My Perfect Day in Key West in 4 Acts

There are strange holes in my travel resume; spots I just haven’t visited for a variety of reasons. Until a few months ago, Key West was on that list, and I couldn’t wait to finally travel to this remote American outpost on the edge of the country. My visit to the Florida Keys was part of a project with Marriott, the Americas to highlight some amazing places around the country, including the always-interesting community of Key West.

Key West Florida

Where to Stay

What helped set the tone for my brief stay in Key West was my very quirky but also very luxurious boutique hotel, The Saint. Part of the Autograph Collection of hotels the distinctive mix of design and decadence matches its central Key West location with ease. A hotel’s location is always important to me, but that was especially true in Key West. The Saint is located in the very heart of the Key West experience, within stumbling distance of the most important sights, restaurants and, of course, bars. Housed in historic buildings that ooze with Key West charm, there are just 34-rooms and 2-suites at this two-story hotel; a number that is guaranteed to make every guest feel unique and special. Although my stay with The Saint was brief, I already know that it will be my go-to hotel whenever I find myself in beautiful Key West.

Key West Florida

What to Eat

The culinary side of Key West was a surprisingly important part of my experience. Since it was my first visit, I was a very corny tourist and had a blast in the process. This meant lunch at Sloppy Joe’s and finding a rooftop bar to soak in one of the sunsets for which Key West is so very famous. In between though I did something a little different – I went out in search of the perfect slice of Key Lime pie. The history of Key Lime pie is actually oddly complicated and fraught with controversy, and my own quest went well beyond Key West to encompass all of the Florida Keys. While in Key West though, I sought out a few different establishments and I actually found a favorite slice at a spot that surprised me. Although the Key Lime Pie Co. was recommended to me, I was still a little hesitant to include it in my tasting spree because it seemed so corporate, so different from the other restaurants on my list. There’s a reason for that, in 2014 the company reached out to entrepreneur Marcus Lemonis – the star of the show “The Profit” – who partnered with the company to help them improve their business. They say that they use a 100-year old recipe, which seems to run slightly counter to historical evidence, but the pies are indeed made fresh every day. I enjoyed this version, although I didn’t think I would. All of the flavors were on point and I like the fact that the filling was extra thick.

Key West Florida

Historical Sites

I’m a history-minded person and, thankfully, there are plenty of spots to visit in Key West that share the history of this odd community. I started at the Hemingway House, a place I’ve wanted to visit for a very long time. This classic Key West home was the residence of the famed author from 1931-1939 and is also home to those equally famous multi-toed cats. Hemingway was given a six-toed cat by a ship’s captain and many of the polydactyl cats around today are descendants of that first furry feline. Touring the home though with a trained guide is a wonderful experience and should be at the top of anyone’s to-do list. Another not to miss home is the Little White House, Truman’s vacation getaway. This was the winter residence for the President, who spent 175 days there over 11 different visits. The home has been painstakingly restored to its period look and is a fun way to learn about the more laid-back side to Truman. Another not to miss spot is the Sails To Rails Museum at Flagler Station. This, the newest museum in Key West, shares the history of Key West from those first ships that sailed into port to Flagler and his famous railroad. The Florida Keys have a fascinating history and the Sails To Rails is the best spot I’ve found to learn all about this colorful past.

Embracing the Weirdness

Key West is an unusual place and always has been. Simultaneously American but also foreign, this port of call has been attracting quirky individuals since its inception. Today it’s a wildly popular vacation destination and with good reason. The history, the culture, the food and the scenery all conspire to create one of the country’s most remarkable hotspots, a designation that I think is well earned. As soon as you cross over onto the Florida Keys though, it’s time to embrace this spirit. In order to truly appreciate the Keys as they are meant to be enjoyed, you have to go with the flow, accept that things are a little bit slower with the knowledge that ultimately, your trip will be made all the better for it.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

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