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Ultimate Key West 3-Day Weekend Itinerary

guests walking through Key West's Mallory Square made up of food booths and carts. In the background, there's a statue of a man riding on a bicycle, two barrels, a sign that says 'Mallory Square' and tables and chairs

Nothing is more thrilling than the prospect of a long weekend around the corner. Since the two most prominent holidays that feature that most welcome Monday off, Labor Day and Memorial Day, occur in the warmer months, visions of outdoor grills, swimming pools, and chilling hard on the old Barcalounger are among the most desirable. However, if you decide you want to level up from the common ‘staycation’, there’s an island situated in the southernmost reaches of the Sunshine State that has been delighting visitors for decades. With its pioneer spirit, off-the-grid appeal and beach town charm, Key West is your ticket to adventure!

  • Admissions Admissions
  • Shopping Shopping
  • Dining Dining
  • Entertainment Entertainment

See the Best First with Old Town Trolley Tours

Our friendly and knowledgeable conductors will take you on a fully narrated journey filled with humor and history as you explore the must-see sights of the Conch Republic. A really handy, time-saving component built into the tour is the freedom to hop on and hop off at any of the 13 stops we service. This means you can take as much time as you like strolling along famous Duval Street with its plethora of bars and restaurants then continue your journey when the next trolley shows up! This entertaining spin through the heart of sunny Key West includes highlights such as the Historic Seaport, Simonton & Greene Streets in the city’s Old Town, Bahama Village, and the East Martello Fort to name just a few.



Pepe’s Café – This Caroline Street mainstay has been feeding locals and visitors since cars still looked like horseless buggies. For all you purists out there who want to sample the traditional recipe that gave rise to it all, Pepe’s pies are the real deal.

The Southernmost Point

key west southernmost pointHaving graced the front of many a postcard, there’s a good chance you’re familiar with the stout, concrete, structure that demarcates the southernmost frontier in the continental United States. This oversized replicated buoy is a very popular spot for the selfie set, but you’ll have to wait your turn. Cuba is only 90 miles south of here, so if you have a high-powered telescope on loan from an observatory, you might be able to see the busy streets of Havana!

Audubon House

key west audubon houseNamed after the famed naturalist and painter, whose proficiency in ornithology informed his popular depictions of birds, this home is among the most majestic on the island. This wonderfully restored estate, with its lush gardens and period furnishings, also used to belong to Captain John Geiger, an affluent entrepreneur who made his fortune as a master wrecker salvaging ships from their watery graves.


El Meson de Pepe – All this Key West adventuring is bound to work up an appetite, so grab a bite, or two, of some of the very best Caribbean delicacies in all of the Conch Republic at El Meson de Pepe. Located in the heart of Key West in historic Mallory Square, this legendary eatery is always buzzing with the rhythms of the other island, just 90 miles away. You’ll delight in all the classics of the Cuban kitchen with a distinctly Key West twist for a culinary experience you can only find here.

Key Lime Pie

You’re on vacation, so put the breaks on that diet and indulge in one of the island’s most delectable creations. This local favorite has a luscious custardy texture, but eats like a cheesecake. The tart, pleasing essence of the Key Lime, with a dollop of freshly whipped cream, makes this a treat all its own. Here are the best places to get your piece of the pie:

Kermit’s Key West Key Lime Shoppe – For over 20 years, Kermit Carpenter and his sister Anita have been making quite a name for themselves with their take on this local specialty. Don’t forget to try their signature creation: a frozen slice skewered on a stick and dipped in dark Belgian chocolate. They also feature a gluten-free version of their tasty pies. Yum!


Explore Mallory Square & Watch the Sunset

When in Rome, it’s the Trevi Fountain. When in the Conch Republic, it’s Mallory Square. This is the perfect end of day for any Key West adventure. This large promenade, extending out from the water’s edge, is a hub of activity surrounded by some of Key West’s most iconic attractions and shops. Soak up the atmosphere in the Sponge Market, explore the island’s roguish past at the Key West Shipwreck & Treasure Museum and, of course, take part in a long-held tradition by attending the Sunset Celebration where hundreds gather, among colorful street performers and local artisans, to salute the sun as it recedes into the sea.



Brunch Spots

Blue Heaven – This Bahama Village gem infuses all the best Key West cuisine is known for with their in-demand brunch. Dig into a version of a Low Country classic like pink shrimp and grits or a fluffy stack of scratch made blueberry pancakes; and definitely leave room for the homemade banana bread and decadent Lobster Benedict with Key Lime Hollandaise! The mimosa menu itself is something to behold with an incredible variety of this brunch staple; and they’re not shy with their pours either!

Moon Dog Cafe – This Whitehead Street favorite serves up good food as well as good vibes. This place is renowned for its baked goods, so if your appetite is craving tartlets with fresh fruit, fresh baked breads or mouth-watering mini quiches, look no further. They also boast one of the few menus in the area that is vegan and vegetarian friendly.

Truman Little White House

key west truman little white houseWhen the 33rd president of the United States wanted a respite from the constant pressures of the most important job in the world, he headed south. Affectionately known as the Winter White House, Harry Truman and his family loved to entertain and relax at this tropical retreat; but it was also the site for many important meetings by the world’s heads of state like President John F. Kennedy when he and British Prime Minister Harold MacMillan met during the Bay of Pigs incident. Even the casual history buff will find plenty to enjoy here!


Key West Butterfly and Nature Conservatory

key west butterfly conservatoryAlong with soothing music and flowing fountains, these enchanting gardens are filled with birds and fish as well as turtles and a dizzying array of butterflies. Surrounded by the beautiful flora and fauna in this incredible habitat, you can take amazing close-up photos of over 60 butterfly species from around the world, along with flamingos and over 20 other exotic species of bird.

Late Lunch at Fisherman’s Cafe

Located on the banks of the historic Key West Seaport where local fishermen can be seen unloading the day’s catch, this local joint is a must-eat! With seafood so fresh, it practically walks its way to your plate, this fourth generation family of ‘Conchs’ serves up the freshest, most delicious lunch on the island. Try the Lobster Enchilao taco’s, healthful salads and ceviches and local, sustainable fish prepared every way imaginable!

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Perfect day to enjoy our patio. 🎣☀️| 📷: @joelle_deroche

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Key West Aquarium

Located in Mallory Square since 1946, the hands-on Key West Aquarium is one of the most historic & interactive attractions on the island. This is a great place to experience the fantastic indigenous marine life that inhabits the offshore ecosystem through a window of wonder that enables visitors to interact with rays, sharks and other sea creatures while expert guides explain the hidden mysteries of the undersea realm surrounding the Florida Keys. You can hold a starfish, pet a shark and get up close and personal with many other aquatic species. Visitors of all ages will enjoy this deep dive into nature.

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This is how we #fishgape when we #Gram! Happy #NationalAquariumMonth! 🐠🦈🐢

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Key West Ghost Tour

Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America. This and more await you on a Key West ghost tour.

Duval Street at Night

Old Town Key West’s main thoroughfare was named after Florida’s first territorial governor, William Pope Duval. If Old Bill were alive today, he would be very pleased with the notoriety the street of his namesake has earned. For a night out on the town and to immerse yourself in the nerve center of this unique town, Duval Street can’t be beat. Here are a few of our top picks for your Duval Crawl:

key west sloppy joesSloppy Joe’s – This iconic watering hole has more stories than Wikipedia and its popularity is celebrated throughout the world. It was the legendary scribe, Ernest Hemingway, an enthusiastic regular, who is credited with the bar’s name, said in jest to then proprietor Jose Garcia because the floors were always covered in melted ice from the seafood that was sold there. Fast forward to today, and you’ll still find a festive crowd, live music and an all-time classic place to satiate that craving for the perfect mojito!

The Smallest Bar in Key West – With all the bigger-than-life bars on the Duval strip, it’s only right to visit the smallest bar in Key West! This 72-square-foot saloon does not disappoint. Beside their diminutive stature, their claim to fame are their rum runners, said to be the very best on the island. Order at the bar and enjoy your cocktail al fresco and watch the people go by.

Nine One Five – It’s a long weekend, so treat yourself. If you’d like to slow things down a bit and take your sweet time to smell the bougainvilleas, this excellent eatery is just the place to wind down with a beautiful bottle of wine. The menu here is known for its inventive Asian-inspired fare and luxurious, house-made pastas. Located inside a breathtaking, two-story, Victorian home complete with gingerbread house accents and a white-picket fence, this is a Key West date night destination for the ages!


It’s time to drift away from the mainland and cruise the ocean blue. Depending on your group preferences and itinerary, there are two excellent options we recommend for water activities on your last day in paradise.

Visit Dry Tortugas Aboard the Yankee Freedom III

(Full Day Trip, Advanced Reservations Required)

Located in the middle of the big, blue Gulf of Mexico, some 70 miles west of Key West, the Dry Tortugas is one of the most remote and fascinating national parks in the United States. Featuring the remnants of a 19th-century fort that was once the American Navy’s largest, you’ll get the feeling that you’ve suddenly become a character in the ‘Swiss Family Robinson’ or are on some far flung expedition for National Geographic. Get lost on a pristine, unspoiled stretch of beach or nature watch the spectacular array of seabirds and coral reefs. A truly remarkable experience, the only way to get there is by booking a trip on the Yankee Freedom III, a state-of-the-art, high-speed catamaran that transports you to and from this amazing place daily.

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Escape the ordinary ☀️ #DryTortugas 📸: @wanderingheartbeat

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Fury Water Adventures

For those looking to get on the water, but don’t have an entire day to spend, Fury has the adventure just for you! Your long weekend should be long on fun and there’s plenty to be had here with special packages that feature everything from parasailing, jet-skiing, and snorkeling America’s only living coral reef to backcountry exploring, and dolphin watch excursions!

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Leaving work on Friday like…

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Now that you’re armed with the ultimate Key West to-do list, it’s your move. Ready…Set…LONG WEEKEND!

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