I visited Key West for a long weekend (Friday – Tuesday) in the middle of August to visit my boyfriend who was there for a 3-week work assignment and have some fun in the sun! This trip was extra special because just prior to this trip in Key West, we had spent almost two months apart due to my digital nomad experience. This trip to Key West was all about reconnection, fun, and adventure! Even though I spent five days there, I condensed the best and most fun activities into 24-hours that will have you feeling carefree, recharged, and reconnected to that special person in your life.

Key West allows you to fully let go of your expectations, and be present having fun, giggling, and excited for what crazy adventure lies ahead on this island. You can unplug, destress, and feel like a kid again. Whether you have 24 hours or 5 days in Key West, you will surely have a good time, I promise.

TRANSPORTATION

Rent a Bike at We Cycle

326 Southard St, Key West, FL 33040

First things first: rent a bike to get around the island. This is the quickest and more importantly, most fun mode of transportation to get you to all of the sites. We used the company We Cycle which charged $10 a day for an adult beach cruiser. This was probably one of my favorite parts of this vacation because it was stress-free and hassle-free compared to a rental car or Uber. Any destination was within a 15-minute bike ride. Riding the bikes at night with the warm, salty air made us feel like kids again. Renting bikes while in Key West is hands-down necessary! And best of all, it’s eco-friendly!

BREAKFAST

Cuban Coffee Queen Downtown

Key Lime Square, 508 Southard St #5, Key West, FL 33040

Now that you’ve got your eco-friendly ride, it’s time for a quick caffeine pick me up before breakfast. My go-to is the cortadito, which I explain all about in my Guide: Cuban Coffee in Key West. This is the perfect local outdoor coffee spot to get your day going.

Date & Thyme Organic Cafe and Market

829 Fleming St, Key West, FL 33040

Since my boyfriend had already been in Key West for two weeks prior to my arrival, he had a favorite local vegan spot on his list. Living in San Diego, this was the perfect cafe to find fresh plant-based food that we are accustomed to. Date & Thyme Cafe and Market has a robust breakfast and lunch menu. It’s a fast casual environment, so you place your order with the cashier, grab your number, and wait for your food on their outdoor patio outfitted with cooling misters, which are oh-so-necessary for the humidity of Key West in August. We ordered the Oatmeal Power Bowl, Buddha Bowl, Peanut Butter Cup Smoothie, and the Daily Detox Organic Juice. This is the perfect place to jump-start your Key West adventure with a fresh organic meal.

*A Local Spot

GET OUTSIDE

Fort Zachary State Park and Beach

601 Howard England Way, Key West, FL 33040
Now that you’re fueled for your day, head on over to Fort Zachary State Park and Beach via a 10-minute bike ride to explore the park, fortress, and beach. It’s a $3 entry fee by bike and can be used all day if you go in and out. Walking along Fort Zachary Taylor shows a glimpse of the history that surrounds Key West, as well as amazing panoramic views of the clear blue ocean that Key West is known for. Since the bf is kind of a history nerd, the fort was a must-see, we opted to do a self-guided tour. Post-fort tour, we walked along the beach and found a nice shady bench to chat. Even though our visit to the beach was lowkey, visitors can snorkel and relax under an umbrella at the beach, which is full-service with rentals, a cafe, and nice bathrooms. We loved this beach in particular because it didn’t feel too crowded, which was a nice respite from the busy Duval Street!

PLAY

Key West Landmark Bike Ride

After you’ve soaked up some sun at the beach, hop back on your bike and make the loop around to the famous Key West landmarks. Almost every hotel will have a local map that shows all of the historic spots around town. Head back into town from Fort Zachary State Park and bike past two historic landmarks including the Truman Little White House and the Hemingway House. The Truman Little White House is set on beautiful grounds and part of the museum has free entry, which is the perfect place to get a blast of AC and respite from the heat. Additional spots to see are the Southern Most Point (a great photo op!), Duval Street, and Mallory Square (the go-to sunset viewing spot).

Cool off at the Splash Park

Felton Road Sigsbee Park Key West, FL 33040
During one of our biking adventures after checking out the Truman Little White House, we stumbled upon the Waterfront Park that was tucked away. The ginormous splash pad/ water park was a welcome oasis! Though it was designed for kids, my boyfriend and I gleefully joined in on running through the spouts of water. If I haven’t mentioned it enough, Key West in August is just pure sticky sweat. We experienced pure bliss from this child-like water entertainment. We even agreed that this was one of our favorite memories from the trip because we felt like we were 10 years old again with no cares or worries!

Enjoy a Sunset Sail

205 Elizabeth Street I, Key West, FL 33040
Sunsets in Key West are absolutely spectacular. They can be viewed from the marina, or even better yet, from an all-you-can-drink sunset boat cruise. We did both during our trip, and the sunset sail on the catamaran came out on top. We used the boating company Sebago, which we happened to see out on the water during the evening we viewed the sunset from the marina. The crew was spectacular and welcoming, and we felt taken care of during the entire 90-minute cruise. Beer, wine, margaritas, and sangria were included in the ticket price as well. Watching the sunset encompassed by a warm breeze with my sweetie was one of the more romantic times during the weekend. And even if you’re traveling with girlfriends or family, this sunset cruise will be a hit to close out your 24 hours in Key West. The boat was full of families, friends, and loved ones celebrating birthdays and spending time together.

DINNER

Frita’s Cuban Burger

601 Howard England Way, Key West, FL 33040
Biking, beaching, and exploring around Key West will sure to leave you famished and a  hearty, local, authentic Cuban meal can be found at Frita’s Cuban Burgers. My boyfriend and I ordered a smorgasbord after our bike ride excursion including the traditional Cuban sandwich and frita burger (what they’re famous for!) for the main course. Fresh sides of tostones with mojo and sweet plantains with guava dip rounded out this insanely delicious meal. We sat on their small outdoor porch right next to the outdoor grill and got to watch the cook make our food which made the experience even better! We were blown away by the superb food and absolutely loved the Cuban hospitality.

Dessert at Mattheessen’s

419 Duval St., Key West, FL 33040

24 hours in Key West wouldn’t be complete without indulging in the city’s famous dessert and popular rambunctious street. Duval Street is a quick bike ride or walk from the marina. Mattheessen’s, a local ice cream and fudge shop located in the middle of Duval Street, sells chocolate-dipped frozen key lime pies on a stick. Get this! To be honest, at first bite, we weren’t sure if we were sold. This is the kind of dessert that the more you eat it, you like it. The dark chocolate nicely offsets the tart creamy frozen lime pie, and the graham cracker crust added a nice crunch. I’ve mentioned all of the friendly restaurant employees in this guide and Matthiessen’s was no exception. The warm, smiley man behind the counter even gave us complimentary fudge. We really loved the hospitality that Key West offered.

LODGING

Key West Lodging

In full transparency, we stayed at the Fly Navy hotel right by downtown since my boyfriend had accommodations setup for work. Not the fanciest of lodging, but it was free! If I were to secure lodging on my own, I would recommend checking out AirBnb before making hotel accommodations, which is a more budget-friendly option. Also checkout the HoteTonight app, which sells unsold rooms for up to a 50% discount.

LOCALS ONLY

Bourbon Bar

801 Burboun Bar: 801 Duval St, Key West, FL 33040

Key West is also known for their epic gay bars and drag shows. My boyfriend and I went to a show at 801 Burboun Bar and it was A. BLAST. This was our first drag show, so we weren’t sure quite what to expect. Upon entering the bar and paying for the show’s admission, the cashier in drag gave me a wink and told me how hot my boyfriend was…with this sign, I knew we were in for a good time! The show featured four drag queens with their own song sets, and boy was it raunchy and entertaining. My boyfriend and I were dealing out cash, clapping our hands and dancing, and fully embracing the wild, fun, crazy show.

BUDGET

BASICS BUDGET: ~$375 FOR TWO

As you can see by my 24-hour all-out Key West adventure, we really treated this trip as an indulgent vacation. Key West can totally be visited on a budget, but that wasn’t our case. The activities listed in this guide for two people, including $120 estimated lodging cost, is $375.
Have you tried any of these spots? Do you have any must-visit places we should know about in Key West, Florida?
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Content compliments of Elise Telford. Image by Keith Luke on Unsplash. Edited by Stranded on Land.
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Elise Telford

Author: Elise Telford

Nourished by connection, doing the unexpected, and committed to overcoming self-doubt to live like never before. Lover of the mountains, good coffee, and conversations with strangers.