The second you cross into Key West along the Florida Keys Scenic Highway you’ll be transported to an island state of mind. The ocean breeze, the aquamarine water and the laid back atmosphere will have you questioning whether two days is enough time to spend in this island paradise. While we can’t get enough of the southernmost point, you can rest assured you’ll be able to explore the most popular attractions and must-visit locales in 48 hours. Key West has something to offer everyone, from romantic weekend getaways to quick trips for families. With little time to waste, let’s get the vacation planning started!

Key West Southernmost Buoy View

Day One


Key West is a small island and all you need is a bicycle to explore over the course of two days. Located just a few blocks away from the iconic Southernmost Point Buoy on famous Duval Street, you’ll find the Fury Bike Shop where you can rent your mode of transportation. Before heading out, you might want to get your energy levels up with a hearty breakfast on the strip! Try the crepes at the Banana Cafe or the wonderful crab meat omelette at the Southernmost Beach Cafe. Biking the area and getting the lay of the land is not only great for a light workout, but you’ll be able to experience the beautiful weather, tropical bougainvillea and pastel conch cottages without a car window in your way. Points of interest to cruise by include the Southernmost Point Buoy, Mallory Square, the Key West Lighthouse and the Truman Little White House and Truman Annex.


On your first day in paradise, you’ll be delightfully overwhelmed by how relaxed you are so there’s no need to rush around trying to do everything. And in our opinion, your Key West vacation doesn’t truly start until you’ve hit the water. Opt for a watersport that allows you to explore Key West while also experiencing the crystal clear waters. Take your pick between an hour-long parasailing adventure or a 90-minute jet ski tour around the island. You’ll see Key West from every angle without taking up too much of your limited stay.

Rise & Shine ☀️🐓

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After some time on the water, you’re sure to work up an appetite. For lunch, head to Elizabeth Street near the Historic Seaport for a delicious, locally-sourced meal at Fisherman’s Cafe. The authentic flavors of Old Key West come out in their fresh catch fish sandwich, fish tacos and blackened key west pink shrimp club wrap. More of a breakfast lover? Fisherman’s Cafe serves breakfast all day – be sure to try their El Cubano Sandwich!

Sunset view of the Fort Zachary Taylor State Park

Still craving more time in the water? Venture to Fort Zachary Taylor State Park for some quality beach time. Soak in the rays on shore, rent snorkel equipment or tour the Civil War-era fort. Even if you get there later in the afternoon, admission is minimal and the park is open until sunset.


It’s nearing the end of your first day in tropical bliss and it wouldn’t be complete with a marvelous sunset. Gather around Mallory Square for the famous Sunset Celebration complete with performers, live entertainment, local vendors and a front row seat to the main show.

el meson de pepe

For dinner, hang around Mallory Square and savor an authentic Cuban meal at El Meson de Pepe. This family owned and operated restaurant serves up tasty appetizers like guacamole and plantain chip nachos. For the main course, choose from classic dishes like rabirubia frita entera (fried whole yellowtail), ropa vieja (stewed shredded beef) and lechon asado (roasted pork). And don’t forget to order a round of mojitos!

Now that the sun has dipped below the horizon, it’s time to experience Key West after dark. Head to the famed Duval Street for a bar crawl like none other. Start at Sunset Pier, near Mallory Square, and work your way toward the southern edge of the island. Hot spots not to be missed include Hog’s Breath Saloon and Smokin’ Tuna Saloon.

Day Two


Yawn, stretch and get ready for another adventurous day in Key West! Hit up breakfast, or bunch, at the legendary Blue Heaven. Made from scratch pancakes, omelets and benedicts is just the start of the menu. And since you’re on vacation, live it up by ordering a Bloody Mary or mimosa and make a toast. The expansive backyard setting is colorful, quirky and totally Key West.

Make a pit stop at Besame Mucho, just up the street from Blue Heaven, to peruse this adorable boutique with one-of-a-kind jewelry, deliciously scented candles and home goods. Pick up a souvenir and bring a little piece of Key West home with you.

Hemingway House


Hop on your bikes and peddle to the Ernest Hemingway Home & Museum on Whitehead Street. This is where the author lived during most of the 1930s and wrote many of his award-winning novels. Take the guided tour for a glimpse into the life of this great American author. No Key West vacation would be complete without learning the island’s history and the stories of its most famous residents.

While in the area, stop by Bahama Village. This 12-block area is home to restaurants, bars and a market. It’s a cultural hub celebrating the first black Bahamian settlers that arrived in Key West during the 19th century. You can also ride by the historic (and haunted) Key West Cemetery and satisfy your sweet tooth at Kermit’s Key West Key Lime Shoppe for a tangy treat. Depending on the time, make your way to the Key West Butterfly & Nature Conservatory. Wander around the scenic conservatory, home to over 60 species of butterflies and 20 species of exotic birds.

Fury Water Adventures Double Dip Snorkel Trip


Take advantage of your last evening in Key West by combining the island’s two best qualities, watersports and the sunset. Fury’s Double Dip Snorkel and Sunset Combo trip departs in the afternoon and returns after sunset. While aboard our catamaran, you’ll visit two reef locations for a once in a lifetime snorkeling adventure. Then, sit back and relax with a complimentary glass of champagne as you toast to another Key West sunset. (Sunset trips offered seasonally)

conch republic seafood company

After kicking around the ocean in your snorkeling fins, it’s time for dinner at Conch Republic Seafood Company. Located along the Historic Seaport, it’s conveniently right next door to where you’ll return from the snorkeling trip. Enjoy a plate of cracked conch followed up by oysters, clams, blackened Key West shrimp or whatever Key West delicacy you’re craving!

Last Updated 12/06/2023