Florida 2020 – Flight Planning

We wanted to fly into Fort Myers and return from Orlando since we were going to rent a car and drive between the two mid-trip.

Flights: Take One

We have a high preference for nonstop flights, especially in the COVID era. We don’t want to be stuck in an airport any longer than necessary. Since we had to cancel our Summer 2020 trip to Hawaii, we had a lot of United points in my account available so that was the first place I checked.

I was happy to see a Saturday morning nonstop flight to Fort Myers which arrived around noon. This would give us most of the weekend before the last few days of school before Christmas. The tickets were only 5,000 points each and with the latest policies from United, the tickets could be canceled and the points refunded without fees. This made a lot of sense so I booked the tickets immediately.

I also found similarly priced tickets for a nonstop United flight returning from Orlando on New Year’s Day around noon. Earlier and later flights and flights on other days were about twice as expensive. The time worked well for us so I booked them quickly. These had the same ability to cancel without fee.

Flights: Take Two

As the fall progressed, we got thinking about the timing of our flights and wondered about ways to maximize our vacation time. Since the boys are in person for school only two days a week, they are remote the rest of the week. We got thinking that we could potentially leave mid-week to get an extra 5 days away (3 weekdays and 2 weekend days). While they would still have to attend remote school, it would be from someplace potentially more inviting than home in December. The plan would be to work from the Hyatt Regency Coconut Point in Fort Myers and the boys would be able to enjoy the water park after school. It would be tough, but I’m sure they’d be up for the “challenge”.

I found that getting a flight might be the real challenge. I was looking for flights on a Tuesday or Wednesday evening that left late enough that the boys wouldn’t need to leave school early. There was a JetBlue flight that we could barely make on Tuesday night, but it was pretty expensive. On Wednesday, the same time flight, which worked better for that day because the boys have an early release that day, was even more expensive on JetBlue. There were flights even later the would have us arrive after midnight that were more reasonably priced, but difficult to justify given the boys would have school the next day.

We didn’t have many good options, but we decided on the earlier Tuesday night flight that would be tight. I put off buying the flight for a day while I was distracted with work and by the time I was ready to buy, the flights were no longer offered. JetBlue and United had both changed their schedules and there weren’t any viable flight schedules to Fort Myers that worked for us all week.

Rather that give up on the new plan, I looked for alternatives. I know that Miami and Fort Lauderdale are only a couple hours away by car. I looked for options to fly into there, thinking we could drive from there to Fort Myers instead of flying into Fort Myers directly since we were going to be renting a car anyways.

I found a reasonably priced flight from Boston to Fort Lauderdale on a Tuesday night. It arrived around 9pm and wouldn’t require the kids to miss any school. We’d have to find a place to stay for one night in Fort Lauderdale as we wouldn’t attempt to drive to Fort Lauderdale that night. We could spend the night Tuesday in Fort Lauderdale, the boys would do remote school on Wednesday until their early release, and then we’d make the drive to Fort Myers for a 7 night stay.

I was able to book the flight using part of a travel voucher credit from an earlier canceled trip. With the flights reserved, next up was booking the hotels.