Year round, Key West boasts tranquil blue waters, fun festivals and some of the best weather in the continental United States. Experience all the island has to offer during the month of February. Whether you’re visiting from out of town or call Key West home, you’re guaranteed to find something exciting to do or see. Read on for the top things to do in Key West during February!

Tourists enjoying a day sail in Key West on a sunny day

Enjoy an Island Style Live Music Day Sail

Sail away on a state-of-the-art 65’ Catamaran and let the live island music set your mind at ease while you enjoy a delectable brunch, Key West style! This day excursion is bound to bring you pure bliss on the water as you cruise along the calm coastline in the Gulf of Mexico and enjoy the majestic scenery of blue skies along with the refreshing ocean breeze.

Mile 0 Festival in Key West, FL

Mile Zero Fest

Jan 28-Feb 1

Fanatics & first-timers alike will be overwhelmed by the star-studded Red Dirt & Americana lineup that showcase their talent during the 4 day music festival. Take in the big shows at Truman Waterfront Park Amphitheater, a brand new state-of-the-art facility located blocks off the hopping streets of Duval, or get into a stripped down acoustic set with your favorite band leader at one of the theaters or bars off Duval. Throw your hat into the ring for one of the charity golf outings or a fishing derby! These are just a few of the many activities and memorable experiences that await you at Mile 0 Fest.

Romantic Sunset Sails

Feb 14

It’s hard to imagine a more well-suited outing for you and your special someone than taking a front row seat to witness one of nature’s most dazzling displays. Our Sunset Cruise lets you enjoy Key West’s explosive sunsets like never before with complimentary food and beverage and live music to make an already perfect evening even better! Learn more about our Valentine’s Day Specials and surprise your loved one with a romantic excursion on the waters of Key West.

Wesley House Valentine’s Day Gala

Feb 14

Something you don’t often see around our laid-back island paradise: getting dressed up for a fancy night out! Valentine’s Day, however, is the exception. This signature event includes dinner, drinking, dancing, a silent auction and live entertainment. All proceeds go directly to Wesley House Family Services. Intrigued yet?

conch republic seafood company

Visit Key West’s Historic Seaport

There aren’t many things more relaxing than an early morning or evening stroll along Key West’s historic seaport. Walk along the boardwalk, and stop by Fisherman’s Cafe for some of the freshest seafood in town. FYI…their lobster enchilau tacos are to die for! Need a little extra energy? Grab a Bucci to go, and enjoy the sights and sounds of the active marina. But before you leave, stop by the Conch Republic Seafood for a great happy hour overlooking the water.

Take Part in Key West House & Garden Tours

Feb 15-16

Sponsored by the Old Island Restoration Foundation, Key West House & Garden Tours celebrate the architectural and cultural heritage of Key West. Get a behind-the-scenes look at the island’s bright, beautiful and one-of-a-kind historic homes and gardens during these unique tours. From intricate restorations to expansive art collections, visitors delight in learning about Key West’s diverse architectural influences.

Dry Tortugas

National Parks Are Free on Presidents’ Day Weekend

Feb 14-16

If you’re looking for a fun outdoor activity over Presidents’ Day weekend, take a trip to the Dry Tortugas National Park. National Parks are waiving entrance fees in honor of Presidents’ Day weekend. Located almost 70 miles west of Key West, the Dry Tortugas National Park is known for its incredible bird watching, remote camping and rich history. Explore the famous Fort Jefferson, snorkel and swim during an adventurous Presidents’ Day weekend.

Old Island Days Art Festival

Old Island Days Art Festival

Feb 22-23

Feeling crafty? The Old Island Art Days Festival is the perfect event for you! During the last weekend in February, over 100 craft artists gather at the Key West Art Center to showcase their work and the opportunity for you to shop to your heart’s desire!

Last Updated 06/10/2020