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Weekend in Key West Itinerary: The Perfect 2 Day Getaway

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A weekend in Key West is the perfect way to escape the hustle and bustle of daily life and indulge in some fun in the sun. 

I live in Naples, and Key West is one of my favorite weekend getaways in Florida. 

I go once every two to three months, and I’ve done it enough times to know the best way to spend a two to three-day weekend in this charming island city.

That’s why I’ve created the ultimate weekend itinerary for Key West, designed for both first-time visitors and frequent travelers looking for a new experience.

From learning about the best things to do in the Southernmost city in the continental United States, where to stay, the best places to eat and drink, and more helpful tips — I’ve included all the information you could possibly need to have the perfect weekend trip to Key West.

You’ll explore historical sites like The Ernest Hemingway Home and Museum and the Key West Lighthouse to more outdoor adventures, such as kayaking through the mangroves, snorkeling around the vibrant coral reefs, and much more. ​​ 

Without further ado, let’s dive in!

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here.

👉 Don’t have time to read the whole post? This incredible food and cultural walking tour allows you to taste local seafood, Cuban dishes, and key lime pie at quaint ‘mom and pop’ spots while learning about the rich history and architecture of Key West in an intimate group setting.

In This Post:

Weekend in Key West Itinerary Overview

Here’s a quick glance at all the fun things you’ll do during your Key West weekend getaway.

Day 1 Overview

  • Visit The Hemingway Home and Museum
  • Take a Photo at the Southernmost Point of the Continental U.S.A.
  • Explore the Key West Lighthouse
  • Learn About History at Fort Zachary Taylor Historic State Park
  • Walk Through the Key West Historic Seaport and Have Lunch
  • Visit The Key West Butterfly and Nature Conservatory
  • Stroll Around Duval Street and Have Dinner
  • Watch the Sunset Celebration at Mallory Square

Day 2 Overview

  • Discover the Sun-Kissed Shores of Key West
  • Go Kayaking and Snorkeling in the Pristine Waters
  • Hit the Seas on a Jet Ski Adventure
  • End the Day With a Key West Sunset Sail

Day 1 in Key West: Explore Old Town Key West and Other Historical Sites

You’ll start the first day of your weekend in Key West by exploring the Old Town. 

Old Town Key West is the island’s heartbeat, with its quirky Conch houses and charming lanes.

This is where you’ll find most of Key West’s historical sites and landmarks, giving you a glimpse into the city’s rich past of shipwrecking, piracy, and literary legends.

The best way to get around the Old Town area is with a trolley tour. 

⭐️ I recommend this hop-on hop-off trolley tour because you can get a one or two-day pass, and you can see all the main historical sites at your own pace without worrying about transportation. 

You can also explore Old Town Key West using the Duval Loop bus, a small group walking tour, a guided bicycle tour, and the Key West Conch Train Tour.

Visit The Hemingway Home and Museum

The Ernest Hemingway Home and Museum in Key West, a two-story yellow house with white trim and a black wrought iron balcony surrounded by lush greenery and tropical trees. Several people can be seen enjoying the balcony, overlooking the well-kept lawn and garden below.
The Hemingway Home & Museum | Photo credit: Buurserstraat38 via Depositphotos

Nestled in the heart of the Old Town, the Ernest Hemingway Home and Museum is a must on this weekend in Key West itinerary for literature buffs and history enthusiasts alike.   

This Spanish Colonial-style mansion, once home to the legendary author Ernest Hemingway, is as charismatic as the man himself.

Walking through its lush, tropical gardens, you can almost hear the clack of Hemingway’s typewriter, where classics like “A Farewell to Arms” and “For Whom the Bell Tolls” came to life.

The estate is not just about the man but also his peculiar companions — about 50 six-toed cats, descendants of Hemingway’s original pet, Snow White, roam freely, adding a whimsical charm. 

Whether you’re marveling at the preserved interior that Hemingway once inhabited or getting inspired in his second-floor writing studio, the Hemingway Home offers a peek into the private life of a literary giant.

📕 If you’re a Hemingway fan, the museum offers free guided tours included with the price of admission every 20-30 minutes. I loved this tour and learning all the little details about Hemingway’s life and writing process. It truly felt like stepping back in time and getting to know the man behind the words.

Take a Photo at the Southernmost Point of the Continental U.S.A.

Tourists gather around the iconic red, black, and yellow concrete buoy marking the Southernmost Point in the continental U.S. in Key West, Florida, with the text
The Southernmost Point Buoy

The Southernmost Point Buoy is as photogenic as it is iconic and has been a beloved symbol of Key West since 1983.

It’s a massive, colorful buoy that marks the spot at the corner of Whitehead Street and South Street, boldly claiming its status as the southernmost point of the continental U.S.A., just 90 miles from Cuba.

Someone once told me that you can see Cuba from Key West. You can’t — I tried, and it didn’t work out.  

The Southernmost Point Buoy has become one of the most popular attractions in Key West, with visitors from all over the world flocking to take a photo with this historic landmark.

📸 I highly recommend getting your photo opp done early, no later than 8 am. The line will get really long during the day since it is a free attraction in Key West, and quite honestly, it isn’t worth standing in line for that long just to get a photo.

Explore the Key West Lighthouse 

The Key West Lighthouse, a white lighthouse stands tall against a clear blue sky, surrounded by lush greenery and flanked by a small white shed with a picket fence and a quaint white house with green shutters.
The Key West Lighthouse | Photo credit: f11photo via 123RF

Standing tall and proud, the Key West Lighthouse is a beacon of history and a testament to the maritime heritage of Key West.

First completed in 1825, the lighthouse has been guiding sailors through the treacherous reefs surrounding Key West for nearly two centuries.

The current lighthouse, opened in 1848, is remarkable not just for its longevity but also for its progressiveness — it had a woman as its Keeper, a rarity in the 19th century. 

Today, you can climb the moderate 88 steps to the top and be rewarded with a 360-degree panoramic view of the island.

Don’t forget to visit the Keeper’s Quarters while you’re there, which now serves as a museum and tells the fascinating story of the lighthouse keepers and their lives, which were as integral to Key West’s history as the structure itself.

📌 The stairs are very narrow, and to be truthful, the view from the top isn’t the most stunning. If you have mobility issues or are afraid of heights, you’re totally fine skipping out on climbing to the top. You can also catch a gorgeous view of it from the nearby Hemingway Home and Museum balcony.

Learn About History at Fort Zachary Taylor Historic State Park

Two palm trees with intertwined trunks on a sandy beach, with a backdrop of calm turquoise waters and a rocky shoreline, under a cloudy sky at Fort Zachary Taylor Historic State Park.
Visiting the beach at Fort Zachary Taylor Historic State Park is a must on any weekend in Key West itinerary.

History meets natural beauty in the most stunning way at Fort Zachary Taylor Historic State Park.  

This unique park is home to a Civil War-era fortress and boasts some of the best beaches on the island.

I recommend exploring the fort first, which was built in the mid-19th century as part of the United States’ coastal defense system. 

Named after President Zachary Taylor, the fort played significant roles in the American Civil War and the Spanish-American War.

As you wander through the fort’s labyrinthine passages, you’ll encounter a wide array of cannons, war artifacts, and exhibits detailing the fort’s rich history.

After you’re done with your history lesson, head over to the beach and admire the crystal-clear waters, soft white sand, and stunning views of the Gulf of Mexico.

There’s also a picnic area nestled among Australian Pines, and you can even see the colorful fish hanging out near the rocks without having to snorkel.

🏖️ If you arrive earlier in the day like I do (it’s my first stop when I spend a weekend in Key West since I’m a history nerd and love to have the whole fort to myself), you can come back later on the same day as long as you have your ticket. The sunsets here are epic, and I recommend trading out the Sunset Celebration at Mallory Square for the sunset here. More on that below!

Walk Through the Key West Historic Seaport and Have Lunch

A smiling woman in an orange t-shirt stands in front of a colorful mural that reads
Cuban Coffee Queen is one of my favorite spots in the Key West Historic Seaport.

Located along the harborwalk waterfront, Key West Historic Seaport is a vibrant hub that beautifully blends the charm of Old Town Key West with modern amenities. 

You can take a stroll along the harborwalk and soak in the sights of historic boats, waterfront restaurants, and bustling activity on the docks.

For lunch, I highly recommend stopping by the Conch Republic Seafood Company for some delicious and fresh seafood dishes. 

This restaurant is known for its fresh catch of the day specials and its famous Key Lime pie. 

My absolute favorites here are the conch fritters, the Caribbean spiced mahi mahi, and the blackened shrimp. 

I wasn’t a huge fan of fish until I had their mahi mahi, and now it’s a must for me on every weekend trip in Key West.

After your meal, explore the shops and galleries and grab an iced Cafe Con Leche from Cuban Coffee Queen for a refreshing pick-me-up.

👉 This Key West Historic Seaport Food Tasting Walking Tour allows you to try delicious seafood dishes at five restaurants in the Historic Seaport while learning about the history of Key West. It’s the perfect way to try a little bit of everything and get a taste of the local flavors that have been shaped by the island’s rich history and culture.

Visit The Key West Butterfly and Nature Conservatory

A vibrant butterfly with black wings highlighted by white, red, and blue patches rests on a glossy red leaf with droplets of water, under a soft-focus backdrop of greenery.
A beautiful butterfly at The Key West Butterfly and Nature Conservatory. | Photo credit: romrodinka via 123RF

The Key West Butterfly and Nature Conservatory offers an enchanting experience — a chance to walk among hundreds of free-flying butterflies of 50-60 species in a glass-domed tropical habitat.

The conservatory is not just home to butterflies but also hosts exotic birds and two glorious flamingos named Rhett and Scarlett.

I easily spent an hour learning about the science and nature of butterflies, their life cycle, and their importance in our ecosystem.

If you’re traveling with kids, this is especially a must on your weekend in Key West itinerary, but it’s a captivating experience for all ages.

Stroll Around Duval Street and Have Dinner

A sunny street scene in Key West with tropical palm trees, colorful umbrellas at an outdoor cafe, and traditional white-painted houses with verandas. Pedestrians walk along the sidewalk, and vehicles, including a scooter and a golf cart, are parked or in motion, under a bright blue sky scattered with clouds.
The infamous Duval Street 😍 | Photo credit: alkanc via 123RF

Duval Street is perhaps the most vibrant, eclectic, and popular street in Key West. 

By day, you can meander through quirky shops and galleries and soak up the local art and culture.

As the sun sets, the famous Duval Street transforms into an energetic hub of nightlife, with live music echoing from the historic bars and restaurants.

You’ll see tons of bachelor/bachelorette parties, street performers, and lively crowds enjoying the island vibes.

One must-visit spot is Sloppy Joe’s, a legendary bar that was a favorite of Ernest Hemingway and still serves up delicious drinks to this day.

I’m not a huge fan of their food, but their drinks are top-notch, and it’s a Key West staple.

🥣 Some of the best restaurants to grab dinner on Duval Street are:

  • DJ’s Clam Shack: A casual spot serving up fresh seafood and killer lobster rolls.
  • Kaya Island Eats: Island fusion cuisine and their ahi poke nachos are amazing.
  • Bagatelle: A little more upscale, and their lobster mac and cheese is a must-try.
  • Seaside Cafe at the Mansion: My absolute favorite restaurant in Key West, and the lobster pizza is to die for.

Watch the Sunset Celebration at Mallory Square

A group of people sit along the waterfront, enjoying a picturesque sunset with warm hues reflecting off the water. Silhouettes of sailboats are visible against the glowing horizon as the sun dips low, casting a tranquil scene over the gathering.
Sunset Celebration at Mallory Square | Photo credit: zhukovsky via 123RF

Mallory Square is another must-visit during your weekend in Key West. 

This waterfront square hosts the famous Sunset Celebration every evening, where street performers, local vendors, and spectacular sunsets all come together to create a lively and unforgettable experience. 

The event starts about two hours before the sunset, and the atmosphere and energy are truly infectious. 

In all honesty, I think there are better sunset spots in Key West, so I recommend checking out the Sunset Celebration when it starts and then heading to one of the quieter spots like Fort Zachary Taylor State Park or a sunset cruise for a more intimate and peaceful view.

Additional Attractions to See in the Historic District

You can easily swap out any of the above recommendations for these additional attractions in the Old Town.

If you’re a fast-paced traveler like me, any of these options are easy to add to your day if you still have some time left to explore around the Old Town.

  • Truman Little White House
  • Key West Shipwreck Treasure Museum
  • Audubon House and Tropical Gardens
  • Mel Fisher Maritime Museum
  • Key West Historic Memorial Sculpture Garden
  • Key West Aquarium
  • Key West Cemetary
  • Key West Museum of Art and History
  • San Carlos Institute
  • Oldest House Museum and Gardens Key West

Day 2 in Key West: Relax on the Beaches and Enjoy Outdoor Activities

On your second day in Key West, take it easy and enjoy the beautiful beaches and outdoor activities. 

Key West is brimming with tropical beaches and crystal-clear waters, perfect for swimming, snorkeling, sunbathing, jet skiing, dolphin watching, water activities, and more. 

Enjoy this day soaking up the sun and reveling in the relaxed island atmosphere!

Discover the Sun-Kissed Shores of Key West

View of a calm turquoise sea with gentle waves, overlooking a coastline with lush greenery and partially constructed buildings in the background under a clear sky.
The stunning shoreline of Key West.

Key West isn’t known for having vast expanses of beaches, but what it lacks in size, it makes up for in charm and beauty.

My two favorite beaches in Key West are Smathers Beach and Higgs Beach.

Smathers Beach is the largest public beach in Key West and offers a variety of water sports rentals, umbrella and lounge chair rentals, and food trucks.

Higgs Beach is a more secluded option, perfect for those looking for a quieter beach experience.

There’s a restaurant and bar on site called Salute! On The Beach, and it’s home to the Higgs Beach Memorial Pier.

Both beaches offer stunning views of the water and are great for swimming, snorkeling, or simply lounging in the sun.

☀️ Other beaches in Key West to check out if you have time:

  • Fort Zachary Taylor Historic State Park
  • South Beach
  • Simonton Street Beach
  • Dog Beach

Go Kayaking and Snorkeling in the Pristine Waters

Key West is a haven for water sports lovers, and there’s no better way to experience the crystal clear waters than by kayaking or snorkeling. 

Snorkeling gives you the opportunity to see a variety of marine life, including colorful fish, coral reefs, and maybe even some dolphins or sea turtles! 

Kayaking in Key West gives you a unique perspective of the island’s diverse ecosystem. Paddling through the mangrove mazes in the backcountry waters, you’ll get an up-close look at a variety of birds and fish.

🤿 I recommend this half-day snorkeling and kayaking tour because it combines both activities in one adventure. 

You get to navigate mangrove-canopied canals that are filled with birds, rays, sport fish, and more.

You also get to snorkel in the waters of the Key West National Wildlife Refuge and swim above a coral reef teeming with 600+ species of marine life. 

Plus, snacks, beer, wine, and soft drinks are included on this tour, and the tour is suitable for all skill levels.

🛶 Book your half-day Key West snorkeling and kayaking cruise!

Hit the Seas on a Jet Ski Adventure

A person in a life vest is riding a yellow and white jet ski over turquoise waters, creating a splash in the sea. They appear focused as they maneuver the watercraft, with a clear sky and the horizon visible in the background.
Jet skiing in Key West is a fun and thrilling way to see the island. | Photo credit: ventdusud via Depositphotos

One of the most exhilarating ways to explore the azure waters of Key West is by jet skiing.

The island is surrounded by the warm and inviting waters of the Atlantic Ocean and the Gulf of Mexico, making it a prime location for this adrenaline-pumping activity.

🐬 This epic Key West jet ski tour is the perfect way to experience the thrill of jet skiing while taking in the stunning scenery of the island.

You’ll discover 28 miles of open ocean on this 1.5-hour guided tour, giving you the chance to see some of Key West’s most iconic landmarks from a unique perspective.

Plus, the second rider is free, so you can bring a friend or loved one along for the ride!

As you glide over the waves, you’ll have the chance to spot a variety of marine life, including dolphins, sea turtles, and a myriad of tropical fish.

🐠 Book your Key West jet ski tour!

End the Day With a Key West Sunset Sail

A serene sunset over calm waters with a sky painted in vibrant shades of orange, red, and yellow. A solitary sailboat is silhouetted against the fiery colors reflected on the water's surface, suggesting a peaceful evening at sea.
The perfect weekend in Key West includes a sunset cruise. | Photo credit: fotoluminate via 123RF

There’s something truly magical about a Key West sunset, and there’s no better way to experience it than on a sunset sail.

As your catamaran glides over the calm waters, you’ll have an unobstructed view of the horizon, where the setting sun paints the sky with vibrant hues of orange, pink, and purple.

⛵️ This small group Key West sunset sail is the perfect way to end your day in paradise, and it’s one of my favorite things to do in Key West.

It includes a wine tasting and beer tasting along with a gourmet cheese platter, making it the perfect romantic activity for couples too.

The experienced crew will take you to some of the best spots for viewing the sunset while also pointing out interesting facts about the surrounding area.

🌅 Book your Key West sunset sail!

Looking for more sunset cruises in Key West? Check out this post that I wrote about the best sunset cruises in Key West! There are so many amazing options to choose from, and I’ve narrowed it down to 13 of the best-rated ones based on my experience.

Additional Water/Beach Activities to Try: 

As with Day 1 of your weekend getaway in Key West, you can swap out any of these activities for other water/beach activities you prefer.

These are some other popular options that you’ll also love:

What If You Have a Long Weekend in Key West?

When I say long weekend, I mean at least three days in Key West. 

If you have the luxury of a few extra days in Key West, here are some additional activities to consider adding to your itinerary:

Dry Tortugas National Park

An aerial view of Fort Jefferson in the Dry Tortugas National Park, surrounded by the stunning turquoise waters of the Gulf of Mexico. The massive coastal fortress with its large brick walls forms a hexagon, encompassing a lush green courtyard, while a sandy spit and a dock extend towards a smaller island nearby.
Dry Tortugas National Park | Photo credit: NationalParked via Depositphotos

Dry Tortugas National Park, located about 70 miles off the coast of Key West, is a unique national park that offers a rich combination of history and natural beauty. 

This park consists of seven small islands and is home to the 19th-century Fort Jefferson, which served as a prison during the Civil War.

Dry Tortugas National Park is surrounded by crystal-clear water, making it a popular spot for snorkeling and diving.

The national park is remote, and the only way you can access it is by ferry or seaplane, which adds to the sense of adventure.

Ferry tickets start at $22, and a seaplane charter starts at $451. 

If you’re visiting Key West on a budget, I don’t recommend making the day trip to Dry Tortugas National Park, as it’s quite expensive.

Bahia Honda State Park

A smiling woman wearing a black Nike t-shirt stands on a balcony with a picturesque view of a beach and lush greenery in the background. She has sunglasses perched atop her head and is holding a smartphone in her hand. Behind her, the clear blue sky meets the calm sea at the horizon.
One of my favorite places to visit in the Florida Keys is Bahia Honda State Park.

Bahia Honda State Park makes for the perfect day trip if you have a long weekend in Key West.

It’s 37 miles north of Key West and is home to three beautiful beaches: Calusa Beach, Loggerhead Beach, and Sandspur Beach.

You can also see the remnants of the Old Bahia Honda Bridge, which was built by Henry Flagler. 

You can walk on the bridge before it breaks off, and you’ll catch gorgeous views of the state park from above.

Another popular activity at Bahia Honda State Park is snorkeling, and you can even rent a kayak or a paddleboard and explore the park from a different perspective.

Florida Keys Road Trip 

A nurse shark swims gracefully through the clear shallow waters over a seabed of marine grass. The shark's elongated tail fin trails behind as it navigates the serene aquatic environment.
An adorable shark that I saw in Key Largo, which makes for a great day trip from Key West and is one of the best small beach towns in Florida.

If you’re feeling adventurous and want to explore more of the Florida Keys, a road trip is the perfect way to do it.

The Overseas Highway, also known as US-1, stretches 113 miles and connects the islands of Key West to mainland Florida, and it is one of the coolest Florida road trips.

The drive is known for its stunning ocean views and iconic bridges, including the Seven Mile Bridge.

Along the way, you’ll pass through charming towns like Big Pine Key, Marathon, Islamorada, and Key Largo, where you can stop and explore what they have to offer.

You can even continue north to spend one day in Miami and experience the bustling city life before heading back down to Key West, but this will make for a very long road trip, so plan accordingly.

Tours for Your Weekend in Key West

Since you’re only spending a weekend in Key West, a tour is a great way to make the most of your time.

Below, I’ve listed a few of my favorite tours I’ve taken in Key West, from food/drink tours to ghost tours and more. 

Key West Food and Drink Tours

Food and drink are an integral part of the Key West experience, so why not take a food tour to immerse yourself in the local cuisine fully?

From fresh seafood at local restaurants to famous key lime pie, these tours will fill your stomach and give you a taste of the island’s unique flavors.

You’ll learn about the history and culture behind each dish and get to try a variety of different foods and drinks. Plus, it’s a great way to meet locals who are passionate about the local food and love to share it with you.

These are the best food and drink tours in Key West:

Key West Ghost Tours

In case you didn’t know, Key West is known for its spooky history and ghostly encounters and is touted as one of the most haunted destinations in the USA.

One of the best ways to experience this side of Key West is through a ghost tour.

There are several different tours available, each offering a unique take on the haunted history of the island.

Some of these tours include stops at haunted locations where you’ll hear spine-chilling stories and maybe even have your own paranormal encounter along the way.

See for yourself the ghostly legends and eerie tales that have been passed down through generations with these handpicked Key West ghost tours:

Where to Eat on a Weekend Trip to Key West

I couldn’t write this weekend in Key West itinerary and not tell you where to find the best food! 

The culinary scene in Key West is a combination of Caribbean, Cuban, and seafood-centric cuisine.

This unique blend of flavors makes for a delicious dining experience and a very happy me. 

Some must-try dishes in Key West include:

  • Conch Fritters: made from the meat of the conch shell, which is deep-fried in batter and often served with a citrusy or spicy dipping sauce. (Conch is pronounced conk. I pronounced it literally when I tried to order them the first time I visited Key West, and the server told me that I had no business ordering something I couldn’t pronounce. Lol.)
  • Key West Pink Shrimp: Sweet, tender shrimp known for their unique pink hue, often served grilled, sautéed, or in ceviches. (Grilled with garlic butter sauce and a side of vegetables is my favorite.)
  • Key Lime Pie: A tart and creamy pie made with Key lime juice, egg yolks, and sweetened condensed milk, set in a graham cracker crust and often topped with whipped cream or meringue. It’s the signature dessert of Key West.
  • Cuban Mix Sandwich: A hearty sandwich that reflects Key West’s Cuban heritage, featuring ham, roasted pork, Swiss cheese, pickles, and mustard on Cuban bread, pressed until crispy.
  • Spiny Lobster: Unlike its Northern cousin, the spiny lobster lacks claws, but its tail meat is grilled to perfection and often served with garlic butter or a citrus marinade.
  • Fish Sandwiches: A staple of beachside dining, fish sandwiches are made with freshly caught local fish, often mahi-mahi, yellowtail snapper, or grouper, and served on a bun with lettuce, tomato, and tartar sauce.
A person is seated with a lobster pizza on the table in front of them, featuring golden cheese and a well-browned crust, on a patterned metal plate. On the glass table, there's another pizza with someone reaching for a slice, two glasses with clear liquid and lime, and a lit candle, suggesting a casual dining atmosphere.
The most delicious lobster pizza at the Seaside Cafe at the Mansion.

Here’s where you can find some of the best food and drinks in Key West. (These are additional recommendations I haven’t mentioned above):

  • Blue Heaven: An iconic outdoor dining spot known for its laid-back atmosphere, roaming chickens, and lush foliage. Blue Heaven serves Caribbean-inspired seafood and American classics and is famous for its Mile High Key Lime Pie. The ambiance is as memorable as the food.
  • Latitudes: Located on Sunset Key, Latitudes offers upscale dining with breathtaking waterfront views. The menu features fresh, local seafood and tropical-inspired dishes in a sophisticated setting. It’s ideal for a romantic dinner or special occasion, and reservations are required. They’ll pick you up on a ferry to take you to dinner — that’s how upscale it is.
  • El Siboney Restaurant: A casual, family-owned spot offering authentic Cuban cuisine. El Siboney is beloved for its generous portions of classic dishes like ropa vieja, Cuban sandwiches, and plantains, providing an authentic taste of Cuba in Key West.
  • Louie’s Backyard: Overlooking the Atlantic Ocean, Louie’s Backyard offers a fine dining experience with a menu highlighting seasonal local seafood and innovative dishes. The outdoor deck is the perfect spot for enjoying a cocktail and the view.
  • Pepe’s Cafe: Established in 1909, Pepe’s Cafe is the oldest restaurant in Key West, offering a mix of American breakfast classics, fresh seafood, and hearty steaks. Its rustic charm and no-frills approach to good food make it a must-visit for breakfast or brunch.
  • Half Shell Raw Bar: A quintessential Key West experience, the Half Shell Raw Bar is located in the historic seaport area and serves fresh oysters, clams, and a variety of seafood in a laid-back setting reminiscent of an old fish house.
  • Kermit’s Key West Key Lime Shoppe: While not a traditional restaurant, Kermit’s is a must-visit if you want to try authentic Key Lime Pie in Key West. They also serve coffee, light snacks, and a variety of Key lime-themed treats, from cookies to candies.
  • Hogfish Bar & Grill: Located on Stock Island, just outside Key West, Hogfish Bar & Grill offers a genuine local experience with its signature dish, hogfish. This laid-back spot is perfect if you’re looking to enjoy fresh seafood in a less touristy setting.

Where to Stay During Your Weekend Getaway in Key West

For a short weekend trip in Key West, I recommend staying in the Old Town area. 

This is where most of the action happens, and you’ll be within walking distance of many popular attractions, restaurants, and bars.

My favorite Key West hotels:

  • Old Town Manor: This 9/10 star rated adult-only bed and breakfast is nestled in the heart of Key West and offers a blend of modern amenities in a classic Key West style lush tropical architecture. Check rates and availability here.
  • Simonton Court Historic Inn & Cottages: This 9.12/10 star rated inn used to be a cigar factory, and now it features elegantly appointed rooms, suites, and cottages in a beautiful garden setting. Check rates and availability here.
  • The Gardens Hotel: The Gardens Hotel is dubbed as the prettiest hotel in Key West and has a 9.6/10 star rating. It was built in the 1800s and is listed on the National Register of Historic Places. It still has its historic charm but has been updated with modern amenities. Check rates and availability here.

How to Get to Key West

There are several ways to get to Key West, which makes it easy for you regardless of how far you’re traveling from. There’s a convenient option for everyone. 

🚗 By car: One of the most popular ways to get to Key West is by doing a Miami to Key West drive. Along the way, you’ll get to enjoy the scenic views of the Florida Keys and make stops at different islands on the Overseas Highway. The drive takes approximately 4 hours without stopping, but there are plenty of places to stop for food, gas, or a quick dip in the ocean.

🛩️ By air: Key West International Airport (EYW) is located 15 minutes from the Old Town and welcomes flights from major cities in the USA. From the airport, you can take a taxi, shuttle service, or rent a car to get to your hotel. Check prices for your flight to Key West here.

🛥️ By boat: An enjoyable alternative to flying or driving is arriving via cruise ship and ferry. Many major cruise lines make stops in Key West, allowing you to explore the island for a day or longer. The Key West Express operates daily ferry services from Fort Myers and Marco Island, making it an easy and scenic way to reach the island.

How to Get Around Key West

One of my favorite things about visiting Key West is how easy it is to get around the island. 

I don’t recommend renting a car because the Old Town is walkable, and parking can be a hassle and pretty pricey. 

Instead, opt for one of these modes of transportation:

🚲 Bicycles: There are numerous rental shops on the island where you can rent bicycles for a day or longer. Biking is a popular way to explore Key West, and there are dedicated bike lanes throughout the town.

🛵 Scooters/Mopeds: If biking isn’t your thing, consider renting a scooter. It’s a convenient and fun way to zip around the island. Remember to wear your helmet.

🚎 Trolley: The Key West Hop-On Hop-Off Trolley takes you around the island’s top attractions. It’s an ideal option if you want to learn more about the history and culture of Key West while getting from attraction to attraction. Another option is the Key West Conch Train Tour, and it works in a similar way.

🚌 Public Transportation: The city of Key West also has a public bus system called the Duval Loop. This free shuttle service runs along a loop that covers popular areas on the island, making it easy to get around without spending money on transportation.

🚕 Taxi or Ride-sharing Services: If you need to travel longer distances or prefer not to walk or bike, taxis and ride-sharing services like Uber and Lyft are available in Key West. 

Best Time to Do a Weekend Getaway in Key West

Most people will say that the best time to visit Key West is between March and May. 

During these months, the weather is enjoyable, and the island is less crowded than during peak season (mid-November through March).

However, my favorite time to visit Key West is between June and November. 

This is the rainy season, and it also happens to be hurricane season. The best part is that it doesn’t rain all day — it’s usually just for a short period of time, so you can duck into a bar or café and wait it out.

While this may seem like a downside, I find that the island is much quieter, and hotels are more affordable during these months. 

On the other hand, if you’re looking for a lively party scene and don’t mind higher prices, visiting during peak season (December through February) may be more suitable for you.

Weekend in Key West, Florida Packing List

Here’s a quick packing checklist for a weekend trip to Key West, Florida, so you can make sure you’re not forgetting anything:

  • Swimsuit: Key West is surrounded by beautiful beaches and clear waters, so a swimsuit is a must-have for swimming, snorkeling, or just lounging on the beach.
  • Sunscreen: Given Key West’s sunny and tropical climate, you’ll need a good sunscreen to protect your skin. Consider a coral reef-safe brand to help protect the local marine life.
  • Lightweight Clothing: The weather in Key West can be quite warm. Pack lightweight, breathable clothing to stay comfortable.
  • Rain Jacket: Key West can experience brief rain showers, especially in the summer, so it’s a good idea to pack a light rain jacket.
  • Insect Repellent: Mosquitoes can be an issue, particularly during the summer months, especially in the evening.
  • Snorkel Gear: If you plan to explore the rich underwater world around Key West, bring your own snorkel gear.
  • Hat and Sunglasses: Protect yourself from the strong Florida sun. A wide-brimmed hat and UV-protection sunglasses are ideal.
  • Comfortable Walking Shoes: Key West is best explored on foot, with many attractions within walking distance. Comfortable shoes are a must.

Tips for Making the Most of Your Weekend in Key West

Here are some quick tips to help you make the most of your weekend in Key West:

  • Plan Ahead: Key West can be busy on weekends, especially during peak seasons. Make sure to book your accommodations and any special tours or activities in advance.
  • Check Out Local Events: There are often festivals, concerts, or other events happening in Key West over the weekend. Ask your hotel concierge or check online for any upcoming events during your stay.
  • Keep Your Belly Full: The food in Key West is simply delicious, and if you’re not eating something every two or three hours, you’re doing it wrong. Speaking of, take advantage of happy hour specials.
  • Respect Local Wildlife: From the roaming chickens to the marine life, remember to respect all creatures. Don’t feed wildlife, and keep a safe distance.

Map of Attractions on This 2 Days in Key West Itinerary

I’ve included this map to help you visualize the locations of all of the attractions and restaurants mentioned in this Key West itinerary. 

Simply click on the map below to open it in Google Maps and easily navigate to each spot during your visit.

Interactive map highlighting points of interest in Key West, Florida, with categories for attractions and dining. Notable locations such as The Hemingway Home and Museum, Southernmost Point, and various beaches are marked with red and blue pins, while top dining spots like DJ's Clam Shack and Blue Heaven are indicated with red check marks.

Weekend in Key West FAQs

Is Key West Expensive?

Yes, Key West is considered expensive compared to many other destinations in the United States. Its popularity as a tourist destination, limited space on the island, and high demand for accommodations, dining, and attractions contribute to higher prices for visitors.

Is Key West a Good Weekend Trip?

Yes, Key West is an excellent destination for a weekend trip, offering a rich mix of beautiful beaches, historic sites, vibrant nightlife, and unique culinary experiences, all within a compact area that’s easy to explore over a couple of days.

Is 2 Days in Key West Enough?

​​Yes, two days in Key West is enough to see the main attractions, enjoy some local cuisine, and experience the nightlife, making it a suitable duration for a brief visit. However, a longer stay allows for a deeper exploration of the island’s charm, hidden gems, and relaxed pace.

Is Key West Crowded on Memorial Day Weekend?

Yes, Key West is crowded on Memorial Day weekend. The island hosts several events and festivals during this holiday weekend and attracts a large number of visitors seeking to enjoy the warm weather and long holiday weekend.

Is Key West Fun for Non-Drinkers?

Yes, Key West is fun for non-drinkers, offering a variety of activities such as snorkeling, historic tours, beach outings, and exploring the island’s rich arts and cultural scene, ensuring there’s plenty to enjoy without participating in the drinking culture.

Final Thoughts: The Ultimate Weekend in Key West

A weekend in Key West promises to be the ultimate getaway, filled with exploration of the island’s charm, hidden gems, and diverse range of activities. 

From indulging in delicious local seafood to taking part in water sports and exploring historical landmarks, you’ll find something to do around every corner of the town.

Spend day one exploring the Old Town, with its quaint streets lined with colorful conch-style houses, boutique shops, and art galleries. 

Spend your second day exploring the beaches and doing water sports activities such as snorkeling, kayaking, and going on a sunset cruise.

If you have a long weekend in Key West with a third day, you can go on a day trip to nearby parks and explore other towns in the Keys. 

No matter how you spend your weekend in Key West, one thing is for sure — you’ll leave feeling relaxed, rejuvenated, and wanting to come back for more on another USA weekend trip!

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