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Showing 71cruise vacations: All Destinations,January 2026 - May 2026
2 Sailors , 1 Cabin
Showing 71 cruise vacations that match your search
Dominican Daze
Miami, Florida • Puerto Plata • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,590
per Cabin
Departing on:
Aruban Sights & Antiguan Nights
San Juan • Oranjestad • Willemstad • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
SAVINGS TO WRITE HOME ABOUT
80% off your 2nd Sailor + free drinks
Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.
Cozumel, Grand Cayman & Bimini
Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Miami to the Cayman Islands
Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida
Getaways for 80% off 2nd Sailor
Fire & Sunset Soirées
Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,272
per Cabin
Departing on:
Cayman Isles & Jamaican Miles
Miami, Florida • George Town • Ocho Rios • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
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
Riviera Maya
Miami, Florida • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,590
per Cabin
Departing on:
Grand Turk Tranquility & St. Croix Charm
Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida
Getaways for 80% off 2nd Sailor
Miami, Grand Turk (& back)
Miami, Florida • Grand Turk • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,592
per Cabin
Departing on:
San Juan, Samaná & Bimini
Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
St. Kitts, Barbados, Martinique & More
San Juan • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
Miami to San Juan
Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,502
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
Cayman Coves & Jamaican Waterfalls
Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,948
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
San Juan Sunrises & Dominican Dreams
Miami, Florida • Puerto Plata • San Juan • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$2,086
per Cabin
Departing on:
Magnetic Miami to Gorgeous George Town
Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida
Getaways for 80% off 2nd Sailor
Cartagena, Aruba, Antigua & More
San Juan • Cartagena • Willemstad • Oranjestad • St. John's • St. Croix • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
From Miami to St. Croix
Miami, Florida • Puerto Plata • San Juan • Philipsburg • St. Croix • Miami, Florida
Getaways for 80% off 2nd Sailor
Antigua, Martinique, & Barbados & More
San Juan • Philipsburg • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan
Getaways for 80% off 2nd Sailor
Sunny Miles of Tropical Isles
San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan
Getaways for 80% off 2nd Sailor
Aruban Sunsets & Calm Cayman Days
Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida
Getaways for 80% off 2nd Sailor
Quaint Castries to Elegant Antigua
San Juan • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan
Getaways for 80% off 2nd Sailor
Gorgeous Antigua, St. Kitts & Bimini
Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Costa Mayan Caves & Honduran Waves
Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • 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
Puerto Rican Nights & St. Croix Delights
Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida
Getaways for 80% off 2nd Sailor
Panama Canal & Pacific Wonders
Miami, Florida • Cartagena • Colón • Panama Canal (Cruising) • Puntarenas • Puerto Quetzal • Cabo San Lucas • Los Angeles, California
Getaways for 80% off 2nd Sailor
Saint (Isles) & Seas of the Caribbean
San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg • San Juan
Getaways for 80% off 2nd Sailor
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
The Big Apple to Bermuda
New York City, New York • Kings Wharf • New York City, New York
Getaways for 80% off 2nd Sailor
Insider cabins from
Price$1,790
per Cabin
Departing on:
Brilliant Lady LA MerMaiden
Los Angeles, California • Santa Barbara, California • San Diego, California • Ensenada • Los Angeles, California
Getaways for 80% off 2nd Sailor
California (and Mexico) Dreamin'
Los Angeles, California • Cabo San Lucas • Mazatlàn • Los Angeles, California
Getaways for 80% off 2nd Sailor
Bermuda Beauty to East Coast Elegance
New York City, New York • Kings Wharf • Nassau • Charleston, South Carolina • New York City, New York
Getaways for 80% off 2nd Sailor
Puerto Plata, San Juan & Tortola
Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida
Getaways for 80% off 2nd Sailor
Hollywood Sunsets & Mexican Horizons
Los Angeles, California • Cabo San Lucas • Mazatlàn • Puerto Vallarta • Los Angeles, California
Getaways for 80% off 2nd Sailor
Transatlantic to Spain & Morocco
Miami, Florida • Gran Canaria • Casablanca • Valencia • Barcelona
Getaways for 80% off 2nd Sailor
LA Lights & Vancouver Vistas
Los Angeles, California • Catalina Island, California • San Francisco, California • Astoria, Oregon • Victoria • Vancouver
Getaways for 80% off 2nd Sailor