Top 25 Things To Do in Key West

From sunset celebrations to literary landmarks, this quirky island paradise offers a perfect blend of relaxation and adventure.

West Parker
By
West Parker
July 1, 2024

As the sun dips below the horizon at Mallory Square, a motley crew of street performers, tourists, and locals gather to bid farewell to another day in paradise. This nightly ritual captures the essence of Key West - a place where time seems to slow down and worries melt away like ice in a mojito. But Key West is more than just stunning sunsets and tropical drinks.

This tiny island at the southernmost tip of the continental United States packs an impressive array of attractions into its 4-mile by 1-mile frame. From literary landmarks to coral reefs, historic forts to hidden beaches, Key West offers a unique blend of culture, history, and natural beauty. Whether you're a first-time visitor or a returning traveler, the Conch Republic has something new and exciting to offer. So grab your sunscreen and sense of adventure as we explore the 25 best things to do in Key West.

Watch the Sunset at Mallory Square

Lively Mallory Square sunset celebration in Key West with street performers and tourists gathered to watch the sun go down
Caught this amazing fire juggler at Mallory Square's sunset celebration. The energy here is electric every single night!

As the day winds down, Mallory Square comes alive with an electric energy that's pure Key West. Street performers, from jugglers to tightrope walkers, entertain the gathering crowd while local artisans sell their wares. But the real star of the show is Mother Nature herself. As the sun sinks into the Gulf of Mexico, painting the sky in a riot of oranges, pinks, and purples, you'll understand why this nightly celebration has become a Key West institution. Grab a drink from a nearby vendor, find a spot along the water's edge, and prepare for a sunset you won't soon forget.

  • Location: 400 Wall St, Key West, FL 33040
  • Hours: The celebration begins about two hours before sunset daily
  • Admission: Free

Why Visit: It's the quintessential Key West experience, blending natural beauty with the island's quirky charm.

Insider Tip: Arrive early to snag a prime viewing spot and catch the best acts. The area can get crowded, especially during peak tourist season.

Explore the Ernest Hemingway Home and Museum

Six-toed cat relaxing on vintage furniture at Ernest Hemingway's Key West home, showcasing the writer's legacy and famous feline residents
Met one of Hemingway's famous six-toed cats at his Key West home. These felines live like royalty in this beautiful old house!

Step into the world of one of America's greatest writers at the Ernest Hemingway Home and Museum. This Spanish Colonial villa, where Hemingway lived and wrote for over a decade, offers a fascinating glimpse into the author's life and work. Wander through rooms filled with Hemingway's personal belongings, including his typewriter and extensive library. The lush gardens are home to descendants of Hemingway's famous six-toed cats, adding a touch of whimsy to the literary pilgrimage. As you stroll the grounds, you might even feel inspired to pen your own island tale.

  • Location: 907 Whitehead St, Key West, FL 33040
  • Hours: Open daily, 9:00 AM - 5:00 PM
  • Admission: Adults $17, Children (6-12) $7

Why Visit: It's a must-see for literature lovers and history buffs alike, offering unparalleled insight into Hemingway's life and work.

Insider Tip: Join one of the 30-minute guided tours for fascinating anecdotes about Hemingway's time in Key West.

Snorkel at Fort Jefferson in Dry Tortugas National Park

Aerial view of Fort Jefferson in Dry Tortugas National Park, showcasing the historic fortress surrounded by crystal-clear Caribbean waters
Took a seaplane to Dry Tortugas and was blown away by Fort Jefferson. It's like stepping back in time surrounded by the most beautiful water I've ever seen.

Seventy miles west of Key West lies a true hidden gem: Dry Tortugas National Park. This remote paradise is home to Fort Jefferson, a massive 19th-century fortress surrounded by crystal-clear waters and vibrant coral reefs. After exploring the fort's impressive brick walls and learning about its rich history, don your snorkel gear and plunge into the warm waters. You'll be greeted by a kaleidoscope of tropical fish, colorful corals, and perhaps even a sea turtle or two. The contrast between the imposing fort and the delicate underwater ecosystem is simply breathtaking.

  • Location: 70 miles west of Key West (accessible by ferry or seaplane)
  • Hours: Open 24/7, but ferry service operates on a set schedule
  • Admission: $15 per person for 7 days, plus transportation costs

Why Visit: It's one of the most unique national parks in the U.S., offering a perfect blend of history and natural beauty.

Insider Tip: Book your ferry tickets well in advance, especially during peak season. Consider splurging on a seaplane trip for breathtaking aerial views and more time at the park.

Tour the Key West Butterfly and Nature Conservatory

Vibrant butterflies resting on exotic flowers in the Key West Butterfly and Nature Conservatory, a tropical paradise in the heart of the island
Felt like I was in a magical fairy tale at the Butterfly Conservatory. These little guys aren't shy at all - one even landed on my shoulder!

Enter a tropical paradise within a paradise at the Key West Butterfly and Nature Conservatory. As you step inside the climate-controlled habitat, you'll be surrounded by hundreds of colorful butterflies fluttering freely among exotic flowers and plants. The sound of cascading waterfalls and chirping birds creates a serene atmosphere that feels worlds away from the bustling streets of Key West. Keep an eye out for the conservatory's resident flamingos, Rhett and Scarlett, who add a touch of pink to this magical environment.

  • Location: 1316 Duval St, Key West, FL 33040
  • Hours: Open daily, 9:00 AM - 5:00 PM
  • Admission: Adults $15, Children (4-12) $11

Why Visit: It's a magical, hands-on experience that's perfect for nature lovers of all ages.

Insider Tip: Visit early in the morning when the butterflies are most active and the conservatory is less crowded.

Kayak Through the Mangroves

Kayakers exploring the serene mangrove tunnels in Key West, offering a unique perspective of the island's natural beauty
Kayaking through the mangroves was like entering another world. So peaceful and we saw so much wildlife - even spotted a manatee!

Paddle your way through the intricate waterways of Key West's mangrove forests for a unique perspective on the island's ecosystem. As you glide through the narrow channels, keep your eyes peeled for a variety of wildlife, from colorful tropical fish darting beneath your kayak to herons and egrets perched in the twisted mangrove roots. The peaceful rhythm of your paddle and the gentle lapping of water against your kayak create a meditative experience that's a world away from the lively atmosphere of Duval Street.

  • Location: Various launch points around the island
  • Hours: Vary by tour operator, but morning tours are recommended
  • Price: Around $50-$80 per person for guided tours

Why Visit: It's an eco-friendly way to explore Key West's natural beauty and get up close with local wildlife.

Insider Tip: Opt for a clear kayak tour for an unobstructed view of the underwater world beneath you.

Visit the Key West Lighthouse and Keeper's Quarters

Historic Key West Lighthouse standing tall against a clear blue sky, offering visitors panoramic views of the island
Climbed to the top of the Key West Lighthouse today. The view is absolutely worth the 88 steps - you can see the whole island!

Climb to the top of Key West's history at the Key West Lighthouse and Keeper's Quarters. Built in 1848, this beacon guided ships through treacherous waters for over a century. Today, it offers visitors a glimpse into maritime history and stunning panoramic views of the island. As you ascend the 88 steps to the top, imagine the lighthouse keepers of yesteryear making this climb several times a day. The adjacent Keeper's Quarters museum houses fascinating artifacts and exhibits that bring the lighthouse's storied past to life.

  • Location: 938 Whitehead St, Key West, FL 33040
  • Hours: Open daily, 9:30 AM - 4:30 PM
  • Admission: Adults $14, Children (6-12) $5

Why Visit: It offers unparalleled views of Key West and a fascinating peek into the island's maritime history.

Insider Tip: Visit late in the afternoon for a chance to catch a spectacular sunset from the top of the lighthouse.

Relax at Fort Zachary Taylor State Park

Snorkelers enjoying the clear waters at Fort Zachary Taylor State Park beach, with the historic fort visible in the background
Best beach day at Fort Zachary Taylor State Park! Great snorkeling right off the shore and the old fort adds such a cool backdrop.

Escape the crowds and discover Key West's best beach at Fort Zachary Taylor State Park. This hidden gem offers crystal-clear waters perfect for snorkeling, a sandy shoreline ideal for sunbathing, and shaded picnic areas for a leisurely lunch. After soaking up the sun, take a stroll through the historic fort, which played a significant role in the Civil War and Spanish-American War. The juxtaposition of military history and natural beauty makes for a uniquely Key West experience.

  • Location: 601 Howard England Way, Key West, FL 33040
  • Hours: Open daily, 8:00 AM until sunset
  • Admission: $6 per vehicle, $2 for pedestrians and bicyclists

Why Visit: It's the perfect spot to combine beach relaxation with a dose of history.

Insider Tip: Bring water shoes to navigate the rocky shoreline, and snorkel gear to explore the underwater world just off the beach.

Take a Sunset Sail

Silhouette of a sailboat against a vibrant Key West sunset, capturing the romance and beauty of an evening sail
Nothing beats a Key West sunset from the water. This sail was the perfect end to a perfect day - complete with champagne!

Experience Key West's famous sunset from a different perspective – on the deck of a beautiful sailboat. As you glide out into the Gulf of Mexico, the worries of the world seem to disappear with the shoreline. Sip on a cold beverage, feel the warm breeze on your face, and watch as the sky transforms into a canvas of vibrant colors. The silhouette of Key West against the setting sun creates a postcard-perfect scene that captures the magic of this island paradise.

  • Location: Various marinas around Key West
  • Hours: Typically depart 1-2 hours before sunset
  • Price: Around $60-$100 per person, often including drinks and light snacks

Why Visit: It's a romantic and relaxing way to end a day in Key West, offering unobstructed sunset views.

Insider Tip: Book a smaller sailboat for a more intimate experience, and bring a light jacket as it can get breezy on the water.

Discover Key West's Past at the Shipwreck Museum

Antique diving equipment and treasure chest displays at the Key West Shipwreck Museum, showcasing the island's maritime history
Discovered the fascinating world of shipwreck salvage at this museum. Can't believe how heavy those old diving suits are!

Dive into Key West's maritime history at the Shipwreck Museum. Housed in a recreated 19th-century warehouse, this museum brings to life the era when Key West was the richest city in Florida, thanks to its lucrative wrecking industry. Through artifacts recovered from actual shipwrecks, interactive exhibits, and costumed actors, you'll learn about the dangerous yet profitable business of salvaging goods from ships that ran aground on nearby reefs. Climb to the top of the 65-foot lookout tower for a bird's-eye view of the island – just as wreckers did in the 1800s to spot ships in distress.

  • Location: 1 Whitehead St, Key West, FL 33040
  • Hours: Open daily, 9:30 AM - 5:00 PM
  • Admission: Adults $17.95, Children (4-12) $9.95

Why Visit: It offers a unique perspective on Key West's history and the industry that shaped its early days.

Insider Tip: Don't miss the live demonstrations of how divers salvaged goods from sunken ships.

Stroll Down Duval Street

Lively scene on Duval Street in Key West, with colorful shops, bars, and tourists enjoying the island's main thoroughfare
Duval Street is always buzzing! Found the cutest boutiques and best people-watching spots. Don't miss the famous Sloppy Joe's bar!

No visit to Key West is complete without a stroll down its most famous thoroughfare, Duval Street. This mile-long stretch is the beating heart of Key West, lined with an eclectic mix of restaurants, bars, shops, and galleries. By day, browse quirky boutiques and art galleries showcasing local talent. As night falls, the street comes alive with music spilling out of lively bars and the chatter of revelers enjoying the island's famous nightlife. From upscale dining to casual watering holes, Duval Street offers a taste of Key West's diverse and vibrant culture.

  • Location: Duval St, Key West, FL 33040
  • Hours: Varies by establishment, but the street is always open
  • Price: Free to stroll, costs vary for shopping and dining

Why Visit: It's the epicenter of Key West's famous nightlife and a great place to people-watch.

Insider Tip: For a quieter experience, explore Duval Street in the morning before the crowds arrive. Don't miss the side streets for hidden gems and local favorites.

Visit the Truman Little White House

Exterior of the Truman Little White House in Key West, a historic site showcasing presidential history in a tropical setting
Toured President Truman's "Little White House" today. So cool to see where he worked and relaxed during his Key West visits!

Step into presidential history at the Harry S. Truman Little White House. Originally built as naval officers' housing in 1890, this unassuming house served as the winter White House for President Truman during his tenure. Today, it's a living museum that offers a fascinating glimpse into mid-20th century American politics. As you tour the perfectly preserved rooms, you can almost imagine the weighty decisions and light-hearted moments that took place within these walls. The tropical gardens surrounding the house provide a serene backdrop that must have been a welcome respite for the president.

  • Location: 111 Front St, Key West, FL 33040
  • Hours: Open daily, 9:00 AM - 4:30 PM
  • Admission: Adults $22.50, Children (5-12) $10

Why Visit: It's a unique piece of American history tucked away in tropical paradise.

Insider Tip: Take the guided tour for insightful stories about Truman's time in Key West and how the island influenced his presidency.

Explore the Key West Cemetery

Unique above-ground tombs with humorous epitaphs at the Key West Cemetery, reflecting the island's irreverent spirit
Key West's sense of humor extends even to its cemetery! Some of these epitaphs had me laughing out loud. A surprisingly fun visit!

Tucked away in the heart of Old Town, the Key West Cemetery is a fascinating open-air museum that tells the story of the island's history and its colorful inhabitants. Established in 1847, the cemetery is known for its above-ground graves and unique epitaphs that reflect Key West's irreverent sense of humor. As you wander among the tombstones, you'll find graves of notable residents, victims of the USS Maine explosion, and even a plot dedicated to "devoted fan" of singer Julio Iglesias. The cemetery offers a quiet, contemplative space that's a stark contrast to the lively streets just a few blocks away.

  • Location: 701 Pauline St, Key West, FL 33040
  • Hours: Open daily, 7:00 AM - 7:00 PM
  • Admission: Free

Why Visit: It's an off-beat attraction that offers insight into Key West's history and unique culture.

Insider Tip: Pick up a self-guided tour map at the cemetery entrance to locate some of the most interesting graves and epitaphs.

Take a Jet Ski Tour Around the Island

Jet skiers enjoying a high-speed tour around Key West, with the island's shoreline visible in the background
What a rush! Jet skiing around the entire island gave us a whole new perspective on Key West. Definitely a must-do activity!

For an adrenaline-pumping way to see Key West, hop on a jet ski and zoom around the island. These guided tours take you on a 26-mile loop around Key West, giving you a unique perspective of the island from the water. You'll zip past landmarks like the Southernmost Point, Mallory Square, and Sunset Key, with stops at sandbars and shallow areas where you might spot marine life. The wind in your hair and the spray of the sea create an exhilarating experience that's hard to beat.

  • Location: Various departure points around Key West
  • Hours: Multiple tour times daily, typically lasting 1.5-2 hours
  • Price: Around $150-$200 per jet ski (can accommodate 1-2 people)

Why Visit: It's an exciting way to see Key West from a different perspective and cool off on a hot day.

Insider Tip: Book an early morning tour for calmer waters and a chance to see the island wake up.

Visit the Key West Butterfly and Nature Conservatory

Step into a tropical paradise at the Key West Butterfly and Nature Conservatory. As you enter the climate-controlled glass dome, you'll be surrounded by hundreds of free-flying butterflies from around the world. The lush landscape, complete with flowering plants, waterfalls, and trees, creates a serene environment where these delicate creatures thrive. Keep an eye out for the conservatory's famous residents, Rhett and Scarlett, a pair of pink flamingos who add a touch of whimsy to the already magical atmosphere.

  • Location: 1316 Duval St, Key West, FL 33040
  • Hours: Open daily, 9:00 AM - 5:00 PM
  • Admission: Adults $15, Children (4-12) $11

Why Visit: It's a magical, hands-on experience that's perfect for nature lovers of all ages.

Insider Tip: Visit early in the morning when the butterflies are most active and the conservatory is less crowded.

Sample Key Lime Pie at Kermit's

No trip to Key West is complete without indulging in a slice of authentic Key lime pie, and Kermit's Key West Key Lime Shoppe is the place to do it. This vibrant green shop serves up what many consider to be the best Key lime pie in the Keys. Tart, sweet, and creamy, with a graham cracker crust, it's a taste of Florida sunshine in every bite. Can't decide between traditional or frozen chocolate-dipped? Get both – you're on vacation, after all!

  • Location: 200 Elizabeth St, Key West, FL 33040
  • Hours: Open daily, 9:00 AM - 9:00 PM
  • Price: Around $6-$8 per slice

Why Visit: It's the quintessential Key West dessert, and Kermit's version is consistently rated as one of the best.

Insider Tip: Try the Key lime pie on a stick – it's dipped in dark chocolate and frozen, perfect for a hot day.

Explore the Mel Fisher Maritime Museum

Treasure displays featuring gold coins and jewelry at the Mel Fisher Maritime Museum in Key West
Felt like a real treasure hunter at the Mel Fisher Museum! The story of the Atocha discovery is incredible. They even let you hold a real gold bar!

Dive into the world of underwater treasure hunting at the Mel Fisher Maritime Museum. This fascinating museum showcases the artifacts recovered by famed treasure hunter Mel Fisher, including gold, silver, and jewels from the Spanish galleon Nuestra Señora de Atocha, which sank off the Florida Keys in 1622. The museum brings to life the excitement of maritime archaeology and the allure of sunken treasure. Interactive exhibits allow you to lift a real gold bar and learn about the techniques used to discover and recover these priceless artifacts.

  • Location: 200 Greene St, Key West, FL 33040
  • Hours: Open daily, 9:30 AM - 5:00 PM
  • Admission: Adults $17.50, Children (6-12) $8.25

Why Visit: It offers a unique blend of history, adventure, and glittering treasures that captivate visitors of all ages.

Insider Tip: Don't miss the Spanish coin exhibit where you can see how these centuries-old coins were minted.

Take a Ghost Tour

Costumed guide leading a ghost tour through the dark streets of Key West, sharing spooky stories of the island's past
Our ghost tour guide really got into character! Whether you believe in ghosts or not, the stories of Key West's haunted history are fascinating.

As night falls, uncover Key West's spooky side with a ghost tour through the island's historic streets. Led by knowledgeable (and theatrical) guides, these tours blend local history with tales of hauntings and supernatural occurrences. You'll visit allegedly haunted locations like the Artist House, home to the infamous Robert the Doll, and learn about the island's darker past. Whether you believe in ghosts or not, these tours offer a unique and entertaining way to explore Key West after dark.

  • Location: Various starting points in Old Town
  • Hours: Usually begin after sunset, around 8:00 PM
  • Price: Around $30-$40 per person

Why Visit: It's a fun and slightly spooky way to learn about Key West's history and folklore.

Insider Tip: Bring a camera – you never know what might show up in your photos!

Visit the Key West First Legal Rum Distillery

Interior of Key West First Legal Rum Distillery, showcasing copper stills and aging barrels used in the rum-making process
Learned all about rum making at this cool distillery. The free samples were a nice bonus - their key lime rum is dangerously good!

Quench your thirst for knowledge (and rum) at the Key West First Legal Rum Distillery. Housed in a former Coca-Cola bottling plant, this small-batch distillery offers free tours where you can learn about the rum-making process from start to finish. See the copper pot still in action, learn about the history of rum in the Florida Keys, and best of all, sample some of their unique rum flavors. From traditional white rum to creative infusions like key lime or coconut, there's a flavor for every palate.

  • Location: 105 Simonton St, Key West, FL 33040
  • Hours: Open Monday to Saturday, 10:00 AM - 5:00 PM
  • Admission: Free tours and tastings

Why Visit: It's a fun and educational experience that ends with a tasty rum tasting.

Insider Tip: Try their rum cake – it makes for a great souvenir or gift.

Bike Around the Island

Bicycles parked in front of vibrant conch houses in Key West, illustrating the island's bike-friendly nature and charming architecture
Rented bikes for the day and it was the best decision! Such a fun way to explore all the little streets and hidden corners of Key West.

One of the best ways to explore Key West is on two wheels. Rent a bike and pedal your way around the island, taking in the colorful Conch-style houses, lush tropical vegetation, and historic landmarks at your own pace. The flat terrain and compact size of Key West make it ideal for cycling. Follow the Florida Keys Overseas Heritage Trail for stunning coastal views, or meander through the quiet back streets of Old Town to discover hidden gems off the tourist track.

  • Location: Various bike rental shops around the island
  • Hours: Most shops open daily from 9:00 AM - 5:00 PM
  • Price: Around $15-$20 for a full day rental

Why Visit: It's an eco-friendly and fun way to explore the island at your own pace.

Insider Tip: Many hotels offer free or discounted bike rentals to guests – check with your accommodation before renting.

Relax at Higgs Beach

Serene view of the long pier at Higgs Beach in Key West, extending into calm, turquoise waters
Found a bit of tranquility at Higgs Beach. The pier is perfect for a morning stroll or watching the sunset. Keep an eye out for the wild chickens!

Escape the crowds and unwind at Higgs Beach, a local favorite that offers a more laid-back beach experience than some of Key West's more popular spots. This small beach boasts soft sand, clear waters, and plenty of amenities including a pier, tennis courts, and a dog park. History buffs will appreciate the African Cemetery near the beach, a solemn reminder of Key West's role in the transatlantic slave trade. As you relax under a swaying palm tree, keep an eye out for the wild chickens that roam freely around the island – they're as much a part of Key West as the sunset celebrations.

  • Location: 1000 Atlantic Blvd, Key West, FL 33040
  • Hours: Open daily, sunrise to sunset
  • Admission: Free

Why Visit: It's a quieter alternative to Smathers Beach, with a mix of recreation options and historical significance.

Insider Tip: Rent a chair and umbrella from the nearby concession stand for a comfortable day at the beach.

Tour the Oldest House in South Florida

Exterior of the Oldest House in South Florida, a well-preserved example of early Key West architecture surrounded by lush gardens
Stepped back in time at the Oldest House in South Florida. It's amazing how well-preserved it is - you can really imagine life in early Key West here.

Step back in time at the Oldest House in South Florida, a beautifully preserved example of colonial architecture dating back to 1829. This historic home offers a glimpse into the daily life of Key West's early settlers, with period furnishings and artifacts that tell the story of the island's past. The lush garden surrounding the house is a tranquil oasis, featuring native plants and a replica of the cook house where meals were prepared.

  • Location: 322 Duval St, Key West, FL 33040
  • Hours: Open daily, 10:00 AM - 4:00 PM
  • Admission: Adults $10, Children under 12 free

Why Visit: It's a well-preserved piece of Key West history that offers insight into the island's early days.

Insider Tip: Don't miss the ship's harpoon in the master bedroom – it's said to have belonged to Richard Cussans, the house's builder.

Enjoy a Drag Show at 801 Bourbon Bar

Vibrant drag performance at 801 Bourbon Bar in Key West, capturing the island's lively and inclusive nightlife scene
What a show at 801 Bourbon Bar! The queens are fabulous and hilarious. Definitely a Key West must-do for a fun night out!

For a night of unforgettable entertainment, head to 801 Bourbon Bar for one of their famous drag shows. This Key West institution has been entertaining locals and tourists alike for decades with their high-energy performances and witty banter. The talented queens lip-sync, dance, and interact with the audience, creating a lively and inclusive atmosphere that embodies Key West's accepting spirit. It's a perfect way to cap off a day of sightseeing and embrace the island's vibrant nightlife.

  • Location: 801 Duval St, Key West, FL 33040
  • Hours: Shows typically start at 9:00 PM and 11:00 PM
  • Price: Cover charge varies, usually around $10-$20

Why Visit: It's a Key West tradition that showcases the island's inclusive and fun-loving spirit.

Insider Tip: Arrive early to get a good seat, and bring cash for tipping the performers.

Visit the Audubon House and Tropical Gardens

Beautiful tropical gardens at the Audubon House in Key West, featuring colorful orchids and lush vegetation
The gardens at the Audubon House are a hidden oasis. I could spend hours looking at all the different plants and Audubon's detailed bird prints.

Immerse yourself in 19th-century Key West at the Audubon House and Tropical Gardens. While John James Audubon never actually lived here, he visited in 1832 and created paintings of local birds for his famous "Birds of America" folio. Today, the meticulously restored house showcases period furnishings and Audubon's exquisite bird prints. The surrounding gardens are a botanical delight, filled with tropical plants and orchids that Audubon might have encountered during his visit.

  • Location: 205 Whitehead St, Key West, FL 33040
  • Hours: Open daily, 9:30 AM - 4:15 PM
  • Admission: Adults $16, Children (6-12) $5

Why Visit: It's a beautiful blend of art, history, and horticulture in the heart of Old Town.

Insider Tip: Take time to relax in the tranquil gardens – they're a perfect spot for a quiet moment away from the bustle of Duval Street.

Catch a Show at the Waterfront Playhouse

Illuminated marquee of the Waterfront Playhouse in Key West at night, highlighting the island's vibrant arts scene
Illuminated marquee of the Waterfront Playhouse in Key West at night, highlighting the island's vibrant arts scene

Experience Key West's thriving arts scene at the Waterfront Playhouse, one of the oldest continuously operating theaters in Florida. This intimate venue hosts a variety of productions throughout the year, from classic plays to contemporary works and musicals. The theater's location in Mallory Square puts you right in the heart of Key West's entertainment district, perfect for dinner and a show. The high-quality performances and cozy atmosphere make for a memorable evening of culture and entertainment.

  • Location: 310 Wall St, Key West, FL 33040
  • Hours: Vary by performance, typically 8:00 PM showtime
  • Price: Varies by show, typically $40-$50 per ticket

Why Visit: It's a chance to experience Key West's cultural side and enjoy professional theater in an intimate setting.

Insider Tip: Check their website for special events like staged readings and cabaret nights.

Explore Fort East Martello Museum

Exterior view of Fort East Martello Museum in Key West, showcasing its distinctive red brick architecture and Civil War history
Fort East Martello is full of surprises! From Civil War history to weird art installations (and don't forget Robert the Doll!). A truly unique Key West experience.

Delve into Key West's Civil War history and folk art scene at Fort East Martello Museum. Built in the 1860s to defend against Confederate sea assault, this never-completed fort now houses a fascinating collection of artifacts and art that tell the story of Key West. From Stanley Papio's whimsical scrap metal sculptures to the famous Robert the Doll (said to be haunted), the museum offers a unique blend of history and local lore. The fort's distinctive red brick architecture and circular design make it a photographer's dream.

  • Location: 3501 S Roosevelt Blvd, Key West, FL 33040
  • Hours: Open daily, 9:30 AM - 4:30 PM
  • Admission: Adults $17, Children (6-12) $8

Why Visit: It's a quirky mix of military history, folk art, and local legends that's quintessentially Key West.

Insider Tip: Don't forget to climb to the top of the central tower for panoramic views of the Atlantic Ocean.

Structuring Your Key West Adventure: A 7-Day Itinerary

Now that we've explored the best things to do in Key West, let's put it all together into a week-long itinerary. Remember, this is just a suggestion – feel free to mix and match activities based on your interests and energy levels.

Day 1: Getting Oriented

  • Start your day with a ride on the Conch Tour Train to get an overview of the island and its history.
  • Walk down Duval Street, popping into shops and galleries.
  • End your day with the Sunset Celebration at Mallory Square.

Days 2-3: History and Culture

  • Visit the Ernest Hemingway Home and Museum in the morning.
  • Explore the Truman Little White House.
  • Take a stroll through the Key West Cemetery.
  • Spend an evening on a Ghost Tour.
  • The next day, visit the Mel Fisher Maritime Museum.
  • Tour the Oldest House in South Florida.
  • End with a show at the Waterfront Playhouse.

Days 4-5: Natural Beauty and Outdoor Adventures

  • Start early with a day trip to Dry Tortugas National Park.
  • The next day, relax at Fort Zachary Taylor State Park.
  • Visit the Key West Butterfly and Nature Conservatory.
  • Take a sunset sail in the evening.
  • Rent bikes and explore the island at your own pace.

Day 6: Off-the-Beaten-Path Experiences

  • Visit Fort East Martello Museum in the morning.
  • Tour the Key West First Legal Rum Distillery.
  • Explore the Audubon House and Tropical Gardens.
  • End your day with a drag show at 801 Bourbon Bar.

Day 7: Relaxation and Last-Minute Must-Dos

  • Spend a relaxing morning at Higgs Beach.
  • Climb the Key West Lighthouse for panoramic views.
  • Do any last-minute shopping on Duval Street.
  • Don't forget to sample some Key Lime Pie at Kermit's!

Remember, Key West is all about relaxation and going with the flow. Don't be afraid to stray from the itinerary if something catches your eye – some of the best experiences in Key West are the unexpected ones.

Whether you're a history buff, a nature lover, or just looking to unwind in a tropical paradise, Key West has something for everyone. From the lively atmosphere of Duval Street to the serene beauty of its beaches and gardens, this tiny island packs a big punch when it comes to attractions and experiences.

As you plan your visit, remember that the real magic of Key West lies not just in its attractions, but in its laid-back attitude and welcoming spirit. So slip into island time, embrace the local motto of "One Human Family," and prepare for a vacation you'll never forget. Who knows? Like so many before you, you might just find yourself planning your return trip before you've even left the island.

West Parker
West Parker
Article updated:
August 7, 2024 9:14 AM

West Parker, a Cornell University School of Hotel Administration graduate, has spent two decades as the secret weapon of the jet-set elite, crafting bespoke adventures that redefine luxury travel. Now a resident writer for Town & Tourist, this 45-year-old "Architect of Extraordinary Journeys" combines razor-sharp insights with unparalleled industry connections to deliver experiences that even the most discerning globetrotters can't help but rave about. West's expertise spans from exclusive real estate to fine dining, making him the go-to strategist for those who demand nothing but the extraordinary in their travels.

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