Complete Old Town Key West Guide & Fun Things to Do

Upholding a rich and storied history of a town that may seem all surface level to those who haven’t taken the time to acquaint themselves is Old Town Key West. Also known as Key West’s Historic District, this little pocket of island paradise puts conch culture on full display with museums, attractions, restaurants, and more. It’s the best place to get to know where Key West comes from in an enthralling way — fully immersed in the most fascinating attractions on the island. If you’re not a history buff, Key West’s Historic District may just change your mind and introduce you to your new favorite lunch spot at the same time. So, hurry on down! Old Town Key West awaits!

A Brief History of Old Town Key West

At the time of the City of Key West’s founding in 1822, Old Town Key West was designated as the city’s center. Today, it serves as the center for Key West’s Historic District, and in turn, the city’s premier tourist location. The history of the area began with a boom with Key West’s wrecking industry of the 19th century, making it the richest city in the United States per capita at the time. It was the site of the founders’ shipping docks, warehouses, restaurants and grand homes.

In addition to wrecking, Old Town Key West received a population influx upon becoming an official territory of the United States. For reasons political, economic and more, many prominent Bahamian citizens transported their homes from the Bahamas to Key West in the 19th century, establishing a distinct architectural style for years to come.

Today, thanks to the City of Key West, this standard of construction is most stringently maintained in Old Town Key West as a means of preserving Key West’s Historic District’s original glory.

Know Before You Go

Old Town Key West occupies the vast majority of the western half of the island. It hosts a great deal of the tourist attractions Key West has to offer, making it a must-see destination on your Key West vacation.

Key West’s tropical climate ensures warm weather year-round, even in those winter months of December, January and February. In the season spanning September to February, Key West sees its slower tourist season and temperatures ranging in the 70’s & 80’s (considered great beach weather in the Northeast)! From March to August, encompassing events such as spring break, Juneteenth and the Fourth of July, Key West experiences its busiest tourist season, as well as hotter temperatures.

While Key West’s Historic District is certainly walkable (as is most of Key West), there are some ways to get around that you might find easier and more fun. Consider a Hop On, Hop Off Tour with Old Town Trolley. It’s a great way to get the best views Key West has to offer above traffic, as well as take you from one popular attraction to another as you wish! With all-day service, it’s a value you can’t beat. Bicycles are also a popular mode of transportation in Key West for those looking to capitalize on those Key West sunbeams. And, what’s even faster and more fun than a bicycle is a Fury golf cart rental. These fun-mobiles ensure that even the transport from one place to another is a great time. Zipping through the streets of Key West in a golf cart may even prove to be the highlight of your trip!

Nearby Attractions

When you are in Old Town Key West, you are in the city’s tourist hub. Here are some of the attractions Key West’s Historic District has to offer that you just can’t miss. In no particular order…

Aerial view of the Fury Afternoon Snorkel Tour

#1 Fury Morning Snorkel

When you’re on vacation, waking up bright and early is best! Fury sees that, and invites you to their Morning Snorkel trip. Be the first ones to the reef and watch it wake up before your very eyes. Head out on a state-of-the-art catamaran, put on Fury’s top-of-the-line snorkel gear and explore beneath the surface all morning. When you’re ready to get back on the boat, enjoy complimentary beverages, such as mimosas, beers, wine and sodas. Spend the rest of your day reflecting on your marvelous sunrise experience!

#2 Fury Commotion on the Ocean Sunset Sail

After one evening in Key West, it will become abundantly clear to you how remarkable a Key West sunset is. Experience the best sunset on the East Coast out on the Atlantic with a drink in hand and live music that makes you want to dance the night away. A party like you’ve never experienced before, Fury’s Commotion on the Ocean Sunset Sail shows you the natural beauty of the evening sky in the grandest fashion. Book your Sunset Sail now! You won’t regret it.

#3 Fury Ultimate Adventure H2.0

When Fury says “Ultimate Adventure,” they mean it! This is truly an all-encompassing, 3.5 hour excursion with fun and excitement in every second! Soar through the sky on a parasail, make some serious wakes on a Jet Ski, zip through the waters on a thrilling banana boat ride, and play your hardest at the largest ocean water park in Florida! Refreshing Snacks and beverages all included, all you need is your favorite swimsuit and a desire to have a blast. Fury’s Ultimate Adventure H2.0 will take care of the rest!

#4 Fury Golf Cart Rentals

There is nothing like the simple fun of zipping through the streets of Key West in a golf cart from Fury, putting that razor-sharp handling to the test, parking wherever is convenient for you. A simple treat that makes getting around Key West’s Historic District a breeze, coincidentally keeping the breeze in your hair the whole time, ditch the hassle of arranging rides and choose fun with Fury’s golf cart rentals.

#5 Mallory Square’s Sunset Celebration

Located on the waterfront in Old Town Key West, Mallory Square is said to be where legendary playwright of the 20th century, Tennessee Williams, stood to applaud the brilliant Key West sunset every evening. Today, Mallory Square’s Sunset Celebration is still the greatest place for a land lover to bask in the glory of a painted sky. The waterfront of the Key West Historic District are lined with artists, performers, food vendors and more, all there because the sunset is the reason for the celebration. At the Mallory Square Sunset Celebration, the heart of Key West is on proud display.

#6 Key West Aquarium

The best way to experience marine life without getting in the water, the Key West Aquarium is loaded with breathtaking experiences for people of all ages. At the Key West Aquarium, visitors can enjoy the spectacle of shark feedings, get up close and personal in the exhilarating touch tank and take an informative Sea Turtle Conservation Tour. Only a fraction of what this one-of-a-kind attraction has to offer, get your tickets to the Key West Aquarium today!

#7 Ernest Hemingway House

For all those who love American literature, the Ernest Hemingway House is a must visit. Roam the grounds and put yourself in the shoes of a writer who changed the course of 20th century literature in the grandest fashion. Gaze out on the waters that inspired his masterpiece, The Old Man and the Sea, and become acquainted with the descendants of Hemingway’s pet cat, as there are a number of felines that call the Hemingway House home. An opportunity to sit in the same house as a literary giant, the Ernest Hemingway House is a piece of Key West history like no other.

#8 Truman Little White House

History buffs visiting Key West’s Historic District would be remiss if they didn’t venture to the Truman Little White House, former president Truman’s home away from home. With special permission, Truman conducted a number of important works out of his Key West home, making it a historic location not only unique to Key West but to the entire country. With a number of tours offered to visitors, one could receive an unparalleled presidential experience with almost full access to all that Truman’s Little White House has to offer.

Old Town Trolley driving through Key West carrying guests who are waving at the camera

#9 Old Town Trolley Key West Tour

Old Town Trolley offers visitors the best views of Old Town Key West above traffic. Their Hop On, Hop Off Tour takes you from one exciting attraction to another, with expert tour guides narrating the scenic journey along the way. To be enjoyed at your own leisure all day, a Hop On, Hop Off Tour with Old Town Trolley is a value that can’t be beat. Don’t worry about transportation once in Key West. Trust Old Town Trolley.

#10 Key West Lighthouse

In the past, the Key West Lighthouse was quite literally a beacon for ships in the night navigating the dangerous, rocky waters surrounding Key West. Today, it is an homage to the nearly extinct, truly unique lifestyle of the lighthouse keeper. A real window into history, the Key West Lighthouse takes a second to consider the lives of those whose names would not cross our minds but did so much for the world around them.

FAQs

Where do you park?

Tricky at times, there are a number of streets in Old Town Key West offering metered parking. There are also places such as the Old Town Parking Garage.

How do you get there?

Old Town Key West occupies roughly the western half of the island. Arriving by car is always an option; however, bicycles and golf carts are also popular modes of transportation in Key West.