Castaway Cay Twice?!: Disney Cruise Line Reveals 2026-2027 Itineraries

Some itineraries include two stops at Castaway Cay, and for the first time - a stop at Puerto Plata in the Dominican Republic

As time marches on, it’s time to start thinking about 2026 and 2027 vacations, and Disney Cruise Line is right on time with their announcement of itineraries in that cruising season.

What’s Happening:

  • An expanded sailing season is on the horizon for Texas and California families with the release of fall 2026 and spring 2027 Disney Cruise Line itineraries.
  • Early bookings open on August 25th, 2025 for select Disney Cruise Line Castaway Club members, and general bookings open September 2nd, 2025. All bookings will begin at 8 a.m. ET / 8 p.m. SGT.
    • Monday, August 25, 2025: Castaway Club Pearl Members
    • Tuesday, August 26, 2025: Castaway Club Platinum Members, Golden Oak and Walt Disney World Club 33 Members
    • Wednesday, August 27, 2025: Castaway Club Gold Members
    • Thursday, August 28, 2025: Castaway Club Silver Members, Disney Vacation Club Members and Adventures by Disney Adventure Insiders
    • Tuesday, September 2, 2025: General bookings open
  • Disney Cruise Line is returning to favorite destinations, including Mexico, The Bahamas, Eastern Caribbean and Western Caribbean.
  • Several itineraries include stops at both of Disney’s island destinations, Disney Castaway Cay and Disney Lookout Cay at Lighthouse Point. Some sailings will stop not once but twice at Disney Castaway Cay.
  • For the first time, Disney Cruise Line will call on a new port, Puerto Plata in the Dominican Republic.

Ship by Ship:

  • The Disney Magic will kick off the sailing season in October 2026 from San Diego, California with three-, four-, five-, six- and seven-night voyages before heading to Galveston, Texas in November. The ship will stop in Catalina Island, California, as well as Cabo San Lucas, Ensenada and Puerto Vallarta, Mexico. Between November 2026 and April 2027, the Disney Magic will offer four-, five- and seven-night sailings to everywhere from Cozumel, Mexico, the historic Progreso, Mexico, and even offering guests the chance to experience a Bahamian vacation under the palm trees at Disney Castaway Cay or Nassau.
  • The Disney Wonder will make its way to San Diego in October 2026 as well, offering everything from three- to seven-night sailings through April 2027.
  • The Disney Destiny, joining the family in November of 2025, will offer four-, five- and seven-nights from Fort Lauderdale to The Bahamas, Eastern Caribbean and Western Caribbean.
  • The Disney Dream will begin fall 2026 with three-, four-, five- and six -night cruises to The Bahamas and seven-night sailings to the Eastern Caribbean from Fort Lauderdale, as well as seven-night sailings to the Southern Caribbean from San Juan, Puerto Rico. The ship will then make its way to Port Canaveral for more three- and four-night Bahamian vacations.
  • The Disney Fantasy will call on Disney Castaway Cay, Disney Lookout Cay and Nassau between October 2026 and May 2027 during three-, four- and five-night voyages.
  • The Disney Wish will visit Disney Castaway Cay, Disney Lookout Cay and Nassau. Three- and four-night sailings from Port Canaveral will be offered on the Disney Wish.
  • Seven-night sailings aboard the Disney Treasure from Port Canaveral will offer itineraries visiting Cozumel, Disney Castaway Cay, San Juan, Puerto Rico, and the Caribbean between October 2026 to May 2027.
    The Disney Adventure is setting sail later this year, and will return with three- and four-night cruises from Marina Bay Cruise Centre in Singapore from October to December 2026.
  • Halloween on the High Seas is returning on select sailings from September to October 2026, and Very Merrytime Cruises will begin in early November. These holiday themed sailings will be available on select domestic Disney Cruise Line itineraries.

As A Reminder:

  • Several days ago we learned that Disney Cruise Line will not be returning to Australia after the upcoming seasons, so don’t be too surprised by the lack of that destination in these itinerary announcements.
  • As in year’s past, we don’t get the Alaska season itineraries at this point, but if you’re looking for an Alaska Cruise in 2027, sit tight as those will probably be announced as we get closer to that season.
  • For more information about the new itineraries and to book your voyage aboard the Disney Cruise Line, be sure to reach out to our friends at Mouse Fan Travel, who can assist with all your planning needs.

Laughing Place recommends MouseFanTravel.com for all your Disney Cruise travel planning
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Tony Betti
Originally from California where he studied a dying artform (hand-drawn animation), Tony has spent most of his adult life in the theme parks of Orlando. When he’s not writing for LP, he’s usually watching and studying something animated or arguing about “the good ole’ days” at the parks.
View all articles by Tony Betti