Planning a Trip to the Florida Keys

When we decided to settle in one spot in Florida for a while, we knew we wanted to continue our monthly trips to get away and explore as we did in Virginia. The first place I wanted to visit was the Florida Keys.

The Keys are not conducive to boondocking, so I started exploring VRBO.com for a place to stay for a few days. As it turned out, I found an affordable reservation over our anniversary weekend.

As we got married a month after our vacation last year during the Covid shutdown, we did not go on a honeymoon. I hoped to put away enough money for a trip to Hawaii for our first anniversary instead. With both of us losing our jobs, that didn’t happen.

Since October, we have done a lot of traveling, so planning a vacation at our usual time in March seemed silly. We decided a romantic trip to Key West for our anniversary would be a perfect getaway. I booked the cottage and waited excitedly for our anniversary weekend to arrive.

New Yorker Daily Eats Tampa Florida

A Great Start to the Trip

One of our favorite vacation activities has always been exploring great places to eat. We haven’t eaten out much since the pandemic started. With the numbers dropping and more people getting vaccinated, we decided this would be the weekend we would attempt eating out again. Eating in restaurants would put us outside of our comfort zone, but we felt it was time.

Our trip started at Daily Eats in Tampa, our favorite breakfast spot. We timed our departure to arrive at the restaurant right after they opened and planned to sit outside on the patio. There were a few other customers when we got there. The hostess allowed us to pick our table, so we chose the one at the end of the patio with no other tables nearby. As usual, the food was terrific, and the service was fantastic. It was a perfect start to our adventure.

As we journeyed south, we passed a car on the side of the road, fully engulfed in flames. We were happy to see the driver was safely in the grass on his phone, presumably calling for help. Another driver had stopped to lend a hand, so we felt comfortable continuing on our way. As we drove, we saw the fire trucks heading in that direction.

Black Vulture Fort Myers Florida

When we stopped at a rest area for a short break, we were surprised to see a large black vulture hanging out. The rest of our trip was uneventful until we reached the Miami area. Traffic was heavy, slowing us down, but soon we were on the road to the Keys.

The Keys

We planned to stop for lunch in Key Largo at Pilot House Restaurant. I was excited to eat on the glass floor over the marina. We had good timing, and the restaurant was not busy. We felt comfortable eating on their deck. Unfortunately, they no longer have a glass floor. While lunch was less than a stellar experience, I enjoyed our sandwich.

Sailboat Key Largo Florida

After a welcome break, we continued our scenic ride through the Keys. One of the beauties of the Keys is the drive. It is about 100 miles from Key Largo to Key West, mainly on a two-lane road. Most of the two-hour drive is within sight of the most spectacularly colored blue-green water. The view is breathtaking. We enjoyed seeing all the boats out on a gorgeous Saturday afternoon.

There are plenty of passing zones along the way to keep from getting stuck behind a slow driver. At one point, the GoogleMaps directed us to turn onto a small side road. I didn’t understand why until we saw a traffic backup on the main road. The side street took us to the front of the traffic jam, saving us a lot of time.

Cudjoe Key

As we crossed the bridge to Cudjoe Key, a flock of pelicans flew directly over us. It was as if they were welcoming us to the island. I took it as a sign that we were bound for a fantastic weekend. Our cottage on Cudjoe Key was not fancy but had everything we needed for a lovely weekend. We could see the water from our screened porch, and there was a pool behind us. We walked down to the water where we could see a variety of fish swimming. I enjoyed seeing the many lizards running around the property. Twice some of them got into the porch through a small hole in the screen, giving Chris an excuse to catch them to set them free.

With our late lunch, we decided on a late dinner as well. We had picked The Square Grouper Bar and Grill for dinner because it had good reviews and was nearby. When we went online to put our names on the waitlist, we realized that they were busy, so we decided to order our food to go.

Key Deer

We drove over two Keys to go to the grocery store for a few supplies we wanted for the weekend. Big Pine Key is one of the places that has Key Deer, an endangered subspecies of white-tailed deer, found exclusively in the Florida Keys. They are the smallest species of deer in North America. I had read about them while researching things to do in the Keys but didn’t expect to see any.

Key deer with rooster Big Pine Key Florida

As we pulled into the store parking lot, I was delighted to see not one but three of the precious creatures. Unfortunately, some children were feeding and petting one of the deer, even after someone leaving the store told them that it was illegal to feed or touch them. I can understand their fascination as the tiny deer are adorable.

I took some photos of the other two deer and the rooster that was hanging out with them. When we left the store, I attempted to get a few more pictures of the deer. I heard the rooster, but when I looked, I couldn’t see the creature. I walked over to where I heard the noise and realized that he was up in a tree. As I looked, I realized there were six more roosters perched in the tree with him.

Rooster in a tree Big Pine Key Florida

We picked up our food on the way back from the store, enjoying the beautiful sunset reflecting over the water. The famous white blimp over Cudjoe Key was lovely, with the pink light bouncing off it.  After a spectacular dinner, we called it a night as we had an early morning planned.

Driving Through the Florida Keys Gallery