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October 2026

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54% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

May 1, 2027 - May 8, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$479pp

Jim's Onboard Credit

57% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Oct 9, 2027 - Oct 17, 2027 (8 Nights)

Tampa • George Town, Cayman Islands • Roatan, Honduras • Belize City • Cozumel • Tampa

Average Starting Price

Jan 23, 2028 - Jan 30, 2028 (7 Nights)

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

Average Starting Price

Dec 6, 2027 - Jan 3, 2028 (28 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • St. George's • Bridgetown, Barbados • St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

$13,699pp

Jim's Onboard Credit

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

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

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

Average Starting Price

Apr 23, 2027 - Apr 28, 2027 (5 Nights)

Miami • Bimini • George Town, Cayman Islands • Miami

Average Starting Price

Nov 22, 2027 - Dec 3, 2027 (11 Nights)

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Panama Canal, Panama • Colon, Panama • George Town, Cayman Islands • Bimini • Fort Lauderdale

Average Starting Price

$2,082pp

Jim's Onboard Credit

Norwegian Aqua

Norwegian Cruise Line

May 9, 2027 - May 16, 2027 (7 Nights)

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

Average Starting Price

34% OFF

Jul 4, 2027 - Jul 10, 2027 (6 Nights)

Miami • Celebration Key • Fun Day at Sea • Ocho Rios, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami

Average Starting Price

Sep 27, 2027 - Oct 2, 2027 (5 Nights)

Miami • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

$695pp

Jim's Onboard Credit

28% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Nov 4, 2027 - Nov 18, 2027 (14 Nights)

New York, New York • Great Stirrup Cay • La Romana, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Dec 28, 2027 - Jan 4, 2028 (7 Nights)

Miami • Nassau • Ocho Rios, Jamaica • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

$2,023pp

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!

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