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4% OFF
Carnival Horizon
Carnival Cruise Line
Jan 10, 2027 - Jan 16, 2027 (6 Nights)
Miami • Celebration Key • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami
Average Starting Price
$409pp
Jim's Onboard Credit
32% OFF
Carnival Breeze
Carnival Cruise Line
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Isla Tropicale, Roatan • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,148pp
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!

Resilient Lady
Virgin Voyages
Jan 23, 2028 - Jan 29, 2028 (6 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Bimini • Miami
Average Starting Price
$774pp
Jim's Onboard Credit
Vista
Oceania Cruises
Nov 25, 2028 - Dec 5, 2028 (10 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$4,199pp
Jim's Onboard Credit
Celebrity Beyond
Celebrity Cruises
Jan 23, 2028 - Jan 29, 2028 (6 Nights)
Fort Lauderdale • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$869pp
Jim's Onboard Credit
14% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Dec 29, 2026 - Jan 14, 2027 (16 Nights)
Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Acapulco, Mexico • Cabo San Lucas • San Diego • Los Angeles
Average Starting Price
$15,349pp
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!

36% OFF
Carnival Liberty
Carnival Cruise Line
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
New Orleans • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fun Day at Sea • New Orleans
Average Starting Price
$844pp
Jim's Onboard Credit
Radiance of the Seas
Royal Caribbean
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
Tampa • Cozumel • Costa Maya • George Town, Cayman Islands • Tampa
Average Starting Price
$682pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Gem
Norwegian Cruise Line
Jan 4, 2027 - Jan 14, 2027 (10 Nights)
Tampa • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Tampa
Average Starting Price
$899pp
Jim's Onboard Credit
Explorer of the Seas
Royal Caribbean
Dec 21, 2026 - Dec 28, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Grand Bahama Island • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,437pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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 Jewel
Norwegian Cruise Line
Jan 4, 2027 - Jan 14, 2027 (10 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$739pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 29, 2026 - Jan 10, 2027 (12 Nights)
Fort Lauderdale • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal Partial Transit New Locks, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale
Average Starting Price
$1,359pp
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!

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