Cruise Lines
Cruise Lines
Ships
Ships
Departure Ports
Departure Ports
Regions
Regions
Ports of Call
Ports of Call
Star Pride
Windstar Cruises
Dec 20, 2026 - Jan 3, 2027 (14 Nights)
San Juan, Puerto Rico • At Sea • St. George's, Grenada • Bequia, St Vincent and the Grenadines • Mayreau, St Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay • 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
$10,384 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!

Star Pride
Windstar Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • At Sea • St. George's, Grenada • Bequia, St Vincent and the Grenadines • Mayreau, St Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay • San Juan, Puerto Rico
Average Starting Price
$3,846 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 Flora
Celebrity Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Baltra Island, Ecuador • Egas Port, Ecuador • Rabida, Ecuador • Elizabeth Bay • Tagus Cove, Ecuador • Sullivan Bay • Bartolome Island, Ecuador • Las Bachas, Ecuador • Daphne Island, Ecuador • North Seymour Island, Ecuador • Puerto Baquerizo, Ecuador • Punta Pitt, Ecuador • Puerto Ayora, Ecuador • Baltra Island, Ecuador
Average Starting Price
$16,919 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
MSC Seascape
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Galveston • At Sea • At Sea • Costa Maya • Roatán, Honduras • Cozumel • At Sea • Galveston
Average Starting Price
$763 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!

Viking Aton
Viking
Dec 20, 2026 - Dec 31, 2026 (11 Nights)
Cairo, Egypt • Cairo, Egypt • Cairo, Egypt • Luxor, Egypt • Qena, Egypt • Luxor, Egypt • Esna, Egypt • Aswan, Egypt • Aswan, Egypt • Kom Ombo, Egypt • Edfu, Egypt • Luxor, Egypt • Cairo, Egypt • Cairo, Egypt
Average Starting Price
$6,999 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!

58% OFF
MSC Bellissima
MSC Cruises
Dec 20, 2026 - Dec 24, 2026 (4 Nights)
Keelung, Taiwan • Miyako, Japan • Naha, Japan • Ishigaki, Japan • Keelung, Taiwan
Average Starting Price
$491 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!

22% OFF
MSC World Europa
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Pointe-à-Pitre, Guadeloupe • St. Maarten • At Sea • St. John's, Antigua and Barbuda • St. Kitts • Dominica • Fort-de-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,369 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!

58% OFF
MSC Sinfonia
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Barcelona, Spain • Marseille, France • Genoa, Italy • Florence/Pisa, Italy • Rome, Italy • At Sea • Valencia, Spain • Barcelona, Spain
Average Starting Price
$831 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!

Nieuw Statendam
Holland America Line
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay, Bahamas • At Sea • Ocho Rios, Jamaica • George town, Cayman Islands • Cozumel • At Sea • Fort Lauderdale
Average Starting Price
$1,409 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!

25% OFF
MSC Musica
MSC Cruises
Dec 20, 2026 - Dec 26, 2026 (6 Nights)
São Paulo, Brazil • Ilhabela, Brazil • Rio de Janeiro, Brazil • Ilha Grande, Brazil • Buzios, Brazil • At Sea • Paranaguá, Brazil
Average Starting Price
$1,009 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!

35% OFF
MSC Musica
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
São Paulo, Brazil • Ilhabela, Brazil • Rio de Janeiro, Brazil • Ilha Grande, Brazil • Buzios, Brazil • At Sea • Paranaguá, Brazil • Itajaí, Brazil
Average Starting Price
$739 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!

22% OFF
MSC Seaview
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
São Paulo, Brazil • Camboriú, Brazil • At Sea • Punta del Este, Uruguay • Buenos Aires, Argentina • At Sea • At Sea • São Paulo, Brazil
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!

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