Spending 29 hours in beautiful Key West, Florida

This is a blog post that I’ve been meaning to write for months. My only excuses are pretty good ones, I’d say. Between the Christmas holiday, our daughters’ birthdays, bringing home a new puppy, and taking on more freelance writing work, it’s been a whirlwind. Anyone else still shocked that we’re already on our way to St. Patrick’s Day and Easter? BUT I’d be remiss to not do my best to recall what were an incredibly fun, key lime pie-filled 29 hours in Key West, Florida last December.

As a lifelong Parrothead, a trip to Key West has felt like a necessary bucket list item. Yet the logistics can be a little tough, and trips just for me and my husband are rare. That’s why when we planned to spend a week in Naples, Florida with my parents after Thanksgiving, it felt like the perfect opportunity to sneak away for a quick Key West visit and let the girls have some extra grandparent time.

Thanks to the Key West Express out of Ft. Myers, we could leave at 8:00am and get to Key West in about four hours by boat, which is much faster than driving. Based on the ferry schedule and our trip dates, we decided to travel down to the Keys on a Thursday morning and return the following evening. Thanks to the late departure time coming back, we’d have 29 hours to enjoy all that we could before heading back.

While that doesn’t seem like nearly enough time, we had guidance from friends and family about their favorite places, and also had our own can’t-miss spots. We managed to cover a lot of ground. Not to mention, a lot of key lime pie. Here’s what we did!

Arriving at the dock right around lunchtime our first day, we ventured straight to a place recommended by family friends: B.O.’s Fish Wagon. We were told they had amazing fish tacos, and boy did they hit the spot after a long morning of boat travel.

B.O.’s Fish Wagon is an open-air shack covered in random bumper stickers and artifacts from all around the world. I even spotted a U.P. bumper sticker on our way out. This was a great introduction to the laid back Key West way of life.

From there, we walked to our bed and breakfast, The Conch House. There were several recommendations for hotels and bed and breakfasts in Key West, and so many of them sounded great. Because we decided to book our night there without a ton of notice, many of the most popular places were booked up.

Luckily, we were able to get a wonderful room at The Conch House, which is a close walk to Blue Heaven, Hemingway House, and Duval Street. I liked the idea of being a little bit away from the main drag while remaining walking distance from the places we wanted to visit. I loved how every place had Christmas decor up, but in the most Florida way possible.

After getting checked into our room and freshening up, we ventured out to get our bearings. We walked toward the Hemingway House and there wasn’t a line at the gate. We overheard a guide mention that a tour was starting in a couple of minutes, so we decided to buy our tickets right then and join the tour.

I loved learning about Hemingway’s wives, secrets about the house, their many cats, and fun bits of trivia. Our guide was hilarious and shared so many funny stories about Hemingway. It was a magical place and I can see why it’s a must-visit.

After Hemingway House, we walked over to Duval Street to check out the shops, bars, and restaurants. We enjoyed our first taste of key lime pie at the Southernmost Key Lime Pie Shop before walking up toward Captain Tony’s Saloon, a popular Jimmy Buffett spot.

Southernmost Key Lime Pie shop pie

After walking around for a few hours, we went back to Conch House to get changed for dinner at the Sunset Celebration at Mallory Square. This is another tradition that many people familiar with Key West recommended we experience. Mallory Square fills up with vendors, performers, musicians, and food carts as it gets close to sunset time. The area by the square offers a beautiful view of the sunset and a chance to applaud as a group when the sun disappears into the water. The night we were there it ended up being a little cloudy, so it was hard to tell when the sun actually set, but nevertheless it was cool to experience.

After the sunset celebration, we walked around Mallory Square before heading over to The Flaming Buoy Filet Co. for dinner. We had gotten several great dinner recommendations from friends, but decided to try this place based on reviews and their menu offerings. I’m allergic to shellfish, so sadly a lot of the recommended places predominantly featured shellfish items. Flaming Buoy was a really eclectic looking restaurant on the inside, with lots of Star Wars decor mixed into what is otherwise a very snazzy bistro type of place. We both loved our meals there.

During our walk after dinner, we decided to give another key lime pie shop a try. This one, the Key West Key Lime Pie Co., ended up having my favorite key lime pie of the trip. What set it apart from the others is that you could order it extra tart, and the whipped cream topping was added when we ordered the slice, making it even fresher tasting.

The next morning, we beelined over to Blue Heaven for breakfast, because we were going to eat as much in Key West as we could, obviously. Everyone recommends Blue Heaven for their breakfast and patio area, and it also inspired Jimmy Buffett to write his song “Blue Heaven Rendezvous.” We arrived shortly after they opened and got a table in the outdoor seating area. Much like everywhere we went in Key West, roosters roamed around. We each had a delicious breakfast (the eggs benedict was divine) and shared, you guessed it by now, another slice of key lime pie.

The pie at Blue Heaven is famous for its tall layer of meringue on top. Though amazing and delicious, I have to give the edge to Key West Key Lime Pie Co. for their traditional slice.

After breakfast, we walked over to the Key West Butterfly and Nature Conservatory. What a magical place! This also came highly recommended by our family friends, and I was so happy we visited. We got discounted tickets when we were at Hemingway House, which also helped. As soon as we walked into the building, we were greeted by hundreds of butterflies and birds. It felt like being in a movie. You’re not supposed to reach out for the butterflies, but oftentimes they would land on people.

I could have spent hours inside the habitat, and can’t recommend it enough to anyone who loves butterflies/has a soul.

We weren’t too far from the Southernmost Point buoy, so we walked in that direction and waited in a short line for a photo. Luckily, it’s a popular enough spot that we were able to take a family’s photo in exchange for them taking ours.

After the photo, we took our time walking toward Santiago’s Bodega, a small plates restaurant where we had a lunch reservation. My friend Erin recommended this spot, and it had fantastic reviews. We enjoyed a few small plates and a glass of sangria while eating out on the patio (truly, is there anything better than eating outside?) and watching the roosters walk by.

Our host at Conch House recommended the Mel Fisher Maritime Museum as a place to check out if we wanted to sneak in another activity before we had to get on the ferry boat to go back to Ft. Myers. I think that it would be a fun place to visit for families, but I wouldn’t need to see it more than one time. It was cool to walk around and learn about the shipwreck and treasure that was found after years of searching.

After the museum, we hit up one more key lime pie shop, Kermit’s Key West Key Lime Pie Shoppe. I’d read a lot about this one online prior to our trip. It also had a lot of great key lime-themed treats for me to bring back home to friends. In the ranking of key lime pies, it was third for me.

We walked back to Conch House to grab our bags and get a ride up to the docks for the Key West Express. There was one more spot on my Key West list that I wanted to check out: Cuban Coffee Queen. We were a little early for the boat, so we stopped by their original location by the water so I could grab a coffee. I ordered a delicious cold brew, which was so good.

Their cold brew has coffee ice cubes, so even as they melt, it doesn’t get watered down. This Cuban Coffee Queen location is also home to this awesome Key West mural, so even if you don’t love coffee, it’s a great photo op spot.

We went over to the Key West Express for boarding and settled in for the long journey back to Ft. Myers.

All in all, we had a solid 29 hours in Key West and made the most of our time there. I’m hoping we’ll get back there again soon and spend at least one extra night in order to enjoy everything at a slower pace.

And even more key lime pie. Alllll the key lime pie.


Have you been to Key West? Where are your favorite spots there?