Key West, Florida, is one of the most desired vacation spots and road trips in the country. It is only 90 miles from Cuba and one of the only parts of the Florida Keys archipelago that people recognize the name of. Known for its laid-back charms and spectacular water adventures, Key West is a sensational place to get to know. From the iconic drive getting there (Atlanta Ocean on one side, the Gulf of Mexico on the other) to cocktails at sunset and delicious key lime pie, here are 33 things you won’t want to miss in Key West to add even more fun to your visit.
Table of Contents
- 1. Old Town Trolley Tours
- 2. Sipping Cocktails
- 3. Eating a Tasty Key Lime Treat
- 4. Taking Nature Photos
- 5. Staying in a Luxury Hotel
- 6. Discovering the Butterfly Conservatory
- A Bonus: Exploring Fort Jefferson
- 7. Seeing the Cemeteries
- 8. Touring the Hemingway House
- 9. Eating Breakfast at Harpoon Harry’s
- 10. Go Clubbing
- 11. Hanging Out at the Hard Rock
- 12. Climbing the Lighthouse
- 13. Checking Off the Southernmost Point
- 14. Strolling Duval Street
- 15. Hearing Live Music
- 16. Riding Bikes Around Key West
- 17. Visiting the Little White House
- 18. Exploring the KW Sculpture Garden
- 19. Indulging in Blue Heaven
- 20. Visiting the Key West Aquarium
- 21. Hitting the Beaches
- 22. Selfies at Mile Marker Zero
- 23. Watching Local Artists
- 24. Living Like a Mermaid at Parrot Key Hotel and Villas
- 25. Touring the Shipwreck Treasures Museum
- 26. Feasting on Seafood
- 27. Watching a Magnificent Sunset
- 28. Seeing the Historic Seaport in Holiday Attire
- 29.Getting a Dose of Cuba
- 30. Admiring the Strand
- 31. Touring the Audubon House
- 32. Riding the Conch Tour Train
- 33. Browsing the KW Museum of Art & History
- Key West: A Favorite Vacation Destination
1. Old Town Trolley Tours
See the best of Key West on the 13 stops aboard Old-Town Trolly Tours, showcasing over 100 points of interest. Stops include the Rum Factory, Hemingway House, Little White House, and Mallory Square, to name a few. Old Town Trolley runs every 30 minutes (from each stop) from 9 AM to 4:30 PM and gives you freedom from searching for a parking space. Get the most from your tour by riding the entire loop (90 minutes) before deciding which stops you want to take—children 12 and under ride for free. Buy your tickets online for bonus savings.
2. Sipping Cocktails
Key West is the ultimate outdoor setting for enjoying tasty cocktails. One of our favorite places to do so is First Flight Island Restaurant and Brewery, an aviation-themed eatery serving American-style dishes. First Flight Island Restaurant is where the first Pan-Am flight tickets were sold in 1927. Beer lovers might fancy a Southern Clipper Wheat or Havana Red Ale at this Southernmost Microbrewery. I recommend the First Flight Mules, available in blueberry, orange, basil, or strawberry.
3. Eating a Tasty Key Lime Treat
Indulge in a world-famous chocolate-dipped Key Lime Pie on a Stick, or one of the other classic favorites at everybody’s preferred key lime shop in the Keys, Kermit’s Key West Key Lime Shoppe. You may even catch Kermit outside of the store as he waves to the passersby encouraging them to stop for a look. Kermit’s creations range from cheesecake to salsas and cookies to cocktail sauce. My favorite? The Strawberry Key Lime pie.
4. Taking Nature Photos
Take a selfie or group photo in front of the enormous, sacred Kapok tree in the heart of Key West. If you are not familiar with these majestic trees, Mayans believed that souls of their dead climbed a (mythical) kapok tree’s branches to reach heaven. Key West also has beautiful banyan trees— another perfect photo opportunity. You’ll find much more natural beauty as you venture out and about in Key West.
5. Staying in a Luxury Hotel
Oceans Edge Key West Resort Hotel & Marina is a luxury hotel (with all rooms facing the ocean) offering plush accommodations, free Wifi, and six outdoor pools. The setting is fantastic, with an heir of privacy, excellent customer service, and stellar amenities being their top goal. Though located on Stock Island, Key West’s friendly neighbor, you are afforded beautiful harbor views and have much less traffic. A hotel shuttle will take you to the popular Key West attractions, and you won’t have to fight for a parking space.
6. Discovering the Butterfly Conservatory
My #1 thing to see and do in Key West is to visit the Butterfly and Nature Conservatory. I can’t say that I’m a butterfly lover, but this museum, with the vibrant blooms, gorgeous flamingos, and a great gift shop is truly a place I could visit daily and never tire of. You’ll have to see for yourself as you wander the indoor paradise that is a treasure trove filled with colorful and even rare butterflies.
A Bonus: Exploring Fort Jefferson
Located 70 miles from Key West, either via boat ride or seaplane, explore the history of Fort Jefferson, a magnificent National State Park, and an unfinished coastal fortress. The fort and national park are located on the Dry Tortugas Island, a remote area with water every bit as beautiful as the Caribbean islands.
Fort Jefferson spreads over 16 acres on the island and contains 16 million bricks, all of which had to be transported and hand-carried to this remote location. Bring your bathing suit and enjoy swimming or snorkeling at the world’s third-largest reef while you are there. The array of fish you can see is second to none!
7. Seeing the Cemeteries
Key West has fascinating cemeteries. First of all, the graves are above ground since the city is at sea level. Then, the 19-acre cemetery, estimated to have at least 100,000 people buried there, is known for some unexplained or haunted happenings. I double-dog dare you to walk through at midnight.
8. Touring the Hemingway House
Hemingway is one of America’s most prolific writers and Nobel Prize winners. He penned some of his greatest novels and short stories from his modest estate home in the Florida Keys, including A Farewell to Arms. The historic Spanish-Colonial home became a US National Landmark in 1968 and continues to draw thousands of visitors each year who want to see where the magic took place.
While at the Ernest Hemingway Home and Museum, be on the lookout for Hemingway’s six-toed cats, still wandering around the property. You can also see the Key West Lighthouse across the street.
9. Eating Breakfast at Harpoon Harry’s
Harpoon Harry’s is one of those beloved Key West eateries (and best diner) that you’ve just got to experience once during your travels. Arrive early to beat the crowds, come with cash as credit cards are not accepted, and feast on the delicious array of omelets, biscuits & gravy, steak & eggs, and key lime French toast from the breakfast menu.
10. Go Clubbing
It wouldn’t be a trip to the Florida Keys without letting your hair down and getting funky at one of the countless bars, clubs, drag shows, or discos in Key West. It’s always 5 o’clock somewhere in the Keys. From traditional bars to risqué clubs, there is plenty of fun for everyone in this particular location.
Mary Ellen’s Bar and Restaurant is a dive bar with a relaxed vibe, a tasty menu (gourmet grilled cheeses, y’all!), and nightly events/entertainment. 801 Bourbon Bar and Bourbon Street Pub (both LGBT) were perfect for people watching, live entertainment, great music, and a vibrant atmosphere. Bull and Whistle and Green Parrot Bars are other popular choices.
11. Hanging Out at the Hard Rock
One of the places I recommend sitting for a spell and enjoying adult libations is the gorgeous three-story Victorian Hard Rock Cafe in Key West. Sitting on Duval Street, the Hard Rock has a massive collection of rock & roll memorabilia on display to be browsed and talked about. Need drink suggestions? How about a stiff hurricane or the passion fruit mai tai?
12. Climbing the Lighthouse
The Key West Lighthouse, circa 1825, was built to help ships entering the port steer clear of the dangerous reefs. Visitors come today to collect a bucket list check or climb the 88 steps to the top for scenic panoramic photographs. Admission also includes grounds and Keeper’s Quarters tours, complete with antiques, vintage pictures, and plenty of treasures.
13. Checking Off the Southernmost Point
A bucket list item of yours might be seeing or having your photo made at the Southernmost Point landmark (in the continental US), a popular spot for tourists to capture the memory of Key West. You can also see the tip of Cuba from this point. Be prepared to wait in a line, but the big red-striped concrete buoy photo is a must in Key West. Around three million people visit the Southernmost Point each year.
14. Strolling Duval 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.
15. Hearing Live Music
Key West is fantastic for getting out and listening to music. YOu’ll find all sorts of music—reggae, classic rock, country, pop, karaoke, polka, smooth jazz, you name it—in restaurants, bars, nightclubs, hotels, and even on the sidewalks. I couldn’t imagine being in Key West without this key component to adding much fun and culture to your vacation experience.
16. Riding Bikes Around Key West
An excellent way to really soak up the sights in Key West is by bicycle. If you are a Floridian or local, perhaps you travel to the Florida Keys with your bike, or if not, then you can rent them. I’ve even seen many hotels offer bikes as one of the amenities and a great one in my book. You can cover a lot of ground by bicycle, plus have epic views and not have to worry about finding a parking spot.
17. Visiting the Little White House
Take a guided tour of the only Florida Presidential Museum on the National Register of Historic Places. The Truman Little White House was built for a military commandant (officer in charge) and paymaster in 1890. Still, the dual residence was converted into a single-family dwelling that attracted US presidents. Clinton spent the weekend there, FDR came three times, JFK prepared for a summit before the Bay of Pigs Invasion, and Eisenhower recovered at the house after a heart attack. It is also where the Department of Defense was created.
Nobody loved or spent more time at the Little White House than Harry Truman. Truman spent 11 working vacations at the charming house where he and his wife Bess loved having friends and dignitaries over for card games and entertaining. The name of the house was changed in his honor years later.
18. Exploring the KW Sculpture Garden
A new encounter I had on my latest Key West visit was to explore the Key West Historic Memorial Sculpture Garden, only a minute from Mallory Square. Here, 36 bronze busts of people who have impacted Key West have been on display since 1997. James Mastin is the talented sculptor behind this marvelous creation. A few of the faces you will see in the garden are John Geiger, Henry Flagler, Ellen Russell Mallory, and Ernest Hemingway.
19. Indulging in Blue Heaven
Key West’s Blue Heaven has been charming the socks off guests through Floribbean food, fun, and funky for years now. I recommend going for breakfast and dine in the courtyard, amidst beautiful art on display for purchase and with the colorful chickens and cats. Though it may be too early for key lime pie, you should still take a piece of this award-winning pie with baked meringue on top with you. It is the most unique key lime pie recipe on the island.
20. Visiting the Key West Aquarium
I’ve passed by the Key West Aquarium numerous times until my last visit. What an incredible gem right in the heart of Key West at Mallory Square. The aquarium is small but mighty, with well-labeled tanks full of exotic sea creatures and jellyfish. The touch tank (sea cucumbers, urchins, horseshoe crabs, conchs, sea stars) and shark exhibit seemed to be the family favorites, but I was glued to the Caribbean Reef octopus tank. The octopus was mesmerizing to watch as he gracefully climbed the glass of his tank. Purchase your ticket online to save a few bucks.
The Key West Aquarium touts the claim of being the top-rated attraction since 1946…impressive.
21. Hitting the 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, and Ft. Zachary Taylor Historic National Park.
22. Selfies at Mile Marker Zero
The Mile Marker Zero sign is one of the most popular Key West attractions and a place you must get a photo of. The US-1 Mile Marker Zero sign is an Instagram-Worthy stop, but like the Southernmost Point, it serves as proof of your being in Key West. The 2,369-mile interstate runs from upstate Maine to Key West.
23. Watching 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. Living Like a Mermaid at Parrot Key Hotel and Villas
My friend Sara and I found the best pool selections of them all at Parrot Key Hotel and Villas in Key West. This treasure-trove offers not only adorable side-by-side apartment-style lodging (villas) but three swimming pools to choose from, each with a different vibe and offers. The pools are surrounded by five acres of lush tropical gardens and stellar grounds. Don’t miss the hammocks along the waterfront; also an ultimate spot for watching the magnificent sunset.
25. Touring the Shipwreck Treasures Museum
The family-friendly Key West Shipwreck Museum is a gold mine of artifacts and film that tell the story of a long-time ago shipwreck in the Florida Keys. At night, it is part of the ghost adventures on a separate tour and ticket. The 19th-century warehouse setting is wall-to-wall ship treasures and educational info with the best observation tower in town. Be sure to climb to the top for the awesome panoramic photos.
26. Feasting on Seafood
Two Friends Patio Restaurant is one of the popular dining spots in Key West, where the seafood is abundant and delicious. Though I skimped with a pound of hot peel & eat shrimp (delicious, I might add), my friend enjoyed the steamed snow crab legs dinner, complete with baked potato, salad, and steamed broccoli. Two Friends is open for breakfast, lunch, and dinner.
Fun fact: This building is one of the few remaining Old Key West establishments.
27. Watching a Magnificent Sunset
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. Seeing the Historic Seaport in Holiday Attire
Christmas is an excellent time to visit Key West or the Florida Keys. The traffic is minimal, hotel rates are low, and the island is decorated beautifully. I enjoyed the holiday lights around Mallory Square, especially this clever tree creation.
29.Getting a Dose of Cuba
The Cuban influence is alive and well in Key West, only 94 miles away. Experience a Cuban cigar from one of the local shops, Cuban food from El Meson De Pepe’s Restaurant, and a perfect cup of Cuban coffee from Cuban Coffee Queen. I recommend dining on ropa vieja, marinated skirt steak with peppers, tomatoes, onions, and red wine, along with black beans and yellow rice. At the coffee bar, try a Cortadito (Cuban coffee, white sugar, evaporated milk), my favorite coffee of them all.
30. Admiring the Strand
Something that caught my eye on my first Key West visit was the gorgeous art-deco Strand Theater. Though it no longer shows movies, the previous home of Ripley’s Believe It Or Not attraction until 1993 is now a Walgreens. Keep this in mind when you are looking for snacks, soda, sundries, magazines, and that type of thing, but at least admire the beautiful facade and original features inside this classic building.
31. Touring the Audubon House
Take a self-guided tour of the amazing Audubon House and Tropical Gardens in the heart of Key West. Stroll through the gardens, full of blooming flowers, tropical and rare plants, and exotic palms. Then, go inside and admire the prints collection, art exhibits, and priceless pieces in the 19th-century home of Captain John Huling Geiger. Hours are 9:30 AM to 5 PM daily.
32. Riding the Conch Tour Train
A cheesy but fun way to see Key West is by the Conch Tour Train. This 90-minute narrated sight-seeing attraction has been raking in tourists since 1958. The Conch Tour Train runs from 10:15 AM to 4:45 PM daily and stops at the Lighthouse Museum, Historic Seaport, Hemingway House, Key West Aquarium, and Mel Fisher’s, to name a few.
33. Browsing the KW Museum of Art & History
Another prized museum in Key West is the Museum of Art and History, chock full of interesting exhibits ranging from paintings by Tennessee Williams to sketches from Guy Harvey’s “Old Man and the Sea” sketches. The museum (US Custom House) is sprawling, and each room and area offers exciting and educational artwork. Henry Flagler’s Overseas Railway exhibit was my favorite and taught me a great day. Mario Sanchez’s pieces were the coolest.
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 this site.
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