Explore over 320 cruise vacations
Showing 29 cruise vacations: All Destinations, December 2024 - October 2026
Departs San Juan, Puerto Rico
Showing 29 cruise vacations that match your search
Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,740
per Cabin
Departing on:
Sunsets in the Lesser Antilles
San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,226
per Cabin
Departing on:
SAVINGS TO WRITE HOME ABOUT
80% off your 2nd Sailor + free drinks
Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.
Resilient Valentine's Voyage
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,710
per Cabin
Departing on:
San Juan, Barbados & Beyond
San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$3,430
per Cabin
Departing on:
Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on:
Puerto Rican Daze & Caribbean Nights
San Juan • Tortola • St. John's • Basseterre • Fort-de-France • Castries • Bridgetown • Kingstown • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,700
per Cabin
Departing on:
Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,824
per Cabin
Departing on:
San Juan to Spanish Island Nights
San Juan • Santa Cruz de Tenerife • Casablanca • Palma de Mallorca • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,660
per Cabin
Departing on:
Sunny Miles of Tropical Isles
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
per Cabin
Departing on:
Sun-Soaked Seas & Saint Isles
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
Cartagena & Caribbean Faves
San Juan • Cartagena • Willemstad • Oranjestad • Fort-de-France • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,060
per Cabin
Departing on:
St. Lucia, St. Maarten, Barbados & More
San Juan • Basseterre • Castries • Roseau • Bridgetown • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
Valiant Caribbean Holidays
San Juan • Philipsburg • Basseterre • St. John's • Castries • Tortola • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,368
per Cabin
Departing on:
Valiant New Year’s Ahoy!
San Juan • Philipsburg • Basseterre • Castries • Bridgetown • St. Croix • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,768
per Cabin
Departing on:
Aruban Sights & Antiguan Nights
San Juan • Oranjestad • Willemstad • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
Virgin Island Views & Saint Isle Blues
San Juan • Tortola • Bridgetown • Kingstown • Basseterre • St. Croix • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
St. Kitts, Barbados, Martinique & More
San Juan • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
Barbados, Antigua, BVI & More
San Juan • Tortola • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,946
per Cabin
Departing on:
Quintessential Caribbean Highlights
San Juan • Philipsburg • Basseterre • St. John's • Fort-de-France • Castries • Kingstown • Bridgetown • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,780
per Cabin
Departing on:
Cartagena, Aruba, Antigua & More
San Juan • Cartagena • Willemstad • Oranjestad • St. John's • St. Croix • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,058
per Cabin
Departing on:
Antigua, Martinique, & Barbados & More
San Juan • Philipsburg • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
Quaint Castries to Elegant Antigua
San Juan • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,228
per Cabin
Departing on:
Tortola, Charleston, Newport & More
San Juan • Tortola • Puerto Plata • Charleston, South Carolina • Newport, Rhode Island • New York City, New York
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,684
per Cabin
Departing on: