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Cruise Dates

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October 2026

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Carnival Festivale

Carnival Cruise Line

May 29, 2027 - Jun 6, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

Sep 25, 2027 - Oct 2, 2027 (7 Nights)

Miami • Costa Maya • Roatan, Honduras • Cozumel • Perfect Day Cococay • Miami

Average Starting Price

$1,659pp

Jim's Onboard Credit

Norwegian Sun

Norwegian Cruise Line

Mar 13, 2027 - Mar 24, 2027 (11 Nights)

Miami • Falmouth, Jamaica • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Harvest Caye, Belize • Cozumel • Miami

Average Starting Price

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

Fort Lauderdale • Nassau • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,389pp

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!

Star Pride

Windstar Cruises

Nov 1, 2027 - Nov 15, 2027 (14 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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

$4,224pp

Jim's Onboard Credit

26% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Dec 7, 2027 - Dec 18, 2027 (11 Nights)

Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

Nov 28, 2027 - Dec 10, 2027 (12 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami

Average Starting Price

Jan 24, 2028 - Jan 29, 2028 (5 Nights)

Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • Nassau • Fort Lauderdale

Average Starting Price

Dec 22, 2027 - Jan 14, 2028 (23 Nights)

Fort Lauderdale • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • 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

$6,014pp

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!

36% OFF

Seven Seas Voyager

Regent Seven Seas Cruises

Mar 18, 2028 - Apr 1, 2028 (14 Nights)

Miami • Great Stirrup Cay • Royal Naval Dockyard, Bermuda • Horta (Azores), Portugal • Cadiz, Spain • Valencia, Spain • Barcelona, Spain

Average Starting Price

Nov 27, 2027 - Dec 4, 2027 (7 Nights)

San Juan, Puerto Rico • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • St. Thomas • Cayo Levantado, Dominican Republic • Ocean Cay • Miami

Average Starting Price

Sep 19, 2027 - Sep 24, 2027 (5 Nights)

Baoshan, China • Yatsushiro, Japan • Fukuoka, Japan • Baoshan, China

Average Starting Price

$832pp

Jim's Onboard Credit

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