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Cruise Dates

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October 2026

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Celebrity Ascent

Celebrity Cruises

Mar 29, 2027 - Apr 9, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Jun 26, 2027 - Jul 3, 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

Jan 13, 2027 - Jan 21, 2027 (8 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Dec 17, 2027 - Dec 27, 2027 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

$3,599pp

Jim's Onboard Credit

20% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 5, 2027 - Mar 17, 2027 (12 Nights)

Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Tortola • Miami

Average Starting Price

4% OFF

Nov 29, 2026 - Dec 11, 2026 (12 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale

Average Starting Price

Feb 20, 2027 - Feb 27, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 22, 2027 - Jan 5, 2028 (14 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Tortola • Miami

Average Starting Price

$4,399pp

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!

Viking Sky

Viking

Dec 19, 2027 - Dec 29, 2027 (10 Nights)

Average Starting Price

Nov 21, 2027 - Dec 5, 2027 (14 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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jan 22, 2028 - Feb 2, 2028 (11 Nights)

Miami • Philipsburg, St. Maarten • Fort-De-France, Martinique • Castries, St. Lucia • Grenada • Oranjestad, Aruba • Miami

Average Starting Price

Jan 15, 2028 - Jan 25, 2028 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Fort-De-France, Martinique • Grenada • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • St John's, Antigua • St. John • San Juan, Puerto Rico

Average Starting Price

$4,500pp

Jim's Onboard Credit

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