Hello to the land of Jimmy Buffett, endless watering holes, live music, rainbow flags, roaming roosters, and the “come as you are” mentality.

My family and I go to Key West for vacation every year during the winter months of January or February - the weather is perfect & it’s so nice to have a break from the cold weather. If you are planning a trip to Key West or you need a sign to book a vacation to somewhere new - you’ve come to the right place!

I’m here to let you in on a little secret of my favorite spots to sip a cocktail, let my foodie flag fly high, & fully embrace the vibrant atmosphere of Key West.

Food • Drink

Blue Heaven

American Cuisine

Blue Heaven is a crowd-favorite! The atmosphere feels like you are smack dab in the middle of a treehouse in the jungle. The food is absolutely incredible and Blue Heaven is owned by a fellow North Carolinian - need I say more?

Pro Tip: You will most likely have to wait at any time of the day for a table - it’s one of the most popular restaurants in Key West. Put your name down at the host stand, grab a drink at the tiki bar & listen to the live music while you wait. You might see a rooster or two while dining :)

Banana Café

French Cuisine

Banana Cafe, Je vous aime. Banana Cafe is a casual, charming French bistro with Caribbean flair. The cafe is known for their crepes but you honestly cannot go wrong with ordering anything on the menu. The seating options are indoor, on the outdoor patio, or on the rooftop balcony upstairs.

Pro Tip: They serve breakfast, lunch, and dinner daily, but I recommend going for breakfast. You might have to wait for a table depending on the time of day that you go and your party size, but it’s totally worth it.

La-Te-Da

American Cuisine

La-Te-Da just makes me happy as soon as I walk through the doors! Located on the infamous Duval Street, it is a hotel, restaurant, & bar. I love to grab a table outside by the pool & sip on a cocktail.

Pro Tip: Casual dining during the day, white tablecloth at night. There is a caberet show upstairs that is a hit.

Latitudes

Island Cuisine

Oh, Latitudes, you are pure paradise! Latitudes is an oceanfront fine-dining restaurant located on Sunset Key, a private island community.

Pro Tip: You must take a ferry to get to Latitudes. Once you book your reservation, Latitudes will tell you a time/location to meet to take your party over to Sunset Key.

Southernmost Beach Resort Beach Bar

Unless your hotel has a private beach, you venture off to Smathers Beach for the day, or you dock the boat at a sandbar, there aren’t too many public beach options with access to Duval St. in Key West besides the Southernmost Beach Resort Cafe. If you’re looking to get a little sun and to get your booze on, you can rent a beach chair and hang by the bar for the day. The cafe is located next to the Southernmost House of Key West, a historic beachfront boutique hotel.

Pro Tip: Go during happy hour!

A&B Lobster House

Seafood

A&B Lobster House is located at the A&B Marina, a historic seaport in Key West. Facing the harbor waterfront, A&B is an upscale restaurant with fresh local seafood from KW & Maine.

Pro Tip: There are bars, shops, and restaurants all along the marina. Go when the sun is setting and stroll along the boardwalk before dinner. Book your resy on OpenTable.

Café Solé

Seafood, French, Modern European Cuisine

Cafe Sole is an adorable, tucked away restaurant that you might mistake for a Key West cottage. This quaint, candlelit cafe has delicious food for all appetites and the presentation is unreal.

Pro Tip: Cafe Sole is only open for dinner. Book your resy on Yelp.

Better Than Sex

Dessertery

If you have a sweet tooth and are ready for an experience, head to Better Than Sex after dinner one night. The menu has selections of hilariously named cocktails, wine, beer, and gourmet desserts. We ordered the rimmed wine and the “Popcorn Pimp Cheesecake”, which is one of the tamer names of dessert on the menu - it was fantastic. Will you see a nude photo hung on the wall in the restaurant? 100%.

Pro Tip: Book your resy on Zomato.

Frenchie’s Café

French Cuisine

Frenchie’s is a walk-up French inspired breakfast and lunch cafe that is rumored to have the best coffee in town. Grab a bite to-go or hang out on the adorable patio outside.

Dives

Sloppy Joe’s

Sloppy Joe’s is well-known for its live music scene, with bands performing by day and night. There is always a crowd and it is the epitome of Key West islander vibes.

Pro Tip: Sloppy Joe’s serves casual bar food, so I wouldn’t recommend for a sit-down dinner, unless you’ve been boozing all day and need a chicken tender or six.

Hog’s Breath

Despite the name, Hog’s Breath Saloon is one of my favorite pubs to hit while on Duval St. Hog’s Breath is in Old Town Key West and has a tropical indoor/outdoor vibe with frozen drinks and a raw bar.

Capt. Tony’s

Capt. Tony’s is an old-school historic landmark that was named after the late Mayor of Key West. Total dive, total vibe.

Schooner’s Wharf

My hands down favorite dive bar in Key West is Schooner’s. Located on the Historic Harbor Walk at A&B Marina, Schooner’s is a little piece of Old Key West that is a funky open-sided outdoor bar, with a small stage for live music and umbrella-covered tables. Schooner’s is covered with signed dollar bills, license plates, and bumper stickers galore, giving it the ultimate dive feel.

Fat Tuesday

Home of the frozen drink wall, Fat Tuesday is a great *touristy* bar to grab a souvenir drink to-go while you walk down Duval.

Pro Tip: If you get the 190 Octane…goodnight, we will see you in the morning.

Activities

Duval St.

Duval St. is the main street of restaurants, dives, pubs, & shops in downtown Key West. Duval’s atmosphere is loud, it’s crazy, it’s an absolute blast.

You’ll want to book your hotel or Airbnb close by, so that you can walk everywhere during your stay.

Ernest Hemingway House & Museum

Explore the many rooms of Ernest Hemingway’s house through a self-guided or professionally guided tour of the museum. There are approximately 60 free-roaming cats that live on the property, so take note if you have allergies. Fun fact: Ernest Hemingway named all of his cats after famous people and that tradition has carried over to the cats that live on the grounds today - I would like to meet Britney Spears, please.

Pro Tip: Walk-ins are welcome - tickets do not need to be purchased ahead of time.

Key West Lighthouse

Take the 88 steps to the top of the Key West Lighthouse to check out the aerial views of The Keys. The lighthouse was opened back in 1848 to assist the U.S. Navy base. It is tight corridors going up and down the stairs of the lighthouse, so if that’s not your jam, stay on the ground.

Pro Tip: Tickets are few dollars cheaper online than if purchased in person.