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Norwegian Escape
Norwegian Cruise Line
May 21, 2028 - May 28, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,229pp
Jim's Onboard Credit
Nieuw Statendam
Holland America Line
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,284pp
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 Jewel
Norwegian Cruise Line
Jan 3, 2028 - Jan 13, 2028 (10 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$1,249pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Mar 26, 2028 - Apr 1, 2028 (6 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Nassau • Fort Lauderdale
Average Starting Price
$1,415pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings
60% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
Dec 23, 2027 - Dec 28, 2027 (5 Nights)
Tampa • Key West, Florida • George Town, Cayman Islands • Tampa
Average Starting Price
$829pp
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 Epic
Norwegian Cruise Line
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$569pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Nov 16, 2028 - Dec 3, 2028 (17 Nights)
Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Corinto, Nicaragua • Puerto Quetzal, Guatemala • Acapulco, Mexico • Puerto Vallarta, Mexico • Los Angeles
Average Starting Price
$8,399pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
Tampa • Bimini • Key West, Florida • George Town, Cayman Islands • Tampa
Average Starting Price
$642pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Nov 21, 2026 - Dec 5, 2026 (14 Nights)
Miami • Key West, Florida • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Miami
Average Starting Price
$2,024pp
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!

6% OFF
Carnival Horizon
Carnival Cruise Line
Feb 21, 2027 - Feb 27, 2027 (6 Nights)
Miami • Celebration Key • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami
Average Starting Price
$434pp
Jim's Onboard Credit
45% OFF
Carnival Venezia
Carnival Cruise Line
Aug 29, 2027 - Sep 4, 2027 (6 Nights)
Miami • Celebration Key • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami
Average Starting Price
$510pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Jun 20, 2027 - Jun 27, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,349pp
Jim's Onboard Credit
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