Travel Guide to Key West, Florida

December 9, 2018

by Kate O

While there are lots of benefits to a November birthday, for most of us the weather isn’t one of them! This year I decided to symbolically jump ship on Winter and run as far away from it as I could reasonably get in a weekend, in this case, to the Southern tip of Florida.
Key West is the last stop of the scenic Florida Keys, the westernmost island and southernmost town of the chain. Discovered in 1521, it didn’t officially join the US until 1822, and industries like wrecking, salvaging, and turtling quickly made it the richest city (per capita) in the country. Though that’s no longer the case, its popularity as a tourist destination remains strong. The draw is entirely understandable, with its rich history, Caribbean undertones, and walkable distances it’s a truly unique place to explore. Of course, I also have to mention the weather, with its coldest temperatures averaging 21°c (69°f) – it gives you a taste of the tropics without having to leave the US!

Getting There

Coming from Miami, there are two ways to get to the island at the end of the world that is Key West. It’s a long enough drive along the Overseas Highway (US 1). In theory it’s 3 ½ hours but it took me double that, courtesy of the Friday night traffic that plagues cities everywhere (beware!). While the drive is long, the road is almost entirely straight once you leave the city and the scenery is beautiful, including the 7-mile bridge (one of the largest in existence when it was built) and Key Largo. As the road name suggests, you’re surrounded by ocean views almost the whole way down.
Alternatively, you can fly direct to the local Key West airport, which takes around 50 minutes, and seems entirely painless.

Where to Stay

While there are lots of options available in Key West, ranging from chain motels to quaint guesthouses, all within walking distance of most attractions, I can only recommend the hotel that I stayed in: The Southernmost House. It’s oozing with charm, the building itself looks as if the house from Alfred Hitchcock’s Psycho was dipped in a pastel paint box, and the view of the ocean out across the swimming pool cannot be beaten. Though there’s no restaurant, they do have a bar, and offer a continental breakfast that can be enjoyed on the classic wraparound porch. Our room itself was across the street in an equally quaint old house, with a covered porch and a little kitchen.

Where to Eat

As someone with several food allergies including diary and gluten, and a childish dislike of fish, I have to admit that I didn’t have the most options in Key West where Southern cooking meets fresh seafood. However, I did sample several local restaurants while I was there.

Old Town Mexican Café

Tucked into a corner, we stumbled upon this vibrant and colourful Mexican restaurant with lots of options and massive portions. The terrace is ideal for people-watching on Duval street, but there’s also tree coverage that makes you feel like you’ve found a hidden gem away from the world.

Southernmost Beach Café

Right next door to our hotel, this adorable open-air restaurant had lots of seafood options and an imaginative chef, complete with a beautiful view out onto the ocean. They have everything from breakfast to a full bar. Side note (literally): while they helpfully indicate their gluten free options, their sides are very limited for someone with my kind of restrictions.

La Te Da

Good for a nice lunch, this is a slightly more upscale place with a French inspired menu. Even though they don’t have dedicated gluten free options, they were very friendly about adjusting my order. It’s also a cabaret and piano bar in the evenings!

Banana Café

Finally, we found this cute French restaurant at the south end of Duval street where we had a delightful Sunday-morning breakfast. While I couldn’t enjoy the signature crêpes myself, I was told they were delicious!

What to See

Hemingway House

As a big fan of Hemingway, Key West is a treasure trove of references. Most notably, the house that he lived in with his second wife from 1931 to 1940, featuring the first in-ground pool in Key West. It’s full of personal paraphernalia, anecdotes, and most importantly cats! The entry fee of $14 includes a long and detailed tour by very capable guides which really enhanced the whole experience.

Sloppy Joe’s

Sloppy Joe’s is also a staple of Hemingway-lore, it was his local bar where he frequently drank himself into a stupor before making questionable decisions – Including once dragging a 100lb urinal home with him. The place still exists, and it has a certain Cuban quality to it which I find to be a common thread of many of Hemingway haunts. It’s an atmospheric bar and restaurant with wood panelled walls and live music, very loud and very down to earth.

Southernmost Point

Tucked away in a little corner by the ocean, is a concrete buoy marking the Southernmost Point of the Continental United States. It’s a great spot for a photo op, but during the day there’s often a large queue, I’d recommend going early morning for the best shots and some privacy.

Duval Street

Duval Street is the main artery of tourism in Key West, running 14 blocks between the Gulf of Mexico and the Atlantic Ocean (fun fact!). Apart from the usual bustling bars, restaurants and souvenir shops, it’s a unique and vibrant street full of everything from a Butterfly sanctuary, to an antique store selling sculptures of balloon animals. If you do nothing else, I personally found just wandering along this street gives you a real sense of the atmosphere of Key West, and plenty to experience without committing to going inside.

Worth Noting

Mile Marker 0

Key West is home to the southern end of the US 1 highway (the longest north-south road in the country), marked by a very famous green road-sign, indicating Mile 0. It’s become a local attraction, and the logo is everywhere you look. From key chains to t-shirts, it’s a staple.

Little White House

Situated inside a gated community that used to house military officers, this Presidential residence initially served as the naval station’s command headquarters during the Spanish-American War, and both world wars. In 1946, it became the winter home of President Truman. For around $20, tours are offered throughout the day, by knowledgeable and enthusiastic guides.

Oldest House in Key West

A quaint house museum dating back to 1829, the house was originally built on Whitehead Street, but like many buildings on the Island it has since been moved and can now be found on Duval Street. Nestled among the grand Southern mansions with wrought iron balconies, this one-and-a-half storey family home offers a glimpse back into the lives of ordinary Key West residents in the 19th century. It has survived many hurricanes, and originally housed 9 people. It’s also free, which is always a bonus!


Originally erected in 1847, it’s since been updated and modified, but the lighthouse still has a lot of old charm to it, and now serves as a maritime heritage museum. For $12 admission, you can explore details about the life of the keepers who ran it until 1969, as well as climb it’s 88 steps to the top and catch a great view over the entire island. It’s right next to the Hemingway house, and legend says that he used to use it to find his way home when he was drunk (so most of the time).

Kate O

By Kate O

I'm Kate, a loud, enthusiastic, third-culture kid from Belgium. I have lived in 7 places in 8 years and I specialise in being perpetually foreign and confused, I love to travel and talk about travel, and generally feel a sense of adventure as often as possible. .


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