Cruise Lines
Cruise Lines
Ships
Ships
Departure Ports
Departure Ports
Regions
Regions
Ports of Call
Ports of Call
Seabourn Ovation
Seabourn
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Barbados • St. Lucia • At Sea • Little Bay • St. John's, Antigua and Barbuda • St. Kitts • Great Harbour, British Virgin Islands • St. Maarten • Soper's Hole, British Virgin Islands • St. Kitts • At Sea • Les Trois-Îlets, Martinique • Bequia, St Vincent and the Grenadines • St. George's, Grenada • Barbados
Average Starting Price
$8,619 pp
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!

Seabourn Ovation
Seabourn
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Barbados • St. Lucia • At Sea • Little Bay • St. John's, Antigua and Barbuda • St. Kitts • Great Harbour, British Virgin Islands • St. Maarten
Average Starting Price
$4,069 pp
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!

Icon of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Miami • At Sea • At Sea • St. Maarten • St. Thomas • At Sea • Perfect Day Cococay • Miami
Average Starting Price
$2,009 pp
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!

53% 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
$529 pp
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!

Celebrity Apex
Celebrity Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • At Sea • Puerto Plata, Dominican Republic • St. Thomas • St. Kitts • At Sea • At Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,512 pp
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!

Insignia
Oceania Cruises
Dec 19, 2026 - Jan 24, 2027 (36 Nights)
Miami • Key West, Florida • At Sea • At Sea • Curacao • Aruba • Santa Marta, Colombia • Cartagena, Colombia • Panama Canal • At Sea • At Sea • Manta, Ecuador • Guayaquil, Ecuador • At Sea • Lima, Peru • Lima, Peru • Pisco, Peru • At Sea • At Sea • Coquimbo, Chile • Santiago, Chile • At Sea • Puerto Montt, Chile • Puerto Chacabuco, Chile • Laguna San Rafael, Chile • Cruising the Chilean Fjords • Cruising the Chilean Fjords • Punta Arenas, Chile • Cape Horn • Ushuaia, Argentina • At Sea • Port Stanley, Falkland Islands • At Sea • Puerto Madryn, Argentina • At Sea • Punta Del Este • Buenos Aires, Argentina
Average Starting Price
$11,499 pp
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!

Insignia
Oceania Cruises
Dec 19, 2026 - Jan 3, 2027 (15 Nights)
Miami • Key West, Florida • At Sea • At Sea • Curacao • Aruba • Santa Marta, Colombia • Cartagena, Colombia • Panama Canal • At Sea • At Sea • Manta, Ecuador • Guayaquil, Ecuador • At Sea • Lima, Peru • Lima, Peru
Average Starting Price
$4,399 pp
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!

Zuiderdam
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
$2,769 pp
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!

Celestyal Discovery
Celestyal Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Tarragona, Spain • Tarragona, Spain • At Sea • Malaga, Spain • Gibraltar, Gibraltar • Casablanca, Morocco • Cádiz, Spain • Lisbon, Portugal
Average Starting Price
$649 pp
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!

Celestyal Discovery
Celestyal Cruises
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Tarragona, Spain • Tarragona, Spain • At Sea • Malaga, Spain • Gibraltar, Gibraltar • Casablanca, Morocco • Cádiz, Spain • Lisbon, Portugal • Lisbon, Portugal • Tangier, Morocco • At Sea • Valencia, Spain • Palma, Spain • Sete, France • Tarragona, Spain
Average Starting Price
$1,299 pp
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!

Celestyal Discovery
Celestyal Cruises
Dec 19, 2026 - Jan 10, 2027 (22 Nights)
Tarragona, Spain • Tarragona, Spain • At Sea • Malaga, Spain • Gibraltar, Gibraltar • Casablanca, Morocco • Cádiz, Spain • Lisbon, Portugal • Lisbon, Portugal • Tangier, Morocco • At Sea • Valencia, Spain • Palma, Spain • Sete, France • Tarragona, Spain • Tarragona, Spain • Nice, France • Rome, Italy • Napoli, Italy • Messina, Italy • At Sea • Kusadasi, Turkey • Athens, Greece
Average Starting Price
$1,419 pp
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
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
Miami • At Sea • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Maarten • At Sea • At Sea • Bimini • Miami
Average Starting Price
$1,192 pp
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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