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Celebrity Apex
Celebrity Cruises
Apr 17, 2027 - Apr 24, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Key West, Florida • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,248pp
Jim's Onboard Credit
49% OFF
MSC Grandiosa
MSC Cruises
Nov 18, 2027 - Nov 28, 2027 (10 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Port Canaveral (Orlando), Florida • Ocean Cay • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$1,045pp
Jim's Onboard Credit
Norwegian Gem
Norwegian Cruise Line
Nov 30, 2027 - Dec 11, 2027 (11 Nights)
Miami • Great Stirrup Cay • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$1,519pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Oct 30, 2027 - Nov 27, 2027 (28 Nights)
Miami • Nassau • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • Santa Domingo, Dominican Republic • San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Castries, St. Lucia • Port of Spain, Trinidad • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Belize City • Cozumel • Progreso, Mexico • Miami
Average Starting Price
$6,584pp
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 Princess
Princess Cruises
Mar 28, 2027 - Apr 9, 2027 (12 Nights)
Fort Lauderdale • George Town, Cayman Islands • Ocho Rios, Jamaica • Limon, Costa Rica • Colon, Panama • Oranjestad, Aruba • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$874pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Mar 28, 2027 - Apr 4, 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
$629pp
Jim's Onboard Credit
Eurodam
Holland America Line
Nov 21, 2027 - Dec 1, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$2,574pp
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!

40% OFF
Carnival Horizon
Carnival Cruise Line
Mar 21, 2027 - Mar 27, 2027 (6 Nights)
Miami • Celebration Key • Fun Day at Sea • Ocho Rios, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami
Average Starting Price
$633pp
Jim's Onboard Credit
Norwegian Sun
Norwegian Cruise Line
Mar 24, 2027 - Apr 5, 2027 (12 Nights)
Miami • Ocho Rios, Jamaica • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$1,649pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
New York, New York • Tortola • St John's, Antigua • Basseterre, St. Kitts and Nevis • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$4,149pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Dec 20, 2027 - Dec 27, 2027 (7 Nights)
Miami • George Town, Cayman Islands • Ocho Rios, Jamaica • Bimini • Miami
Average Starting Price
$1,113pp
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!

42% OFF
Carnival Spirit
Carnival Cruise Line
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Tampa • Fun Day at Sea • George Town, Cayman Islands • Ocho Rios, Jamaica • Fun Day at Sea • Cozumel • Fun Day at Sea • Tampa
Average Starting Price
$679pp
Jim's Onboard Credit
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