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Caribbean Princess
Princess Cruises
Dec 22, 2028 - Jan 2, 2029 (11 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados
Average Starting Price
$1,870pp
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!

Norwegian Pearl
Norwegian Cruise Line
Dec 8, 2026 - Dec 18, 2026 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$609pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Feb 25, 2029 - Mar 11, 2029 (14 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,634pp
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!

Celebrity Summit
Celebrity Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Tampa • Nassau • Bimini • Cozumel • Tampa
Average Starting Price
$905pp
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 • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$4,392pp
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!

Norwegian Dawn
Norwegian Cruise Line
Jan 2, 2027 - Jan 7, 2027 (5 Nights)
Jacksonville • Great Stirrup Cay • Grand Bahama Island • Jacksonville
Average Starting Price
$249pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Dec 5, 2026 - Dec 13, 2026 (8 Nights)
Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort Lauderdale
Average Starting Price
$1,661pp
Jim's Onboard Credit
Adventure of the Seas
Royal Caribbean
Mar 21, 2027 - Mar 27, 2027 (6 Nights)
Fort Lauderdale • Falmouth, Jamaica • George Town, Cayman Islands • Nassau • Fort Lauderdale
Average Starting Price
$754pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Wind Surf
Windstar Cruises
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,677pp
Jim's Onboard Credit
Disney Magic
Disney Cruise Line
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Galveston • Nassau • Disney Castaway Cay, Bahamas • Galveston
Average Starting Price
$2,943pp
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!

Norwegian Joy
Norwegian Cruise Line
Dec 26, 2026 - Dec 31, 2026 (5 Nights)
Miami • Cozumel • Great Stirrup Cay • Miami
Average Starting Price
$749pp
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!

29% OFF
Carnival Liberty
Carnival Cruise Line
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
New Orleans • Fun Day at Sea • Fun Day at Sea • Isla Tropicale, Roatan • Belize City • Cozumel • Fun Day at Sea • New Orleans
Average Starting Price
$1,249pp
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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