Top 12 Ways to Travel Single in Key West
Make Friends in Key West! It's easy when everyone is chill and happy! That's how Key West is!
Single? But want... need a vacation? Key West is your vacation place!
Many vacation sites flaunt romantic pictures of couples kissing on the beach or holding hands as they snorkel. There is plenty of that in Key West, but one amazing thing about this gorgeous little island is that there is a ton to do as a single person here. The vibe in Key West is so open and laid back, that there really is no place you can’t go alone and not feel comfortable.
That said, here are the Top 12 Ways to get the most out of your singles trip to Key West:
1. Bar Hop on Duval Street
Key West’s famous Duval Street is packed with legendary bars like Sloppy Joe’s, Green Parrot, and Irish Kevin’s. It’s perfect for solo travelers looking to meet new people or just enjoy great live music and tropical cocktails. Take a look at some of the favorite bars in Key West!
2. Join a Group Key West Snorkel or Sunset Cruise
Hop on a catamaran for a snorkeling tour to the reef or a sunset sail with drinks included. Companies like Fury or Sebago offer group excursions that are friendly and social—ideal for meeting other travelers. Take a look at Key West things to do!
3. Rent a Bike or Scooter and Explore Freely
There’s no better way to feel the Key West vibe than by zipping around solo. Ride through the historic district, past quirky homes, the Southernmost Point, and the Hemingway House at your own pace. Find Key West sightseeing tours!
4. Belly Up to the Bar
Key West’s famous Duval Street is packed with legendary bars like Sloppy Joe’s, Green Parrot, and Irish Kevin’s. It’s perfect for solo travelers looking to meet new people or just enjoy great live music and tropical cocktails. Whether you are there for a drink or there to have a meal, belly up to the bar and you are sure to make new friends. The bartenders are outgoing in Key West, and you will probably see other singles sitting at the bar too. After a shot or two of liquid courage, you will find yourself chatting it up with new friends as if you’ve known each other for years. Find Key West Bars!
5. Find a Stage - Sing Karaoke at a Local Bar
Unleash your inner rock star with some karaoke! Places offer fun, low-pressure karaoke nights that are popular with locals and visitors alike—great for solo travelers looking to let loose and make friends. Find a fun Key West bar here!
6. Attend a Local Event or Festival
Key West is known for its parties and parades. Check out the event calendar for happenings like Fantasy Fest, Hemingway Days, or live music nights at the Key West Amphitheater—perfect for mixing with locals and visitors alike.
7. Make it a Beach Day
Hang Out at Fort Zachary Taylor Beach. Bring a book or snorkeling gear and unwind at Key West’s best beach. You’ll find locals and tourists mingling, and it’s a peaceful yet social setting to enjoy the island’s natural beauty solo. See our beaches here!
8. Take a Guided Bar Stroll, Walking Tour or Ghost Tour
Explore the island’s colorful history and spooky folklore with a walking tour or a ghost tour after dark. These small group activities are perfect for solo travelers looking to connect with others. Bar strolls of all kinds are fun! Find Tours & Attractions here!
9. Go to the Art Galleries
There is a huge arts scene in Key West – many of the locals are artists themselves. Whether you are gallery hopping by day, or taking in a musical or a campy drag show by night, there is sure to be a throng of singles enjoying the bustling art and performance scene in Key West. To See Theater options, click here. To see Art Galleries, click here.
10. Ride the Wave and take an excursion in Key West
Don’t think for a second that water excursions like snorkeling, diving, fishing, and sunset sails are for couples only. Many snorkeling and sunset tours offer group excursions that are friendly and socially—ideal for meeting other travelers. With all the singles on this beautiful island, the water activities are catered to every type of traveler. In fact, you are bound to meet other singles on any water adventure you embark on. Find Key West Watersports here!
11. Book a Fishing Charter Adventure
You don’t need a full group to go fishing. Many charter boats offer split charters where you can join others for reef or offshore fishing adventures. It’s social, exciting, and a great way to spend time on the water. Find your Key West fishing charterboat here!
12. Watch the Sunset Celebration at Mallory Square
Every evening, locals and tourists gather at Mallory Square to celebrate the sunset with street performers, artists, food vendors, and musicians. It’s a festive, communal experience that’s ideal for solo travelers soaking up Key West’s magic. Find your Key West Sunset Celebration here!
Ready to plan your trip? Explore MORE at FloridaKeys.com and start builing your ultimate solo-travel itinerary.