Click for possible route/stop changes on the day of your tour.
So, you’re heading to the southernmost city in the USA? Lucky you! There is so much to do and see in this island paradise, from intriguing attractions and historical sights to water sports, entertainment and world-famous points of interest. If you want to see the best of Key West in one day, hop aboard Old Town Trolley.
The best way to start the day is with a delicious breakfast at Fisherman’s Café, making it the first stop on your itinerary. Located on Elizabeth Street, in the Historic Seaport a few blocks away from Mallory Square, this Key West classic features a charmingly nostalgic ambience and delicious local cuisine. Serving up island favorites with a modern twist, this walk-up eatery is the rebirth of an old local favorite, where conchs came to swap stories and catch up on the news of the day. Stop in for a café con leche and a hearty breakfast sandwich before heading out to explore the rest of paradise on your 1 day getaway.
Now that you’re full of energy from that big breakfast, it’s time to explore one of the most popular locations in all of Key West – Mallory Square! Home to shops, restaurants, museums, theaters, live entertainment and the world’s best sunsets, it’s hard to find a more vibrant spot anywhere else throughout paradise. Take a stroll down the street and marvel over the local handcrafted goods. Make sure you save at least two hours to explore a few of the incredible museums located within the area, like the Key West Shipwreck Treasure Museum and Harry S. Truman Little White House. Both museums are filled with fascinating facts and authentic views into the rich history of Key West. Whether you’re a history buff or just looking for a fun local activity, both museums will help showcase what makes this island such a unique treasure.
A Key West vacation itinerary is not complete without hopping aboard the Old Town Trolley. A Key West institution for over 30 years, those venerable green and orange trolleys consistently rank at the top of things to do in Key West. With the single largest fleet in the city, you’ll spend less time waiting and more time sightseeing. Their friendly and knowledgeable conductors will take you on a fully narrated journey filled with humor and history. Explore the must-see sights of the Conch Republic. A really handy, time-saving component built into this Key West tour is the freedom to hop on and hop off at any of the 13 stops they service, allowing you to maximize your 1 day vacation.
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Next on the itinerary is finding the perfect lunchtime spot! Located in downtown Key West, right next door to the historical Hemingway House in Bahama Village, is the Moondog Cafe & Bakery. This delightful eatery features delectable vegetarian, vegan, and gluten-free meals. Plus, intoxicating fresh aromas coming straight out of their in-house bakery. With vibrant artwork and a unique personality flowing throughout the restaurant, you’ll find yourself never wanting to leave your table.
Next stop on your 1 day vacation itinerary in Key West is exploring the Ernest Hemingway House Museum. As always, we recommend traveling via the Old Town Trolley as this is stop #5 on their route. This lovely Key West home is where legendary author Ernest Hemingway lived and worked for more than ten years. The famed author was known to have an affinity for the island life and spent many days fishing out on the open water. Lovers of his work will want to make sure this is on their itinerary. The home and gardens are visited by thousands of people each year, offering a glimpse into Hemingway’s life and a chance to meet some of the descendants of his beloved six-toed cat, Snowball.
Take a quick stroll through Mel Fisher’s Maritime Heritage Museum. You’ll learn all about his 17-year expedition and amazing discovery of the shipwrecked Spanish Galleon. Then, if you’re hungry, grab a bite at one of the many nearby restaurants. Stop by some of Key West’s most famous watering holes, including Hog’s Breath Saloon, Green Parrot Bar, and Sloppy Joe’s.
The Key West Butterfly and Nature Conservatory is really unique. Take a tour inside to witness these graceful creatures in their natural habitat. After, take a walk down Duval Street towards Mallory Square. It is a scenic stroll with lots of shops, restaurants and art galleries to view along the way. You should arrive in time to see the street vendors setting up for the nightly Sunset Celebration. It’s a perfect way to end your day in Key West or catch the cruise ship in port. Sample some homemade conch fritters, order an ice-cold mojito at the bar just outside Cayo Hueso and then head out to the edge of the seawall to witness the spectacle of the famous Key West sunset.
For over 40 years, this family-owned historic landmark has been serving the finest local seafood for lunch and dinner. From conch fritters to the best island steaks and ribs, Two Friends Patio offers true Key West flavor, making it a must see on your single day in paradise. Conveniently between the famous Mallory Square and Front Street, it features premiere outdoor dining experiences. Plus, the best happy hour and karaoke shows on the island – making it the perfect spot for dinner on your 1 day Key West vacation.
No Key West vacation itinerary is complete without a sunset celebration in Mallory Square! The Key West Sunset Celebration invites everyone to partake in watching the glowing pink and red sun sink into the Gulf of Mexico horizon. The nightly festival hosts visitors from all over the world who come to take part in the magicians, jugglers, clowns, psychics, local musicians, artists, and food vendors that combine for an incredible cultural experience. It is a fusion of friends and talents that has captivated tourists and locals alike. This nightly party has everything any local or guest could ever hope to stumble upon.
Cap off your 1 day in paradise with a frightful experience aboard the Trolley of the Doomed. Ghosts and Gravestones invites guests on an exciting and spine chilling tour through the grim history of Key West, in search of the forgotten souls. This spooky trip through the paranormal is a unique and fun experience for all fans of ghosts and ghouls. This 1 hour and 35 minute Key West tour will show you exactly why Key West is considered one of the top ten, most haunted cities in America.
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Key West is an island filled with rich history and a blissful ambiance, unlike anywhere else in the country. With so much to offer nature lovers, foodies, beach goers and good-time seekers, it’s no wonder why people keep coming back for more. Hopefully this itinerary helps provide you with all the tools and resources you need, for the perfect 1 day experience through the beautiful island. And if you couldn’t get through all of Key West in a day, never fear because paradise will always be here!