad, Curaçao
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • San Juan, Puerto Rico
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Sea View cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Sea View cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on:
DEAL

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
Insider cabins from
per Cabin
Loading
7 nights
Valiant Lady
+ Balcony upgrades
70% off 2nd Sailor
Insider cabins from
per Cabin
Loading
Departing on: