Your Family-Friendly Guide to Key West in 2026

Key West is full of experiences that make family vacations unforgettable. Staying at Parrot Key Hotel & Villas puts you near the island’s most memorable events and attractions, making it easy to plan a schedule packed with fun. From music festivals to local markets and petting zoos, there are activities that appeal to every age. Here’s a guide to some of the best things to do in Key West for 2026.

Jam Out at Mile 0 Fest

Truman Waterfront Amphitheater, Key West / January 27 - January 31, 2026

Families can enjoy five days of Red Dirt and Americana music at Mile 0 Fest, set against the island’s sun-soaked outdoor venues. 

• A Welcoming Vibe: The festival blends lively performances with a laid-back atmosphere, giving everyone space to dance, sing, or just relax on the grass. 
• Plenty to Eat: Food vendors and local shops add to the experience, so you can enjoy snacks and shop for unique items between sets. 
• Finding New Artists Together: Kids and adults alike can discover new artists, soak in the island vibes,  and enjoy moments that bring the whole family together.

Get a Taste of Florida Keys Seafood Festival

Truman Waterfront Park, Key West | February 14-15, 2026

Seafood lovers will find plenty of activities to enjoy at the Florida Keys Seafood Festival. Attendees can experience it all, from trying fresh, local dishes and dancing along to live performances to discovering interactive activities for kids. 

• An Air of Excitement: Celebrating its 20th year, the festival is alive with tradition and energy. Walking through the festival feels like stepping into a celebration of island culture, with the smell of fried fish baskets igniting your appetite, drinks flowing, and vibrant merchandise for sale. 
• Family-Friendly Atmosphere: Families can sample a variety of dishes, enjoy performances, and take part in hands-on activities designed for younger visitors, like the Children’s Eco Discovery Zone. 
• Opportunities to Learn: The festival also showcases Key West’s sustainable fishing practices, adding an educational element to the festival. Several of the conservatory organizations on-site offer access to marine life exhibits along with key info about how to enjoy seafood responsibly.

Enjoy Local Produce at Truman Waterfront Farmers Market

Truman Waterfront Market, Key West | Every Thursday

Shopping at the Truman Waterfront Farmers Market is a colorful, engaging outing for families, letting kids learn what’s in season while connecting with members of the local community. 

• Something for Everyone: Fresh produce, ready-to-eat meals, and artisan goods line the stalls, giving visitors plenty to explore. Kids can enjoy tasting local snacks while adults browse crafts and meet local vendors.
• Idyllic Vistas: The market’s waterfront location provides scenic views, making a stroll between stalls relaxing and enjoyable. It’s a place to connect with the community, discover new foods, and pick up one-of-a-kind souvenirs.

See Ben Harrison Live in Concert

Key West Theater, Key West | January 8 & 21, February 5 & 17, March 5 & 25, 2026

Ben Harrison’s concerts at the Key West Theater bring humor, personality, and original music together in a small, intimate setting. 

• A Peek Into Island Life: Audiences experience the island’s character through his witty anecdotes and songs inspired by local life. Older children and teens will enjoy the playful energy, while adults can appreciate the clever humor and rich storytelling. 
• Enjoy a Unique Point of View: Each performance feels personal, drawing the audience into the experience. It’s an opportunity to enjoy music and entertainment that is quintessentially Key West.

Explore Animal Lovers’ Paradise at the Animal Farm

Stock Island, Key West | Second and Fourth Sundays of each month, 2026

Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara. 

• A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational. 
• For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.

Enjoy Local Art at The Art Walk

White Street, Key West | Third Thursday of each month, 2026

The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene. 

• A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers. 
• Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs. 

Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.

Cast a Line at the Key West Sailfish Tournament

Kick Off at Dante’s Key West Pool Bar and Restaurant | March 26 – 28

Set out on Key West’s sparkling blue waters, home to some of the best sports fishing in the world, and compete to reel in the biggest catch.

• Fish Alongside the Best: If you’re a fishing aficionado, this is your opportunity to compete in the most prestigious sailfish series in the country.
• Head to the Docktail Party: On Saturday, enjoy complimentary cocktails on Dock Harbor Dock, sponsored by Deep Eddy Vodka.
• Celebrate the Wins: The Awards Ceremony will take place where it all began at Dante’s Pool Bar and Restaurant, featuring dinner and drinks from Deep Eddy and Caymus Wines. You’ll catch the after party and raffle at Tattoo's and Scars Saloon.

Celebrate Key West’s Independence at Conch Republic

Various Locations | April 17 – 26

This 10-day party embodies the island’s weird and wonderful history with a lineup of unique events.

• Meet the Local Legends: Learn the real stories behind Captain Tony, Mel Fisher and Captain Finbar, three of the saltiest characters who once called Key West home, on this riveting walking tour.
• Compete via Conch: Why not give conch blowing a shot? Join the conch blowing contest, followed by dancing under the stars.
• See the Action at The Sea Battle: Long live the Conch Republic! This battle commemorates the 44th anniversary of Key West “seceding” from the US, so you can see how it all began during this reenactment. 
• Catch the World’s Longest Parade on Duval: Stretching from the Atlantic Ocean to the Gulf of Mexico, this world-famous, quirky, parade celebrates Conch Republic Independence. Pick your favorite float as they move through the excitement.

Pick Up the Pace at the Cow Key Bridge Run

Cow Key Channel Bridge | April 19

Lace up your running shoes for this “0k” run across Cow Key Bridge. 

• Show Off Your Costume at the Pre-Part y: Dress up in your wackiest race gear, and get your costume judged in the pasture before the “big race.”
• Moooove It: Start your day with a good old-fashioned mooing contest to get you in the moooood for the rest of the events.
• The Main Event: Head to the bridge for the “run.” Breaking a sweat is optional. There will be heats for fastest, slowest, bass-ackwards, relay, people & pets, stampede to Stock Island, and bibless walk of shame!

Listen to Rising Stars at the Key West Songwriters Festival

Multiple Venues | April 23 – May 3

Long known as a country music career starter, this festival gives music lovers the chance to get to know some of the industry's rising talent.

• Discover Budding Artists: The festival has been instrumental in the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris.
• Hop from Show to Show: With over 50 shows at various venues, it’s the perfect excuse to venture off Duval and discover  lesser-known gems in Key West.

Taste the Island’s Best at Mango Fest

June 2026, Exact Dates and Location TBD

Key West is bursting at the seams with mangoes this time of year, and this festival is an homage to the wonderful, tropical fruit.

• Support a Good Cause: This event is typically organized alongside the Key West Police Athletic League (PAL), a youth-focused nonprofit that raises funds through festival activities.
• Experience All Things Mango: You’ll find a mango-themed vendor village, fruit tastings, cooking demos, and more, so get ready to celebrate everything you love about mangoes.

Key West has something for every family, from music festivals and seafood celebrations to markets, art, and animal encounters. Staying at Parrot Key Hotel & Villas makes it easy to access these experiences while enjoying the beauty of the island. And with our One More Night in Paradise offer, you can extend the fun by booking a three-night stay and enjoying the third night on us (Available on Suites and Villas for stays through July 31, 2026). It’s the perfect excuse to linger a little longer by the pool, savor tropical-inspired dining, try watersports, and soak up even more island adventure. Whether your family loves live music, local flavors, or creative arts, Key West offers endless opportunities to create lasting memories together.