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Crown Princess
Princess Cruises
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,049pp
Jim's Onboard Credit
47% OFF
Carnival Firenze
Carnival Cruise Line
May 2, 2027 - May 8, 2027 (6 Nights)
Miami • Celebration Key • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami
Average Starting Price
$504pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 8, 2027 - Nov 15, 2027 (7 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$2,411pp
Jim's Onboard Credit
Viking Octantis
Viking
Sep 22, 2028 - Nov 22, 2028 (61 Nights)
Milwaukee, Wisconsin • Mackinac Island, Michigan • Alpena, Michigan • Detroit, Michigan • Point Pelee, Ontario • Niagara Falls (Port Colborne), Ontario • Welland Canal, Ontario • Toronto, Canada • Toronto, Canada • Scenic Sailing: St. Lawrence Seaway Locks • Trois Rivieres, Canada • Quebec City, Quebec • Tadoussac, Canada • Havre-Saint-Pierre, Quebec • Woody Point, Newfoundland • Sydney, Nova Scotia • Halifax, Nova Scotia • Halifax, Nova Scotia • Sail the Atlantic Ocean • New York, New York • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Gulf of Mexico • San Salvador, Bahamas • Man of War Bay (Great Inagua), Bahamas • Port Antonio, Jamaica • Sail the Caribbean Sea • Scenic Cruising: Panama Canal • Panama City (Fuerte Amador), Panama • Sail the Pacific Ocean • Sail the Pacific Ocean • Sail the Pacific Ocean • Lima, Peru • Sail the Pacific Ocean • Sail the Pacific Ocean • Iquique, Chile • Sail the Pacific Ocean • Sail the Pacific Ocean • Valparaíso, Chile • Sail the Pacific Ocean • Scenic Sailing: Chilean Fjords • Chacabuco, Chile • Scenic Sailing: Chilean Fjords • Explore Chilean Glaciers • Explore Chilean Glaciers • Scenic Sailing: Chilean Fjords • Punta Arenas, Chile • Explore Chilean Glaciers • Garibaldi Glacier, Chile • Scenic Cruising: Cape Horn • Ushuaia, Argentina • Sail the Drake Passage • Explore Antarctica • Explore Antarctica • Explore Antarctica • Explore Antarctica • Explore Antarctica • Explore Antarctica • Explore Antarctica • Sail the Drake Passage • Scenic Cruising: Cape Horn • Ushuaia, Argentina
Average Starting Price
$54,999pp
Jim's Onboard Credit
Viking Mars
Viking
Jan 6, 2028 - Jan 16, 2028 (10 Nights)
Fort Lauderdale • Sail the Caribbean Sea • Progreso, Mexico • Progreso, Mexico • Cozumel • Belize City • Sail the Caribbean Sea • Limon, Costa Rica • Colon, Panama • Scenic Cruising: Panama Canal • Panama City (Fuerte Amador), Panama
Average Starting Price
$5,299pp
Jim's Onboard Credit
Disney Believe
Disney Cruise Line
Feb 12, 2028 - Feb 17, 2028 (5 Nights)
Fort Lauderdale • Cozumel • Disney Castaway Cay, Bahamas • Fort Lauderdale
Average Starting Price
$1,879pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Mar 21, 2027 - Apr 11, 2027 (21 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 • Kralendijk, Bonaire • Willemstad, Curacao • Cabo Rojo, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,169pp
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!

Azamara Quest
Azamara
Nov 6, 2027 - Nov 14, 2027 (8 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$2,369pp
Jim's Onboard Credit
Disney Wish
Disney Cruise Line
Nov 16, 2027 - Nov 19, 2027 (3 Nights)
Port Canaveral (Orlando), Florida • Nassau • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,114pp
Jim's Onboard Credit
Oosterdam
Holland America Line
Dec 22, 2027 - Jan 2, 2028 (11 Nights)
Fort Lauderdale • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,249pp
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!

49% OFF
MSC Opera
MSC Cruises
Apr 29, 2027 - May 13, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,908pp
Jim's Onboard Credit
Disney Dream
Disney Cruise Line
Jul 2, 2027 - Jul 5, 2027 (3 Nights)
Port Canaveral (Orlando), Florida • Nassau • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,400pp
Jim's Onboard Credit
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