Ahoy, Stephanie! Welcome to planDisney and the first step toward booking your third sailing aboard the Disney fleet. It sounds like you are already a proud Silver Member of the
Disney Cruise Line Castaway Club, but are taking on the booking process yourself for the first time. I know it can be intimidating at first, but let me give you a few tips to help ensure smooth sailing.
There are three main dates to keep in mind: booking date, advance booking window, and when online check-in opens. Remember that as a Silver Castaway Club Member, you have access to special benefits, including: the ability to book new itineraries at least one day before the general public, an advance booking window for cruise activities 90 days prior to sailing, and the ability to complete online check-in 33 days prior to sailing.
As you mentioned, only the itineraries for early 2027 sailings have been released, so bookings are open for cruises setting sail on dates as far out as January to May 2027. I highly recommend making sure that you are signed up for the official Disney Cruise Line email updates because they bring news like itinerary announcements right to your inbox. Once your desired timeframe is announced, then you can narrow down your cruise search by timeframe, destination, departure port, and other filters to determine the best options for you and your sailing party. Just click on the
“Plan a Cruise” tab at the top of the main website and then use the white boxes labeled “Leaving,” “Sailing to,” and “Departing from” to specify your desired cruise details. It sounds like you are only interested in the longer itineraries, so you can also click where it says “More Filters” and scroll down to the second question that asks “How many nights?” to eliminate the shorter cruises from your results list.
You should be able to book both of your back-to-back cruises once the dates are released, but keep in mind that your advance booking window and check-in timeframes will be separate for each cruise based on the embarkation date. After your cruise balance is paid in full and your advance booking window opens for each specific sailing date, then you can book activities online or through the Disney Cruise Line Navigator App. The advance booking window is the first date that you are able to make advanced reservations for certain activities, including port adventures, adult-exclusive dining options, and more. The specific onboard activities vary by ship, sailing date, and are always subject to availability, which is why booking these particular options early is recommended and you get the benefit of earlier access as a Castaway Club member.
Finally, you will need to complete your online check-in for both cruises in your back-to-back sailing. Each one will open up separately, but the first one will be your priority. Part of the check-in process is selecting your Port Arrival Time, which is a 15-minute period (e.g., 11:30 AM-11:45 AM) when you and your party are designated to arrive at the cruise terminal. For the first cruise, you will want to complete online check-in as soon as possible to get the earliest Port Arrival Time, but it doesn’t really matter for your second cruise. See my friend Dustin’s
answer for more details on the logistics of switching from your first cruise to your second cruise.
I hope this information gives you a place to start and helps you understand the most important dates to keep in mind as you plan your dream vacation. We are always here to help at planDisney if you have more questions. Happy sailing in 2027!
Catherine