The Bull & Whistle Bar is one of The 15 Best Places for People Watching in Key West.

1. The Bull & Whistle Bar

7.8
224 Duval St (Caroline St), Key West, FL
Rock Club · 43 tips and reviews

David M.David Minkin: Best people watching on the island is from the balcony of the Whistle bar on the 2nd floor.

Greta P.Greta Perry: Fun place to people watch and good drink prices.

Emily R.Emily Ross: Great place to people watch on rival street!

Amigos Tortilla Bar Mexican Restaurant is one of The 15 Best Places for People Watching in Key West.

2. Amigos Tortilla Bar Mexican Restaurant

8.4
425 Greene St (at Duval St.), Key West, FL
Mexican Restaurant · 76 tips and reviews

Vanessa H.Vanessa H.: The fish tacos with Mango-Chili sauce are amazing,as are the Lobster Tacos. Freshly made tortillas on site and great people watching. Cheap too!

John J.John Jaworski: Make sure you get a seat at the street side bar.. Klerk place for people watching.... And there is always a lot to watch in Key West!

Beth v.Beth von Behren: Loved my taco salad, but wished I had ordered the Mexican version of Coca Cola, rather than a margarita, which was good but nothing special. Suggest you sit at counter, facing out, and people watch.

Caroline's Cafe is one of The 15 Best Places for People Watching in Key West.

3. Caroline's Cafe

8.3
310 Duval St (at Caroline St), Key West, FL
American Restaurant · 92 tips and reviews

PaulPaul: Cuban Press is decent and cheap. Nothing life changing, but cheap for Duval St. and great people watching (especially from the bar). Cops eat here, so it must be decent.

Madeline C.Madeline Clark: Best place on Duval to people watch.

Jenn T.Jenn Tofanelli: Lettuce wrap salad. Or order the cheese steak except with chicken. Super delish. And fantastic people watching.

Cork and Stogie is one of The 15 Best Places for People Watching in Key West.

4. Cork and Stogie

8.7
1218 Duval St (Between Louisa & United), Key West, FL
Beer Garden · 18 tips and reviews

Sean R.Sean Reardon: Great cigars and good people. Awesome place for people watching. You get to see escorts come and go across the street!

Eric W.Eric Wolf: Good selection of cigars - excellent selection of beers. Grab a drink and a stick, sit on the comfortable front porch and enjoy the people watching.

ElizabethElizabeth: Not just wine and cigars - they have a small but well-curated selection of craft beer, too. The porch is an awesome spot to have a drink.

Fogarty's and Flying Monkey's is one of The 15 Best Places for People Watching in Key West.

5. Fogarty's and Flying Monkey's

8.4
227 Duval St (at Caroline St), Key West, FL
Bar · 141 tips and reviews

Florence D.Florence Diehl: Great food and excellent staff!! Also great place to people watch!!!

Kari P.Kari Pettit: Love the drinks! Fun to people watch on the rail too.

Jan D.Jan Dorr: Fish tacos! People watching. Beer.

Dante's is one of The 15 Best Places for People Watching in Key West.

6. Dante's

8.3
955 Caroline St, Key West, FL
Cuban Restaurant · 50 tips and reviews

Thea Y.Thea Yatras: Great food, great drinks, and the pool is some of the best people watching in Key West!

Brianna B.Brianna Birtles: great people watching. stay out of the pool

paul m.paul menta: Beverage, swim and the game.....yep

Sloppy Joe's Bar is one of The 15 Best Places for People Watching in Key West.

7. Sloppy Joe's Bar

8.6
201 Duval St (at Greene St.), Key West, FL
Bar · 191 tips and reviews

RobinRobin: No matter how touristy....the food is fab, the bands are cool, and the people watching is amazing! Black bean quesadillas w salsa are to die for....pizza is also very good!

Leigh P.Leigh Price: Great people watching place!! Especially if there is a bachelor's party going on!!!

Julie M.Julie Mann: Must visit if you are in key West, great live band and great for people watching!

Rum Bar at the Speakeasy Inn is one of The 15 Best Places for People Watching in Key West.

8. Rum Bar at the Speakeasy Inn

8.4
1117 Duval St, Key West, FL
Hotel Bar · 49 tips and reviews

Megan P.Megan Peterson: Painkillers and people watching on the porch.

Kelly D.Kelly DeHart: great outside tables for people watching and the goombay smash was delicious!

Stephanie B.Stephanie Bolton: Bob is awesome! Let him recommend something for you.

Hard Rock Cafe Key West is one of The 15 Best Places for People Watching in Key West.

9. Hard Rock Cafe Key West

8.0
313 Duval St, Key West, FL
Theme Restaurant · 76 tips and reviews

Jon C.Jon Cobb: Great people watching

Theresa P.Theresa Pomfret: Sit out the front & people watch as you enjoy a tasty meal with friendly staff.

Taylor J.Taylor Johnson: I'm so fuckin drunkk right nowwwww

Rick's Bar is one of The 15 Best Places for People Watching in Key West.

10. Rick's Bar

7.5
208 Duval St, Key West, FL
Bar · 45 tips and reviews

Jan D.Jan Dorr: Perfect place to people watch on Duvall

Gabriel H.Gabriel Hayes: Has a great view of Duval upstairs. Great for people watching.

Matt H.Matt Hope: Great for people watching on Duval St

Nine One Five is one of The 15 Best Places for People Watching in Key West.

11. Nine One Five

8.0
915 Duval St, Key West, FL
Mediterranean Restaurant · 64 tips and reviews

Garry S.Garry Smithwick: Table on the porch is good for people watching.

Hannah W.Hannah Weeks: Great with friends, splitting rounds of appetizers is a must! Porch was great fun for people watching and enjoying the balmy weather.

Mary Margaret M.Mary Margaret McLeroy: The tuna dome is a house specialty & a must try - amazing!

Mallory Square is one of The 15 Best Places for People Watching in Key West.

12. Mallory Square

9.1
1 Whitehead St (Wall St.), Key West, FL
Plaza · 126 tips and reviews

Scott D.Scott Dunham: Love the buskers, people watching at sunset!

WalgreensWalgreens: Take a great sunset picture: Find a location with an interesting foreground full of objects that would look good in silhouette form. Then, frame the sunset in the top or bottom third of your picture.

Sarah W.Sarah Warfield: Great place for family's. Street performances...lots of shopping...great sunsets

The Porch is one of The 15 Best Places for People Watching in Key West.

13. The Porch

8.8
429 Caroline St (at Duval St), Key West, FL
Beer Garden · 69 tips and reviews

Sarah D.Sarah Dunn: Great place to people watch from the balcony

Matt S.Matt Sheehan: If you see Larry here tell him to go to hell

Bradley G.Bradley Garrison: Hey James W!..... Suck it

Conch Republic Seafood Company is one of The 15 Best Places for People Watching in Key West.

14. Conch Republic Seafood Company

8.5
631 Greene St (at Elizabeth St.), Key West, FL
Seafood Restaurant · 187 tips and reviews

Jan D.Jan Dorr: Panko crusted dolphin is phenomenal. Dogs are allowed. They will bring your pup a water dish to stay cool. Great views of the marina. Perfect place to people watch

Barbara M.Barbara Mommsen: Views & People Watching

Sean L.Sean Lux: Royal reds are the best seafood in the world. Not on the menu, but at $25 its the best deal ever. You can't buy them anywhere else in Key West

Willie T's is one of The 15 Best Places for People Watching in Key West.

15. Willie T's

8.4
525 Duval St (Southard Street), Key West, FL
Restaurant · 65 tips and reviews

Renee B.Renee Bogacz: Fun place to relax and people watch!

Sean R.Sean Rosenberg: Jump off a table onto the bouncy mechanical bull pit and run out the back entrance before security yells at you

Amy M.Amy Murphy: Best Mojito's EVAH!!! The Banana Daiquiri's aren't bad either!