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October 2026

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Celebrity Ascent

Celebrity Cruises

Mar 27, 2028 - Apr 7, 2028 (11 Nights)

Fort Lauderdale • Puerto Plata, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Panama Canal, Panama • Colon, Panama • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

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

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

Average Starting Price

$765pp

Jim's Onboard Credit

Norwegian Aqua

Norwegian Cruise Line

Aug 29, 2027 - Sep 5, 2027 (7 Nights)

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

Average Starting Price

Dec 12, 2026 - Dec 26, 2026 (14 Nights)

Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Key West, Florida • Miami

Average Starting Price

$2,099pp

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!

35% OFF

Carnival Venezia

Carnival Cruise Line

Jun 6, 2027 - Jun 12, 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

Jan 6, 2028 - Jan 22, 2028 (16 Nights)

Los Angeles • Ensenada • Cabo San Lucas • Acapulco, Mexico • Puerto Quetzal, Guatemala • Puntarenas, Costa Rica • Panama Canal, Panama • Cartagena, Colombia • George Town, Cayman Islands • Miami

Average Starting Price

44% OFF

Oct 24, 2027 - Oct 31, 2027 (7 Nights)

New Orleans • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fun Day at Sea • New Orleans

Average Starting Price

May 24, 2027 - May 29, 2027 (5 Nights)

Miami • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

Feb 28, 2027 - Mar 12, 2027 (12 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale

Average Starting Price

$2,629pp

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!

21% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Dec 21, 2026 - Jan 4, 2027 (14 Nights)

Tampa • George Town, Cayman Islands • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$12,399pp

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!

20% OFF

Seven Seas Splendor

Regent Seven Seas Cruises

Dec 11, 2026 - Dec 28, 2026 (17 Nights)

Galveston • Montego Bay, Jamaica • Port Royal, Jamaica • Cap Cana (Punta Cana), Dominican Republic • San Juan, Puerto Rico • Tortola • St John's, Antigua • Gustavia, St. Barts • Philipsburg, St. Maarten • George Town, Cayman Islands • Galveston

Average Starting Price

52% OFF

Feb 13, 2027 - Feb 21, 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

$658pp

Jim's Onboard Credit

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