1 Week Key West Vacation Itinerary

Smathers Beach in Key West with palm trees in the background under blue sunny skies

Located at longitude 24.5551° N and latitude 81.7800° W, at the southernmost tip of the continental United States, you will find one of the most remarkable destinations in the United States.

Key West, Florida, dubbed ‘Bone Key’ by Spanish explorer Ponce de Leon almost 500 years ago due to the island’s use as a communal graveyard by its indigenous population, has a history suitable for a Hollywood movie. Pirates, sunken treasure, bootleggers, and haunted lore are all part of a larger story that gets more fascinating as time goes on. This is a place where people come to get away from it all, sometimes for a weekend, other times, forever. Ernest Hemingway fell in love with the island, making a home and penning one of his masterworks there. With its tropical charm, carefree lifestyle and bohemian vibe, you’re sure to fall for Key West too!

Here are the best things to see and do during your weeklong vacation in the Conch Republic!

 

DAY 1 - GET OUT & EXPLORE


OLD TOWN TROLLEY TOURS


There’s no better way to get a comprehensive lay of the land than on this wildly popular trolley tour. These ubiquitous green and orange vehicles criss-cross the island with 13 stops along the way. The highly-knowledgeable narrators regale you with colorful anecdotes and inside scoops about Key West’s dynamic past. One of the best features of the tour is that it’s Hop-on Hop-off, meaning you can disembark at any stop at any time and explore the surrounding area at your own pace. Afterward, when you’re ready to continue your adventure, you simply re-board at any of the spots you choose. This tour will set the tempo for the rest of your stay for sure!

MALLORY SQUARE


Easily the most popular meeting place on all the island, this wide-open promenade perched at the water’s edge is a treasure trove of stores selling shells and other types of souvenirs, restaurants, several attractions, and you’ll probably get to see the massive cruise ships that pull in and out of port next door. The thing to do here, however, is to converge upon the public square at dusk for the traditional sunset salute. Mallory Square transforms into something of an open air carnival with street performers of every stripe and local vendors selling food and handmade goods all gathered in one place to bid farewell to the sun as dazzling oranges, pinks and purples streak across the sky.

DAY 2 - THE DRY TORTUGAS


YANKEE FREEDOM III



It’s time to find paradise lost with a bold, new adventure to one of America’s most wondrous National Parks! Located on a series of remote islands roughly 70 miles west of Key West, The Dry Tortugas National Park is a haven for bird-watchers, marine life, and all those with wanderlust in their hearts. A virtually unspoiled coastline makes you feel like your very own stretch of beach. Snorkel the many reefs that are mere feet from shore and definitely make time to go on a tour of Fort Jefferson. Much of what remains of this massive naval fort is very much intact and the ranger-guided tour is truly enlightening and a highlight of your visit. Book your trip with Yankee Freedom III, a state-of-the-art, high-speed catamaran that provides the only transportation to and from the island. Don’t forget your sunscreen and your camera and get set for an adventure of a lifetime!

 

DAYS 3-4 - MUST-SEE MUSEUMS & SIGHTS


TRUMAN LITTLE WHITE HOUSE


The Truman Little White House was once a naval command station that later became the winter White House for the 33rd President of the United States, Harry S. Truman, and his family. Aside from serving as a respite from the pressures of Washington DC, the home hosted many important heads of state and played a role in several significant historical events including the infamous Bay of Pigs when President John F. Kennedy met with British Prime Minister Harold McMillan. The museum contains many articles and artifacts from the era to explore and the lush grounds surrounding the property are often used to show outdoor films, cook-offs, special events, and even weddings!

KEY WEST AQUARIUM


The hands-on Key West Aquarium is a great place to experience the indigenous marine life that inhabits the offshore ecosystem. This window of discovery 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 close to numerous other aquatic species like moray eels, barracuda and sea turtles without getting wet. The welcoming Key West Aquarium is a popular attraction where nature and animal lovers of all ages can learn about the marine inhabitants and their incredibly bio-diverse habitats.



SAILS TO RAILS MUSEUM


A relative newcomer to Key West’s many attractions, the Sails to Rails Museum at Flagler Station chronicles Key West’s epic 500-year history to the present day. Learn of opportunistic pirates, shipwrecks and how it all lead to Key West’s first industry. Check out all the hands-on, interactive exhibits and even hold a salvaged bar of silver in your hands! One of Florida’s most central figures, industrialist Henry Flagler, looms large here as the story of how his Florida East Coast Railway was extended south to Key West is told through some compelling exhibits. There are worlds to be discovered here sure to spark a whole new perspective as you travel the Conch Republic!

KEY WEST SHIPWRECK & TREASURE MUSEUM


Relive the glory days of “Wrecking” as you explore two floors of shipwreck artifacts and treasures dating from the Spanish galleons of the 17th and 18th centuries, through the merchant ships of the 1800s, up to modern day. Guests will hear tales of the Spanish galleons that were lost and found throughout the Florida Straits, about the families whose fortunes were made by salvaging wrecks along treacherous reefs, and how all this led to Key West becoming the wealthiest city in the U.S. Make sure to climb up the 65’ observation tower that sits atop the museum for some spectacular views!

THE ERNEST HEMINGWAY HOME & MUSEUM


Among the many must-see attractions in the Conch Republic, the home of prolific author and raconteur Ernest Hemingway ranks near the top of any list. Hemingway had a reputation for being a rough and tumble troublemaker; but he was a romantic at heart and his two-story villa is reflective of that. Manicured gardens and swaying palms make the home an oasis in the middle of Key West. Wander through the fragrant foliage and peaceful calm that inspired several prominent works. The 1861 home still contains all the original furniture as well as a healthy brood of friendly felines that roam the property freely, said to be the descendants of the cats Hemingway owned when he was alive.

SOUTHERNMOST POINT


Having graced every postcard at one time or another, there’s a good chance you’re familiar with the stout, concrete, structure resembling a giant buoy that demarcates the southernmost frontier in the continental United States. This is a very popular spot for the selfie set, so you’ll have to wait your turn before you hit ‘share.’ 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!

 



 










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Southernmost Point ????????


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DAY 5 -

SHOP ‘TILL YOU DROP IN MALLORY SQUARE

Besides being the island’s epicenter and preferred gathering place to watch brilliant sunsets, there’s a wide array of shops to browse for that perfect Key West keepsake. Here are two of our favorites:
  • THE SPONGE MARKET - Home to Key West’s largest collection of natural sponges in all conceivable colors, sizes, and shapes. The market also features a museum exhibit that tells the story of the area’s lucrative sponge trade.
  • SHELL WAREHOUSE - Discover rare shells from around the world and those harvested locally at this old converted warehouse. Grab gifts for yourself or someone else that are quintessential Key West including coral, shark teeth, jewelry, and even home furnishings.

TAKE A WALK ON THE DARK SIDE WITH GHOSTS & GRAVESTONES


The lost souls and restless spirits of Key West’s murky past await you on the Trolley of the Doomed! This devilishly delightful departure is great for ghost-hunting hobbyists, curiosity-seekers, or anyone that likes a good scare. One of the tour’s highlights is a visit to the East Martello Fort, a Civil War-era fortress that houses a rather sinister figure known, simply, as Robert the Doll. Before you take his picture, though, make sure to ask him first! Shed a light on Key West’s dark side with a trip to some of the island’s most haunted places.

DAYS 6-7 - KEY WEST WATER ACTIVITIES


FURY WATER ADVENTURES


For those looking to get on the water, Fury has the adventure just for you! Your week should be long on fun and there’s plenty to be had here with special packages that suit every taste! If you’re looking to max out your time with a little bit of everything, sign up for the Ultimate Adventure! Parasailing, jet skiing, snorkeling and slipping and sliding on a floating water park are all on the menu alongside complimentary beverages and a delicious breakfast and lunch to keep you revved up and active for your day on the water!

 



 










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Leaving work on Friday like...


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SMATHERS BEACH


For some prime sun-worshiping, head on down to Key West’s largest beach. This half-mile stretch of coastline is ideal for those who just want to run their toes in the sand and gaze at an endless sea.

HIGGS BEACH


This county beach/park features a wide, sandy beach, calm waters, and a long-wooden pier that gets you closer to the action at sea. There are plenty of amenities available to make a day of it like picnic tables, chair rentals, playgrounds, and even a dog park.

EAST MARTELLO FORT


This brick outpost on the road to Key West International Airport once enjoyed life as a naval fort in the 19th century. Though it never saw any action in its day (the fort was never even armed), it still has a history worth telling and, as such, became the first museum in Key West. The museum now houses works by Cuban folk artist Mario Sanchez and Robert the Doll.


THE BEST OF THE REST


KEY LIME PIE


This Caribbean confection is as American as...well, you get it. There are fine examples of this beloved dessert up and down the island proper; but these are our fav spots to get your pie game right.

  • 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.

  • Pepe’s Café - 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.





 










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Happy #PiDay from all of us at Kermit’s


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DUVAL STREET


The main drag where many a Key West story, and tall tale, gets its start, is right here on old Duval Street. There’s a certain laid-back hustle and bustle on this strip that really picks up energy when the local nightlife venues kick into gear. Here are some must-sees:

  • SLOPPY JOE’S - Ernest Hemingway, an enthusiastic regular, 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 - This 72-square-foot saloon does not disappoint. Besides 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.


CUBAN BREAKFAST AT EL MESON DE PEPE


The carousing and bar-hopping is over (for now, anyway) and you need the perfect pick-me-up to set your sails right. Pay another visit to Mallory Square and pop into one of the island’s best Cuban eateries for a hearty and comforting breakfast. Eggs, anyway way you like them, chorizo, a perfectly-pressed crispy side of Cuban toast and a café con leche makes it complete. (Dunking the toast in the coffee is optional, but highly recommended!)






 










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So close, you can ~taste~ it ???????????? ????: @sweetxapple


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MUST-EAT Key West SEAFOOD RESTAURANTS


Newsflash: Key West is surrounded by water! Making sure you sample the delicacies of the sea during your week-long vacation is a no-brainer. Here are some of our favorite places to reel them in:

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 brings it! 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 tacos, healthful salads and ceviches and local, sustainable fish prepared every way imaginable!

 



 










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Happy #LobsterDay! ????We're celebrating our favorite holiday with our Lobster Enchilau tacos. Come get your claws on some!


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A&B LOBSTER - On the other side of the culinary spectrum and a most excellent way to start a special night out on the town, is this Key West institution. With its wrap-around balcony and dreamy views of the Key West Bight, it's a definite tone-setter for a romantic evening. They’ve been around since 1947, so you know the food, especially their array of lobster dishes, has got to be out-of-this-world!

You may have heard this about other places, but Key West is not only an amazing vacation destination, it’s moreso, a state of mind. Time slows down here, people aren’t in a rush to make a meeting or beat traffic, and the views and tropical weather are simply divine. Your week in paradise will go faster than you think, so make the most of every moment. We hope this guide will make all your Key West dreams come true!

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