The drive to Key West on the Overseas Highway is one of the designated All-American Roads, an honor received by only 31 of the nation’s Scenic Byways. It is 110 miles and takes at least 4 hours, depending on the number of stops.
We chose one stop, both ways, at Robbie’s in Islamorada at mile marker 77.5. On the way down we had lunch and fed the tarpon, which was exciting. On the way back, we just used the restrooms. There are lots of opportunities to stop and buy souvenirs and take pictures with giant crustaceans, but we just drove and enjoyed the views. We spent a lot of time talking about how great it would be to be boating instead of driving, and the logistics of trailering, driving, or chartering to make that happen.
what to listen to on the drive
Audible (books on tape)
Audible (books on tape) – anything by Carl Hiaasen, but specifically books that include the character Andrew Yancy, and Razor Girl, which takes place in the Keys. WARNING: Inappropriate Content, not suitable for all ages
Jimmy Buffet
The Weather is Here I Wish You Were Beautiful; Margaritaville; and It’s 5 O’Clock Somewhere
Songs to Add to the Mix
Key Largo
Drive South
Cruise
Time To Move On
making a plan
The most important thing for a trip, any trip, is to know your audience and get buy-in. The best way to do that is to let everyone choose a special activity. This particular trip was with my son for two nights; we needed to find mother-son activities for a new graduate, who likes adventure. We were joining Baby Sis and three of her kids for the Keys segment of their Florida trip, so there were several different ages and interests.
Joseph’s activity was to ride jet skis and I chose to take the seaplane to the Dry Tortugas. Renting jet skis – was fun, but terrifying. Because the Keys are still reopening after the pandemic, we had a private tour. The guide was in a hurry to be rid of us, so he told me that the ride is smoother the faster you go – not true. He and Joseph were full throttle, about 45 mph – which I tried, but it rattled my brain. I trailed behind at 25 mph (very fast!) for the 30 miles around the island. They were doing tricks and weaves, and making spray… I was happier enjoying the views. After all it was Joseph’s activity, and the slower I went, the more time he had on the jet ski. You’re welcome!
dry tortugas national park
The park is collection of small islands and corals reefs, located about 70 miles offshore from Key West. The remoteness makes it one of the least visited of the national parks. There are several ways to get there: private boat, ferry, or seaplane. The ferry is a long day! It’s 10 hours, with more than half of that time on the ferry. Click HERE to read about the ferry.
The flight is 45 minutes, which goes very quickly. The pilot spots turtles, sharks, and shipwrecks and gives a bit of history and commentary. What I wish I knew, and I will share here, is that the best views are on the right side going out. Try very hard to snag a seat on the right as you board the plane. The pilot encourages everyone to stay on the same side of the plane for the return trip, so that you see different things. I got to sit in the cockpit on the way back, which was awesome, but never got the good picture of the fort from the air.
There are two flights per day: 8 am and 2 pm. Click HERE for details about the seaplane. We are locals, and know that the afternoons in June are likely to include storms ~ it’s a pattern, so we obviously wanted the morning flight. They could not accommodate us, so we ended up on the afternoon flight. This is an example of things working out because it stormed all morning that day, and the afternoon was beautiful!
After we landed, the ferry left 10 minutes later, so there were only campers, people from private yachts, and the rangers left on the island. It was very easy to socially distance. We walked around the fort for an hour and found that our favorite place was the middle level, opposite the entrance – it had shade, a breeze, and a view of the lighthouse on Loggerhead Key.
Afterwards we had some time to go swimming and snorkeling, but not a lot. Then it was time to gather our things because it was time to leave. We definitely would have liked to stay another hour, but another 3-4 hours? I’m not sure.
BRING: a sandwich and water, even though water is included with the ticket, I needed more; dry clothes and a towel; flip flops; optional – tennis shoes were good for walking around the fort, and I’m glad I had them; also, a bag for wet clothes.
getting around in key west
We drove, so had SUVs to get around, but that isn’t the moment. I would imagine that as the Keys open up more, traffic will be an issue, and parking, but we didn’t have to deal with that. They have the Conch Train and a Trolley Tour, but we only had the morning before we were going to get on the plane to the Dry Tortugas, so we opted for renting a 6-seat golf cart. This allowed us to go on our own timeline, and was less money than buying everyone trolley tickets.
We pulled up the stops on a self-guided Key West app and started checking them off. We took our picture at the buoy, which you should do early because it’s better light and there isn’t a huge crowd. The museums were opening late, so we started at the cemetery, when the wheel came off – literally. You can read about it HERE.
I don’t recommend the cemetery as an activity – just a drive-by. There are lots of iguanas living in the opened crypts – it was unsettling to watch them slither into the tombs. Ugh.
We spent a lot of time on Duval St. looking in the windows at the offensive tee-shirts and inappropriate souvenirs. We did a drive-by of the lighthouse, and got some sandwiches for the afternoon.
where to eat
The Keys Coffee Co.
505 Southard St.
The first day I ordered Avocado Toast, which comes with two poached eggs, and it a total mess to eat, but so good. The next day I went back and tried the Havana, also very good.
Sunset Pier
0 Duval Street
We ended up here to watch the sunset, I was late because we walked from the hotel, and the sun didn’t wait. But it was time to eat, and the ceviche was very good, as was the burger. Sometimes touristy places on the main drag are only ok, but this place was solid.
Uber Eats: Indian Harbor
What to do when the skies open up and it’s dinner time? Drink wine in the room and have a picnic. Unfortunately, it was my bed that served as the picnic blanket, so that was poor planning.
where to stay
Winslow’s Bugalows
725 Truman Ave.
This is a charming little complex of attached bungalows, two pools, and parking. It’s very nice, and it felt like we were the only people there. It’s perfect for couples or groups, who want to be a bit off the main drag and chaos of Duval St.
What I didn’t like: it’s a hike to Mallory Square for the sunset views; the bikes that are available for all of their guests are ‘first come, first serve’ and even with the hotel at 25% capacity (about 22 rooms, with our group being 3 of those rooms) the bikes were all taken, as was the parking. What is it like when the hotel is full?
After reading through the website’s amenities, I didn’t see any sign of a boozy welcome, or an afternoon refresher… Also, we had some severe thundershowers, and there are no breezeways and very little shelter when leaving the rooms. The breakfast area is very small and there was little protection from the rain.
want to see more?
Just in case you haven’t seen enough… here is a link to the gallery of everything from the visit! The photos on this page are at a reduced resolution for ease of loading, the originals are much larger files, and are available for download.
buy a vintage poster
