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Cruise Dates

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October 2026

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Resilient Lady

Virgin Voyages

Apr 4, 2027 - Apr 11, 2027 (7 Nights)

Miami • Key West, Florida • Ocho Rios, Jamaica • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

Feb 20, 2028 - Feb 26, 2028 (6 Nights)

Fort Lauderdale • George Town, Cayman Islands • Falmouth, Jamaica • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

48% OFF

Mar 5, 2028 - Mar 19, 2028 (14 Nights)

Miami • Nassau • Ocean Cay • George Town, Cayman Islands • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

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!

54% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

May 15, 2027 - May 22, 2027 (7 Nights)

Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami

Average Starting Price

Jun 12, 2027 - Jun 19, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

Fort Lauderdale • Bimini • Nassau • Cozumel • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

47% OFF

Nov 11, 2027 - Dec 2, 2027 (21 Nights)

Miami • Kralendijk, Bonaire • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami

Average Starting Price

$2,060pp

Jim's Onboard Credit

Norwegian Sun

Norwegian Cruise Line

Feb 6, 2027 - Feb 17, 2027 (11 Nights)

Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Harvest Caye, Belize • Cozumel • Miami

Average Starting Price

$1,499pp

Jim's Onboard Credit

Brilliance of the Seas

Royal Caribbean

Mar 4, 2028 - Mar 12, 2028 (8 Nights)

Tampa • George Town, Cayman Islands • Cozumel • Roatan, Honduras • Costa Maya • Tampa

Average Starting Price

Dec 30, 2026 - Jan 10, 2027 (11 Nights)

Fort Lauderdale • Cozumel • Belize City • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Fort Lauderdale

Average Starting Price

$5,600pp

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!

26% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Feb 6, 2028 - Feb 16, 2028 (10 Nights)

Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Falmouth • George Town, Cayman Islands • Miami

Average Starting Price

$8,699pp

Jim's Onboard Credit

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