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Cruise Dates

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October 2026

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50% OFF

MSC Opera

MSC Cruises

Jul 19, 2027 - Jul 26, 2027 (7 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic

Average Starting Price

Feb 21, 2027 - Mar 7, 2027 (14 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

47% OFF

Oct 30, 2027 - Nov 20, 2027 (21 Nights)

Marseille (Provence), France • Genoa (Portofino), Italy • Naples, Italy • Messina (Taormina), Italy • Valletta, Malta • Barcelona, Spain • Palma de Mallorca, Spain • Alicante, Spain • Malaga, Spain • Las Palmas (Gran Canaria), Spain • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique

Average Starting Price

Jan 30, 2028 - Feb 6, 2028 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jul 10, 2027 - Jul 17, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

12% OFF

Apr 4, 2027 - Apr 11, 2027 (7 Nights)

Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

Aug 29, 2027 - Oct 9, 2027 (41 Nights)

Kangerlussuaq, Greenland • Nuuk (Godthaab), Greenland • Iqaluit, Canada • Diana Island, Canada • Erik Cove, Quebec • The Seabourn Northwest Passage Experience • Fury and Hecla Strait, Canada • The Seabourn Northwest Passage Experience • The Seabourn Northwest Passage Experience • The Seabourn Northwest Passage Experience • Cambridge Bay, Nunavut • The Seabourn Northwest Passage Experience • The Seabourn Northwest Passage Experience • Sisimiut (Holsteinsborg), Greenland • Evighed Fjord, Greenland • Kangerlussuaq, Greenland • Nuuk (Godthaab), Greenland • Pangnirtung, Nunavut • Kekerten Island, Nunavut • Lady Franklin Island, Canada • Monumental Island (Nunavut), Canada • Lower Savage Islands, Canada • Resolution Island, Nunavut, Canada • Nachvak Fiord, Torngat Mts, Canada • Ramah Bay, Torngat Mts, Canada • Rose Island, Bahamas • Hebron, Canada • Nain, Canada • Indian Harbour, Newfoundland • Battle Harbour, Labrador • L'Anse aux Meadows, Newfoundland • Halifax, Nova Scotia • Carambola Beach, Saint Kitts and Nevis • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

$1,869pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$710pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Dec 25, 2027 - Jan 1, 2028 (7 Nights)

San Juan, Puerto Rico • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Tortola • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$1,959pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Scarlet Lady

Virgin Voyages

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Mar 18, 2028 - Mar 25, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$787pp

Jim's Onboard Credit

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