From water adventures to laid-back charms that’ll capture your heart, Key West has it all. And with this list of 33 must-see attractions, you won’t miss a beat! So get ready to experience the iconic drive, enjoy cocktails at sunset, and savor the tastiest key lime pie you’ve ever had – all in Key West – 90 miles from Cuba!
Table of Contents
1. Old Town Trolley Tours
Experience the top attractions in Key West seamlessly with Old Town Trolly Tours. With 13 stops and over 100 points of interest, you’ll be treated to an unforgettable journey! Whether you’re visiting the Rum Factory, Hemingway House, Little White House, or Mallory Square, there’s something for all ages.
With trolleys running every 30 minutes from morning till early evening, you won’t have to worry about parking. Take advantage of the full 90-minute loop for the complete experience and decide which stops to take. Plus, children 12 and under ride for free!
To save even more, purchase your tickets online.
2. Cocktails at First Flight Restaurant
Get ready to sip on some delicious cocktails with a backdrop of the great outdoors in Key West! Our go-to spot for this is the First Flight Island Restaurant and Brewery, a unique aviation-themed eatery that serves up classic American cuisine.
Fun Fact: in 1927, the first Pan-Am flight tickets were sold here!
For all you beer enthusiasts, check out their selection of Southern Clipper Wheat or Havana Red Ale, brewed right on site at the Southernmost Microbrewery. And don’t miss out on the must-try First Flight Mules, available in mouth-watering flavors like blueberry, orange, basil, or strawberry.
3. Kermit’s Key Lime Shoppe
Treat yourself to the world-renowned Belgian chocolate-dipped Key Lime Pie on a Stick or other delicious classics at Kermit’s Key Lime Shoppe, a must-visit destination for all Key Lime enthusiasts. Keep an eye out for Kermit himself who can often be seen greeting passersby with an inviting wave to come inside.
Explore Kermit’s wide selection of mouth-watering creations, including cheesecake, salsas, cookies, and even cocktail sauce! My personal top pick? The Strawberry Key Lime pie – absolutely divine!
4. Kapok Tree
Come take a selfie or snap a group photo in front of the awe-inspiring Kapok tree located in the heart of Key West. According to Mayan mythology, the souls of their departed would ascend the branches of these majestic trees to reach heaven.
While you’re exploring, don’t forget to check out the stunning banyan trees, also perfect for photos.
5. Oceans Edge Key West: Indulge in Luxury
Oceans Edge Key West Resort Hotel & Marina is where luxury meets relaxation. Each room offers breathtaking ocean views, plush accommodations, and free Wifi. There are six outdoor pools to choose from, and a host of amenities.
Located on Stock Island, Key West’s cozy neighbor, the hotel offers an unparalleled level of privacy and excellent customer service. Relish in beautiful harbor views with much less traffic compared to the hustle and bustle of Key West. Let the hotel shuttle take you to all the popular Key West attractions without the hassle of finding parking.
6. Key West Butterfly & Nature Conservatory
My top thing to see is the amazing Key West Butterfly and Nature Conservatory! Even if you’re not a butterfly person, the vibrant blooms, stunning flamingos, and awesome gift shop make this museum a must-visit.
You’ll step into an indoor paradise filled with rare and colorful butterflies, making it a place you could see every day without ever getting bored. Don’t just take my word for it – come see it for yourself!
7. Dry Tortugas National Park and Fort Jefferson
Discover the rich history of Fort Jefferson, at the impressive Dry Tortugas National Park, only 70 miles from Key West! Accessible by boat or seaplane, this stunning coastal fortress is situated on the idyllic Dry Tortugas Island, boasting water as mesmerizing as the Caribbeans.
Covering a whopping 16 acres and comprised of 16 million bricks, all hand-carried to this remote location, Fort Jefferson is a must-visit destination. Don’t forget your swimsuit and explore the world’s third-largest reef, abundant with vibrant sea life – an underwater experience unlike any other!
8. See the Above Ground Gravesites
Come explore the fascinating cemeteries of Key West! With graves above ground due to the city’s sea level location, the 19-acre cemetery is estimated to hold at least 100,000 people. Legend has it that some unexplained and possibly haunted happenings have taken place in this historic location.
Will you take on the dare to walk through in the eerie midnight hours?
9. Hemingway Home & Museum
Discover the prolific American writer and Nobel Prize winner Ernest Hemingway’s story at his modest Florida Keys estate home. Witness the birthplace of his greatest works, including A Farewell to Arms, now a US National Landmark attracting thousands of visitors each year.
Plus, don’t miss the chance to spot Hemingway’s famous six-toed cats still roaming the grounds and catch a glimpse of the Key West Lighthouse just across the street.
10. Breakfast at Harpoon Harry’s
Harpoon Harry’s is one of those beloved Key West eateries (and best diner) you’ve just got to experience once during your travels. Arrive early to beat the crowds and come with cash as credit cards are not accepted. Feast on the delicious array of omelets, biscuits & gravy, steak & eggs, and Key lime French toast from the breakfast menu.
11. Hard Rock Cafe
Unwind with a few drinks at the beautiful three-story Victorian-style Hard Rock Cafe in Key West. It’s old-school, but still loads of fun. Located on Duval Street, this stunning venue boasts an impressive rock & roll memorabilia collection for you to admire while you sip on your favorite libations.
To get you started, try a deliciously stiff hurricane or a refreshing passion fruit Mai Tai. Cheers to a great time!
12. Key West Lighthouse
Come discover the historic Key West Lighthouse. Built in 1825 to guide ships away from dangerous reefs, it’s now a bucket list destination for visitors and locals alike. Don’t miss the chance to climb the 88 steps to the top for breathtaking panoramic views that will make your Instagram followers jealous.
With admission, you can also explore the beautifully landscaped grounds and learn about the life of the lighthouse keeper in the Keeper’s Quarters, where antiques, vintage pictures, and other treasures await. It’s the perfect adventure for history buffs and aspiring photographers!
13. Southernmost Point
Have you ever dreamed of having your picture taken at the Southernmost Point landmark in Key West? Not only is it a popular bucket list item, but you’ll also catch a glimpse of Cuba from this spot!
Don’t be discouraged by the line – the iconic red-striped concrete buoy photo is worth the wait. Plus, you’ll be among the three million visitors who make their way to this must-see attraction each year. Don’t miss out on the chance to capture this unforgettable memory!
14. Stroll Duval Street
Welcome to Duval Street, Key West’s main thoroughfare! Take a stroll down this bustling street and discover dozens of charming boutiques, art galleries, world-famous bars, irresistible restaurants, and photo opportunities at every turn. And let’s not forget about the colorful chickens and roosters!
Running north to south, from the Gulf of Mexico to the Atlantic Ocean, Duval Street is just a little over a mile long. But don’t be fooled by its size. Everything you’ve heard and imagined about Key West can be found right here, on this lively street.
Duval Street is the main thoroughfare through Key West. On it, you’ll find dozens of boutiques, art galleries, famous bars, restaurants, photo ops, and of course, chickens and roosters.
Duval Street runs north to south, from the Gulf of Mexico to the Atlantic Ocean, and is merely more than a mile long. Still, you’ll find everything you heard and thought about Key West right here in this vicinity, including the Masquerade March during October’s Fantasy Fest.
15. Hear Live Music
This island hotspot has all kinds of jams, from reggae to classic rock, alternative to country, and more. You can catch live performances everywhere – restaurants, bars, hotels — even on the streets! The live music offering will surely enhance your visit to this island paradise.
16. Rent Bikes
Discover Key West’s sights in style! Pedal your way through the island’s beauty on a bicycle. Bring your own or rent one when you get here. Even better, check into one of the many hotels that offer bicycles as an amenity.
You can explore more of the island and enjoy stunning views without stressing about parking spots.
17. The Little White House
Join in on a captivating tour of the Florida Presidential Museum – the only one on the National Register of Historic Places. Originally built in 1890 as a dual residence for a military commandant and paymaster, the Truman Little White House became the go-to vacation spot for several US Presidents.
Clinton, FDR, JFK, and Eisenhower all stayed there at some point in time. And let’s not forget the fact that the Department of Defense was created there too.
The charming house saw a lot of love from Harry Truman, who spent 11 working vacations there. He and his wife Bess delighted in playing card games and hosting dignitaries. In fact, the house was renamed in Truman’s honor years later.
18. Key West Historical Memorial Sculpture Garden
Just a minute from Mallory Square is the incredible Key West Historic Memorial Sculpture Garden. Thanks to the skilled work of James Mastin, 36 bronze busts are on display to honor the people who have impacted Key West since 1997.
Notable faces you may recognize are Tennessee Williams, Henry Flagler, Ellen Russell Mallory, and Ernest Hemingway.
19. Breakfast at Blue Heaven
Blue Heaven, a Floribbean restaurant, has been delighting visitors to Key West with its fun, funky vibe and delicious food for years. Don’t miss dining in the gorgeous courtyard, surrounded by intriguing art mixed with mischievous cats and chickens.
Even if it’s too early for dessert, be sure to take home a slice of their award-winning key lime pie with baked meringue on top – it’s a truly unique recipe you won’t find anywhere else on the island.
20. Key West Aquarium
Discover the hidden gem of Key West at Mallory Square – the Key West Aquarium! Despite passing it numerous times, I only realized the wonders within during my last visit. Though small in size, the well-labeled tanks are teeming with exotic sea creatures and jellyfish.
Make sure to check out the favorite family touch tank, where you can interact with sea cucumbers, urchins, horseshoe crabs, conchs, and sea stars. The shark exhibit is also a must-see, but I found myself captivated by the Caribbean Reef octopus tank. Watching him gracefully climb the glass was mesmerizing.
Don’t forget to purchase your tickets online to save a few bucks (currently $20.99 for adults, $11.99 children 4-12). And did you know that the Key West Aquarium has been the top-rated attraction since 1946? That’s truly impressive!
21. Hit Key West’s Beaches
Explore one of the six beaches of Key West while you work on your tan, read a good book, or relax. The nearby Key West beaches are:
- Higgs
- Smathers
- South
- Dog
- Simonton Street Beaches
- Ft. Zachary Taylor Historic National Park
22. Selfies at Mile Marker Zero
Looking for the perfect Key West photo-op? Look no further than the Mile Marker Zero sign! A must-see for any traveler, this historic sign marks the end of the 2,369-mile US-1 interstate from upstate Maine to sunny Key West.
Not only is it Instagram-worthy, but snapping a pic with this iconic sign is also a fun way to prove that you were truly here and a part of Key West’s vibrant community. I am pictured below with my youngest daughter on a memorable Florida Keys road trip from Vero Beach.
23. Watch Local Artists
Please keep your eyes open for the many painters and artists practicing their craft around town. I’ve seen people painting from the trunks of their truck bed to cool setups like this gals, showcasing her gorgeous pieces that are for purchase on the spot.
Key West is an artist haven!
24. Live Like a Mermaid at Parrot Key Hotel and Villas
Looking for the ultimate pool experience in Key West? My friend, Sara, and I discovered it at Parrot Key Hotel and Villas. This somewhat hidden gem boasts not one, not two, but THREE swimming pools to choose from. And with its apartment-style lodging, the villas are as adorable as they are convenient.
But it’s not just the pools that make Parrot Key special– the lush tropical gardens and gorgeous grounds are the perfect backdrop for your getaway. Oh, and don’t forget to check out the hammocks along the waterfront– they offer the perfect vantage point for catching an incredible sunset.
25. Key West Shipwreck Museum
Discover the fascinating Key West Shipwreck Museum – perfect fun for the whole family! Delve into the treasure trove of artifacts and films that bring to life the gripping tale of a shipwreck from long ago in the Florida Keys.
By night, ghosts roam the halls and give thrill-seekers an eerie adventure on a separate tour and ticket. The 19th-century warehouse setting is an educational experience and is packed floor-to-ceiling with ship treasures and interesting info, with the added bonus of the best observation tower in town.
Don’t miss the chance to climb to the top for stunning panoramic photos!
26. Eat Seafood from Two Friends Patio
Two Friends Patio Restaurant is a popular dining spot that offers an abundance of fresh and tasty seafood dishes, sure to satisfy any craving.
If you’re a fan of shrimp, I recommend the pound of hot peel & eat shrimp – they’re wonderful. But if you’re in the mood for a heartier meal, the steamed snow crab legs dinner is the way to go. It comes complete with a baked potato, salad, and steamed broccoli. Two Friends Patio serves breakfast, lunch, and dinner.
27. Catch a Sunset from Mallory Square
Visitors and locals alike pile into Mallory Square for possibly the best sunsets they’ve ever seen. There is nothing like a Key West sunset. While it may sound redundant, people come out daily at sundown to experience the magnificent showing night after night.
Along with the sunset showing are food vendors, street performers, music, and other entertainment, making this a lively part of town.Mallory Square is also where you will find some of Key West’s best shopping, including Shell Warehouse and Caribbean Congo. Come early, as the square gets very busy when it gets to be that magical time of evening.
28. Go Clubbing
It’s no surprise that Key West is a party hearty address. Let your hair down and join the ranks at some of the coolest places for house music and entertainment.
My two top picks happen to be the 801 Bourbon Bar and Bull and Whistle, both LGBTQ+ friendly and definitely not for those under 21.
29. Eat and Drink Real Cuban Food and Coffee
Looking for a taste of Cuba without the travel? You’ll find it right here in the Florida Keys. Indulge in a world-renowned Cuban cigar from one of the local shops, feast on authentic Cuban cuisine at El Meson De Pepe’s Restaurant, and sip on a satisfying cup of Cuban coffee from the beloved Cuban Coffee Queen.
Try the flavorful ropa vieja – skirt steak marinated and cooked to perfection with peppers, tomatoes, onions, red wine, black beans, and golden rice. And don’t miss out on a Cortadito – my personal favorite coffee made with Cuban coffee, white sugar, and evaporated milk – at the Cuban Coffee Queen bar.
30. Admire The Strand
When you’re in Key West, don’t miss the stunning art-deco Strand Theater. While it’s no longer a cinema, the building once housed Ripley’s Believe It Or Not! attraction until 1993, and now you’ll find a Walgreens inside.
Still, take a moment to appreciate the magnificent facade and interior of this classic structure before stocking up on snacks, sodas, magazines, and other essentials.
31. Tour the Audubon House
Experience the beauty of Audubon House and Tropical Gardens at 205 Whitehead Street in Key West with a self-guided tour. Wander through the lush gardens, where rare plants, exotic palms (hello lipstick palms!), and vibrant flowers are in full bloom. Step inside the 19th-century home of Captain John Huling Geiger to view an impressive collection of prints, antiques, art exhibits, and priceless treasures.
The Audubon House is open daily from 9:30 AM to 4:15 PM. Adult tickets are $15. Children under six are free.
This is an attraction that will take you by surprise and provide a great deal of joy, inside and out.
32. Ride the Conch Tour Train
The Conch Tour Train is a for a fun and cheesy way to discover Key West. This 90-minute narrated sightseeing adventure has been delighting tourists since 1958. With daily runs from 10:15 AM to 4:45 PM, the train stops at some of Key West’s most iconic landmarks, including the Lighthouse Museum, the Historic Seaport, Hemingway House, the Key West Aquarium, and Mel Fisher’s.
33. Key West Museum of Art & History
Discover artistic treasures and fascinating history at the Museum of Art and History in Key West, featuring a wide range of exhibits too great to miss. Admire stunning paintings by Tennessee Williams and sketches from Guy Harvey’s “Old Man and the Sea.”
As part of the US Custom House, this sprawling museum offers educational artwork in every room and area. You’ll also see Henry Flagler’s Overseas Railway exhibit, which taught me so much, and the gorgeous pieces by Mario Sanchez.
Key West: A Favorite Vacation Destination
This coveted Southernmost destination remains sacred for sipping cocktails, watching sunsets, and enjoying a low-key vacation with plenty of fun for the entire family. I hope these 33 things will help you plan your trip and see the best of Key West.
Thanks to the Florida Keys and Visit Florida for hosting my adventures. As always, opinions and reviews are 100% mine and unbiased. Thank you for reading.
You can learn more about the Key West and the Florida Keys by visiting the tourism site.
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Jeff
Tuesday 23rd of April 2019
Drag queen bingo at 801 Bourbon bar is a must. It’s fun, hilarious, and raises money for a different charity each month. Sunday afternoons.....free pizza.
MelodyPittman
Friday 26th of April 2019
I would have loved to done that!