Spring 2020 – Planning

We usually try to do a trip during the weeks the boys have off from school in February and April. In February we had gone to Spain for 10 wonderful days. April is a little more constrained because of soccer schedules. In 2019 we had a great trip to Los Cabos in Mexico but were planning something closer to home in 2020.

Choosing the Destination

We had originally looked at going to Chicago because it’s relatively easy to get to and there are a lot of great things to see and do. I’ve never really been but my wife has and it seemed like an interesting destination.

For whatever reason, we started yearning for a warmer destination, though. At the time we were looking to build up our Hyatt status and had been looking for unique destinations within their brand. We found several posts along the lines of the “Best Family Hyatt Hotels” and most had a hotel near Fort Myers, FL as their top choice.

The Hyatt Regency Coconut Point Resort and Spa has it all. It has a full blown water park with slides and a lazy river. It has access to a private beach (via water shuttle). It has a climbing wall and tons of other lawn games and outdoor activities. The reviews we read were all glowing and we were pretty excited about the destination.

I was able to find 5 nights available on points that were an excellent value as well. This looked to be our April destination!

Booking Flights

We found nonstop flights on JetBlue from Boston arriving on a Sunday evening and returning Friday evening. This would allow the boys to attend their soccer games and maximize our vacation time. We figured we would be able to get a later checkout on the Friday to get as much work done as possible. The flight was not a good value on points so we ended up paying cash.

This Pandemic Thing

As we now know, around mid-March, the pandemic started to hit the northeast. In our town, schools started to go remote so the boys were going to be home. The stores were running low on food and there were threats of shutdowns and lockdowns. This was all long before travel restrictions and masks. We knew a lot less about the virus than we do now.

After a few days of remote learning, we made the decided to “work from hotel” instead since we could use the hotel gym/pool. We had plans to stay in Boston but there were rumors about shutting down restaurants and other things. Again, we had no idea what was to come in the months ahead.

This prompted the idea to see about getting out of town completely. At the time we naively thought things would clear up by the time April came around and we’d be able to go on our trip (ha!). I figured I’d look into moving the trip up and having the boys work remotely from the hotel.

It was a Saturday morning and I was looking at the hotel availability for the next week. There were rooms available on points. Looking at flights for the next day, I saw that flights were surprisingly inexpensive. They were about $50 per person one way. We decided to cancel the April plans and head to Florida!

As we’re almost a year into the pandemic, knowing what we now know, I’m not sure we’d make the same decision, but things seemed pretty dire in the northeast at the time. There were looming shutdowns and shortages of basic supplies and escaping to southern Florida seemed like an attractive option. Our thinking was that worst case we could always rent a car and drive home if it came to that.

That said, I didn’t book a return flight because there was a chance that if things got really bad in MA we might want to stay away longer. I wanted to give ourselves that flexibility at the risk of having to pay a lot for a flight home. We were willing to take that risk.

In the end, we changed our plans last minute and had booked a flight for the next day to Fort Myers. We had booked 6 nights in the Hyatt Regency Coconut Point Resort and Spa. I had also used a club level upgrade I had recently received so we would have access to free breakfast in the club lounge. We would use Lyft to get around to avoid having to pay for parking and renting a car while building up my Hyatt status.

Time to pack for the sunny weather!