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57% OFF

Dec 19, 2026 - Jan 2, 2027 (14 Nights)

Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • At Sea • Puerto Plata, Dominican Republic • At Sea • At Sea • Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • At Sea • Cozumel • Costa Maya • At Sea • Port Canaveral (Orlando), Florida • Port Canaveral (Orlando), Florida

Average Starting Price

Jim's Onboard Credit

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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!

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Celebrity Silhouette

Celebrity Cruises

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

Fort Lauderdale • At Sea • At Sea • Curacao • Aruba • Bonaire • At Sea • At Sea • Fort Lauderdale

Average Starting Price

Jim's Onboard Credit

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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!

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23% OFF

MSC World Europa

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Fort-de-France, Martinique • Pointe-à-Pitre, Guadeloupe • St. Maarten • At Sea • St. John's, Antigua and Barbuda • St. Kitts • Dominica • Fort-de-France, Martinique

Average Starting Price

Jim's Onboard Credit

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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!

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56% OFF

MSC World America

Dec 19, 2026 - Jan 2, 2027 (14 Nights)

Miami • At Sea • Roatán, Honduras • Costa Maya • Cozumel • At Sea • Ocean Cay • Miami • At Sea • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • At Sea • At Sea • Ocean Cay • Miami

Average Starting Price

Jim's Onboard Credit

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Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

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Holland America Line

Dec 19, 2026 - Jan 2, 2027 (14 Nights)

Fort Lauderdale • At Sea • Grand Turk • San Juan, Puerto Rico • St. Thomas • At Sea • Relaxaway Half Moon Cay, Bahamas • Fort Lauderdale • Relaxaway Half Moon Cay, Bahamas • At Sea • Ocho Rios, Jamaica • Grand Cayman • Cozumel • At Sea • Fort Lauderdale

Average Starting Price

Jim's Onboard Credit

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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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Holland America Line

Dec 19, 2026 - Jan 2, 2027 (14 Nights)

Miami • At Sea • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay, Bahamas • At Sea • Key West, Florida • Miami • At Sea • Grand Turk • San Juan, Puerto Rico • St. Thomas • At Sea • Relaxaway Half Moon Cay, Bahamas • Miami

Average Starting Price

Jim's Onboard Credit

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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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Norwegian Cruise Line

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Galveston • At Sea • Cozumel • Roatán, Honduras • Harvest Caye, Belize • Costa Maya • At Sea • Galveston

Average Starting Price

Jim's Onboard Credit

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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!



Holland America Line

Dec 19, 2026 - Jan 3, 2027 (15 Nights)

San Diego • At Sea • Cabo San Lucas • Puerto Vallarta, Mexico • At Sea • Huatulco, Mexico • At Sea • Puerto Quetzal, Guatemala • At Sea • Puntarenas, Costa Rica • At Sea • Panama Canal • Panama Canal • Panama Canal • Cartagena, Colombia • At Sea • At Sea • Fort Lauderdale

Average Starting Price

Jim's Onboard Credit

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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!

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Pride of America

Norwegian Cruise Line

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Honolulu • Kahului, Hawaii • Kahului, Hawaii • Hilo, Hawaii • Kona, Hawaii • Nawiliwili, Hawaii • Nawiliwili, Hawaii • Napali Coast, Hawaii • Honolulu

Average Starting Price

Jim's Onboard Credit

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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!

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Adventure of the Seas

Royal Caribbean

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

Fort Lauderdale • Nassau • At Sea • Cabo Rojo, Dominican Republic • Curacao • Aruba • At Sea • At Sea • Fort Lauderdale

Average Starting Price

Jim's Onboard Credit

FREE Specialty Dining Meal

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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!



Holland America Line

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Fort Lauderdale • At Sea • Grand Turk • San Juan, Puerto Rico • St. Thomas • At Sea • Relaxaway Half Moon Cay, Bahamas • Fort Lauderdale

Average Starting Price

Jim's Onboard Credit

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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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38% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Dec 19, 2026 - Dec 23, 2026 (4 Nights)

Tampa • At Sea • Cozumel • At Sea • Tampa

Average Starting Price

Jim's Onboard Credit

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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!

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