Upcoming Disney Wish Sailings: Choose the Perfect Trip 

Disney Wish sailings in 2025 and 2026 include trips from Port Canaveral to Bahamian paradises and Disney island destinations. Depending on the sailing you choose, you may dive into a pirate-themed feast, go trick-or-treating, or even sing holiday carols.  

Looking for the perfect trip with just the right amount of swashbuckling or decking the halls? Here’s your complete guide to upcoming Disney Wish sailings.

Note that sail dates are subject to change. View the latest Disney Wish cruises on the Disney Cruise Line site for itineraries.

Curious seafaring scallywags often wonder: “Do pirate nights happen on every Disney Wish sailing?”  

Our answer? Aye, aye!  

But there are a couple of details to keep in mind, me hearties. While each sailing turns salty with a piratey-fun celebration, the 3-night and 4-night sailings differ in style. 

For 3-night sailings on the Disney Wish, enjoy a fabulous meal as usual at one of the rotational dining locations, then don your bandana and join the Pirate’s Rockin’ Parlay Party on deck. During 4-night sailings, you will be treated to a special pirate menu at dinner before joining the fun.  

Get more info on Pirates Night festivities and schedule your next Disney Wish sailing. 

Get ready to unleash your inner pirate for an unforgettable night on deck, exclusive to the Disney Wish, Disney Treasure, and Disney Destiny. Leading the charge is Captain Redd, a fiery descendant of the iconic red-headed auctioneer from the Pirates of the Caribbean attraction, backed by her high-energy crew of guitar-shredding buccaneers.  

Together, they deliver a setlist packed with classic rock hits, capped off with a bold, amped-up version of the classic anthem “Yo Ho (A Pirate’s Life for Me).” She’ll bring forth famous pirate captains, including Captain Jack Sparrow, as the night concludes in a sparkling fireworks display at sea. 

As you board the Disney Wish for Halloween on the High Seas, you will enter not-so-scary regions beyond. The Grand Hall will be fully transformed into a Halloween wonderland centered around the Magical Pumpkin Tree.  

Halloween on the High Seas brings all manner of fall fun onboard, including Mickey’s Mouse-querade, a lively “scare-a-bration” where kids of all ages are encouraged to dress up and dance alongside Disney characters in their Halloween best. 

Throughout the cruise, you’ll find themed character meet and greets, featuring favorites like Minnie, Daisy, and Clarabelle dressed as the Sanderson sisters from Hocus Pocus—a perfect photo op for fans of the film.  

Dive into hands-on Halloween activities, including spooky crafts and seasonal games that add a creative twist to the festivities. And of course, no Halloween celebration is complete without spine-tingling treats— indulge in themed desserts and beverages and enjoy trick-or-treating around the ship. It’s an exciting and festive experience packed with Disney magic at every turn. 

All Halloween on the High Seas sailings on the Disney Wish will leave from Port Canaveral to embark on either a 3-night, Friday- through- Monday covering the weekend, or a 4-night, Monday- through- Friday sailing throughout the week. Itineraries include visits to Nassau, Disney Castaway Cay, and even Disney Lookout Cay at Lighthouse Point. 

Look out for Lookout Cay: One Halloween on the High Seas sailing in 2025 will head to Lookout Cay at Lighthouse Point, departing on Oct 6.

‘Tis the season for a Very Merrytime sailing leaving from Port Canaveral with stops at Bahamian destinations in Nassau, Castaway Cay, and Lookout Cay at Lighthouse Point. 

It’s a winter wonderland at sea when you come aboard the Disney Wish during a Very Merrytime Cruise sailing. Here, guests can see that the decks have been, well, decked, inside the Grand Hall and beyond. A glorious Christmas tree shines underneath the dazzling chandelier, where Santa will soon make a festive entrance and greet little ones.  

On one special evening of the cruise, be sure to head up to Deck 11 for Mickey & Minnie’s Holiday Party, where Mickey & Friends put on a cheerful yuletide show, culminating in a flurry of “snow.” Special themed treats and activities abound during the sailing, and you will even see some of your favorite characters in their holiday best.  

Very Merrytime sailings also offer holiday-themed fireworks show at sea, exclusive holiday merchandise at Mickey’s Mainsail, and seasonal movies shown at Never Land Cinema, like “Frozen” and “Mickey’s Once Upon a Christmas.” With plenty of holiday cheer, a Very Merrytime Cruise creates lasting memories through festive activities, enchanting shows, and magical moments for all ages. 

With 14 Very Merrytime sailings to choose from aboard the Disney Wish, you’ll jingle all the way from Port Canaveral to the sparkling seas. 

Watch for Double-Dip Dates: Three 4-night Very Merrytime sailings in 2025 will head to both Castaway Cay Lookout Cay at Lighthouse Point (noted below). These popular “double-dip” sailings will keep your family in the Disney magic from ship to shore! 

When Disney Cruise Line started offering sailings that visited Castaway Cay twice in one trip, guests started calling this the “double-dip” opportunity to soak in the Disney magic from ship to shore.  

Now, with the new Lookout Cay at Lighthouse Point joining in the fun, a double-dip sailing can now offer two different shores with the same Disney quality of service, exciting offerings, and even an all-out Junkanoo celebration.  

Slipping away to Castaway Cay and Lookout Cay isn’t just a tropical detour; it’s a curated extension of the Disney Cruise Line experience. Guests can expect the same level of storytelling, service, and immersion, all ashore a beautiful island destination designed by Disney. 

Just like on the Disney Wish, Castaway Cay and Lookout Cay at Lighthouse Point are sectioned into specific areas to focus on the fun. Choose from family areas, adults-only lounging spaces, water play zones, and kids’ activities. From the smiling crew members who greet you on the dock, to the island cookout buffets, every detail is taken care of.  

Note that all of the 2025 and 2026 double-dip sailings are 4-night sailings with a day at sea, and all sailings in 2025 are Very Merrytime Cruises. 

Is your perfect Disney Wish sailing on this list? Check out our full list of itineraries here, and stay tuned to Disney Parks Blog as we update with new offerings and dates.  

_{Note that sail dates are subject to change. View the latest Disney Wish cruises on the Disney Cruise Line site for itinerary dates.}