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October 2026

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Viking Sea

Viking

Nov 27, 2027 - Dec 7, 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

Nov 29, 2027 - Dec 9, 2027 (10 Nights)

Average Starting Price

Mar 12, 2027 - Apr 2, 2027 (21 Nights)

Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

$4,154pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Grandeur of the Seas

Royal Caribbean

Oct 23, 2027 - Oct 30, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

8% OFF

Nov 22, 2027 - Dec 19, 2027 (27 Nights)

Fort Lauderdale • Cozumel • Belize City • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Limon, Costa Rica • Colon, Panama • Cartagena, Colombia • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Pointe-à-Pitre, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale • Roseau, Dominica • St John's, Antigua • Gustavia, St. Barts • Tortola • Fort Lauderdale

Average Starting Price

Mar 29, 2027 - Apr 5, 2027 (7 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico

Average Starting Price

Dec 23, 2027 - Dec 30, 2027 (7 Nights)

Miami • St. Thomas • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$4,685pp

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!

Norwegian Prima

Norwegian Cruise Line

Nov 27, 2027 - Dec 4, 2027 (7 Nights)

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

Average Starting Price

31% OFF

Jan 29, 2028 - Feb 12, 2028 (14 Nights)

Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • St John's, Antigua • St. Lucia • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston

Average Starting Price

$1,326pp

Jim's Onboard Credit

25% OFF

Seven Seas Voyager

Regent Seven Seas Cruises

Dec 19, 2027 - Jan 13, 2028 (25 Nights)

Miami • Tortola • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Jan 19, 2029 - Mar 31, 2029 (71 Nights)

Fort Lauderdale • Grand Turk • Samana, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • St. Kitts • St. Barts/Gustavia, French West Indies • San Juan, Puerto Rico • St. Barts/Gustavia, French West Indies • Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Scarborough (Tobago), Trinidad and Tobago • Devil's Island, France • Fortaleza, Brazil • Recife, Brazil • Maceio, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Santos (Sao Paulo), Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Punta del Este, Uruguay • Puerto Madryn, Argentina • Port Stanley, Falkland Islands • Ushuaia, Argentina • Cruising the Cape Horn • Punta Arenas, Chile • Cruising the Chilean Fjords • Cruising the Chilean Fjords • Laguna San Rafael, Chile • Chacabuco, Chile • Castro, Chile • Puerto Montt, Chile • Valparaíso, Chile • Valparaíso, Chile • Bahia CoQuimbo, Chile • Iquique, Chile • General San Martin, Peru • Lima, Peru • Salaverry (Trujillo), Peru • Manta, Ecuador • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • Roatan Island, Honduras • Santo Tomas de Castilla, Guatemala • Belize City • Cozumel • Progreso, Mexico • Fort Lauderdale

Average Starting Price

$47,000pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

49% OFF

MSC Seashore

MSC Cruises

Nov 20, 2027 - Dec 5, 2027 (15 Nights)

Miami • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Miami • Ocean Cay • Puerto Plata, Dominican Republic • Grand Turk • Miami

Average Starting Price

$1,540pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

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