Weekend getaway in Key West

Florida Keys

Tropical Key West scene with colorful architecture and clear skies.

Recommend flying into Miami, grab some croquettes from the Cuban restaurant at the airport, and drive to Key West. The Florida Keys drive is about a 3 1/2 hour covering 150 miles, absolutely worth it! Gulf of Mexico one side and the Atlantic Ocean on the other with beautiful blue water surrounding you. Check out the partial original 7 mile bridge and railroad track along the way.

Grab lunch at Hogfish bar and grill, my fave is the hogfish tacos. My Conch Sistas highly recommend the smoked fish dip!!!

I stay with family when visiting. Recommend a B & B, they are mostly historic conch houses in Old Town near Duval street. Other options, the Casa Marina or La Concha, historical hotels.

Cruise the island on bikes for the weekend and visit the local destinations: the Southernmost Point, Ernest Hemingway’s House, the Big Little Lighthouse, and Truman’s House. Recommend bikeman bike rentals.

After exploring the island, head over to Mallory Square for the sunset, where you also can watch the street performers. Other locations with good sunset views (and cocktails) are The Pier at Ocean Key Resort or Lagerhead’s beach.

Dining options:
~Half Shell Raw Bar: casual chill dinner, best oysters in town, and my Conch Sistas recommend the conch chowder.
~Louie’s Backyard: Old Florida restaurant with a great sun deck area for drinks before or after dinner. Food is always great!

~El Meson de Pepe: delicious Cuban Food in historic building

~Garbo’s Grill: scrumptious seafood tacos

~Latitude’s at Sunset Key: You have to take a boat out to a private island - it’s pricey, but excellent food and unbelievable views.

Key West

A must is breakfast at Blue Heaven’s, where the roosters and chickens are always welcomed. It’s a local fav so be prepared for a wait. My Conch Sistas recommend the lobster Benedict.

Best part of Key West is the salt water! Some options for enjoying the salty water:

~Visit the best beach in town, Fort Zachary Taylor, it’s where the Gulf of Mexico meets the Atlantic Ocean.

~ Water sports activity: parasailing, snorkeling, jet skiing, or kayaking through the mangroves. Recommend salty dog adventures and key west water sports.

~Take the ferry or sea plane to the Dry Tortuga for an amazing day of snorkeling and tour of the historic fort.

More dining options: Mangia Mangia, best pasta in town (had my first dinner date with unknowingly future husband). Santiago’s Bodega has great tapas. BO’s fish wagon for a fresh fish sandwich. Locals fav, Sandy’s cafe for a Cuban mix sandwich.

After dinner cocktails/nightlife on the infamous Duval street. Hog’s Breath, Sloppy Joe’s, Irish Kevin’s, Captain Tony’s, The Bull (has a clothing optional bar at the top called Garden of Eden so you may want to avoid that place... or not?), and Virgilio’s Bar.

Key West

Before you head out, go for a run or walk along Smathers beach and enjoy the salt life.

And some other locals favs that you must try:

Cafe con Leche- traditional Cuban coffee drink (expresso with milk and some sugar)

Key West Conch Fritters – you must try conch fritters while in KW, they are always good at the street vendor in front of the Key West Aquarium downtown or most seafood restaurant will have them.

Key Lime Pie – Most places on Duval street are good so order a slice of key lime pie and enjoy that tart delicious dessert! And if you aren’t a fan of key lime pie, check out Flamingo Crossing Ice cream. They have homemade Key Lime Pie Ice Cream, but also fun flavors like mango and Cuban coffee.

Enjoy Cayo Hueso!