9 Fun Activities In Key West In May - Join The May Madness

Key West In May - Beach Party

Welcome to Key West, the vibrant tropical paradise just 90 miles from Cuba! This world-famous island, only two miles wide and four miles long, boasts year-round warm temperatures that make it a perfect getaway. Most of the year the weather is stable, warm, and humid, except for hurricane season when there is a chance of heavy showers or a tropical storm.

With a plethora of attractions and activities for all ages, families, singles, and couples will find a variety of things to do in Key West in May regardless of their budget. As with all islands, you can soak up the sun on beautiful beaches, and experience swimming, snorkeling, water sports, and boat tours including sunset cruises. You will adore Key West with its historic sites and culture that go hand-in-hand with the theaters, bars, and many festivals that take place throughout the year.

Visiting Key West in May is a fantastic choice, especially if you want to avoid the crowds that come during the high season in winter. With so many things to see and do, a full-day trip won’t be enough to fully appreciate the beauty and charm of this island’s many attractions. Discover the beautiful Florida Keys by joining May Madness with these 9 cool activities in Key West.


1) Take A Boat Trip And Visit The Sandbars In Key West

Get ready for an unforgettable adventure with Key West Sandbar Tours! We offer private charters for both small and large groups, and our fleet of small-group boats is simply the best in the region. With our affordable rates and a choice of four outstanding tours, you’ll be creating memories that will leave you with stories to tell for years to come!

Our boat tours are truly unique, with options for small groups of up to six people and large groups of up to 12. Whether you’re traveling solo, as a couple, or with a group of friends, people from all over the contiguous United States come to relax and have a blast exploring the sandbars.

So mark your calendar, pack your sunscreen, and get ready to create memories that will last a lifetime in Key West this May! Gather your family and friends and reach out to Key West Sandbar Tours today. We guarantee that you’ll have the time of your life!

Visit The Sandbars In Key West


2) Sing And Dance At The Key West Songwriters Festival

Calling all country music lovers! Don’t miss the world’s biggest festival of its kind in Key West. Locals and visitors alike can’t get enough of this epic celebration!

  • Music will resound from numerous spots around the island including bars, beaches, boats, resorts, and even theaters

  • For 5 days and nights, you will have the opportunity to see and hear some of country music’s career starters as well as elite performers, all at no cost. Yes, most of the shows are free!

  • Many of today’s well-known country artists started their careers here at the Key West Songwriters Festival

So come along and be a part of the throng of music lovers here in Key West. Don’t miss out on the epic fun and unforgettable vibes!

Songwriters Festival


3) Embark On A Key West Bar Crawl Adventure!

Unleash your inner party animal and get ready for an unforgettable night out in Key West! Get ready for a thrilling bar crawl tour that will take you to the hottest spots in town. Discover hidden gems, sip on iconic drinks, and dance the night away.

As you hop from one bar to another, you’ll be amazed by the vibrant atmosphere and the variety of drinks on offer. From tropical cocktails to craft beers, there’s something to satisfy every taste bud. But the fun doesn’t stop there! A bar crawl adventure is full of surprises that will keep you on your toes. You never know what exciting twist or unexpected treat awaits you at each stop.

So gather your friends, put on your dancing shoes, and get ready to make memories that will last a lifetime. Let the good times roll!

key west in may - Bar


4) Celebrate Cinco De Mayo In Key West

Get ready for a fiesta like no other as Key West comes alive with vibrant colors, delicious flavors, and infectious energy to celebrate Cinco de Mayo! This festive holiday is the perfect excuse to indulge in all things Mexican, from mouthwatering tacos and refreshing margaritas to lively music and traditional dances.

Join the locals and visitors alike as they take to the streets, adorned in sombreros and colorful attire, ready to party the day away. From lively parades to street performances, the atmosphere is electric with excitement and joy.

Don’t miss out on the incredible food and drink specials offered by the local restaurants and bars, where you can savor authentic Mexican cuisine and sip on refreshing margaritas. Dance to the rhythm of live music, try your hand at salsa dancing and immerse yourself in the rich culture and traditions of Mexico.

Head to Key West to celebrate Cinco de Mayo in style. It’s a celebration you won’t want to miss!

Celebrate Cinco De Mayo In Key West


5) All Aboard The Conch Tour Train In Key West!

If you visit Key West in May, don’t miss to hop on board the iconic Conch Tour Train and get ready for a fun-filled adventure through the charming streets of Old Town Key West! This delightful train tour is the perfect way to explore the island’s rich history, vibrant culture, and stunning sights.

As you chug along, a friendly conductor will regale you with fascinating stories and interesting facts about Key West’s past and present. Sit back, relax, and enjoy the scenic views as you pass by colorful architecture, lush gardens, and picturesque waterfronts.

You’ll learn about famous landmarks, legendary figures, and the unique heritage that makes Key West so special. Don’t forget to wave to the locals as you make your way through the streets – they love seeing the train pass by!

The Conch Tour Train In Key West includes the following three stops:

  • First Stop – Truval Village for great shopping and close to the Hemingway House and Museum, Key West Butterfly and Nature Conservatory, the Key West Lighthouse, and the Southernmost Point Buoy.

  • Second Stop – Station Depot, located at the lively corner of Front St. and Duval St. Get ready for a 10-minute pit stop to recharge and indulge in some tasty treats.

  • Third Stop – At Sails and Tails Museum you have the option to hop off and explore the sights of the Historic Key West Seaport.

Whether you’re a history buff, a curious traveler, or simply looking for a fun and relaxing way to explore Key West, the Conch Tour Train is a must-do experience!

Hop On Board The IconicKey West Conch Tour Train


6) Sunsets & Surprises – Mallory Square Is Where The Fun Begins!

Located on Key West’s waterfront with an amazing selection of shops, galleries, bars, and restaurants, Mallory Square features street performers and a daily Sunset Celebration. Daytime and nighttime, live music is the norm in most of the bars so grab a seat and sway to the beat. There’s no shortage of fun things to do here:

  • Great shopping at the Sponge Market and Shell Warehouse

  • Traditional and specialty dining; try a conch fitter or an Island juice cocktail

  • Pay a visit to the open-air Key West Historic Memorial Sculpture Garden with 36 bronze busts of the men and women who have influenced Key West

  • Chill out and spend some time in Mallory Square people-watching or savoring Key Lime Pie

Get ready for a fun day! Grab your sunglasses, bring your friends, and head to Mallory Square – the ultimate hotspot in Key West that you absolutely have to experience!

Fun Sunset Experience At Mallory Square


7) Smathers Beach – Where Fun Meets Sun

Looking for the perfect spot to soak up the sun and dive into crystal-clear waters? This vibrant and lively beach is a paradise for water enthusiasts. Smathers Beach offers a wide selection of Key West outdoor activities and amenities that include:

  • Restroom and shower facilities

  • Jet ski rentals

  • Beach volleyball courts

  • Convenient food cart vendors

  • Calm waters for swimming and snorkeling

Grab your beach towel, slather on some sunscreen, and get ready for a day of fun in the sun. Don’t forget to bring your beach games, frisbees, and a picnic to make the most of your time at Smathers Beach. Embrace the tropical vibes, and create unforgettable memories at this slice of paradise in Key West.

Smathers Beach


8) Duval Street – Where The Party Never Ends

Known as “The Longest Street in the World,” it spans the length of the island from the crystal-clear waters of the Gulf of Mexico to the Atlantic Ocean. Walk its famous 1.25-mile street brimming with diverse shopping, art galleries, and a wonderful selection of eclectic cuisine. Branded as “Party Land,” there are more than 100 bars in 15 blocks. Visiting Duval Street is one of the most popular things to do in Key West in May:

  • Indulge yourself in the fabulous shops ranging from designer clothes to handmade jewelry and authentic Key West souvenirs

  • Experience A-1 entertainment at the world-renowned Hard Rock Café while rock ‘n’ roll aficionados take their time to wander through the memorabilia displayed

  • Great rum tasting at The Rum Bar situated on the first floor of the Speakeasy Inn

Duval Street - Where The Party Never Ends


9) Unlock The Fun At Key West’s Historic Seaport

This vibrant and lively destination is a playground for excitement and entertainment, offering a wide array of activities for visitors of all ages. Step into a world of maritime history as you explore the charming streets lined with colorful buildings and bustling shops. From quaint boutiques to delicious seafood restaurants, there’s something for everyone to enjoy.

For the thrill-seekers, hop aboard a thrilling boat tour and set sail on the sparkling waters surrounding Key West. Dive into the depths of the ocean with a snorkeling or diving excursion, or try your hand at fishing and reel in the big catch of the day.

If relaxation is more your style, find a cozy spot by the waterfront and soak up the sun while sipping on a refreshing drink. Watch as the boats come and go, and feel the cool ocean breeze on your face.

No visit to Key West’s Historic Seaport is complete without indulging in the mouthwatering seafood delicacies. From fresh oysters to succulent lobster, satisfy your cravings and treat your taste buds to a culinary adventure.

Visit To Key West's Historic Seaport


Dive Into Adventure On A Sandbar Hopping Tour

Ready to make a splash and experience the best of Key West? Join us for an unforgettable boat tour that will take you to the other side of paradise! Our qualified captains are here to make your trip the highlight of your vacation.

Get ready to explore a different and enchanting side of Key West that you won’t find on other tours. From hidden sandbars to pristine snorkeling spots, we’ll show you the secret gems that will leave you in awe.

Whether you’re into water sports, snorkeling, or simply relaxing on the boat with a cold drink in hand, our tours have something for everyone. Don’t miss out on the fun! Book your boat tour today in paradise!

3 to 4 hours
Group Size
Up to 12

Sandbar Tour For Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

3 to 4 hours
Group Size
Up to 6

Hopping Sandbars In Key West

What a perfect day to take a boat ride! You will see not one but several different sandbars on this tour! It will only take 25 minutes to get there on our epic adventure, and we can stop as long as you want at those sandbars that interest you the most. This is something you cannot miss!

Experience the mangrove trails of Mud Keys and hang out with locals at Snipe Point after. You won't want the day to end.

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2 hours
Group Size
Up to 6

Key West Sunset Cruise

Ocean, meet our captain! One of the best things about the backcountry waters is how it’s never too crowded. So jump in and enjoy the peacefulness and remoteness as you stand in the "middle of the ocean" with nothing but water around you. Optionally, bring some champagne to enjoy with the sunset as a backdrop. Then, just sit back and relax as you cruise on out into the middle of nowhere, leaving behind any stress or worries.

2 hours
Group Size
Up to 6

Mud Key Mangrove Safari

It's time for some adventure and excitement with a boat trip through the backcountry. After only a short ride, we'll take you on a leisurely cruise down to Mud Key Sanctuary, where you can enjoy the countryside and take in all the wonders of nature that surround you. Stop by the sandbar for a refreshing dip or just stroll around and soak up the sun. Capture your memories and cherish them forever.