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Cruise Dates

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October 2026

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Hero of the Seas

Royal Caribbean

Aug 28, 2027 - Sep 4, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

Jan 9, 2028 - Jan 20, 2028 (11 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St. Kitts • St John's, Antigua • St. John • Miami

Average Starting Price

$6,300pp

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

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

Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$1,010pp

Jim's Onboard Credit

Norwegian Getaway

Norwegian Cruise Line

Jul 9, 2027 - Jul 12, 2027 (3 Nights)

Miami • Great Stirrup Cay • Nassau • Miami

Average Starting Price

49% OFF

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

$1,541pp

Jim's Onboard Credit

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

54% OFF

Carnival Sunrise

Carnival Cruise Line

Sep 4, 2027 - Sep 9, 2027 (5 Nights)

Miami • Fun Day at Sea • Relaxaway Half Moon Cay • Nassau • Celebration Key • Miami

Average Starting Price

$322pp

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

MSC Seaside

MSC Cruises

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

Miami • Nassau • Ocean Cay • Ocean Cay • Miami • Nassau • Ocean Cay • Miami

Average Starting Price

43% OFF

May 21, 2027 - May 24, 2027 (3 Nights)

Miami • Celebration Key • Fun Day at Sea • Miami

Average Starting Price

Jul 10, 2027 - Jul 15, 2027 (5 Nights)

Miami • Grand Turk • Bimini • Miami

Average Starting Price

$1,275pp

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!

Resilient Lady

Virgin Voyages

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

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

Average Starting Price

49% OFF

Sep 4, 2027 - Sep 12, 2027 (8 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$603pp

Jim's Onboard Credit

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