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.
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!
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
601 Howard England Way, Key West, FL 33040
Felton Road Sigsbee Park Key West, FL 33040
Enjoy a Sunset Sail
205 Elizabeth Street I, Key West, FL 33040
601 Howard England Way, Key West, FL 33040
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.
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.
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.