Cruise Lines
Cruise Lines
Ships
Ships
Departure Ports
Departure Ports
Regions
Regions
Ports of Call
Ports of Call
Wind Surf
Windstar Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
St. Maarten • Gustavia, Saint Barthélemy • Falmouth Harbour • Road Bay • Soper's Hole, British Virgin Islands • Jost Van Dyke, British Virgin Islands • Jost Van Dyke, British Virgin Islands • Virgin Gorda / Prickly Pear, British Virgin Island • St. Maarten
Average Starting Price
$3,148 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 - 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
$8,718 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
$3,773 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!

Anthem of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 28, 2026 (9 Nights)
Sydney, Australia • At Sea • At Sea • Bay of Islands, New Zealand • Auckland, New Zealand • Tauranga, New Zealand • At Sea • At Sea • At Sea • Sydney, Australia
Average Starting Price
$2,062 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!

Silver Spirit
Silversea
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
Barbados • Bequia, St Vincent and the Grenadines • Fort-de-France, Martinique • Dominica • St. Kitts • St. John's, Antigua and Barbuda • At Sea • St. Lucia • Barbados
Average Starting Price
$3,700 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!

Wind Star
Windstar Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Colón, Panama • Panama Canal • Fuerte Amador, Panama • Fuerte Amador, Panama • At Sea • Isla Parida, Panama • Puerto Jiménez, Costa Rica • Quepos, Costa Rica • Puerto Caldera, Costa Rica
Average Starting Price
$3,765 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!

Disney Treasure
Disney Cruise Line
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • At Sea • At Sea • Tortola • St. Thomas • At Sea • Castaway Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$2,953 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
$1,272 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!

52% OFF
Carnival Liberty
Carnival Cruise Line
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
New Orleans • Fun Day at Sea • Fun Day at Sea • Nassau • Relaxaway Half Moon Cay, Bahamas • Celebration Key • Fun Day at Sea • Fun Day at Sea • New Orleans
Average Starting Price
$641 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!

38% OFF
Carnival Breeze
Carnival Cruise Line
Dec 19, 2026 - Dec 23, 2026 (4 Nights)
Galveston • Fun Day at Sea • Cozumel • Fun Day at Sea • Galveston
Average Starting Price
$576 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!

36% OFF
Carnival Freedom
Carnival Cruise Line
Dec 19, 2026 - Dec 23, 2026 (4 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Relaxaway Half Moon Cay, Bahamas • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$539 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!

Caribbean Breeze Travel Logo
Hours: 24/7
Site Links
FAQ
Contact Us
Transfer Cruise
My Booking
Welcome to the CBT Family!
Contact Us Cruise Search