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Cruise Dates

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October 2026

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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

Feb 29, 2028 - Mar 4, 2028 (4 Nights)

Fort Lauderdale • Key West, Florida • Nassau • Fort Lauderdale

Average Starting Price

Feb 18, 2027 - Feb 22, 2027 (4 Nights)

Miami • Key West, Florida • Bimini • Miami

Average Starting Price

Nov 20, 2027 - Nov 27, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Key West, Florida • George Town, Cayman Islands • Grand Bahama Island • Port Canaveral (Orlando), Florida

Average Starting Price

Nov 21, 2027 - Nov 27, 2027 (6 Nights)

Fort Lauderdale • Nassau • George Town, Cayman Islands • Key West, Florida • Fort Lauderdale

Average Starting Price

46% OFF

Apr 10, 2027 - Apr 17, 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

Jan 20, 2027 - Jan 29, 2027 (9 Nights)

Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami

Average Starting Price

$6,260pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

Tampa • Key West, Florida • Belize City • Costa Maya • Tampa

Average Starting Price

Jan 23, 2028 - Jan 29, 2028 (6 Nights)

Miami • Key West, Florida • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

Dec 7, 2028 - Dec 19, 2028 (12 Nights)

Miami • Key West, Florida • St. John • St John's, Antigua • Road Bay, Anguilla • St. Kitts • Virgin Gorda, British Virgin Islands • Grand Turk • Miami

Average Starting Price

$5,900pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Vista

Oceania Cruises

Dec 28, 2028 - Jan 7, 2029 (10 Nights)

Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami

Average Starting Price

$5,149pp

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!

EXPLORA IV

Explora Journeys

Mar 4, 2028 - Mar 11, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami

Average Starting Price

$3,915pp

Jim's Onboard Credit

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