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52% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
Sep 4, 2027 - Sep 9, 2027 (5 Nights)
Tampa • Key West, Florida • Cozumel • Tampa
Average Starting Price
$399pp
Jim's Onboard Credit
54% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Sep 4, 2027 - Sep 9, 2027 (5 Nights)
Miami • Key West, Florida • Bimini • Freeport • Miami
Average Starting Price
$549pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 2, 2027 - Feb 23, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$4,249pp
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!

Brilliance of the Seas
Royal Caribbean
Jan 25, 2027 - Jan 29, 2027 (4 Nights)
Fort Lauderdale • Key West, Florida • Bimini • Fort Lauderdale
Average Starting Price
$661pp
Jim's Onboard Credit
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
Celebrity Summit
Celebrity Cruises
Mar 4, 2028 - Mar 9, 2028 (5 Nights)
Fort Lauderdale • Costa Maya • Key West, Florida • Fort Lauderdale
Average Starting Price
$448pp
Jim's Onboard Credit
46% OFF
Carnival Dream
Carnival Cruise Line
Mar 27, 2027 - Apr 3, 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
$686pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Dec 5, 2027 - Dec 11, 2027 (6 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Nassau • Fort Lauderdale
Average Starting Price
$510pp
Jim's Onboard Credit
Norwegian Dawn
Norwegian Cruise Line
Jan 19, 2027 - Jan 24, 2027 (5 Nights)
Jacksonville • Key West, Florida • Great Stirrup Cay • Jacksonville
Average Starting Price
$319pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 11, 2027 - Jan 29, 2027 (18 Nights)
Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami
Average Starting Price
$9,975pp
Jim's Onboard Credit
Vista
Oceania Cruises
Nov 13, 2028 - Dec 5, 2028 (22 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$8,699pp
Jim's Onboard Credit
Silver Ray
Silversea
Feb 4, 2029 - Feb 15, 2029 (11 Nights)
Miami • St. John • Road Bay, Anguilla • St John's, Antigua • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Key West, Florida • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
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