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Cruise Dates

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October 2026

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Celebrity Constellation

Celebrity Cruises

Feb 13, 2027 - Feb 20, 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

Jan 8, 2028 - Jan 18, 2028 (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

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

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St. Croix • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$553pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Seabourn Quest

Seabourn

Dec 6, 2026 - Dec 20, 2026 (14 Nights)

Miami • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Little Bay, Montserrat • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

Feb 24, 2027 - Mar 6, 2027 (10 Nights)

Average Starting Price

Jan 5, 2028 - Mar 22, 2028 (77 Nights)

Miami • Cozumel • Belize City • Roatan, Honduras • Limon, Costa Rica • Bocas Del Toro, Panama • Panama Canal (Cruising) • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Manta, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • La Serena (Coquimbo), Chile • Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Sailing In The Chilean Fjords • Sailing In The Chilean Fjords • Punta Arenas, Chile • Punta Arenas, Chile • Ushuaia, Argentina • Sailing Snow Island • Sailing Bransfield Strait • Sailing Gerlache Strait • Sailing Paradise Bay • Sailing Wilhelmina Bay • Sailing Penguin Island • Sailing King George Island • Port Stanley, Falkland Islands • Punta del Este, Uruguay • Montevideo, Uruguay • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Saint George's, Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Nov 13, 2028 - Dec 5, 2028 (22 Nights)

Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami

Average Starting Price

$8,699pp

Jim's Onboard Credit

19% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Dec 19, 2026 - Dec 29, 2026 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

$11,799pp

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!

Vision of the Seas

Royal Caribbean

Dec 19, 2027 - Dec 27, 2027 (8 Nights)

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

Average Starting Price

Mar 11, 2028 - Mar 18, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Fort-De-France, Martinique • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 8, 2027 - Jan 17, 2027 (9 Nights)

Fort Lauderdale • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Jan 25, 2027 - Feb 5, 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

$3,558pp

Jim's Onboard Credit

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