top of page

Our Favorite Restaurants & Bars in Key West

If you’re anything like me, I easily gain 5+ pounds when I go on vacation. I love food and plan my day around meals and snack breaks, especially while on vacation. In my humble opinion, vacation is not a time for dieting. You should be experiencing the local cuisine, culture, and living it up! The island of Key West has a plethora of food options with many great establishments in which to experience them. These are some of my go-to’s in the Old Town tourist area.

Winni Wanderer | Our Favorite Restaurants & Bars in Key West

Caroline’s Café

Caroline’s is an open-air American/Caribbean cuisine restaurant on Duval Street. They have seating that line the sidewalks making it a convenient place to people-watch. They have great seafood and sandwich options such as conch fritters and Cajun chicken. Don’t forget to try the Cookie Monster dessert!

The Conch Republic Seafood Company

The Conch Republic is a large waterfront restaurant. The menu will satisfy even the pickiest of eaters and children alike. They have a large bar and drink menu, so you’re sure to find something that fits the most discerning tastes. They have a raw bar, delicious sandwiches, and even steak options. I have never eaten anything I did not like at The Republic. The Conch Republic has a great atmosphere, and they often have live music for entertainment.

Two Friends Patio

This is my favorite breakfast place! It has breakfast options after a late night of drinks and entertainment. Two Friends is a popular breakfast place boasting a covered patio with views of Front Street, all while giving a private, intimate feel. The Bloody Mary’s are spectacular. There is a wide range of menu options to choose from including eggs, French toast, and waffles.

Boat House Bar & Grill

Boat House Bar & Grill is a waterfront, boardwalk restaurant. It also happens to be where a lot of local events occur, so be aware if you go during Fantasy Fest or Hemingway Days as it may be crowded. The traditional-style American menu is a hit. I had the filet mignon, and it was delicious. The more formal upscale Commodore restaurant is located upstairs on the second floor of Boathouse. The owners recently bought the old Turtle Kraals restaurant and were doing renovations when I was last there. The new location is expected to open sometime in 2022 and may already be open at the time of this article’s publication.

Hard Rock Café

Most of us has been to a Hard Rock café. Hard Rock Key West has a similar American style menu. It’s “familiar” food for all those unadventurous eaters. On your way out, pick up your Hard Rock Key West swag to add to your collection.

Harpoon Harry’s

Harry’s is another option for breakfast with many diner-like food options. Harry’s has tasty drinks, delicious food, and the staff is friendly. I hear wonderful things about the crab cake eggs benedict and Cuban egg sandwich! Heads up, this establishment is cash only.

The Flaming Buoy

This small, chic restaurant has a modern feel but don’t be surprised if you find the food is ‘out of this world.’ If you look around at the décor, you’ll notice a Star Wars theme. Very friendly service and outstanding food. This place is a must visit on your trip!

Barhopping in Key West

I can’t talk about dining out in Key West without mentioning a few of my favorite bars as well. My husband and I always have a blast here and really enjoy meeting and talking with other travelers and locals at these 5 spots:

· Sloppy Joes

· Irish Kevin’s

· Willie T’s

· Jack Flats · Island Dogs Bar

Winni Wanderer | Our Favorite Restaurants & Bars in Key West

Writing all of these tips has given me Key West fever, so I’m off to plan my next trip…I’ll probably just book something now, and tell my husband later (read more about that story here). 😉


By Jen Urban


Hungry for more Key West restaurant recommendations? Check out our readers’ restaurant picks in Key West. Our Favorite Restaurants & Bars in Key West



bottom of page