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50 Things to Do and See in Key West

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Key West is a small little island less than seven and a half square miles in all. So how could there possibly be 50 things for someone to do on such a tiny island. Truth is, we stopped at 50!!! There is so much more that this slice of heaven has to offer. But here is a quick list just to get you started.

1. Kayak through Mangrove Tunnels
2. Catch a World-Famous Sunset at Sunset Pier


Sunset Image

3. Dive the Vandenberg Shipwreck

4. Experience 'Blue Heaven'

5. Have a drink at the Smallest Bar in Key West

 6. Meander up and down World-Famous Duval Street. And if you are up for it, sign up for the 'Duval Crawl'

Duval Street

7. Ride the Old Town Trolley

8. Stop in at the Ernest Hemingway House and Museum

Hemingway House

9. Climb to the top of the Key West Lighthouse

10. Enjoy the 'Sound Check' at the Green Parrot

11. Forget a car, rent a scooter.


12. Catch the Cabaret at La Te Da

13. Tour, sunbathe, swim at Fort Zachary State Park

14. Go for a breathtaking sunset sail

15. Snorkel the Florida reef

16. Grab a photo at the Southernmost Point Buoy

Southernmost Buoy

17. Savor Mattheessen's; a terrific dessert shop (their cookies are half a pound)

18. Relish the best Conch Fritters at the Conch Shack

19. Visit the Truman Little White House

20. Take in the scenic Key West Conch Houses

21. Take pics of the Key West Chickens - (Don't worry, they are everywhere)

KW Chickens

22. Visit the Butterfly and Nature Conservatory (and the squawking flamingoes)


23. Find BP "Pearl" Roberts epitaph. "I Told You I Was Sick" at the Historic Key West Cemetery

24. Take a seaplane or boat over to Dry Tortugas for a day

25. Sip the 'Bad Bitch' at Key West Legal Rum, the first local rum distillery

26. Jet Ski around Key West Island

Jet Ski

27. Catch the Sunset Celebration at Mallory Square

28. Go fishing out of the famous Key West Charter Boat Row

Scott fishing

29. Rent a golf cart to tool around town

Golf Cart driving

30. Snag a true Cuban Coffee from the Cuban Coffee Queen

31. Stroll through the Key West Historic Seaport

32. Hang out at Higgs Beach with its long pier and steps down into the warm crystal-clear turquoise water

Higgs Beach Pier

33. Enjoy the craft of cigar rolling at the family-owned award-winning Rodriguez Cigar Factory

34. Keep and eye out for the green iguanas (If it gets too cold they may fall out of the trees and on your head...REALLY!!)

35. Pepe's, the oldest eatery in Key West. Serving breakfast, lunch, and dinner since 1909. (Damn good!!)

36. Take the Southernmost Food and Cultural Walking Tour

37. Bike your way around Key West. Tours available too

Biking by Sloppy Joes

39. Hop on the Ghosts and Gravestones Trolley Tour

40 Love cocktails? Take the Key West Craft Cocktails walking tour

41. Audubon House; a must-see for bird lovers, with John Audubon's artwork on display

42. Attend Fantasy Fest...IF YOU DARE!!!!

43. Stop by the BEVY of indoor-outdoor bars, featuring live music across the island

Girl sitting at bar happily

44. Prove you were at the start or end of it all; grab a photo at the US 1 Mile 0 Marker

Mile 0 guy

45. Crash into the Key West Shipwreck Museum

46. Enjoy browsing through the Award-Winning Museum of Art and History at the Custom House

47. Check out Smathers Beach - swim, kayak, parasail, get the picture

48. The Key West Kapok Tree with its incredible trunk is another unique photo-op

49. Pick up some tropical artwork or eye-popping photos at the Guild Hall Gallery

50. Entertainers abound at the Songwriters Music Festival the first weekend each May

Songwriters number 50

We had to stop somewhere and 50 seemed just about right. There are so many fabulous tropical flowers, trees, and birds. We barely mentioned many of the terrific shops, restaurants, bars, clubs, and festivals.

Key West is a true tropical paradise to cherish. Stop on down for a few days, or a week, or a month, or…you get the picture. And while you are here, visit the only location in the United States where the address is simply the number “0". That would be Zero Duval Street, our Madda Fella store. We would love for you to come on by. 

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