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Cruise Dates

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October 2026

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48% OFF

MSC World America

MSC Cruises

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

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami

Average Starting Price

$1,551pp

Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Sonata

Oceania Cruises

Jan 6, 2028 - Feb 19, 2028 (44 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 • Philipsburg, St. Maarten • Fort-De-France, Martinique • Castries, St. Lucia • Grenada • Oranjestad, Aruba • Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Cruising the Straits of Florida • Cozumel • Roatan, Honduras • Harvest Caye, Belize • Costa Maya • Cruising the Straits of Florida • Miami

Average Starting Price

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

Port Canaveral (Orlando), Florida • St. Thomas • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

48% OFF

Oct 23, 2027 - Oct 31, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$606pp

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!

39% OFF

Carnival Vista

Carnival Cruise Line

May 1, 2027 - May 9, 2027 (8 Nights)

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

Average Starting Price

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

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Samana, Dominican Republic • Bimini • Miami

Average Starting Price

$1,032pp

Jim's Onboard Credit

57% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

Aug 14, 2027 - Aug 21, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Oct 29, 2027 - Nov 5, 2027 (7 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

Apr 23, 2027 - Apr 27, 2027 (4 Nights)

San Juan, Puerto Rico • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Fort Lauderdale

Average Starting Price

49% OFF

Nov 6, 2027 - Nov 18, 2027 (12 Nights)

Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Ocean Cay • Port Canaveral (Orlando), Florida

Average Starting Price

Nov 7, 2027 - Nov 14, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$864pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Norwegian Bliss

Norwegian Cruise Line

Nov 8, 2027 - Nov 20, 2027 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Thomas • Tortola • Philipsburg, St. Maarten • Manhattan

Average Starting Price

$1,469pp

Jim's Onboard Credit

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