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Sky Princess
Princess Cruises
Nov 21, 2027 - Dec 5, 2027 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$1,608pp
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
Seven Seas Grandeur
Regent Seven Seas Cruises
Dec 22, 2027 - Jan 6, 2028 (15 Nights)
Miami • Key West, Florida • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Limon, Costa Rica • Colon, Panama • Panama Canal, Panama • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$10,549pp
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!

Explorer of the Seas
Royal Caribbean
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
Fort Lauderdale • Labadee, Haiti • Falmouth, Jamaica • Costa Maya • Fort Lauderdale
Average Starting Price
$778pp
Jim's Onboard Credit
Vista
Oceania Cruises
Oct 30, 2028 - Nov 13, 2028 (14 Nights)
New York, New York • Nassau • Puerto Plata, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$5,699pp
Jim's Onboard Credit
Norwegian Jewel
Norwegian Cruise Line
Dec 20, 2027 - Dec 30, 2027 (10 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$1,559pp
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!

Independence of the Seas
Royal Caribbean
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
Miami • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Costa Maya • Miami
Average Starting Price
$1,473pp
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 Escape
Norwegian Cruise Line
Sep 10, 2028 - Sep 17, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$949pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 1, 2027 - Dec 22, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$4,894pp
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!

Norwegian Gem
Norwegian Cruise Line
Mar 12, 2027 - Mar 20, 2027 (8 Nights)
Tampa • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • Nassau • Tampa
Average Starting Price
$789pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$629pp
Jim's Onboard Credit
51% OFF
MSC Seaside
MSC Cruises
Dec 21, 2026 - Jan 4, 2027 (14 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Ocean Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Miami
Average Starting Price
$1,913pp
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!

Symphony of the Seas
Royal Caribbean
Jan 9, 2028 - Jan 15, 2028 (6 Nights)
Fort Lauderdale • Nassau • Perfect Day Cococay • Falmouth, Jamaica • Fort Lauderdale
Average Starting Price
$746pp
Jim's Onboard Credit
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