Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (2023)

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

Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (1)Having 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

Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (2)Named 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.

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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

Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (3)When 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!

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We love our #TrumanKeyWest adventure patch! 🇺🇸 💙 What’s your favorite #TrumanKeyWest souvenir? 📸: @jessdev081

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Key West Butterfly and Nature Conservatory

Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (4)Along 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!

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.

(Video) Florida Keys / Key West 6 Day Itinerary Mommy Daughter Trip

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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:

Best 3 Days In Key West | Ultimate Key West Weekend Getaway Itinerary (5)Sloppy 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)

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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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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!

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


Is 3 days in Key West Enough? ›

Three days is absolutely enough time to spend in Key West. The island is small and offers the perfect 3-day vacation experience. With that said, there's so much to enjoy that you can easily extend your trip and not get bored.

Can you do Key West in a weekend? ›

Key West is worth a day trip, but the more time you have, the better! You could easily spend a week in Key West, but 3-4 days is optimal if you want to do it all and still have time to relax. If you only have three days, here's an easy weekend itinerary to help you get the most out of your stay.

How do you do the keys in 3 days? ›

Detailed Itinerary
  1. Day 1: Key Largo and Marathon Key. A beach on Key Largo. ...
  2. Day 2: Explore Key West, Snorkeling and Sunset Adventure. Colorful houses on Duval Street. ...
  3. Day 3: Back to Miami with a stop in Islamorada. Seven Mile Bridge.

What should I not miss in Key West? ›

Don't miss the two pink flamingos in the wading pool.
  • Key West Cemetery. Photo courtesy of Dale M. ...
  • Key West Lighthouse Museum. Old Town. ...
  • The Ernest Hemingway Home & Museum. Old Town. ...
  • Harry S. ...
  • Conch Tour Train. ...
  • Florida Keys Eco-Discovery Center. ...
  • Mallory Square Sunset Celebration. ...
  • Dry Tortugas National Park.

What is the cheapest month to go to Key West? ›

Go during the off season, roughly June to November. (September and November are the cheapest of all.) Shop around for accommodations and compromise on amenities or location. Seek out affordable, casual restaurants.

What is the best month to go to Key West? ›

The best time to visit Key West is between March and May. The winter crowds will taper off, the hotel rates become reasonable and the weather is remarkably similar to winter's blissful 70s and 80s. Speaking of winter – that season is the island's busiest and priciest.

What is there to do in Key West for 3 days? ›

Best Places to visit in Key West in 3 Days – Key West Weekend Getaway Edition!
  • Walk around Duval Street.
  • Take a picture with the Southernmost Point Buoy.
  • See the magical Key West Butterfly & Nature Conservatory.
  • Time for lunch.
  • See marine life at the Key West Aquarium.
  • Watch the sunset at Mallory Square.

Can you get around Key West without a car? ›

If you decide to not have a car in Old Town, be assured that there are many ways to get around Key West, including: walking, bicycling, taxis, electric rental cars, mopeds, pedi-cabs, city buses, trolleys, and hotel shuttles.

IS Key West worth the hype? ›

Is Key West worth visiting? If you're looking for a multi-purpose destination - lively nightlife, exceptional water-sports, Old Town atmosphere, plus plenty of literary and political history - then quirky Key West should suit you down to the ground.

Which key is best to visit? ›

Best islands to stay in Florida Keys
  • Key West (the most famous of all) ...
  • Key Largo (scuba diving and water sports) ...
  • Marathon (family friendly) ...
  • Islamorada (adventure galore) ...
  • Big Pine Key (relax and isolation) ...
  • Key Largo (for the adventure couple) ...
  • Key West (laid-back and boutique stay) ...
  • Big Pine Key (romantic and isolated)

What is the best way to get around the Keys? ›

Here are some of the best ways to get around Key West.
  1. Take the Old Town Trolley Tour. ...
  2. Tour the City on a Bike. ...
  3. Hop in an Electric Car. ...
  4. Rent a Car. ...
  5. Cruise around by Boat. ...
  6. Call a Cab or Limo Service.

IS Key West worth the drive? ›

The drive to Key West will be one of the best parts of your trip. I highly recommend driving the Overseas Highway while you are in Key West. The Overseas Highway is a 113-mile highway, with 42 bridges (one bridge is 7 miles long!)

Do I need jeans in Key West? ›

Locals live in shorts. Unless, of course, there's a cold snap which typically happens in the fall months. Add a pair of jeans, sweater, and tennis shoes to your stacks of shorts and T-shirts to be safe. Winter in Key West is comfortable, with an average high of 75°F and average low of 65°F.

What is Key West most known for? ›

Key West, the southernmost point in the United States, is famous for watersports, lively nightlife, beaches, historic sites and its pastel, conch-style architechture.

What is the busiest month in the Florida Keys? ›

Winter (November through February) is the busiest season, and while the island is lively and fun, expect expensive flights and car rentals and for hotels and vacation rentals to be at capacity. Conversely, you'll find unbelievable deals every June through October, but at a price—it's during Atlantic hurricane season.

What is the cheapest time to vacation in Key West? ›

Visit Key West in the off-season

The fall (September–November) is the low season in Key West, and room rates can drop by 50 percent or more. The hot, storm-prone summer months also see lower prices, and you'll find decent discounts in April and May after the winter crowds thin out.

What is the best airport to fly into to go to Key West? ›

EYW — Key West International Airport — Visitors can fly to Key West International Airport via connections or direct flights from a host of Florida cities. The airport offers a host of ground transportation options, including local shuttle buses and rental cars. Getting around Key West is fun and easy!

What months are hurricane season in Key West? ›

The Atlantic hurricane season formally begins June 1 and ends November 30. Historically, the chances of hurricane activity are greater between August 15 and October 15. Can I travel to the Florida Keys during hurricane season? Absolutely.

Why does the water smell in Key West? ›

That ubiquitous smell is decaying sargassum, islands of floating, brown sea algae that is piling up along the beaches of Key West, the Florida peninsula, Mexico and other Caribbean islands. Happens every summer when the winds and currents come from the south.

Can you drink alcohol on the street in Key West? ›

A common misperception is that open containers of alcohol are permitted in Key West city limits. While in fact, the opposite is true. The Key West Municipal Code, § 18-87 prohibits open containers of alcoholic beverages in public.

What is the best way to explore Key West? ›

What Are the Best Ways to See Key West?
  1. By Foot. If you're staying in Old Town, the great thing about Key West is that most of the island can be experienced on foot. ...
  2. By Bicycle. Renting a bicycle opens up a whole world of possibilities in Key West. ...
  3. By Adventure Vehicle.
  4. By Trolley.
  5. By Scooter.
  6. By Jet Ski.
  7. By Parasail.
  8. By Boat.
22 Mar 2018

Is there more to do in Key West or Key Largo? ›

Key West is a party town filled with nightlife and activity, while Key Largo is more laid-back and relaxed. This means you'll find more activity available during every waking hour you spend on Key West. You'll also find more gift shops, boutiques, and restaurants geared toward visitors on Key West than Key Largo.

How do you spend a weekend in the Florida Keys? ›

Detailed Itinerary
  1. Day 1: Key Largo and Marathon Key. A beach on Key Largo. ...
  2. Day 2: Explore Key West, Snorkeling and Sunset Adventure. Colorful houses on Duval Street. ...
  3. Day 3: Day Trip to Dry Tortugas National Park. Aerial view of Fort Jefferson on Garden Key. ...
  4. Day 4: Back to Miami with a stop in Islamorada. Seven Mile Bridge.

Is there a free trolley in Key West? ›

This FREE hop-on hop-off bus service runs from the City's Park and Ride on Grinnell Street, along Caroline Street, right on Simonton Street, around Front Street, up the length of Whitehead, through Truman Waterfront, then returns down the length of Simonton to Fleming.

Do I need a rental car in the Florida Keys? ›

Should I rent a car in Florida Keys? While there are some public transportation options available in the Florida Keys, the area of the Florida Keys is so vast that you almost certainly need a car to get around.

How much does the trolley cost in Key West? ›

Pricing is different for each tour. The Old Town Trolley, being the longer tour, is $44.95 for each adult passenger and $15.00 for children 4 to 12 with children under 4 riding free. The Conch Tour Train is $34.95 for each adult passenger and $15.00 for children 4-12 with children under 4 riding free.

What is the most popular street in Key West? ›

World-famous Duval Street is known as the party epicenter of Key West and is the island's “main drag.” Running north and south, the thoroughfare is lined with bars, pubs, outdoor cafes, shops, galleries, restaurants, and celebrated attractions.

What is the most popular drink in Key West? ›

Created in the 1950s at the Tiki Bar of Holiday Isle in Islamorada, the rum runner is the quintessential cocktail of the Florida Keys.

What is the prettiest key? ›

While Key Largo is undoubtedly the prettiest of all the Florida Keys, it's also one that's home to plenty of activities for the avid beachgoer.

Why are there no beaches in Key West? ›

The Keys don't have wide sandy beaches because the coral reefs we enjoy as snorkelers and scuba divers prevent the erosion and sand from building up along the shore. So while the beaches aren't what make the Keys special, there are still some pretty special beaches in the Keys.

What is the most popular key? ›

Song Keys Ranked By Popularity
  • C Major (17%)
  • D Major (12%)
  • G Major (12%)
  • A Major (10%)
  • E Major (9%)
  • F Major (9%)
  • E♭ Major (7%)
  • B♭ Major (6%)

How do most people get around in Key West? ›

The best way to get around Key West is on foot. Mopeds and bicycles are also popular, though mopeds can be dangerous. Taxis are available on the street, as well as in front of the Key West International Airport (EYW) in the middle of the island.

Is all of Key West walkable? ›

Key West is a very walkable town. Many of the best things to do in Key West are located around Mallory Square, along Duval and Whitehead Streets, and down towards the Southernmost Point. The Key West Trolley can be used as a hop-on hop-off bus to get around Key West.

Can you walk everywhere in Key West? ›

One of the best things about Key West is you can walk just about everywhere. Don't bring your car - leave it at home! We rode the bus to our hotel and got a good view of the island before we arrived at our lodging. Once you are in Key West, you can walk to Mallory Square, Sunset Pier, and Duval Street.

Is it worth renting a golf cart in Key West? ›

On Key West, Gas Golf Carts are a real hit with visitors who want to zip around the island the fun way. Fast, stable, comfortable, and well-adapted to the island's tight spaces, a Key West gas golf cart rental is your perfect vacation transportation solution.

What should I do on the first day of Key West? ›

First Time In Key West Vacation Guide
  • Catch a Ride. ...
  • Do the Duval Crawl. ...
  • Stroll the Waterfront. ...
  • Celebrate the Sunset. ...
  • Sail Into the Sunset. ...
  • Amp up the Energy. ...
  • Something to Write Home About. ...
  • History of Presidential Proportion.

How much money should I bring to Key West? ›

How much money will you need for your trip to Key West? You should plan to spend around $441 per day on your vacation in Key West, which is the average daily price based on the expenses of other visitors. Past travelers have spent, on average, $308 on meals for one day and $41 on local transportation.

Which key has the clearest water? ›

Fort Zachary Taylor Park Beach, Key West

Fort Zachary Taylor Historic State Park is a National Historic Landmark that offers some of the clearest blue waters for snorkeling and diving in Key West.

What side of Key West has the best beaches? ›

Most of the top beaches in Key West are located on its southern shore, with the majority clustered along a stretch of water only a little over a mile in length. Key West's largest beach, Smathers Beach, is an exception.

What is the dress code for Key West? ›

The unofficial dress code in Key West is very casual, so you shouldn't worry about trying to fit those high heels in your suitcase. If you want to dress it down even more, go for it! A nicer pair of shorts or jeans won't make you feel out of place either.

Do you have to worry about sharks in the Key West? ›

It's no guarantee that you'll spot a shark while snorkeling in Key West, but it happens more than you might think. We see sharks at the reef at least once a week, and probably more often than that! Should I be scared? No!

Can you swim in the ocean in Key West? ›

Boasting temperate waters and more than 3,400 hours of annual sunshine, the beaches of Key West are some of the most popular destinations on this tropical island paradise. You can enjoy the sun, sand and warm water as well as a variety of activities like swimming, snorkeling and fishing.

Is 3 days enough in Key West? ›

Key West is worth a day trip, but the more time you have, the better! You could easily spend a week in Key West, but 3-4 days is optimal if you want to do it all and still have time to relax. If you only have three days, here's an easy weekend itinerary to help you get the most out of your stay.

What celebrities have homes in Key West? ›

Here's a list of musicians, writers, sitting presidents, celebrities and baseball player who have all called Key West home.
  • Judy Blume, author. ...
  • Jimmy Buffett, singer songwriter. ...
  • Bronson Arroyo, baseball player. ...
  • Ernest Hemingway, author. ...
  • Harry S. ...
  • Sandy Cornish, civic leader. ...
  • Wallace Stevens, poet. ...
  • Shel Silverstein, author.
18 Jun 2018

Can you see Cuba from Key West? ›

“ The problem is that the earth, being round, curves and Cuba, which is about 90 miles from Key West, falls below the horizon when you look towards it from Key West. It means that regardless of how great your eyesight is, and how clear the day is, there is no way you can see Cuba from anywhere in Key West.

How many days do I need in the Keys? ›

While it's always ideal to spend more time in any destination, I recommend staying for at least four days in the Florida Keys, if not longer. To accomplish many things to do in the Florida Keys, you'll need a solid five days.

Is it easy to get around Key West without a car? ›

Key West transportation ranges from taxis, shuttles and car rentals to bicycles, scooters and your own two feet. Duval Street and the Old Town area are very walkable. Setting off on foot is a great way to visit the shops, cafes, art galleries and unique buildings and architecture of this tropical Florida Keys location.


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