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Cruise Dates

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October 2026

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42% OFF

Margaritaville at Sea Paradise

Margaritaville at Sea

May 31, 2027 - Jun 4, 2027 (4 Nights)

Palm Beach • Key West, Florida • Freeport • Palm Beach

Average Starting Price

$249pp

Jim's Onboard Credit

Enchantment of the Seas

Royal Caribbean

Oct 30, 2027 - Nov 5, 2027 (6 Nights)

Tampa • Nassau • Perfect Day Cococay • Key West, Florida • Tampa

Average Starting Price

$659pp

Jim's Onboard Credit

54% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Oct 2, 2027 - Oct 9, 2027 (7 Nights)

Tampa • Key West, Florida • Roatan, Honduras • Belize City • Cozumel • Tampa

Average Starting Price

$589pp

Jim's Onboard Credit

57% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

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

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

Average Starting Price

$799pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Nov 14, 2027 - Nov 21, 2027 (7 Nights)

Tampa • Bimini • Key West, Florida • Nassau • Tampa

Average Starting Price

Jan 15, 2028 - Jan 22, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Key West, Florida • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida

Average Starting Price

46% OFF

Nov 13, 2027 - Nov 20, 2027 (7 Nights)

Mobile, Alabama • Fun Day at Sea • Key West, Florida • Celebration Key • Nassau • Fun Day at Sea • Fun Day at Sea • Mobile, Alabama

Average Starting Price

$567pp

Jim's Onboard Credit

25% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Feb 5, 2028 - Feb 16, 2028 (11 Nights)

Miami • Key West, Florida • Cruising the Gulf • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Cruising the Caribbean Sea • Falmouth, Jamaica • George Town, Cayman Islands • Cruising the Florida Straits • Miami

Average Starting Price

$9,199pp

Jim's Onboard Credit

Norwegian Dawn

Norwegian Cruise Line

Mar 30, 2027 - Apr 4, 2027 (5 Nights)

Jacksonville • Key West, Florida • Great Stirrup Cay • Jacksonville

Average Starting Price

$429pp

Jim's Onboard Credit

25% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Dec 22, 2027 - Jan 6, 2028 (15 Nights)

Miami • Key West, Florida • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Limon, Costa Rica • Colon, Panama • Panama Canal, Panama • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$10,549pp

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!

Norwegian Viva

Norwegian Cruise Line

Feb 21, 2028 - Feb 25, 2028 (4 Nights)

Miami • Key West, Florida • Great Stirrup Cay • Miami

Average Starting Price

43% OFF

Mar 20, 2027 - Mar 28, 2027 (8 Nights)

Mobile, Alabama • Fun Day at Sea • Key West, Florida • Celebration Key • Princess Cays • Nassau • Fun Day at Sea • Fun Day at Sea • Mobile, Alabama

Average Starting Price

$903pp

Jim's Onboard Credit

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