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Cruise Dates

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October 2026

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47% OFF

MSC Grandiosa

MSC Cruises

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

Port Canaveral (Orlando), Florida • Ocean Cay • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Port Canaveral (Orlando), Florida

Average Starting Price

Nov 26, 2027 - Dec 4, 2027 (8 Nights)

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

Average Starting Price

$875pp

Jim's Onboard Credit

Norwegian Joy

Norwegian Cruise Line

Nov 27, 2027 - Dec 7, 2027 (10 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$1,219pp

Jim's Onboard Credit

Norwegian Jewel

Norwegian Cruise Line

Nov 29, 2027 - Dec 9, 2027 (10 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

37% OFF

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

Tampa • Fun Day at Sea • George Town, Cayman Islands • Fun Day at Sea • Isla Tropicale, Roatan • Belize City • Cozumel • Fun Day at Sea • Tampa

Average Starting Price

$933pp

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

Norwegian Gem

Norwegian Cruise Line

Nov 30, 2027 - Dec 11, 2027 (11 Nights)

Miami • Great Stirrup Cay • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Dec 2, 2027 - Dec 14, 2027 (12 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • Oranjestad, Aruba • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

Feb 19, 2027 - Mar 11, 2027 (20 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Nassau • Miami

Average Starting Price

$11,349pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

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

Port Canaveral (Orlando), Florida • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

Dec 19, 2028 - Dec 27, 2028 (8 Nights)

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

Average Starting Price

$4,800pp

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!

Celebrity Xcel

Celebrity Cruises

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

Fort Lauderdale • Bimini • Costa Maya • Cozumel • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

$950pp

Jim's Onboard Credit

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