The Ultimate Key West, Florida Bucket List | 98 Things to Do

A few years ago, I spent a summer working in Key West, Florida. I worked at a little shop right next to the cruise ship docks, only a couple of blocks from Duval Street.

Every day, I rode to work on my little scooter, admired the massive ships and yachts just outside my shop’s window, and if working late, tried to sneak a peek of the sunset from Key West’s sunset celebration.

Every moment that I wasn’t working was spent exploring every inch of the island, way beyond its famous Duval Street.

I found so many of the best things to do in Key West, Florida, including unique places to eat and so many hidden gems to explore.

From my time there, I’ve written so much about the tiny island to help you have an amazing time during your next visit.

Since working in Key West, I’ve returned one more time and hope to return again soon🤞.

This post is written in a different way than most of my posts because I want to dump as many fun Key West bucket list ideas on you as possible. So this is a big list, but it’s full of fun, unique ideas to add to your Key West bucket list!

If you’re looking for the very top things to do in Key West, including popular sites and a few hidden gems, you may want to check out my One Day Key West Itinerary.

*There may be affiliate links in this post.  Read my privacy/disclosure policy to learn more.

🌴 IN A RUSH? HERE ARE OUR KEY WEST FAVORITES

WHERE TO STAY: 

💰😍 The Palms Hotel: Hidden Gem!Apartment-style rooms with an outdoor pool in Old Town Key West! Has amazing reviews, cheap bike rentals and a very affordable price. 

💰💰😍 Beachside Resort & Residences: Oceantfront rooms, outdoor pool, private beach and even units with a kitchen.

💰💰💰😍 Casa Marina Key West Curio Collection by Hilton: Recently renovated beautiful hotel with the largest private beach in Key West, plus 2 oceanfront pools and watersports available directly from the hotel.

KEY LIME PIE WALKING TOUR IN KEY WEST: 

🍰 1.5 Hour Key Lime Pie Tasting Tour in Key West:Taste multiple slices of Key Lime pie with a local while learning about the history of Key West and Key lime pie (like a pub crawl but for pie!😍)

EXCURSIONS WE'VE BOOKED AND LOVED:

🚤 Full Day Key West Ultimate Watersports Adventure:Experience all of the watersports on this full-day trip like jet skiing, parasailing, snorkeling, sunbathing on a catamaran and more!

🚤 Jet Ski Tour of Key West:Experience a thrilling trip around the island of Key West on this Jet Ski tour- share a jet ski and the second rider is free!

🌴 Unique Key West Sandbar Adventure: Experience the backcountry of Key West on this cruise and play on a sandbar in crystal clear water. SUPs and lunch included!

⚓ 1.5 Hour Beautiful Sunset Sail with Drinks Included: Experience the majestic Key West sunsets from the water on a sunset sail! 

🤿 Dolphin Watching and Snorkeling Tour in Key West:Visit the best places to see dolphins in Key West plus visit the backcountry for snorkeling!

HOW WE SAVE MONEY ON OUR RENTAL CARS:

🚘 Economy Bookings Car Rental: Any bit you can save on your car rental is worth it. Our go-to is Economy Bookings.


OUR OTHER TRAVEL FAVORITES:

📸 Tours/Excursions: Viator & Get Your Guide
🚕 Airport Transfers with Car Seats: Welcome Pickups
👉 Travel Strollers: Zoe Traveler & Zoe Double
🍼 Baby Carriers: Tula Carriers, Wildride Hip Carriers 
📱 International Data Phone eSIM: Airalo
🚗 Cheap Rental Cars: Economy Bookings
🏠 Accomodations: Booking, Expedia, VRBO, Airbnb
🌎 Travel Insurance: World Nomads
We receive a fee when you get a quote from World Nomads using the above link. We do not represent World Nomads. This is not a recommendation to buy travel insurance.

How to Get To Key West, Florida

Key West has its own international airport, which is by far the most convenient way to reach the island.

However, flights tend to be more expensive going into Key West than the next closest airports of Ft Lauderdale or Miami, which are about 3.5 hours away.

I personally love the drive down the Overseas Highway from Miami/Ft Lauderdale to Key West. It’s by far one of the most unique drives you’ll ever take.

On the Overseas Highway, you’re almost always surrounded by gorgeous turquoise water as you travel on the many bridges and tiny strips of land connecting all of the Florida Keys.

Most of the time, you feel like you’re floating on water- it’s so unique and beautiful, and I highly recommend it.

If you do choose to fly into Key West for convenience’s sake, I’d recommend taking a day trip up the Florida Keys from Key West to get to experience the Overseas Highway yourself. A great destination would be Robbie’s of Islamorada- my absolute favorite stop in the Florida Keys (you get to feed huge Tarpon fish with your hands!!).

When is the Best Time to Visit Key West, Florida?

I recommend May and June as the best months to visit Key West.

In May and June, you are outside of hurricane season (or just at the very start of it) you’ll have much less expensive lodging, the weather is guaranteed to be warm enough to enjoy the beach and water sports and the island is slightly quieter than during the peak winter season.

The peak season in Key West is generally from mid-December to April, with the off-season from May to mid-November.

December to April is the peak season because the weather in Key West is much milder than the summer heat and it’s not yet hurricane season.

From December to April, you can expect temperatures in the mid-70°s F (sometimes warmer, sometimes colder) and water temperatures in the low 70°s F.

The official hurricane season runs from June 1 to November 30, with the highest chances of storms developing from mid-August to mid-October.

From June to August (while I was there) the temperatures are generally in the high 80°s F with high humidity, and the water temps are also in the mid to high 80°s F which honestly feels a bit like bath water (it’s pretty crazy).

Where to stay in Key West, Florida

Lodging in Key West, Florida, can be pretty pricey, especially in peak season.

In peak season in Key West, standard hotel rooms can cost from $450-$600 per night (and way higher for the nicest of stays).

However, in the off-season, you can expect to find accommodations more in the $200-$300 range (and higher).

If you’d like to save money on food (although Key West does have an awesome food scene) you may want to book accommodations with a kitchen.

Many hotels that are further from Duval Street have a shuttle that conveniently drops you off in Old Town/Duval.

These are some places to stay in Key West high on our list for next time we visit:

💰😍 The Palms Hotel: Hidden Gem! Apartment-style rooms with an outdoor pool in Old Town Key West! Has amazing reviews, cheap bike rentals, and a very affordable price.

💰💰😍 Beachside Resort & Residences: Oceanfront rooms, outdoor pool, private beach, and even units with a kitchen.

💰💰💰😍 Casa Marina Key West Curio Collection by Hilton: Recently renovated, beautiful hotel with the largest private beach in Key West, plus 2 oceanfront pools and watersports available directly from the hotel.

98 Amazing Things To Do in Key West: Key West Bucket List Ideas

If you’re in a rush and want to know some of my very favorite/must-do things to do in Key West, here are the links:

🚤 Unique Key West Backcountry Boat Sandbar Adventure (seriously a must-do in my opinion)

⛵ 1.5 Hour Beautiful Sunset Sail with Drinks Included (such a lovely way to enjoy the sunset)

🌴 Breakfast, lunch, or dinner reservations at Latitudes Restaurant (a lovely restaurant on a PRIVATE ISLAND with gorgeous beach, sunset and Key West views- worth the splurge but you need to book far in advance)

🐓 Brunch at Blue Heaven: (outside with the roosters and live music)

🐟 Robbie’s of Islamorada: (such a unique place in the Florida Keys to feed Tarpon fish from the dock! The best day trip from Key West)

🍰 Kermit’s Key Lime Shop: (my favorite way to eat Key lime pie is on a stick dipped in chocolate)

Key West Bucket List: 98 Unique & Fun Things To DO in Key West

1. Drive the Overseas Highway from Miami to Key West. It’s so magical! | Overseas Highway
2. Walk a portion of the old 7-Mile Bridge | Overseas Highway
3. Watch a picture-perfect sunset from Mallory Square |Mallory Square
4. Tip the street performers during Sunset Celebration | Mallory Square
5. Pet a cat 6-toed cat, while touring Ernest Hemingway’s House | Whitehead Street
6. Paddleboard through mangroves and seagrass (and possibly see some Nurse sharks!) | Paddleboard rental with optional lesson

7. Take a thrilling jet-ski trip around the entire island of Key West with a fun stop at a sandbar. | Ultimate Jet Ski Tour
8. Take a jog along the gorgeous beach path on S. Roosevelt Blvd with crystal clear water next to you. | S. Roosevelt
9. Have breakfast with the roosters at an authentic local favorite, Blue Heaven. Make sure to get a table outside to enjoy the live music. And order the best fruit-filled pancakes you’ve ever had!| Petronia Street
10. Pick up some cheap eats from Key West’s hidden gem, Falafel King. Look for the Falafel King sign pointing you down the alley off Front Street! | Fitzpatrick Street

11. Snorkel at Fort Zachary Taylor State Park– the best Key West beach for snorkeling. Snorkel gear can be rented onsite. | Fort Zachary Taylor
12. Snap a pic at the southernmost point of the USA. | Whitehead Street/South Street
13. Crash a wedding at the famous Smathers Beach | S. Roosevelt
14. Get an Insta-worthy pic with the giant conch shell at Key West High School | Flagler Ave.
15. Rent a scooter or golf cart and explore the island with the wind in your hair
16. Try fried plantain (and other delicious Cuban food) with the locals at El Siboney | Catherine Street
17. Wander through the Key West Tropical Forest and Botanical Garden | Stock Island

18. Hang out on a private sandbar in Key West’s backcountry (it’s seriously sooo dreamy)| Key West Backcountry Sandbar Tour
19. Climb aboard a U.S. Coast Guard ship, USCGC INGHAM, retired in 1988 | Southard Street
20. Let a butterfly land on you at the Key West Butterfly and Nature Conservatory | Duval Street
21. Explore beautiful gardens and the history of a Civil War fort at West Martello Gardens and Fort | S. Roosevelt
22. Take a stroll down Edward B. Night Pier (White Street Pier) and keep a lookout for people catching interesting fish! | Atlantic Blvd.
23. Go deep-sea fishing (people of all skill levels welcome) | Gulfstream Fishing
24. Snap a pic of the famous sign marking Mile 0 of Highway 1 | Whitehead Street
25. Climb on and explore the Civil War era Fort at Fort Zachary Taylor | Fort Zachary Taylor State Park

26. Relax on a hammock surrounded by white sand and palm trees on your own private beach. (Must have reservations at Sunset Keys Lodging) | Sunset Key
27. Eat a sloppy joe at the Famous Sloppy Joes | Duval Street
28. Enjoy a guided bike tour of Old Town Key West (4.9 stars on Viator!)| Old Town Key West Bike Tour
29. Soak in the views from the top of the Key West Lighthouse, which was open in 1848 with a woman as the keeper (which was unheard of at that time💪) | Whitehead Street

30. Wander the beautiful Key West Cemetery from 1847. Graves are organized by faith and ethnicity. See the beautiful statues, above-ground graves, and clever grave inscriptions | Pauline Street
31. Eat at the world’s first Jimmy Buffett Margaritaville | Duval Street
32. Try the must-have Key Lime Pie on a stick from the original Kermit’s Key Lime Shop | Elizabeth Street (my full Key West Key Lime Pie Guide is here)
33. Get your Key Lime Pie dipped in chocolate from Funky Rooster Coffee House | Caroline Street
34. Walk Duval Street (during the day for a quieter time, at night for a lively bar scene) | Duval Street (book a pub crawl here if that’s your thing)

35. Parasail over gorgeous turquoise-blue and emerald-green waters | Fury Parasailing Adventure
36. Take a tour of President Harry S Truman’s Winter White House | Front Street
37. Eat fresh fish in a former turtle cannery overlooking the harbor at Turtle Kraals | Margaret Street Historic Seaport
38. Get the best fresh Mex at Amigos Tortilla Bar with a fun and intimate atmosphere (you’ve got to try their bowls) |Duval Street
39. Snag some yummy Cuban sandwiches or smoothies to go at Cuban Coffee Queen (a local favorite) | Margaret Street
40. Snap a pic at the adorable ‘Welcome to Key West’ postcard mural | Behind Cuban Coffee Queen on Margaret Street

41. Make lunch or dinner reservations at Latitudes on Sunset Key for a perfect meal on the water overlooking Key West. | Sunset Key
42. Check Hard Rock Cafe Key West off your Hard Rock bucket list | Duval Street
43. Shop the fun Bahama Village Market for a Key West trinket | Petronia Street
44. Swing by the cute, local boutique Wanderlust KW for some cute clothes or knick-knacks | Petronia Street
45. Learn about 400 years of shipwreck salvaging in the Florida Keys at the Key West Shipwreck Museum |Whitehead Street

46. Take a boat trip to the Sand Key Lighthouse which is a huge metal tower way offshore and a great place to go snorkeling | Florida Reef Snorkel Tour
47. Take a guided Conch Train tour to get your bearings and an overview of the island | Front Street
48. See an extensive collection of artifacts of 17th-century shipwrecks at the Mel Fischer Maritime Museum | Greene Street
49. Pay respects at the African slave burial/memorial site from 1860 at Higgs Beach | Atlantic Blvd
50. Catch a movie at the retro-style Tropic Cinema | Eaton Street
51. See the gorgeous white-washed Trinity Presbyterian Church with blue accents and lined with palm trees | Simonton Street

52. Admire the huge white-washed St. Paul’s Episcopal Church with multiple towers and a stunning door on the usually hectic Duval Street | Duval Street
53. See The Basilica of St. Mary Star of the Sea with 2 large, silver spires and a beautiful olive green exterior | Truman Ave
54. Stroll Caroline Street to admire beautiful, old Key West homes with traditional Southern charm | Caroline Street
55. Try a Key West-fav, Conch Fritters from a cute stand called Key West Original Conch Fritters | Duval Street
56. Day trip to Dry Tortugas National Park on a spacious catamaran | Dry Tortugas Tour

57. See the Key West Riviera Canals, where homes back up to the water and owners dock their boats | S. Roosevelt
58. Shop the Truman Waterfront Key West Farmers Market every Thursday from 2 pm to 7 pm for local food and crafts | Truman Waterfront
59. Shop the Key West Artisan Market every other Sunday in season (November to April) from 10 am to 3 pm at Higgs Beach | Atlantic Blvd
60. Get a close-up look of what’s under the sea at the (small) Key West Aquarium | Whitehead Street

61. Rent a lounge chair and relax under the sun at Southernmost Beach | Duval Street
62. Buy a cheap T-shirt on Duval Street | Duval Street
63. Order some delicious and cleverly named desserts from Better Than Sex Dessert Restaurant | Simonton Street
64. Hang out at the small but clean Simonton Beach, snacking on some fast food from the beach vendor | Simonton Street
65. Catch some live music near the water at Coffee Butler Amphitheater | Angela Street

66. Enjoy a gorgeous Key West sunset while sailing on a 55-foot sailboat | Sunset Sail
67. Have a meal under the twinkle lights on Sunset Pier (bonus if it’s during sunset)| Near Mallory Square
68. Buy all the kitschy Key West trinkets, Christmas ornaments, and seashells from a quirky shop called Mac’s Sea Garden | Margaret Street
69. Swing by Mo’s Restaurant for home-cooked Creole/Caribbean food | White Street
70. Catch a play or a musical from one of the best professional theaters in Southern Florida, Red Barn Theatre | Duval Street

71. Share a delicious (and huge) ice cream and cookie dessert called the Cookie Monster from Mattheessen’s Homemade | Duval Street
72. Admire original John James Audubon bird paintings and stroll through the area he visited in the 1830s at the Audubon House & Tropical Gardens. | Whitehead Street
73. Wander through Key West’s Historic Seaport | William’s Street

75. Take the stairs into the water from Higgs Beach Pier | Atlantic Blvd
76. Watch the sunset with some tasty snacks from Southernmost Beach Cafe | Duval Street
77. People-watch at the cruise ship docks | Mallory Square
78. See a collection of salvaged Cuban refugee boats to learn a little of what Cuban refugees have experienced traveling to Florida | Key West Tropical Forest and Botanical Garden
79. Visit Key West’s natural history museum: Eco-Discovery Center | Quay Road
80. Play with rescued parrots at Nancy Forrester’s Secret Garden | Elizabeth Street

81. Be in Key West during one of the many festivals that occur each year. For example, Hemingway Days or the Speed Boat Racing Festival. (I recommend steering clear of Fantasy Fest if you want to avoid nudity and a raucous time) | Duval Street
82. Visit the beautiful and unique Kapok Tree in front of Monroe County Courthouse | Whitehead Street
83. Try the French crepes at La Crêperie French Café Key West | Petronia Street
84. Hang out with the huge Banyan tree on the property of the Key West Lighthouse | Whitehead Street
85. Visit the Tennessee Williams Museum to learn about the famous playwright who lived in Key West for 30 years and wrote The Glass Menagerie, A Streetcar Named Desire, and Cat on a Hot Tin Roof. | Duval Street/Truman Avenue

86. Go sailing on a historic Key West schooner | Elizabeth Street
87. Take a clear-bottomed kayak tour to get up close and personal with fish, jellies, and nurse sharks | Clearly Unique Kayak Tours
88. Admire the vintage Strand Theater from the 1920s with bulb lighting and retro colors. It’s now home to the most unique Walgreens you’ll ever see | Duval Street
89. Snap a pic with the huge Conch Republic flag mural at the Key West airport terminal | S. Roosevelt
90. Visit the Key West Aids Memorial at Edward B. Knight/White Street Pier | Atlantic Blvd
91. Take a ride on the Key West Hop-on-Hop-off Trolley Tour | 13 stops on Key West

92. Spend an entire day on the water (breakfast and lunch included) sailing on a catamaran, snorkeling, jet-skiing, parasailing, and playing with water toys on Fury’s Ultimate Adventure (it’s a perfect way to get a taste of all the watersports!) | Greene Street
93. Go thrifting at Key West’s Salvation Army | Flagler Ave.
94. Explore Key West’s two independent book stores: Key West Island Bookstore (charming used-book store), Books and Books (spacious, new-book store) | Fleming Street and Eaton Street

95. Feed the Tarpon at Robbie’s. Pay a few bucks for a bucket of fish to dangle for HUGE tarpon to snatch out of your hand around the docks | Islamorada (1.5. hours from Key West)
96. Wander the adorable outdoor market at Robbie’s | Islamorada (1.5 hours from Key West)

97. Try fried Key Lime pie (yes, fried pie) at Porky’s Bayside right on the water | Marathon (1.5 hours away)
98. Relax by the water with food or drinks at the Hungry Tarpon Restaurant | Islamorada (1 hour away)

And that’s everything I recommend adding to your Key West bucket list! Please let me know if you have any questions about things to do in Key West, Florida in the comments below- I’ll be sure to get back to you.

🌴🐚 LOOKING FOR MORE ABOUT KEY WEST?

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🌴 The Ultimate Itinerary for a Day Trip to Key West

🤤 Ultimate Key West Food Guide | 18 Places You Must Try

❗ 17 Things You Need to Know Before Visiting Key West, Florida

🚤 8 Key West Excursions Definitely Worth the Money

🤿 10 Best Things to do at Fort Zachary Taylor State Park in Key West Florida

☀️ The 7 Most Beautiful Places You Need Watch the Sunset in Key West

🚤 5 Reasons You Need to Rent Jet Skis in Key West + How to Rent

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