Should You Fly A Day Before A Cruise? Yes (Cautionary Tale)

Take a moment and ​imagine the joy and excitement that comes with planning a ​​vacation. You go over all the options and itineraries, let your budget and wish list go through an epic battle, and finally book your dream vacation. You meticulously plan all the details (or have your travel agent do it), and it’s finally time to book your flights. Now the question is, “Should you fly a day before a cruise?”

Spoiler alert: Yes!

A Vacation Dream Turned Nightmare

With only a few weeks before ​her family ​vacation, one of our clients, Michelle,​ had only a few things on her mind: ​crystal clear waters, ​bright sunshine and warm temperatures, and cocktails with little umbrellas. Unfortunately, the airlines and Mother Nature ​​had something else in mind.​

should you fly in a day before a cruise?
Vacation daydream: Crystal clear waters, beautiful blue skies.

​One of the compromises in ​her budget vs wish list battle was flying in the same day as her cruise instead of a day or two early to avoid the expense of a hotel room​.

​Mother Nature is known to have a quirky sense of humor (​which nobody finds funny), and ​saw an opportunity. ​An alert let us know ​Michelle’s flight had been delayed by an hour. Then three. ​She was going to miss her connection. Jennifer, my business partner at JJ Travel Associates called the airline and made arrangements for Michelle to be on an entirely different flight, without connections. Crisis averted.

The original flight was canceled but that didn’t ​matter anymore. Then the new flight was delayed an hour. Then two. No problem, though, it was direct and there was plenty of time to get to the port. Another delay, now three hours total. Still no problem. Finally, it was time to board the plane. Everyone seated, seat belts fastened, cross check completed, and away we go!

​”Folks, this is your captain. With all the delays and cancellations, we’re going to have to find a new crew to ​serve you on this flight,” came the voice over the speakers. “With your comfort in mind, ​we’re going to deplane and have you wait at the gate until a crew is found and arrives. The gate agents will have more updates for you throughout the day.”

Fly in a day early
Canceled flights are frustrating!

Ultimately, a storm came blustering through the area and all the flights going to her destination the rest of the day were canceled​.

​I called the cruise line, explained the situation, and arranged for Michelle and her family to meet the cruise ship the following day at the next port. They collected their luggage, and went home heartbroken while I made arrangements with the airline to change her final destination.

​The flight went off without a hitch the following day. Michelle and her family were on the way to a small airport where they would run through the airport, find the car service we had arranged, and get to the port with an hour to spare. Phew!

​Then the unthinkable happened. With all the flight cancellations and delays, customs and passport control was overwhelmed by the number of people coming at one time. The line was longer than the eye could see, and slow moving. Michelle and her family were going to miss the ship again.

​It’s not always possible, but for this itinerary, they would be able to board the ship the following day at the next port. We got them a hotel for the night and made arrangements for them to meet the ship at the next port. Thankfully, they were able to board the ship and enjoy the remaining five days of their cruise.

The High Cost of Unforeseen Delays

By the time Michelle and her family ​finally ​boarded the ​ship, ​they had not only ​had a less than relaxing ​first two ​days of vacation but ​were too tired to explore the second port. ​Plus the added expenses of ​four additional limo rides (airport to home, home to airport, airport to hotel, hotel to cruise port) and a night in a hotel. 

​Fly a Day (Or Two!) Before a Cruise

​​As ​Michelle’s story illustrates, things can go wrong. Flights can ​be delayed or canceled for multiple reasons, and while the airlines do their best to help, it’s not always possible. And, ​cruise lines aren’t particularly sympathetic to these issues. They’ve got schedules to keep and oceans to conquer!

​By arriving at least a day early, you give yourself a buffer ​to manage any unexpected hiccups. Not to mention, it gives you a chance to kickstart your vacation vibes by exploring the departure city. It’s a win-win!

​In conclusion, when it comes to vacation planning, ​arriv​ing ​early, ​saves you money and gives you extra peace of mind, knowing you’ve set yourself up for smooth sailing.

About Joel 225 Articles
Joel is a co-owner of JJ Travel Associates (a Dream Vacations franchise), blogger-in-chief at, lover of all things travel (especially UNESCO World Heritage Sites), wannabe comedian, and the person you should call if you're thinking of planning a vacation.