We Almost Missed Our Disney Wish Cruise

My wife and I had just finished our first sailing on the Disney Wonder. A repositioning cruise from San Diego to Vancouver. That cruise sold us on Disney Cruise Line. From then on, it was every day, every week, checking Disney cruise itineraries, saying to each other, where do we want to go next?

One day I received an email from Disney promoting a Disney Cruise Special. A guaranteed stateroom with $250 in onboard credit. We eagerly booked a three-night guaranteed veranda on the Disney Wish for Labor Day weekend. The best part? The cruise was just a little over 90 days away.

The Plan

The plan was straightforward. On Thursday evening, the day before the cruise, we would leave work at 5:00 PM, fly out of San Jose International at 8:45 PM, connect in Las Vegas, and arrive at Orlando International at 6:00 AM on the day of departure. From there, we would hang around the terminal, catch Disney transportation to Port Canaveral, and board the Wish. Clean, simple, stress-free.

At least that was the plan.

Captain J.J. — Chief Officer

I was packed in the carry-on. Characteristically unbothered.

The Problem

On Thursday, our travel day, the first text message from Southwest Airlines arrived. Our flight was delayed five minutes. No problem. Flights get delayed all the time. Sometimes they make up the time.

An hour later, another text. Ten minutes now. Still fine.

An hour after that, fifteen minutes. Easy to make up.

The updates kept coming. The delays stretched a little further each time. By around 4:00 PM, the message read forty-five minutes. Now I was starting to get concerned. A big enough delay, and we would miss our connection in Las Vegas. Still, we left work at 5:00 PM as planned. Bags were already in the car. We drove forty-five minutes to San Jose International. We dropped the car at long-term parking, took the shuttle to the terminal, and arrived at the Southwest check-in counter at 6:15 PM. Plenty of time for an 8:45 PM departure.
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The Scramble

At the airport, we walked up to the Southwest kiosk to print our luggage tags and boarding passes. Instead, we got an error message. See the counter attendant. That was odd. We walked over, explained what had happened, and the agent pulled up our flight. Then she told us our flight had been canceled.

I said, “What do you mean canceled?”

The flight was coming from Seattle, she explained. Because of bad weather, the flight was delayed. It would not make it to Las Vegas in time for our connection to Orlando. She said she would look for alternatives.

She checked all Southwest flights out of San Jose International, Oakland International, and San Francisco International. The result was the same at every airport. The soonest they could get us to Orlando was 4:00 PM the following afternoon on Friday, right about the time the Wish would be pulling away from the pier. That was not going to work.

My wife and I pulled out our phones and started searching. We started with flights to Orlando from San Jose, then expanded to all the Bay Area airports. My wife found a flight out of San Francisco departing at 8:45 on a booking app — I honestly could not tell you which one at this point. I said, ” F*** it, book it. Put it on the card. I do not care what it costs. We were going on that ship. We were going to see the Star Wars lounge, and we were going to make this happen.

The Mad Dash

So we paid for the tickets, turned around, took the shuttle back to long-term parking, retrieved the car, and jumped on the highway from San Jose to San Francisco. If you know the Bay Area, you know that drive is thirty minutes on a good day and two hours on a bad one. It was Labor Day weekend, and it was already prime commute traffic, so things were looking sketchy.

Somewhere around Mountain View, my wife’s phone started ringing. She had been letting it go, assuming it was spam, but something told her to pick up. She answered, and it was an agent from the booking app. They asked whether we were already at the airport in San Francisco. We were not. It was 7:00 PM. The agent told us we would not make our flight if we were not on airport premises already, and we had not yet checked in. They were going to cancel our tickets.

I asked what else they could find. They put us on hold. Ten or fifteen minutes later, the agent came back with one option. The last two seats leaving at 11:30 PM on a United red-eye flying direct from San Francisco to Orlando, arriving at 5:30 in the morning. The catch was that we would not be able to sit together. I said we would take it. With what we had already paid, the total addition was enough to make me wince. I said book it. Charge the card.

By this point, our flights had cost nearly as much as the cruise itself. We had thought we were getting a bargain. A new ship for us to sail on, onboard credit, and Labor Day weekend. It had not quite worked out that way.

We pressed on to San Francisco. Rather than waste time hunting for long-term parking and waiting for a shuttle, we pulled into short-term parking. Three days. We would eat that cost too.

We reached the airport just after 8:00 PM, checked our bags, cleared security, and sat down in the terminal. We got something to eat and waited for our boarding call. From that point on, it was smooth sailing. We landed in Orlando at about 5:50 AM in the morning, found a spot in the terminal, and waited for Disney Cruise Line transportation to open. We checked in with them, boarded the bus, and walked onto the Disney Wish at a little after 12 PM that Friday afternoon. Then we went ahead and enjoyed our $250 in onboard credit on a three-night Caribbean cruise, with stops at Nassau and Castaway Cay.

Disney Transportation from Orlando Airport

If you fly into Orlando International and use Disney Cruise Line’s ground transportation to Port Canaveral, here is something worth knowing. When you check in with DCL at the airport, they give you a wristband. When you arrive at the port, that wristband gets you into an expedited boarding line. You have already completed your check-in at the airport. All that remains is walking through security and straight onto the ship. No waiting in the general check-in area, no paperwork, nothing to fill out. It is a genuinely smooth process and, after the night we had, we were grateful for every minute it saved us.

Captain J.J. — Chief Officer

I conducted a brief inspection of the boarding area and issued a preliminary verdict of three anchors, pending full review of the stateroom and pool deck situation.

What We Learned

In the end, we paid close to the cost of another cruise just to get on this one. The $250 onboard credit was no longer worth the savings.

Here is what we would do differently.

• Book a direct flight whenever possible. Each connecting flight is a point of failure.
• Build in a travel day. Flying the night before a cruise is a calculated risk. Flying in on the morning the ship is departing is not a plan.
• Get travel insurance. It will not make the flight run on time, but it will soften what happens when it does not.
• Know your airport options. The Bay Area has three major airports, which in the end allowed us to be on a cruise.

The $250 onboard credit was a fine deal. The impulsive, last-minute booking attached to it was not. The story, however, is excellent. The Hyperspace bar on the Wish, was totally worth it.

Captain J.J. — Chief Officer

I do not consider the connecting flight strategy sound and will not be endorsing it. The humans performed adequately under pressure. That is the most I will offer.

If this helped you plan a better cruise, there’s more where that came from. Subscribe to The Magical Navigator and join the crew to get new posts, port tips, and the occasional unsolicited opinion from Captain J.J. delivered straight to your inbox.

Captain J.J.’s Verdict
⚓⚓ — Fine, he supposes.