Rachel’s Guide to Key West’s Best Restaurants and Bars

So you’re coming to Key West for a wedding or to have a great time with family or friends. Whether you're tying the knot or celebrating a loved one's big day, congratulations! Key West is a wonderful island to stay for a few days - or in my case - over 11 years! Many of my photography clients and their guests ask me for local restaurant recommendations. Showcasing my island home is one of my favorite things, so without further ado, here is a list of the best places for food and drink here in Key West! 

Blue Heaven

Blue Heaven is a Key West icon and a favorite among visitors and locals alike. They serve incredible Floridian-Caribbean cuisine in a funky, tropical setting inhabited by free-roaming chickens and cats. The wait can be long, especially for brunch and dinner on the weekends, but there’s no need to stress! Just grab a drink from the bar, play some ping pong, listen to some low-key live music, and dream of Key Lime Pie.

Rachel’s Favorite: The Lobster Benedict for brunch! Add bacon! Bloody Marys and other signature drinks are perfect while you wait! For dinner you must have the scallops followed by the yellowtail snapper special. Oh my. You will thank me later. :) The wine list is fabulous here so definite take a look at Richards selections! By far the best Key Lime pie in town. Don't forget to check out the cool gift shop on your way out! 

Hogfish

Located on Stock Island, Hogfish is another locals’ favorite. This open-air restaurant is named for the buttery-tasting fish, and it serves wonderfully fresh seafood. Its relaxed atmosphere gives you a taste of authentic “Old Key West.”

Rachel’s Favorite: Shrimp Bisque and Hogfish Tacos are a must! Worth the drive up to Stock Island. Pet Friendly. 

Little Pearl

Off the beaten path, Little Pearl just opened in 2017 on Olivia Street and is a welcome gem of an addition to the island! In a cool and intimate atmosphere, savor a lovely array of beautifully presented seafood, as well as an impressive wine list at this "neighborhood wine bar & fish house." 

Rachel’s Favorite: Love the serene, nautical vibe here! My favorite dishes are the Seared Scallops with a tahini soy vinaigrette and the tamarind and pineapple glazed Grilled Shrimp Skewers - they are both unbelievably yummy! And if you're feeling adventurous, try the Bangkok Octopus!

Bad Boy Burrito

This small window on Simonton Street is legendary around Key West. Well, it doesn't hurt that they were featured on Diners, Drive-Ins and Dives! You can "build" a burrito or tacos exactly how you want from delicious fresh ingredients and wash them down with a smoothie, a Mexican Coca-Cola, or hibiscus tea. 

Rachel’s Favorite: Anything with the Key West Pink Shrimp! 

HarbourView Café at Pier House Resort & Spa

At the end of Duval Street, HarbourView Café is part of the elegant Pier House Resort & Spa and offers a perfect setting overlooking the Gulf of Mexico. The menu features island-inspired and Caribbean cuisine, including fresh Key West seafood.

Rachel’s Favorite: Fish Tacos are AMAZING and the Lobster BLT. Don't forget to try the conch chowder. White based. Definitely sit outside and enjoy the view!  

Alonzo’s Oyster Bar

Oysters and mussels and clams, oh my! And let’s not forget shrimp, lobster, conch, and calamari! If you like seafood, you’ll be in heaven at Alonzo's! Especially during their legendary happy hour from 4:00 - 6:00 pm, when drinks and appetizers are half off!

Rachel’s Favorite: Steamed Beer Shrimp, Granny Smith apple coleslaw,and the potato cake. The mojito and the Key Lime Pie martini are must haves! 

Santiago’s Bodega 

One of my absolute favorite restaurants here in Key West, Santiago’s is a charming and cozy place that serves an amazing array of international-inspired tapas. The happy hour from 3:00 - 6:00 pm is a great time to try some options and wine/sangria at half price!

Rachel’s Favorite: Everything! No, seriously the lamb rack, saganaki, avocado and pear salad, yellowfin tuna ceviche, shrimp and chorizo skewers. Pair the bread pudding with a white port to finish off the best meal you will have in a long time! I also love the white Cava sparkling sangria! Ask for Fernando at the bar if he is working! 

2 Cents

This restaurant has a very Key West vibe, both inside the unique bar and outside in their lovely courtyard. The fare ranges from new American to Asian fusion, and it’s also a great choice for Sunday brunch. Happy hour here is a ton of fun; you roll dice to determine your drink cost!

Rachel’s Favorite: The Bacon Wrapped Jalapeño Poppers and the kale caesar.  The nightly fish special is also worth checking in to! Amazing! 

Michael’s

A hidden gem in a quiet neighborhood, Michael’s is one of Key West’s best restaurants, hands down. Its sophisticated menu and intimate, garden-like setting make it perfect for special occasions, but the atmosphere is laid-back enough for any outing.

Rachel’s Favorite: The scallops and brie are my absolute favorites. I also love the beef carpaccio and the wedge salad. The filet with the blue cheese and the nightly fish special are always on point! Ask for Suzzette or Nancy if you sit at the bar! 

The Cafe

Get your veg on at this chill spot with funky local art. The menu features inspired vegetarian, vegan, and Asian dishes. There is seafood as well, but even the veggie options are so savory that even carnivores wouldn’t complain!

Rachel’s Favorite: I love everything here. Favorites include the spring rolls, baby Bok Choy, and the polenta sticks. The pizza and the salads are all good and are ever changing. Love their mocktails too. If you are going for brunch I would recommend the Polenta Benedict! 

Salute! On the Beach

Salute! is Blue Heaven’s sister restaurant. As you soak in views of Higgs beach or lazily spectate a volleyball game, Salute! offers a lovely selection of seafood and Italian dishes, and elegant yet comfortable atmosphere, and wonderful live music. 

Rachel’s Favorite: Scallops  and the yellowtail! Nightly soup specials are wonderful.  Tell Holly the manager I said hello! :) Pet friendly. 

Louie’s Backyard

Another great choice for celebrating special occasions, this sophisticated restaurant offers Caribbean-American cuisine and service as spectacular as its ocean views. Upstairs, Louie's Upper Deck is a great place for small plates and wine by the glass.

Rachel’s Favorite: Make reservations around sunset so you can go early and watch the sunset from the deck.  Reservations can be made at the top where tapas are served or the bottom where a full menu will be featured. Both are amazing. Service is excellent and the view is the best in town! 

Better than Sex

Ready for dessert? This indulgent restaurant may have a racy name, but the experience is nothing but tasteful. Literally, the treats here are absolutely delicious! Giggle at the cheeky menu descriptions with a loved one and enjoy a glass of wine with a rim dipped in chocolate!

Rachel’s Favorite: My favorite is her pumpkin pie but that seasonal. :)  The key lime pie, chocolate grilled cheese, and anything chocolate will do! Don't forget a cider glass dipped in caramel or a red wine glass dipped in chocolate. Did I mention chocolate!? 

The Porch / Caroline's Other Side

Tucked away just off Duval Street, a spectacular old mansion contains two fantastic bars. The Porch is a quirky and quaint hangout with a varied selection of artisanal beers and wines. Right next door, The Other Side offers some of Key West's best craft cocktails. 

Rachel’s Favorite: Craft cocktails on the other side will be like no other cocktail you have had on Duval Street. If you just want a good ol craft beer head in to the left side at the Porch and grab one. They do have Radler in stock!  Be prepared to chill on the Porch and people watch. You may get lucky enough to talk to a crazy local. 

Grand Vin

At Key West's first wine bar, you can try or buy wines from all over the world while sitting on one of Key West's best porches. It's a a front row seat for people-watching on Duval Street!

Rachel’s Favorite: Always a way to have a nice night cap and stay away from the madness on the other end of Duval. Have a glass or stay for a bottle. You can also buy a bottle to take back home too!