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Windstar Cruises

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

San Juan, Puerto Rico • St. John's, Antigua and Barbuda • Gustavia, Saint Barthélemy • St. Kitts • St. Maarten • Jost Van Dyke, British Virgin Islands • Virgin Gorda / Prickly Pear, British Virgin Island • San Juan, Puerto Rico

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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Windstar Cruises

Dec 27, 2026 - Jan 17, 2027 (21 Nights)

Ha Long Bay • Cruising Halong Bay • At Sea • Hoi An, Vietnam • At Sea • Nha Trang, Vietnam • Cruising Saigon River • Ho Chi Minh, Vietnam • Ho Chi Minh, Vietnam • At Sea • Phnom Penh / Sihanoukville • Koh Kood, Thailand • Cruising Chao Phraya River • Bangkok, Thailand • Cruising Chao Phraya River • Koh Kood, Thailand • Ko Samui, Thailand • At Sea • At Sea • Singapore, Singapore • Singapore, Singapore • Port Klang, Malaysia • Grand Cayman • Krabi, Thailand • Ko Yao Noi, Thailand • Phuket, Thailand

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 27, 2026 - Jan 2, 2027 (6 Nights)

Fort Lauderdale • At Sea • Grand Cayman • Cozumel • At Sea • Bimini • 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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Celebrity Summit

Celebrity Cruises

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

Tampa • At Sea • Key West, Florida • Bimini • Nassau • At Sea • 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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Disney Cruise Line

Dec 27, 2026 - Dec 30, 2026 (3 Nights)

Port Canaveral (Orlando), Florida • Castaway Cay • At Sea • 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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36% OFF

Dec 27, 2026 - Jan 5, 2027 (9 Nights)

Buenos Aires, Argentina • At Sea • At Sea • Ilhabela, Brazil • Rio de Janeiro, Brazil • Copacabana, Brazil • Copacabana, Brazil • Ilha Grande, Brazil • At Sea • At Sea • Punta del Este, Uruguay • Buenos Aires, Argentina

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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61% OFF

Dec 27, 2026 - Jan 7, 2027 (11 Nights)

Port Canaveral (Orlando), Florida • At Sea • At Sea • Puerto Plata, Dominican Republic • At Sea • Nassau • Ocean Cay • Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Ocean Cay • 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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65% OFF

Dec 27, 2026 - Jan 7, 2027 (11 Nights)

Split, Croatia • Venice, Italy • At Sea • Katakalon, Greece • Heraklion, Greece • Rhodes, Greece • Limassol, Cyprus • Port Said, Egypt • Alexandria, Egypt • At Sea • At Sea • Split, Croatia

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!



Norwegian Cruise Line

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Great Stirrup Cay • At Sea • Ocho Rios, Jamaica • Grand Cayman • Cozumel • At Sea • 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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Nieuw Statendam

Holland America Line

Dec 27, 2026 - Jan 10, 2027 (14 Nights)

Fort Lauderdale • Nassau • At Sea • Grand Turk • Amber Cove, Dominican Republic • At Sea • Relaxaway Half Moon Cay, Bahamas • 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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34% OFF

Carnival Horizon

Carnival Cruise Line

Dec 27, 2026 - Jan 4, 2027 (8 Nights)

Miami • Celebration Key • Fun Day at Sea • Fun Day at Sea • Aruba • Curacao • Fun Day at Sea • Fun Day at Sea • Miami

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!



21% OFF

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

Itajaí, Brazil • Ilhabela, Brazil • Rio de Janeiro, Brazil • Ilha Grande, Brazil • Buzios, Brazil • Copacabana, Brazil • Copacabana, Brazil • Paranaguá, Brazil • Itajaí, Brazil

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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