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46% OFF
Carnival Liberty
Carnival Cruise Line
Aug 29, 2027 - Sep 5, 2027 (7 Nights)
New Orleans • Fun Day at Sea • Key West, Florida • Celebration Key • Nassau • Fun Day at Sea • Fun Day at Sea • New Orleans
Average Starting Price
$568pp
Jim's Onboard Credit
Norwegian Gem
Norwegian Cruise Line
Feb 12, 2027 - Feb 21, 2027 (9 Nights)
Tampa • Key West, Florida • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Falmouth, Jamaica • George Town, Cayman Islands • Tampa
Average Starting Price
$1,029pp
Jim's Onboard Credit
38% OFF
Margaritaville at Sea Paradise
Margaritaville at Sea
May 10, 2027 - May 14, 2027 (4 Nights)
Palm Beach • Key West, Florida • Freeport • Palm Beach
Average Starting Price
$229pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 13, 2027 - Mar 6, 2027 (21 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,109pp
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!

55% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
May 22, 2027 - May 27, 2027 (5 Nights)
Tampa • Key West, Florida • Progreso, Mexico • Tampa
Average Starting Price
$449pp
Jim's Onboard Credit
59% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jun 26, 2027 - Jul 3, 2027 (7 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Miami
Average Starting Price
$829pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Nov 7, 2027 - Nov 13, 2027 (6 Nights)
Fort Lauderdale • Key West, Florida • Cozumel • George Town, Cayman Islands • Fort Lauderdale
Average Starting Price
$723pp
Jim's Onboard Credit
46% OFF
Carnival Dream
Carnival Cruise Line
Apr 24, 2027 - May 1, 2027 (7 Nights)
Galveston • Fun Day at Sea • Key West, Florida • Celebration Key • Nassau • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$676pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Jan 6, 2028 - Jan 15, 2028 (9 Nights)
Miami • Cozumel • Costa Maya • Santo Tomas de Castilla, Guatemala • Belize City • Key West, Florida • Ocean Cay • Miami
Average Starting Price
$5,375pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Nov 6, 2027 - Nov 13, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Key West, Florida • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$794pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 20, 2027 - Feb 5, 2027 (16 Nights)
Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$9,185pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Nov 21, 2027 - Nov 28, 2027 (7 Nights)
Tampa • Grand Bahama Island • Key West, Florida • George Town, Cayman Islands • Tampa
Average Starting Price
$784pp
Jim's Onboard Credit
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