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October 23rd
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2019 Key West Events

Vacation Homes of Key West brings you an updated calendar of Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.


January 2019

59th Annual Key West House & Garden Tours

Jan 18 to Jan 19

Tour elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements each. January tours are offered 3 to 7 pm each day. Transportation between homes is available via Conch Train for $40 each, seating is limited. Tickets without transportation are $30 in advance and $35 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.


February 2019

Cuda Bowl

Feb 1 to Feb 2

Shallow water flats anglers and guides are invited to hook-up and fight their barracuda rivals. Event is to be headquartered at Hurricane Hole Marina, Stock Island. Prizes and trophies are to be awarded for top angler and guide in light tackle spin and fly divisions.

59th Annual Key West House & Garden Tour

Feb 15 to Feb 16

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and interior design that complements each. February and March tours are offered 10 am to 4 pm each day. Transportation between homes is not provided. Tickets are $30 in advance and $35 on tour days. Proceeds benefit the foundation's Oldest House Museum, grant and scholarship programs.

Key West Cemetery Stroll

Feb 23 to Feb 24

Learn about Key West’s vast history through volunteer guides as they visit numerous graves and monuments within the Key West cemetery. Tours will be conducted at 9:30 am and 12 noon. Cost is $20 per person. Advanced reservations required. Call for more information.

54th Annual Old Island Days Art Festival

Feb 23 to Feb 24

Open-air art show and market featuring oil paintings, watercolors, sculpture, photography and other works. 10 am – 5 pm on Whitehead Street & Caroline Street, Key West.


March 2019

57th Annual Conch Shell Blowing Contest

Mar 2

An island tradition for over 50 years, this unique contest celebrates the historic importance of conch in the Keys and features contestants in several age categories attempting to make "music" with fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Registration begins at 10 a.m., contest starts at noon.

The Smallest Parade in the Universe

Mar 2

Now in its fourth year, this event has Key West’s creative community exhibiting its artistic and satirical talents. Tiny parade floats, all must be under 18 inches long, ride down a mini Duval Street set in a hysterical exhibit of whimsy and humor. Cash prizes, including $1000 for 1st place. This event marks a continued locals’ movement to make Fantasy Fest more about creativity rather than raunch, and we welcome the effort. This event sells out early, and costs $25 to enter. 6pm at Key West Theater, 512 Eaton Street. For more information, visit

19th Annual Open Air Art & Music Affair

Mar 2

Arts and craft vendors display their creations at one of Key West’s favorite watering holes. Live music from local performers. Schooner Wharf Bar, Lazy Way Lane (end of William Street) 10am – midnight.

10,000 Maniacs in Concert

Mar 7

Billboard-topping rock group from the 80’s plays at the intimate Key West Theatre. Although Natalie Merchant has moved as lead singer, this talented act is sure to have you tapping your toes to the numerous big hits they produced. 8pm show, 512 Eaton Street. For more information, call 305-985-0433. Tickets cost $59.50 – $79.50

59th Annual Key West House & Garden Tour

Mar 15 to Mar 16

Visit five Key West homes and tropical gardens. 10am – 4pm. Tickets are $30 in advance, $35 day of the tour.

Saint Patrick’s Day

Mar 17

Key West loves a reason to celebrate and St. Patricks Day is one of our favorite holidays. There are events happening all over town including a pub crawl complete with green beer!

NAS Key West 2019 Southernmost Air Spectacular

Mar 30 to Mar 31

The U.S. Navy Flight Demonstration Squadron the Blue Angels will be taking to the skies at Naval Air Station Key West. The 2019 theme is "Women in Aviation" with a focus on the "Future of Flight." Organizers expect highlights to include civilian performers like an all-female parachute jump team, the Misty Blues, Patty Wagstaff flying an Extra 330SC, Ashley Shelton, Wing Walker and the world famous Shockwave Jet Truck.

Naval Air Station Key West Southernmost Air Spectacular 2019

Mar 30 to Mar 31

The Blue Angels air squadron will be performing their amazing acts of flight synchronicity. Air show will also feature parachute teams and other aeronautical performers. Boca Chica Naval Air Field, mile marker 7. Gates open at 9am. Blue Angels perform at 2:30pm. Free To Attend


April 2019

Beach Boys in Concert

Apr 4

The world-famous California band performs outdoors on the Sunset Green Lawn, 3820 N Roosevelt Blvd, 6:00pm (show starts at 7:30pm). $99, general admission.

The Revivalists in Concert

Apr 6

Popular major band performs at the new Key West Amphitheater, overlooking the Key West harbor. Doors open at 5pm, showtime is 6:30 at 21 Quay Road (Truman Waterfront Park, end of Southard Street). Tickets cost $45-75 + tax & service fee.

38th Annual 7-Mile Bridge Run

Apr 6

The longest bridge in the Florida Keys, and an engineering marvel, is home to one of the most anticipated and contested running races. Each year, approximately 1500 runners traverse the bridge while surrounded by stunning ocean scenery. Registration is online only in early February 2019. Only 1500 entries are allowed and this event quickly sells out.

6th Annual Cow Key Channel Run

Apr 7

This 300-foot mock marathon over the tiny Cow Key Bridge features hilarious costumed runners, walkers, relay teams, and even pets. Prizes awarded for fastest, slowest, best costumed, best theatrical performance, and many more. This year’s theme is “Pirates of the Cowibbean.” FREE to participate. Check-in at 10-11:30am at Stock Island side of Cow Key Channel. Registration costs $10 for bib only, or $35 with bib, shirt, and koozie. Race begins at noon.

24th Annual Taste of Key West

Apr 15

For the benefit of AIDS Help, more than fifty Key West restaurants offer delicious tapas-sized portions at Mallory Square – each taste costing between $3 – $8. Always well attended, this lively event will have you bouncing from cuisine to cuisine, all the while enjoying the generous selection of fine wines available in a collectible wine glass. 6pm – 9pm, Mallory Square (400 Wall Street, Key West). Admission to the event is FREE. Food tickets sold in $1 increments.

37th Annual Conch Republic Independence Celebration

Apr 19 to Apr 28

A celebration of Key West’s brief secession from the United States. Event highlights include bed races on Duval Street, conch shell blowing contest, arts & crafts show, Duval Street Parade, and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale Cuban bread at Coast Guard vessels and each other in a mock secession. Kick-off party at the Schooner Wharf bar on Friday, April 19th, 7pm.


May 2019

4th Annual Papio Kinetic Sculpture Parade

May 3 to May 5

In recognition of Florida Keys artist Stanley Papio, known for his re-purposing of found objects into whimsical sculpture, this event showcases Key West’s creativity and whimsy with a parade of human-powered artworks. Competition categories include art bikes and kinetic sculptures. The parade begins Saturday, May 4 at noon in front of Customs House at 281 Front Street.

24th Annual Key West Song Writers Festival

May 8 to May 12

Features more than two-hundred top songwriters performing at a variety of venues in Key West, including a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and a free concert on Duval Street.

12th Annual Keys 100 Ultra

May 18 to May 19

100 and 50-mile ultramarathons starting near Key Largo and in Marathon FL, finishing in Key West. Cost: $150 to $275 for individuals (depending on race length and time of registration), and $720 to $840 for teams (depending on race length and time of registration). Be aware of traffic if driving through the Florida Keys during the race.


June 2019

43rd Annual Swim Around Key West

Jun 1

Presented by the Key West Athletic Association, this 12.5 mile swim around the island of Key West must be completed in 8 hours and typically has 200 participants, including solo and team swimmers. Cost for registration by March 15 is $165 for a solo swimmer, $300 for two-person relay, and $420 for the three-person relay. Deadline to register is May 18.


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