9+ Things to Do in Key West in February

1. 33rd Annual Fort Taylor Civil War Heritage Days

February 1-3, 2019. This 3 day event portrays the time period of 1861-1862 at a Federal fortress. First person interpretation, weapons demonstrations and camp life are featured on a daily basis. It’s an historical re-enactment of when Fort Taylor was active during the American Civil War in the 1860s. This fortress was one of three fortresses in Florida that was held by Federal forces throughout that conflict. Learn more.

2. 34th Annual Wrecker’s Cup Race

Participate in this fun race series that recalls the tradition of the wreckers in the Key West of the 1800’s. Vessels with rich cargoes from Gulf and Caribbean ports often became victims of the unmarked reefs 7 miles off Key West. The first wrecker to reach the site had the responsibility to save the passengers and crew, but they also won the right to salvage the cargoes. Buy Wrecker’s Cup Race tickets.

3. Try a New Restaurant or Bar

Looking to try a new Key West bar or restaurant since your last visit? We’ve got your covered. What’s new in Key West.

4. Spend the Day like a Local, on the Water

How do the Key West Local’s spend their days off? On the water! Enjoy the local sandbars and remote islands, with an island charter or boat rental. Have a vacation of a lifetime!



5. Mile 0 Fest Key West

January 29th-February 2nd. Mile 0 Fest Key West is a brand-new music festival assured to be a “must see” in the burgeoning Red Dirt & Americana music scene. Take in the big shows at Truman Waterfront Park Amphitheatre, 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 theatres or bars off Duval. Learn more.

6. Historic Key West Cemetery Stroll

February 23, 2019. During the stroll, small groups of visitors will be escorted to gravesites where interpreters will tell the stories of the deceased in brief monologues. Among the gravesites to be visited are those of the Los Martires de Cuba, the Figueredo plot, the Benjamin Albury family restoration, the Otto plot, and Piedad Ayala. Learn more

7. 59th Annual Key West House & Garden Tours

February 15 – 16, 2019. Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. Proceeds benefit the foundation’s Oldest House Museum, grant and scholarship programs. Learn more

8. Watch A Burlesque Show

Key West burlesque celebrates Valentine’s Day, and love in general, with an all-star cast of characters in this 21 and over event. Crowd favorites Moana Amour, Cheeky Derrière, Chief Peach, Velvet Garcia, and Dark n Stormy will be rocking seductive performances in “Key West – We Love You!” Learn more.

9. 54th Annual Old Island Days Art Festival

February 23-24, 2019. This annual juried outdoor fine art festival features oil paintings, watercolors, sculpture, photography and other offerings by more than 100 artists from around the United States and beyond. The event takes place on lower Whitehead Street in historic Old Town. Learn more.


10. Check out a concert at the Key West Theater

Always a great place for events, checkout their calendar.


Deck Boat Rentals

Boat Rentals

Perfect for small or large groups!
Deck Boat or Pontoon Rentals

Local Day Sandbar Charters

Local Sandbar Charters

Spend the day like the locals! Sandbars, Island Hopping, Dolphins, Snorkeling, Sunsets

Sunset Cruise

Sunset Cruise

Sunset Sail or Sunset Dinner Cruise
FREE Open Bar and live music!

Book Today - 305-797-8954

Best Price. No Coupon Required.