2016 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 2016

Florida Keys Paddle Challenge 2016

Jan 15 to Jan 22

Enjoy a true island paradise, paddling beside sea turtles and railroad visionary Henry Flagler's 'Eighth Wonder of the World' in the azure waters of the Florida Keys. You'll journey 77 miles beside white sand beaches and mangrove islands, from Long Key State Park to Key West. Register by: January 1, 2016

Key West Outdoor Movies

Jan 15 to May 20

Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events.

Historic House and Garden Tours

Jan 15 to Jan 16

A unique opportunity to see incredible interiors, creative renovations, and beautiful gardens of a select few Key West homes. Transportation between the homes is provided on the Conch Tour Train. Winding though Key West neighborhoods on the train is part of the fun!Tickets

Florida Keys Seafood Festival

Jan 16 to Jan 17

The 11th Annual Florida Keys Seafood Festival is tentatively set for Saturday, January 16 and Sunday, January 17, 2016, at Bayview Park, at the corner of Truman Avenue

Quantum Key West - Key West International Yacht Race Week

Jan 17 to Jan 22

This exciting challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. More than 100 racing yachts compete for class championships in this international regatta. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West's Atlantic-front restaurants, resorts and beaches.

The Key West Food and Wine Festival

Jan 27 to Jan 31

From Last Year's Event - "Welcome to the 2015 Key West Food and Wine Festival showcasing our tropical paradise’s distinctive restaurants, fresh seafood, funky atmosphere, stunning sunsets and gorgeous weather. Our world-class restaurant, arts and lodging community is an integral part of our island and the well-being of our economy. We are proud to pay tribute to our culinary community while promoting their vast talent, unique island fusion food style and fine wines"


February 2016

Cuda Bowl

Feb 4 to Feb 6

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.

Civil War Heritage Days

Feb 5 to Feb 8

An unforgettable three day event staged at Fort Zachary Taylor State Park that portrays the time period of 1861 - 1862 at a Federal military fortress. Period correct artillery demonstrations and soldier camp life are portrayed by actors in Union and Confederate constumes. This event includes a parade up Duval St., a sea battle, a military trial, and more. For more information, contact Park Services at 305-292-6850.

Red Barn Theatre Presents: Buyer and Cellar

Feb 8 to Mar 12

'Barbara Streisand' hires an out-of-work actor to be the clerk in the basement arcade of her Malibu estate, where she is the only buyer. The Red Barn Theatre has been presenting professional theater in Key West for 36 years, at 319 Duval St. (rear), Key West. Treat yourself to this smash hit comedy from New York, written by Jonathan Tolins. Buy tickets now on-line http://www.redbarntheatre.com/tickets/ or call 305-296-9911

House and Garden Tours

Feb 12 to Feb 13

Tour a series of elegant and unique private homes of Key West, ranging from exquisite restorations to creative renovations, and the interior design that complements their architecture and adds a unique Key West flavor. Transportation between homes on the famous Conch Train is provided by Historic Tours of America. Tickets

Key West Theater presents: Locura, A World Premiere

Feb 17 to Mar 18

"Locura" is a Spanish word that translates to “insanity” or “madness.” Local playwright Michael Marrero captures some of the craziness of Key West in the early 1980’s. Based on some of Marrero’s youth with his father in Key West, the play portrays an uncle and his nephew as they make their way through rooster fights, Monkey Island, Big Pine, shrimpers, and the open ocean. Presented in the recently renovated Key West Theater, at 512 Eaton St., Key West. Visit their website- http://www.thekeywesttheater.com/ (305)985-0433

Fringe Theater of Key West presents: The Lion in Winter

Feb 18 to Mar 5

Celebrating their fifth year, the local Fringe Theater of Key West presents James Goldman's 'The Lion in Winter.' Staged at St. Paul's Church Sanctuary, at 401 Duval St., Key West, this beautiful room is an ideal setting for this play set in 1811, where King Henry II summons his treacherous crown-seeking sons to choose a successor. And the rest is history ... For more information - email: info@fringtheater.org Call (305)707-4053

Key West Theater presents: Winter Concert Series

Feb 20

Featured performer is Robert Randolph and the Family Band, his accompanists, with Caffeine Carl. Randolph calls his "thing" really upbeat, uptempo, with great guitar riffs. Key West Theater located at 512 Eaton Street. Tickets available online.

The Red Barn Theatre presents: Conchs, Cowboys and Tales of Old Key West

Feb 22 to Mar 7

The Red Barn Theatre presents: Conchs, Cowboys and Tales of Old Key West – A rousing musical by the Red Bar’s most popular local musical group featuring some of Key West favorites – John Wells, Gary McDonald, Paul Cotton, Tom Murtha, George Halloran, plus special guests. (305)296-9911


March 2016

Happy Birthday Tennessee Williams!

Mar 1 to Mar 31

Key West will celebrate Tennessee Williams 105th birthday and his life in Key West, during the entire month of March, 2016. Different venues around the island will feature a variety of events including a series of classic movies adapted from William’s award winning plays, staged readings from his plays, letters and journals, a poetry contest, to name a few. Stop in to tour the educational and historic exhibit about Tennessee Williams at 513 Truman Avenue, and purchase event tickets. Find more information at www.twkw.org Call: (305)842-1666

Waterfront Playhouse presents: The Producers

Mar 1 to Mar 26

Winner of 12 Tony Awards, including best musical, the cast of the Waterfront Playhouse presents promises to thrill all with their performance. Based on Mel Brooks' hilarious classic film, you can count on an evening of laughing out-loud comedy and "16'wickedly witty songs and gloriously outrageous dance numbers." The Waterfront Playhouse was named "The Best Professional Theater in Florida," by the Florida Monthly Magazine. Buy tickets on line at: https://www.waterfrontplayhouse.org/tickets/ Call: (305)294-5015

Historian Tom Hambright presents: Key West's Buffalo Soldiers and The Spanish American War

Mar 3

This is a perfect reason to visit Key West's Eco Discover Center at the Truman Waterfront and enjoy a free presentation by Tom Hambright, our own island historian, who will share some intriguing facts about the Spanish-American War that we are pretty sure you haven't learned yet. Call: (305)393-9777

54Th Anniversary Key West Conch Blowing Contest

Mar 5

This will be the 54th year that Key West has celebrated our heritage by competing with each other to see who can blow the conch shell the best! An Old Island Days tradition, this unique contest features novel sounds produced by contestants in several age categories as they attempt to make “music” by blowing on conch shells. Winners are chosen for the quality, duration, loudness and novelty of the sounds they make.Trophies are awarded in multiple age categories. Contestants include all level of shell blowers from novices to talented “pucker pros.” Come join in on the family fun, as the Old Island Restoration Foundation celebrates the historic importance of the the conch in our Florida Keys island life. Held at the Key West's Oldest House, 322 Duval Street, at 12:00 noon. Call: (305)294-9501

Key West House and Garden Tour - 56th Annual

Mar 11 to Mar 12

If you love Key West houses like we do, don't miss the annual Key West house tours. These tours are sponsored by the Old Island Restoration Foundation. Each tour features lovely and unique homes and gardens reflecting the varied tastes and originality of their owners. March 2016 tours are offered 10 a.m. to 4 p.m. each day. Transportation between homes NOT included. Tickets and times available online. Proceeds help benefit the Old Island Restoration Foundation. Email: tickets@oirf.org Contact: 305-294-9501

9th Annual Florida Keys SPCA Spring Social

Mar 11

Animal lovers don't miss this first-class dining event to help raise funds to benefit our animal shelter. Restaurants from all over Key West will provide their best. Delicious tables of food, and there is a VIP champagne reception prior to the event. Music, auction, silent auction, raffles, complimentary been and wine and more. Held at the Key West Golf and Country Club, there is plenty of parking across the street at the Florida Keys Community College, with front door Trolley Service thanks to HTA. Call Tiffany Burton: (305)294-4857

March Merkin Permit Tournament

Mar 14 to Mar 17

A charity flats-and-fly-only tournament with a twist - in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Harbour Yacht Club on Stock Island. Call:


April 2016

35th Annual 7 MIle Bridge Run

Apr 9

One of the most unique running races in the world. 1500 runners gather for a foot race over the 7 Mile bridge spanning across the Overseas Highway. Sponsored by the Marathon Runners Club.

Third Annual Cow Key Channel Bridge Run

Apr 10

Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? Join zany-dressed participants for the world's only Zero K across one of the shortest bridges in the Keys. The event is free to watch.

Key West Art Garden 2016

Apr 15 to Jul 31

Florida Keys artists and sculptors are featured in this open-air exhibit at the Key West Tropical Forest and Botanical Garden. Exhibit is open from 10 a.m. to 4 p.m.; an opening reception is planned April 23 from 12-3 p.m., to meet the artists, enjoy a self-guided tour of the Art Garden, light refreshments. Entrance is free.

19th Annual Earth Day 5k Run/Walk

Apr 16

Local 5k presented by the Southernmost Runners Club to celebrate Earth day! The race begins at McCoy Indigenous Park, located at Atlantic Boulevard and White Street.

Amy Helm & The Handsome Strangers at Fort East Martello

Apr 16

Singer and musician Amy Helm and her band The Handsome Strangers are to perform an outdoor evening concert at historic Fort East Martello, 3501 S. Roosevelt Blvd. They will perform from Helm's debut "Didn't It Rain." Doors open at 4:45. Guests may bring low-profile chairs or blankets for the "backyard casual" setup that will include food and libations from local vendors.

34th Annual Conch Republic Independence Celebration

Apr 22 to May 1

Celebration of Key West’s brief secession from the United States. Event highlights include drag (queen) races on Duval Street, and the infamous bloody battle in Key West harbor where Conch Republic vessels toss stale Cuban bread at Coast Guard vessels in a mock secession. Kick-off party and Conch Shell Blowing Contest at the Schooner Wharf bar at 7pm. Call (305)296-0213

Earth Day 2016 at Key West Turtle Museum

Apr 22

Join the celebration from noon to 4 p.m. The public is invited to tour the Turtle Museum and meet representatives of local organizations that are addressing the concerns and conservation of wildlife in the Florida Keys. Admission is free. The Key West Turtle Museum is located at 200 Margaret St. in Key West's Historic Seaport.

Conch Republic Brew Days

Apr 24

The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer

Key West Paddle Classic

Apr 28 to May 1

Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.


May 2016

Tarponian Fishing Tournament

May 1 to May 4

For avid anglers, springtime is all about the tarpon run. This is a fun 3 - evening tournament that requires that each team fish with a different captain every night. Teams rotate around the 3 major bridge channels in Marathon, FL, so every team gets a crack at the best spots. Contact David Breznicky. (215)542-1492

21st Annual Key West Songwriters' Festival

May 4 to May 8

The largest festival of this kind in the world! Staged in different music venus all over the Key West, "since 1997, BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs." Contact Charlie Bauer @ (305)304-0814

Papio Kinetic Sculpture Parade

May 13 to May 15

Come see human-powered funky art sculptures parade through the streets of Key West. Sponsored by the Key West Art & Historical Society, this art-inspired, family friendly, human-powered art event parades through the streets of Key West. A party and concert follows on parade night. The art machines will be on display all month at the Fort East Martello Tower Museum. For more information call (305)295-6616

Dolphin (Mahi - Mahi) Masters Invitational

May 28

Popular annual fishing challenge based in Key West's Historic Seaport. Angler who scores the highest total combined weight of 3 dolphin catches (mahi - mahi NOT the mammal),gets the top cash prize. No boat limits for participation. Other prizes too. Contact John Stuempfig (305)304-7674


June 2016

Key West Pride

Jun 8 to Jun 12

A celebration of the LGBTA community in Key West. A complete list of events and information on participating can be found on the event website. The schedule is packed full of day-time and night-time parties. The spectacular famous Key West Pride Parade on June 12 where a the largest pride flag in the world is stretched the entire length of Duval Street from the Gulf of Mexico to the Atlantic Ocean. Contact (305)294-4603

Third Annual Mystery Writers' Key West

Jun 10 to Jun 12

A writers' festival featuring acclaimed mystery writers who gather to share insights on their craft with aspiring writers. A great opportunity to meet editors and e-book publishers. For more info, email: info@mysterwriterskeywestfest.com

VFW Fishing Tournament

Jun 11

This family oriented tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee and active service member. Heaviest Dolphin is worth $2,500. All proceeds benefit disabled and/or needy veterans in Monroe County.

Key West Africana Festival

Jun 16 to Jun 19

Come and experience this unique Key West Africana Festival. This three day festival will feature Key West’s Afro-Caribbean culture and is designed as a retreat to promote our islands’ cultural tourism. This three-day destination retreat will integrate music, thought, culture, and wellness programs. Scholars and wellness experts will be featured presenters. Contact: Chris Norwood - cnorwood@keywestafricanafestival.com

Key West Island Swim: Swim Around the Island

Jun 18

Here's your chance to fulfill that fantasy of swimming around an island! This long distance race invites solo swimmers and relay teams of up to 6 people to take the plunge, with or without fins. When you're done you can say you swam through the waters of the Atlantic Ocean and the Gulf of Mexico! All ages welcome. For more info, contact Lori Bosco (305)809-3562


July 2016

Fourth Annual Key Lime Festival

Jul 2 to Jul 4

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime Martini and Margarita Sip and Stroll will kickoff the weekend-long event.

4th of July Fireworks

Jul 4

A fabulous fireworks show staged off the Key West White Street Pier. There is something especially magical about fireworks launched over the ocean. Best place to watch is near the pier at Higgs Beach, or anywhere nearby the water along the south end of the island. This annual event is sponsored by the Key West Rotary Club.

Annual Fourth of July Picnic Benefiting Hospice of the Florida Keys and Visiting Nurse Association

Jul 4

This will be the 32nd annual 4th of July family picnic on the grounds of the luxurious Casa Marina Resort and Beach Club overlooking the Atlantic Ocean. Start the afternoon at 5:00 pm, with old fashioned family fun, and indulge in all the traditional 4th of July picnic foods, like hamburgers and hot dogs, ice cream and much more. There are lawn games for the children, live music, and a silent auction. After the picnic, nestle in to watch the fireworks, of mosey over to the White Street Pier, next door, and watch from there. It's a fabulous 4th of July in Key West.

Del Brown Permit Tournament

Jul 9 to Jul 12

Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.

Hemingway Days

Jul 20 to Jul 25

The 36th annual celebration of the legendary author's work and lifestyle features literary readings, Running of the Bulls, short story competition, fishing tournament, Sloppy Joe's Look-Alike Contest and a birthday "party" commemorating Ernest's July 21st birthday.

The Papa Hemingway Look-Alike Contest 2016

Jul 21 to Jul 23

This is a highlight of the annual Hemingway Days celebrating Papa Ernest Hemingway. Sloppy Joe's Bar once again, hosts the world famous annual Hemingway look-alike contest in 2016. If you think you look like Papa, why not register and see if you can be 'Papa' for the year? The competition starts with the first preliminary round on Thursday, July 21st, second preliminary round on Friday, July 22nd, and finals on Saturday, July 23rd when the winner is announced. You can download the forms on-line. https://sloppyjoes.com/wp-content/uploads/2015/08/EntryForm2016.pdf Otherwise, come and join in on the fun when the Key West celebrates the years Ernest Hemingway live in Key West and wrote some of his most important works.

Hemingway 5K Sunset Run & Paddleboard Race

Jul 23

This is the original and oldest ongoing 5K Run in Key West and takes place as part of the the annual Hemingway Days Festival. The race course is a scenic flat course that runs past Key West's most famous landmarks including the Ernest Hemingway Home, the iconic Southernmost Point and the famous Green Parrot Bar. Visit website for more details.


August 2016

20th Annual Key West Lobsterfest

Aug 11 to Aug 14

All the staff at Vacation Homes of Key West - VHKW, look forward to this festival all year. Indulge in lobster prepared every which way you can imagine by some of the most creative local lobster lovers. This annual event celebrates the beginning of Lobster Season with a 4 day long summer party where thousands enjoy eating lobster, and drinking favorite beverages. Check out the schedule of events here: http://www.keywestlobsterfest.com/Schedule_of_Events.html

Key West Business Guild presents 'Tropical Heat'

Aug 11 to Aug 14

Annual all-male 4 - day gathering with pool and dance parties, adventures on the water, and a fund raising fashion show. Proceeds go to a local non-profit. Contact the Key West Business Guild for more information. (305)294-4603


September 2016

7th Annual Key West Brewfest

Sep 1 to Sep 5

A 5 day Key West party, that goes over the Labor Day weekend, where you can taste more than 150 micro-brews and beers. All collected proceeds are for charity. This is the 7th annual event which benefits the Key West Sunrise Rotary Club's commitment to programs in the Conch Republic. Come and eat and drink like a conch (local) with happy hours, beer dinners, late night parties, beer brunches the next day, and pool parties. Call: (800)354-4455

Phil Peterson's Key West Poker Run - 44th Annual

Sep 15 to Sep 18

For 44 years, a call has been made to all motorcycle riders around the USA to ride down the fabulous Florida Keys scenic highway to Key West. Play poker on the way down to raise money for charity. Winner takes all, AND can win a new Harley Davidson Motorcycle! This outrageous event culminates on Duval St., where thousands of bikes line the street. Motorcycle enthusiasts are all invited to Key West to take in the scene. Contact Drew Peterson: (305)235-4023


October 2016

Goombay Festival - 38th Annual

Oct 21 to Oct 22

2016 marks the 38th Annual Goombay Festival in Key West's Bahama Village. A favorite local's party, this unique party staged in our Afro-Caribbean community, Goombay Festival is a kind of 'kick-off' for Fantasy Fest. Food, music, live entertainment, people hanging out in the streets creates an authentic Caribbean vibe that will have you feeling like you are in The Bahamas. Staff at Vacation Homes of Key West - VHKW, love Goombay Festival, and always take camp chairs, find a favorite spot, and watch the town go by. Check out their Facebook Page at - Bahama Village Goombay Festival

Key West Fantasy Fest - 38th Annual

Oct 21 to Oct 30

2016 marks the 38th year of Key West Fantasy Fest! This annual adult-themed extravaganza goes for 10 days, with every night featuring some kind of contest or event. Get ready for some zany political take-offs in this 2016 election year with the theme - Political Voodoo and Ballot Box Barbarians. All week long fun loving revelers 'let down their guard.' The island really rocks with the culmination of the famous Fantasy Fest Parade that works its way up Duval St. See the official Fantasy Fest website for detailed information and announcements for the annual theme. Call: (305)296-1817

Key West Zombie Bike Ride 2016 - 7th Annual

Oct 23

What started with a few hundred riders, has now grown to over 7,000 people who get dressed up as a ZOMBIE, get on their bicycle, and meet-up at the Fort East Martello Towers, on South Roosevelt Blv, Key West. In a huge reveling crowd of zombie zaniness, everyone rides along the Blvd. in concert with the other ZOMBIES. All ages join in the fun. An ever popular and growing fun-loving October event. Vacation Homes of Key West - VHKW staff members love this family event. Presented by 'We Cycle Bike Shop' who says, 'Ride a bike and change the world!'

Halloween Half-Marathon Series

Oct 23

Dress up as your favorite Halloween costume, be it superhero, super villain, witch, goblin, vampire, werewolf, whatever strikes your fancy. Prizes are awarded for most creative, best group, scariest and funniest characters. Winner medals and awards are to given for overall male and female winners, masters (40 ) male and female winners. Register online. Race starts at 6 p.m. The race takes runners on a scenic loop around the island, along the waterfront for much of the course. Register on-line.


November 2016

Parrotheads 25th Annual Meeting of the Minds

Nov 2 to Nov 6

In the wake of Key West Fantasy Fest, the Parrotheads descend on Key West for fun and philanthropy at their annual 'Meeting of the Minds.' This year their meeting theme is 'Here We Are.' Their giving includes one of the largest blood drives in the Florida Keys. Contact Andrew Talbert, Director of Parrot Head conventions. andrew.talbert@gmail.com

35th Annual Key West World Championship Races (Key West Super Power Boat Week)

Nov 6 to Nov 13

Adrenaline flows strong when international super power boat teams from around the world descend on Key West in November. After serious racing competitions April through October, the biggest and the fastest off shore super boats gather in Key West to race through a portion of Key West harbor, where Key West World Championship racers can gain speed in excess of 140 mph. This is a high-speed event, known internationally as the Indianapolis 500 of powerboat racing. See the website for the schedule of events. Call: (305)296-6166

Key West International Sand Sculpting Competition

Nov 23 to Nov 27

This is some serious sand sculpting. Large-scale artistic creations that thrill participants and spectators . A fun event for every age. This competition features the best sand artist in world, going up against each other for the grand prize. Taking place at The Casa Marina Resort at 1500 Reynolds St., Key West. Great event for a memorable Thanksgiving weekend.


December 2016

New Year's Eve Celebration - Lowering of the Pirate Wench at the Schooner Wharf Bar

Dec 31 to Jan 1

"Rigging in the New Year." New Years Eve tradition at the Schooner Wharf Bar, 202 William St., Key, West, FL "Chief Pirate Wench and co-owner of the bar, Evalena Worthington, is lowered onto the deck of the schooner yacht America 2.0 at midnight, to the fanfare of cannon fire and the release of white doves.

New Year's Eve Giant Shoe Drop of Drag Queen Sushi at the Bourbon St. Pub

Dec 31 to Jan 1

World famous drag queen, Sushi, is lowered in a giant red high heel shoe from the top of The Bourbon St. Pub, 724 Duval St., Key West. Huge crowd cheers below as this major Key West event is broadcast live on CNN. Live entertainment all night.

New Years Eve at Sloppy Joe's Bar - 24th Annual Dropping of the Giant Conch Shell

Dec 31 to Jan 1

World Famous Dropping of 'The Conch Shell' at Sloppy Joe's Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night with confetti, streamers, and lights filling the sky. Crowds start the party in the street at about 10:00 pm and wait til count down to midnight. No Reservations. No Tickets Sold.


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