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

Thinking of heading to Key West? Here is the ultimate Key, West Florida bucket list! A few years ago, I spent a summer working at a color-changing T-shirt shop in Key West, Florida. I think my dad was a little worried and thought I was going to be working at a little shack on the beach bumming my way through the summer.

However, the shop where I worked was right next to the cruise ship docks and only a couple of blocks from Duval Street. So every day I admired the giant cruise ships and amazing yachts riding up to the docks. Then I wandered my way through town on my scooter every night after work.

Because of this, I think I know some of what I’m talking about and even have compiled 17 things you need to know before visiting Key West! Key West, Florida can be known for Duval Street’s drinking and partying each night.

However, I didn’t spend any of my time on the island drinking or partying 🙃 (crazy, right?). Instead, I spent my time exploring every.single.inch of the island (way beyond Duval Street). And I found all of the amazing things to do in Key West, Florida. Plus I found unique places to eat, and hidden gems to explore.

I have since taken my husband back to Key West on an amazing Florida roadtrip. We started at Walt Disney World and then made our way through the Florida Keys to Key West.

However, ever since that roadtrip, I have been daydreaming about returning and spending an entire week just on the island of Key West to be able to fully relax and unwind. Plus this time we’d get to bring along our little tot 😍.

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Getting to Key West

Key West has its own local, international airport. However, I recommend flying into Miami or Ft. Lauderdale instead. Then I recommend you rent a car and enjoy the amazing 3.5-hour drive on the Overseas Highway to Key West. Plus Miami and Fort Lauderdale will most likely have less expensive flights than Key West.

Where to stay in Key West, Florida

Lodging in Key West, Florida can be pretty pricey (booo👎). I’d plan on budgeting *at least* $175 per night for lodging (that’s on the lower end). And, if you are looking at trying to save money, you may be able to find a better deal on an Airbnb.

I recommend looking for an Airbnb with a kitchen because this will help you save a lot of money on eating out! However, staying in a fancy hotel with a private pool and beach sounds pretty amazing too. For example the Casa Marina Key West by Hilton. Maybe one day I’ll have that kind of $$$ 🤞🤞🤞.

Use this link to save up to $65 on your first Airbnb booking.

Related Post:17 Things You Need to Know Before Visiting Key West, Florida

98 Amazing Things You Must 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 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. Rent a bike to explore the island or ride the beach path on S. Roosevelt | Island Safari Rentals
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 Buffet Margaritaville | Duval Street
32. Try the must-have Key Lime Pie on a stick from the original Kermit’s Key Lime Shoppe | Elizabeth Street
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 | 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. Plus get access to Sunset Key’s private beach (trust me, it’s worth it) | 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. RooseveltVisit the quirky and unique Peace Store for unique, feel-good souvenirs and gifts | Caroline Street 
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 sailing the waters of Key West | 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 Restaraunt 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 now is 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 Restaraunt | Islamorada (1 hour away)

And that’s everything I recommend to add 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.

Check out these other Key West posts, I know you’ll love them:

• 17 Things You Need to Know Before Visiting Key West, Florida
• The Ultimate Itinerary for a Day Trip to Key West
• Ultimate Key West Food Guide | 19 Places You Must Try
• 8 Best Places to Try Key Lime Pie in Key West
• The 7 Most Beautiful Places You Need to Watch the Sunset in Key West
• 10 Best Things to do at Fort Zachary Taylor State Park in Key West Florida
• 8 Key West Excursions Definitely Worth the Money
• 5 Reasons You Need to Rent Jet Skis in Key West + How to Rent

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