Fall 2020 Disney Cruise Line Itineraries

Disney Cruise Line has released its Fall 2020 itineraries, with sailings departing from New York, California, Texas, and Florida to the Bahamas, Caribbean, Mexico, and a limited-time return to Bermuda. The September through December 2020 cruise season includes a variety of Halloween and Christmas cruises, and we’ll take a look at the various options followed by commentary on pricing in this post.

Starting with the beginning of the Fall 2020 cruise season, Halloween on the High Seas sailings will be offered aboard select Disney Cruise Line sailings in September and October 2020. Halloween entertainment includes a mouse-querade costume party, ghoulish themed food and beverage, trick-or-treating, seasonal activities for kids, a villainous party for adults, live performances, and a ghostly ship takeover highlighted by the magical pumpkin tree in the ship’s atrium.

In November and December 2020, the Disney Cruise Line fleet is decked from bow-to-stern with yuletide cheer and holiday entertainment during the Very Merrytime Cruises. These Christmas-time sailings feature merry parties, a tree lighting ceremony, festive activities, holiday-themed food and beverage, favorite characters in their holiday finery, a winter wonderland ball with Santa and Mrs. Claus, and snowfall. With Frozen 2 coming out in late November 2019, we’re also expecting more Frozen-related enhancements and entertainment on these sailings.

The Disney Magic returns to New York in October for sailings to Bermuda and Canada, all featuring the aforementioned Halloween on the High Seas. Three 5-night cruises offer two days in Bermuda, with plenty of time for the island’s famous pink-sand beaches, water activities, chic shopping, and Bermuda’s distinct blend of British and Caribbean culture.

One five-night cruise will visit some of Canada’s best seaport cities including Saint John and New Brunswick, Canada’s oldest incorporated city. This sailing also visits Halifax, the provincial capital of Nova Scotia. (Out of all the itineraries, this one sounds coolest to us–given the timing and locations, maybe there it’ll see some last-minute discounts!)

The Disney Wonder sets sail from San Diego in September, with Halloween on the High Seas cruises to Baja and the Mexican Riviera. Baja itineraries range from 2 to 5 nights and feature the region’s famous beaches and water activities with visits to Cabo San Lucas and Ensenada, Mexico. There’s also one 7-night Mexican Riviera cruise, with additional stops in Mazatlán and Puerto Vallarta. On November 6, 2019, the Disney Wonder concludes its California run, departing San Diego for a 14-night Panama Canal crossing.

From late November through December, the Disney Wonder will return to Galveston, Texas for more Very Merrytime Cruises to the Caribbean and Bahamas. These will be 4-7 night sailings with the Caribbean itineraries including stops in Costa Maya and Cozumel, Mexico plus Grand Cayman. Bahamian cruises will include stops in Nassau, Bahamas and Key West, Florida. Of course, these will also include visits to Castaway Cay, Disney Cruise Line’s private island.

Saving the most popular sailings for last, the Disney Fantasy and Disney Dream return to Port Canaveral will sail to the Bahamas and Caribbean from Port Canaveral, Florida. Most sailings include Halloween or Christmas overlays, plus a day at Castaway Cay. The Disney Fantasy will sail Caribbean and Bahamian itineraries ranging from 3 to 8 nights, and the Disney Dream will sail 3 and 4-night Bahamian cruises.

Bookings open to the general public on June 13, 2019, with booking now available for Gold Castaway Club members (and above). Silver Castaway Club members and Disney Vacation Club members will be eligible to book on June 12, 2019. Opening days are popular times to book, so be prepared to wait on hold if you call Disney Cruise Line’s phone lines.   

Rumblings about opening day price-points are starting to make waves on social media (as these itineraries are already available to book for Platinum Castaway Club members), and prices have jumped by quite a bit in some cases. This is not really a surprise at this point, but it’s nonetheless easy to be taken aback when first seeing each year’s prices…especially if you remember what prices were only a few years ago.

It’s worth noting that the fall cruises to the Bahamas and Caribbean are among DCL’s most popular sailings, meaning the opening day stateroom rates are largely on the lower end of the pricing spectrum. As the Bahamian and Caribbean itineraries for Fall 2020 start to book up and stateroom inventory becomes more scarce, rates will invariably increase. Prices on these cruises rarely decrease–they almost always increase.

That’s the bad news. The good news is that if you’re looking at one of the more niche itineraries, you’re likely to have a better chance at a discount. If recent history is any indication, sailings out of places that are not Port Canaveral are the ones most likely to see last-minute discounts. (Still, we wouldn’t recommend banking on it.)

Last year, there were some excellent deals on the Canada itineraries as well as a handful of sailings out of San Diego. These piqued my interest, but they just didn’t work with our plans. We’d still really like to do a sailing to Canada, and the Halloween or Christmas cruises.

The one and only time we were available to take advantage of a good rate on the Halloween on the High Seas cruise, it was during the heart of hurricane season (no wonder there was a discount!). Our cruise ended up being cancelled due to Hurricane Irma, and we got stuck at Walt Disney World. Never one to learn from my mistakes, I’d book another cruise during hurricane season if we could score a great deal!

Based upon what we’ve seen in Disney Cruise Line “discount-stalking,” the itineraries most likely to see deals are similar itineraries during hurricane season, one-way cruises, and sailings out of cities where Cast Members are less likely to take advantage of special rates. (Since those open before general public discounts.)

If you’re only looking at the popular sailings and dates out of Port Canaveral, the opening day prices are likely as good as it’s going to get. It’s a similar scenario as with Walt Disney World–cruise business is booming because consumers are spending freely, so pricing is unlikely to become more favorable until that slows down or Disney Cruise Line’s new ships come on-line to help with demand.

We’ve scored some good deals on Disney Cruise Line over the years (and cover how you can do the same in our How to Save Money on Disney Cruise Line Sailings post), but have had less luck recently. We aren’t optimistic that this trend will change with the Fall 2020 Disney Cruise Line itineraries; if you’re planning on taking one of the popular cruises, booking early is definitely the most pragmatic route!

We really cannot stress this enough with the sailings out of Port Canaveral–the odds of prices dropping are stacked against you. There’s probably (at least) a 90% chance that opening day prices are the cheapest that those sailings to the Bahamas and Caribbean will ever be.

If you want assistance booking these cruises or need personalized recommendations for Disney Cruise Line itineraries, ships, and more, click here to get a cruise quote from a no-fee Authorized Disney Vacation Planner. They can find you all of the best discounts, provide an on-board credit, and help you plan the details of your cruise!


What do you think of these Fall 2020 Disney Cruise Line itineraries? Any that appeal to you? Any thoughts on which you think might have good deals come along later, and which you’d recommend buying now? Do you think Disney Cruise Line is worth the premium pricing? Any other tips to add or recommendations? If you have questions or thoughts, please share them below in the comments!

7 Responses to “Fall 2020 Disney Cruise Line Itineraries”
  1. Devin June 13, 2019
    • Laura October 23, 2019
  2. Keli June 13, 2019
  3. Laura June 12, 2019
  4. JS June 12, 2019
  5. Gina June 12, 2019
  6. Chris June 11, 2019

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