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Showing 142cruise vacations: All Destinations,December 2024 - October 2025
Showing 142 cruise vacations that match your search
San Juan to St. Lucia: Holiday Edition
San Juan • Tortola • Philipsburg • Bridgetown • Fort-de-France • Castries • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Eastern Caribbean Antilles
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,570
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.
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$1,668
per Cabin
Departing on:
Dominican Daze
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$1,290
per Cabin
Departing on:
Resilient Caribbean Holidays
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Resilient New Year's Ahoy
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Scarlet New Year's Ahoy!
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Valiant New Year's Ahoy!
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
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$1,806
per Cabin
Departing on:
Western Caribbean Charm
Miami, Florida • Roatán • Costa Maya • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,428
per Cabin
Departing on:
* Port changes in place on select sailings — see full cruise details
Fire & Sunset Soirées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,192
per Cabin
Departing on:
San Juan, St. Vincent, Barbados & More
San Juan • Tortola • Basseterre • St. John's • Fort-de-France • Bridgetown • Castries • Kingstown • San Juan
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$2,580
per Cabin
Departing on:
Riviera Maya
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$988
per Cabin
Departing on:
Idyllic Caribbean Isles & Colombia
San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Resilient Valentine's Voyage
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Scarlet Valentine's Voyage
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Valiant Valentine's Voyage
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
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$3,152
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
Colombia & Caribbean Islands
San Juan • Cartagena • Oranjestad • Willemstad • Roseau • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Sunny Daze in Puerto Plata & Nassau
Miami, Florida • Puerto Plata • Nassau • Miami, Florida
Getaways for 80% off 2nd Sailor
San Juan to Spanish Island Nights
San Juan • Santa Cruz de Tenerife • Casablanca • Palma de Mallorca • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
Barcelona to France, Italy & Greece
Barcelona • Cannes • Civitavecchia (Rome) • Valletta • Mykonos • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Miami to Casablanca & Barcelona
Miami, Florida • Santa Cruz de Tenerife • Gran Canaria • Casablanca • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
A Virgin Celebration Voyage (Miami)
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Dubrovnik Days & Mykonos Nights
Piraeus (Athens) • Split • Dubrovnik • Kotor • Mykonos • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Greek Island Glow
Piraeus (Athens) • Santorini • Rhodes • Bodrum • Mykonos • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,070
per Cabin
Departing on:
A Virgin Celebration Voyage (Athens)
Piraeus (Athens) • Istanbul • Kusadasi (Ephesus) • Mykonos • Rhodes • Santorini • Chania, Crete • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Barcelona to Palma, Ibiza & More
Barcelona • Cannes • Ajaccio, Corsica • Palma de Mallorca • Ibiza • Barcelona
Getaways for 80% off 2nd Sailor
Mayan Sol
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,490
per Cabin
Departing on:
Barcelona to Rome & More
Barcelona • Civitavecchia (Rome) • Marina di Carrara • Ajaccio, Corsica • Ibiza • Barcelona
Getaways for 80% off 2nd Sailor
Starry Nights in Greece & Croatia
Piraeus (Athens) • Santorini • Bodrum • Mykonos • Dubrovnik • Kotor • Corfu • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$3,372
per Cabin
Departing on:
Barcelona, Palma, Rome & (Many) More
Barcelona • Cannes • Palma de Mallorca • Ibiza • Ajaccio, Corsica • La Spezia • Civitavecchia (Rome) • Barcelona
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
Price$3,278
per Cabin
Departing on:
Southern Spain & Casablanca
Barcelona • Málaga • Cádiz • Casablanca • Valencia • Palma de Mallorca • Ibiza • Barcelona
Getaways for 80% off 2nd Sailor
Sea Terrace cabins from
Price$2,982
per Cabin
Departing on:
Corfu, Dubrovnik & More
Piraeus (Athens) • Kotor • Dubrovnik • Corfu • Mykonos • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,790
per Cabin
Departing on:
Barcelona to Cannes, Rome & More
Barcelona • Cannes • Marina di Carrara • Civitavecchia (Rome) • Ibiza • Barcelona
Getaways for 80% off 2nd Sailor
Florence, Rome, Palma & More
Barcelona • Palma de Mallorca • Cannes • Ajaccio, Corsica • Livorno (Florence/Pisa) • Civitavecchia (Rome)
Getaways for 80% off 2nd Sailor
Istanbul, Santorini & More
Piraeus (Athens) • Istanbul • Kusadasi (Ephesus) • Mykonos • Rhodes • Santorini • Chania, Crete • Piraeus (Athens)
Getaways for 80% off 2nd Sailor
Sea View cabins from
Price$2,838
per Cabin
Departing on:
Spanish & Italian Hot Spots
Civitavecchia (Rome) • Naples • Sicily • Marina di Carrara • Ajaccio, Corsica • Barcelona
Getaways for 80% off 2nd Sailor
Grand Cayman, Costa Maya & More
Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Grand Turk, Puerto Plata & More
Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
A Virgin Celebration Voyage (Lisbon)
Lisbon • Leixoes (Porto) • La Coruña • Portsmouth
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$981.80
per Cabin
Departing on:
England to Iceland & Norway
Portsmouth • Amsterdam • Bergen • Lerwick • Akureyri • Ísafjörður • Reykjavik • Reykjavik
Getaways for 80% off 2nd Sailor
Reykjavik to Amsterdam & Portsmouth
Reykjavik • Reykjavik • Ísafjörður • Akureyri • Lerwick • Amsterdam • Portsmouth
Getaways for 80% off 2nd Sailor
Virgin Voyages Comedy Fest from Miami
Miami, Florida • Costa Maya • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Portsmouth to Ireland, Scotland & More
Portsmouth • Amsterdam • Zeebrugge (Bruges) • Kirkwall • Stornoway, Isle of Lewis • Greenock (Glasgow) • Belfast • Dublin • Portsmouth
Getaways for 80% off 2nd Sailor
Virgin Voyages Comedy Fest from the UK
Portsmouth • La Coruña • Bilbao • Le Verdon (Bordeaux) • Portsmouth
Getaways for 80% off 2nd Sailor
Brilliant Lady New York MerMaiden
New York City, New York • Kings Wharf • New York City, New York
Getaways for 80% off 2nd Sailor
Portsmouth to Amsterdam & Bordeaux
Portsmouth • Amsterdam • Zeebrugge (Bruges) • Le Verdon (Bordeaux) • Portsmouth
Getaways for 80% off 2nd Sailor
The Big Apple to Bermuda
New York City, New York • Kings Wharf • New York City, New York
Getaways for 80% off 2nd Sailor
Portsmouth to Lisbon, Casablanca & Spain
Portsmouth • La Coruña • Lisbon • Casablanca • Málaga • Ibiza • Barcelona
Getaways for 80% off 2nd Sailor
Northeast Atlantic Adventure
New York City, New York • Boston, Massachusetts • Eastport, Maine • Saint John, New Brunswick • Halifax, Nova Scotia • New York City, New York
Getaways for 80% off 2nd Sailor
Nautical Northeast: NYC to Quebec
New York City, New York • Boston, Massachusetts • Eastport, Maine • Saint John, New Brunswick • Halifax, Nova Scotia • Quebec City
Getaways for 80% off 2nd Sailor
Barcelona to Cannes, Rome & Tuscany
Barcelona • Ibiza • Palma de Mallorca • Cannes • Ajaccio, Corsica • Cagliari, Sardinia • Livorno (Florence/Pisa) • Naples • Civitavecchia (Rome)
Getaways for 80% off 2nd Sailor
Canada, Carolina, & Miami
Quebec City • Halifax, Nova Scotia • Saint John, New Brunswick • Eastport, Maine • Boston, Massachusetts • Charleston, South Carolina • Miami, Florida
Getaways for 80% off 2nd Sailor
Italy to France & Spain
Civitavecchia (Rome) • Cagliari, Sardinia • Marina di Carrara • Ajaccio, Corsica • Cannes • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
Scarlet's Haunted Halloween Soirée
Barcelona • Palma de Mallorca • Casablanca • Funchal, Madeira • Santa Cruz de Tenerife • Miami, Florida
Getaways for 80% off 2nd Sailor
Brilliant Lady Miami MerMaiden
Miami, Florida • Philipsburg • Tortola • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Mykonos Moons to Spanish Sunrises
Piraeus (Athens) • Mykonos • Catania, Sicily • Palma de Mallorca • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
Riviera Maya: Halloween Edition
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Dominican Daze: Halloween Edition
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Resilient's Haunted Halloween Soirée
Barcelona • Valencia • Casablanca • Gran Canaria • Miami, Florida
Getaways for 80% off 2nd Sailor
Valiant's Haunted Halloween Soirée
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Honduras, Mexico & Bahamas
Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor