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Cruise Dates

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October 2026

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Silver Nova

Silversea

Dec 21, 2028 - Jan 3, 2029 (13 Nights)

Fort Lauderdale • San Juan del sur, Nicaragua • Gustavia, St. Barts • St. Kitts • Roseau, Dominica • Willemstad, Curacao • Oranjestad, Aruba • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

$8,700pp

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!

Rotterdam

Holland America Line

Dec 29, 2027 - Jan 15, 2028 (17 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,369pp

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!

Crown Princess

Princess Cruises

Dec 19, 2026 - Dec 27, 2026 (8 Nights)

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Apr 29, 2028 - May 6, 2028 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2027 - Dec 18, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

Nov 17, 2026 - Dec 5, 2026 (18 Nights)

Miami • Progreso, Mexico • Roatan, Honduras • Belize City • Ocean Cay • Miami • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • George Town, Cayman Islands • Miami

Average Starting Price

$19,980pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Jan 12, 2028 - Jan 21, 2028 (9 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami

Average Starting Price

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

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

$2,629pp

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!

40% OFF

Carnival Liberty

Carnival Cruise Line

Nov 29, 2026 - Dec 13, 2026 (14 Nights)

New Orleans • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Fun Day at Sea • Cozumel • Fun Day at Sea • New Orleans

Average Starting Price

Nov 21, 2027 - Dec 22, 2027 (31 Nights)

Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Costa Maya • Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

Mar 6, 2027 - Mar 19, 2027 (13 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale • Princess Cays • Grand Turk • Fort Lauderdale

Average Starting Price

$1,924pp

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!

Oosterdam

Holland America Line

Jan 2, 2028 - Jan 23, 2028 (21 Nights)

Average Starting Price

$5,089pp

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!

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