One of the best things about visiting Key West is that you do not need a car to enjoy much of the island. Old Town is compact, many major attractions are close together, and visitors can choose from walking, bicycles, public transportation, taxis, rideshare services, trolleys, golf carts, and other options.
Planning your first trip to Key West should feel exciting, not complicated. The island is compact, colorful and refreshingly easy to enjoy once you understand its rhythm. You can walk from a historic waterfront to lively Duval Street, tour a famous author's home, photograph the Southernmost Point, eat fresh seafood and watch the sun disappear into the Gulf—all without spending your vacation behind the wheel.
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Key West may be famous for sunsets, tropical drinks and turquoise water, but look beyond the island atmosphere and you'll discover one of Florida's most fascinating historical destinations.
For more than two centuries, Key West has been shaped by sailors, wreckers, soldiers, cigar makers, presidents, writers, artists and immigrants from Cuba, the Bahamas and beyond. Its strategic location between the Atlantic, the Gulf and the Caribbean helped turn a small island into a surprisingly important center of maritime trade, military defense and cultural exchange.
Better yet, much of that history is concentrated within Old Town. Arrive aboard Key West Express, and you'll step ashore within easy reach of museums, historic homes and neighborhoods where those stories actually unfolded.
If history is your reason for exploring, here are some of the places—and stories—you won't want to miss.
Discover the Secrets of Historic Key West
Key West is known for its beautiful sunsets, colorful architecture and laid-back island lifestyle, but beneath its tropical charm lies a fascinating history that spans centuries. From Native American settlements and Spanish explorers to literary legends, presidents and treasure hunters, the island has countless stories waiting to be discovered.
Is Key West good for couples? Absolutely. The island brings together tropical scenery, colorful Old Town streets, waterfront dining, beautiful beaches and plenty of places where the two of you can simply slow down.
Whether you’re planning an anniversary, a weekend escape or an easy day away, Key West gives you room to make the trip your own. You can explore historic homes, share a quiet lunch by the water, wander Duval Street or do nothing more ambitious than find two chairs with a view.
And when you travel aboard Key West Express, the getaway begins before you reach the island.
There are so many fun, exciting, and historical things to do in Key West, that even despite challenging times, tourism has stable growth!
Few people are more closely associated with Key West than Ernest Hemingway. Long before the island became one of America's most popular tropical destinations, Hemingway helped put Key West on the map through his writing, adventurous lifestyle, and deep connection to the island.
Turn a Familiar Florida Drive Into an Unforgettable Adventure
A Florida road trip does not have to be a race from one hotel to the next. The most memorable itineraries mix scenery, wildlife, waterfront stops and different ways of traveling. That is what makes a road-and-ferry trip so appealing: you can explore at your own pace, park the car in Fort Myers Beach and finish the journey to Key West across the Gulf.
This flexible route works for couples, families, friends and solo travelers. Begin wherever your Florida plans take you, add one or two natural stops on the way to Southwest Florida, and then let Key West Express turn the final leg into part of the vacation. Instead of spending another long stretch behind the wheel, you can move between climate-controlled seating and open-air decks while the island gets closer.
Every March, Key West trades a little of its tropical color for shamrock green. The island's original St. Patrick's Day Bar Stroll is not a newly invented pub crawl or a generic ticketed party dropped into Old Town. It is a homegrown Key West tradition with roots stretching back to 1979, a collectible shirt, a changing route and more than four decades of stories.
For visitors from Southwest Florida, Key West Express makes it possible to begin the celebration with a Gulf crossing instead of a long drive. Because the stroll continues into the afternoon and participating venues change from year to year, an overnight stay is the most relaxed way to enjoy it without watching the clock.
With all the different options that you have for a Key West Vacation, what should you do and see on your trip to paradise?
