We visited Key West, FL for 4 days in April for our first vacation of 2021. We picked it because we didn’t know how things would be going with Covid, whether we would be vaccinated by then or even generally what would be open/close at that time. Key West is driving distance for us, though the drive took longer than we expected. From West Palm, the drive is about 5 hours, including a stop for lunch. We made a stop about half-way on the drive in Islamorada for a margarita and some fish sandwiches at the Islamorada Fish Company.

We stayed four nights in “Old Town” Key West which is where all the major sites are located, including The Hemingway House, Duval Street, various museums and Mallory Square. We stayed at a relatively new boutique hotel called H2O Suites, which we liked as the Premier Rooms had private plunge pools, it was very modern and clean and there was ample free parking. We were also a block off of Duval Street and walking distance to lots of restaurants, nightlife and shopping.

One of our first sights to see was The Hemingway House. Ernest Hemingway lived in the house with his second wife, Pauline, from 1931 to 1939. After they divorced, the house was still owned by Pauline but she rarely visited and the house was virtually sealed up and left exactly as it was when Hemingway last lived there in the late 1930’s. It’s been very well preserved and they have lots of information and artifacts from his career and life. The property itself is also gorgeous with lush tropical gardens, the famous “last red cent” pool and, of course, the 6-toed cats.

As you can see, the house is left in its original 1930’s state with the same flooring, lighting and even furniture in some rooms. Hemingway’s study, where he wrote much of For Whom the Bell Tolls, was basically locked up with all his animal trophies, pictures and desk left behind (I guess it was an ugly divorce).

I particularly liked all the 6-toed cats on the property, who have complete freedom to roam and sleep anywhere they please. Hemingway was given a polydactyl cat named Snowball by a sea captain back in the 1930’s and all the six-toed cats on the property are his descendant. I believe there around 80 cats on the property with at least half of them bearing an extra toe on their paws.

We also visited Truman’s Little White House but it was, frankly, really run down and shabby looking. Hard to believe that it’s even still used when Presidents visit Key West (which isn’t often).

We also spent some time enjoying the old town charm and walking around between finding some great local seafood places to eat. I love the Key West style homes, which range from Victorians to adorable “eyebrow” cottages. Oh, and there are chickens and roosters everywhere. They wander in and out of restaurants and shops all over town.

We also had some great meals while there (and one really awful meal at A&B Lobster House…sorry to call them out but it was objectively bad food and was our priciest meal of the trip). Our favorite restaurants of the trip were Louie’s Backyard, which overlooks the ocean and is great for sunset, Blue Heaven for brunch, including their key lime pie and famous eggs benedict and then the Half Shell Raw Bar on the marina for beer steamed shrimp and oysters.

We also made a visit to Captain Tony’s Saloon, which is a bar we spent a lot of time in 19 years ago when we came to Key West on our honeymoon. It was just as charming and dirty as I remember. I forced my husband to do a very grainy and dark selfie (he hates selfies) in honor of our 19th wedding anniversary.

Finally, our last activity there was taking a seaplane to the Dry Tortugas National Park, which is the most remote National Park in the U.S. You can only reach it by a 3 hour ferry ride or 40 minute sea plane flight. This was my first time on a sea plane and we loved it. I was a little nervous about the small plane but they fly very low over the water (it’s not pressurized and is basically an “open air” plane) so you can see turtles, shipwrecks and even sharks. You get great views of the shallow waters along the way.

The Dry Tortugas are 70 miles west of Key West and Fort Jefferson, which is located on the main island, is the largest brick and masonry building in the western hemisphere. It was built during the 1850’s and was used during the Civil War as part of the Southern Blockade effort. It also housed prisoners for many years, including Dr. Sam Mudd, who set the leg of John Wilkes Booth and was convicted of treason.

After 2 hours exploring the fort and its beaches, it was back in the sea plane for the return ride. The sea plane is more expensive than the ferry ride but it’s so much faster and if you’re prone to seasickness, this is a much better option! Tickets for the seaplane were about $320 each while the ferry is about $200 each.

All in all, we had a fun few days in Key West. In retrospect, we wish we had taken the risk and gone somewhere outside the state of Florida but I got pretty sick of cancelling plane tickets last year. If you’ve never been to Key West, it’s definitely worth a visit for 2-4 days max. You won’t find great beaches in Key West or anywhere in the keys so it’s more about the history, food, music and nightlife than anything else. We are getting a little old for Duval Street but found plenty of off the beaten path places to enjoy. After Key West, we drove back up the keys and stayed in Miami for 2 nights at my favorite hotel in FL so far – the Four Seasons Surfside….