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Key West Events Calendar

January 2012

January 5-8

  • The seminar’s 2012 topic is “Yet Another World” and will explore dystopias, utopias and created imagined worlds through a diverse program of readings, conversations, lectures, and panel discussions. The Seminar is held at the historic San Carlos Institute. Contact: 888-293-9291

January 6

  • Fight Night in the Keys - This open-air sporting challenge offers spectators the chance to view big-name boxing in a subtropical waterfront setting. The Key West boxing tradition, whose fans included legendary author Ernest Hemingway, is to be celebrated with a bout match scheduled at Mallory Square overlooking Key West Harbor. Fight Night in the Keys is to be highlighted by a 10-round battle between super middleweights Dyah Davis and Alfonso Lopez. The venue at Mallory Square is to open at 6 p.m. ET and the first bout is slated to begin at 7 p.m. Contact: David Johnson 305-292-0486.

January 6-7

  • Ragnar Relay Florida Keys – Miami to Key West - A 199 mile running event that will push you and 11 pals as far south as you can go in the continental U.S. Starting in Miami and finishing in Key West, this relay offers runners a unique opportunity to run near the oceanside and across the southern end of the state of Florida. Along the way you run across multiple bridges including the Seven Mile Bridge, hopping from Key to Key, passing through popular destinations such as Key Largo, Islamorada, Marathon Key and Big Pine Key. The race (and your stamina) will wrap up in the tropics of the southernmost city in the continental U.S., Key West. Clear your calendars for this one, this is a running race you don’t want to miss! 

January 7

  • Harry S. Truman Little White House presents: Governor Bob Graham - The Governor who saved the Little White House, Bob Graham, will be speaking for the first time on the lawn of the Little White House. The presentation, hosted by the Key West Harry S. Truman Foundation, will begin at 4 PM. Bob and Adele Graham will host a cocktail party afterwards inside the Little White House to raise money for the Foundation. Tickets are available for the presentation and the cocktail party. Tickets available at keystix.com. Contact: 305-294-9911.
  • Annie Dillard Exhibit at Gallery on Greene - After an outstanding career in literature, Pulitzer Prize recipient Annie Dillard has focused her creative talents on the visual arts. She is to present a special viewing of her artwork from 1-2 p.m. at The Gallery on Greene, 606 Greene St. Dillard is known for her keen observations of nature, and many of her works are dedicated to the land and sea that surround her at her seasonal abodes. In conjunction with the 2012 Key West Literary Seminar, Dillard will meet art aficionados from 1-2 p.m. January 7 at The Gallery on Greene. Contact: 305-294-1669.

January 8

  • Impromptu Classical Concerts of Key West presents: Firebird Chamber Orchestra - Specializing in Baroque and contemporary classical music, Firebird Chamber Orchestra is a collection of 14 freelance professionals spun out of Miami’s Seraphic Fire Choir in 2007. Since then, Firebird has blazed its own trail of chamber music interpretations, under the artistic direction of Patrick Dupres Quigley, who also directs Seraphic Fire. Its unusual and highly acclaimed interpretation of Vivaldi’s “Four Seasons” is on Sunday’s program. The “With Love, Florence” concert series which hosts Firebird launches an exciting 2012 season. Begins at 4 p.m. at St. Paul’s Church, 401 Duval Street. Children are admitted free; adults $20. Buy tickets online or at the door. 

January 14

  • Seventh Annual Florida Keys Seafood Festival - A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. Free admission; hours open from 11 a.m. – 8 p.m. Bayview Park at Truman Avenue and Jose Marti Drive. Contact: Vicki 305-872-9026. 

January 15-20

  • Premier Racing presents: Key West Race Week 2012 - The 25th-anniversary challenge features world-class competition and yachting teams from more than 12 countries and 24 American states. Nearly 300 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. Contact: 781-639-9545.

January 20-22

  • Key West Harbour King Mackerel Tournament - Big king mackerel migrate to the waters around Key West each winter, and a fittingly large prize awaits the winner of this challenge. The angler who weighs in the heaviest mackerel, also known as kingfish, is to go home with $10,000. Contact: Lee Murray 305-296-0364.

January 20-21

  • 52nd Annual Key West Historic House & Garden Tours - Tour a series of elegant and unique private homes of Key West. Complimentary Conch Tour Train transportation is provided to whisk you from house to house. Proceeds help benefit the Old Island Restoration Foundation. Contact: 305-294-9501. 

January 21

  • Flagler’s 100th Anniversary Gala Costume Ball - Step back in time and enjoy an opulent night of period costumes, dinner, dancing and fireworks, celebrating the glories of the Flagler era. From 6-10 p.m. at the historic Casa Marina – A Waldorf Astoria Resort, located at 1500 Reynolds Street. Seats limited; 180 guests maximum. Open bar cocktails, dinner, beverages, fireworks as well as a silent auction to benefit Friends of Old Seven, a nonprofit organization formed as a community effort to save, enhance and maintain the historic Old Seven Mile Bridge in Marathon, a significant piece of railroad history. NOTE: Although this event is currently sold out, visitors can experience the Casa Marina’s ambiance with casual dining at the Sun-Sun Beach Bar & Grill. 

January 22

  • Key West Half Marathon Run - The perfect place to run in the middle of winter? Key West, during the Key West Half Marathon! Jan. 22 marks the centennial anniversary that Henry Flagler’s Florida Keys Over-Sea Railroad was completed in 1912. Average expected temperature at race time is in the low 70s. Run 13.1 miles, past historic sights such as the Key West Lighthouse and the Hemingway Home & Museum and Key West’s waterfront area. Entry fee $45, $50 day of race. Contact: Barbara Wright 305-296-7182.
  • Flagler Centennial Parade - Everyone loves a parade! Celebrate Henry Flagler’s accomplishment that forever changed the Keys, 100 years after his first train pulled into the station in Key West. Scheduled to start at 1 p.m., this commemorative celebration is to feature historians, dignitaries, perhaps a politician or two in order to mark the milestone occasion. Free and open to the public! Parade route is expected to begin at Higgs Beach, continue along Duval Street and conclude at the Customs House steps, from where Henry Flagler is to address the spectators, visitors and residents of the Florida Keys and Key West. An expanded Speedway to Sunshine exhibit inside the museum at the Customs House is to be unveiled this afternoon as well. 

January 23

  • Friends of Key West Library Lecture Series - Florida historian and author Seth Bramson is to be the evening’s highlight! Lecture and book signing of his new book, The Greatest (Railroad) Story Ever Told: Henry Flagler and the Florida East Coast Railway’s Key West Extension. Seth Bramson is a leading historian, the Company Historian for the Florida East Coast Railway and author of more than 16 books. Located in the main hall at The Studios of Key West, located at 600 White Street. 

January 26-29

  • Key West Food & Wine Festival - Top chefs and restaurateurs showcase their culinary creativity and the Keys’ indigenous cuisine in a tasty schedule of events for food lovers. Attendees also can participate in food-related adventures during the savory celebration. Contact: 800-474-4319; 305-292-1622. 

January 28

  • Anne McKee Artists Fund Auction - Nearly 100 artists are to exhibit and auction their work to raise money for the fund that provides project-based grants to Keys artists. Featured artwork includes original paintings, sculpture, photography, fiber art, ceramics, jewelry and more. Pieces are to be on display two weeks prior to auction, located at Fort East Martello Museum. Viewing begins at 7 p.m.; auction begins at 8 p.m. 

January 28-29

  • 27th Annual Key West Craft Show - Juried artisans and crafters display their talents at a popular show on lower Whitehead and Caroline Streets in historic Old Town. Contact: 305-294-1241.

January 29

  • Key West Master Chefs Classic - Local restaurants vie for top honors in three categories; appetizers, entrees and desserts. Participants get to taste all the food made at this event while judges pick the winners. Held at Westin Key West Resort & Marina Pier at 245 Front Street, open from 4-7 p.m. Tickets available online starting Nov. 1 at keystix.com. Contact: 305-294-9526, ext 25.

February 2012

February 3-4

  • Cuda Bowl - 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 are to be awarded for top angler and guide in light tackle spin and fly divisions, including a substantial gift certificate to Hurricane Hole Restaurant & Bar plus a trophy. Entry fee is $250 for one angler, $300 for two anglers.

February 17-18

  • 52nd Annual Key West House & Garden Tour - Tour a series of elegant and unique homes of Key West. Proceeds help benefit the Old Island Restoration Foundation. Presented by the Old Island Restoration Foundation, this house and garden tour offers a rare opportunity to see inside some of Key West’s magnificent, charming and tropical residences. Contact: 305-294-9501.  

February 18-19

  • Gardenfest Key West - South Florida’s top nurseries are to show bromeliads, orchids, fruit trees, palms, tropical flowers and natives at the Key West Tropical Forest & Botanical Garden’s annual plant sale. Other attractions include landscaping workshops, garden supplies booths, and arts and crafts and docent tours. Contact: 305-296-1504. 

February 25-26

  • Old Island Days Art Festival - The 47th annual juried fine art show is set on lower Whitehead Street and Caroline Street in historic Old Town. The highly acclaimed show, from 10 a.m. to 5 p.m. daily, features oil paintings, watercolors, sculpture, photography and other offerings by artists from around the United States. Contact: Lois Songer 305-294-1243.

February 27

  • Waterfront Playhouse presents: Dinner and Disco at the Flamingo Diner - Get your tickets early because this event is a sell-out every year. Disco, famed diner food, drink and ambiance meld together. Come dressed as your favorite cook, waitress, diner patron, disco diva or dude. Who’s going to win the costume prize this year? At the home of Bert Whitt and Dennis Beaver. Showtime 7 p.m. Contact: Box Office 305-294-5015.

March 2012

 March 3

  • 50th Annual Conch Shell Blowing Contest - An Old Island Days tradition, this unique contest features novel sounds produced by contestants in several age categories as they attempt to make “music” on fluted conch shells. Contest located in the garden of the Oldest House, 322 Duval Street, free and open to all ages. Contact: 305-294-9501.

March 11-15

  • March Merkin Permit Tournament - 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. Contact: Jon Ain 303-888-4546.

March 16-18

  • Key West Fishing Tournament Kick-Off - Fifteen target species and $5,000 in cash prizes highlight this open-to-the-public event, heralding the beginning of more than eight months of exciting Keys fishing. Cash awards await individual participants who catch the heaviest dolphin, kingfish, cobia, blackfin tuna, mackerel, mutton snapper, wahoo, mangrove snapper and grunt, and for boat teams that score the most releases of tarpon, permit, bonefish, barracuda, marlin and sailfish. Junior anglers under age 15 can also fish. Entries in the kickoff also are eligible for the Key West Fishing Tournament, which runs through Nov. 30, 2012. 

March 17-18

  • 52nd Annual Key West House & Garden Tours - Tour five elegant and unique homes of Key West. Proceeds help benefit the Old Island Restoration Foundation. Presented by the Old Island Restoration Foundation, this house and garden tour offers a rare opportunity to see inside some of Key West’s magnificent, charming and tropical residences. Contact: 305-294-9501.

March 17 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

March 22

  • Waterfront Playhouse presents: Beer, Bourbon and Barbecue - Delectable tastings of bourbons and beers accompanied by the Iron Chefs mouth-watering barbecue make this a fun-filled evening. Check our website for more details. Event time 7 p.m. Contact: Box Office 305-294-5015.
March 23-24
  • Cuban Cultural Exposition & Hot Havana Nights - Celebrate Cuba Week finishes with the hottest event of the year; this annual event has returned to the Garden with the sounds of Havana Soul; enjoy mojitos, authentic Cuban food, original Cuban art, live auction and more. This HOT benefit always sells out so make your reservations early! VIP Seating and General Admission tickets available. Contact: 305-296-1504.
March 24
  • Florida Keys Ocean Festival - The southernmost island chain’s vibrant marine environment is to be celebrated with live music, artistry, kids’ activities, educational exhibits and more during the third annual Florida Keys Ocean Festival, set for noon to 6 p.m. More than 30 exhibits are to spotlight the Keys’ conservation efforts and the work of nonprofit organizations, and a like number of marine artists, craftspeople and vendors plan to showcase their wares. Free admission, free parking at the Florida Keys Eco Discovery Center, on the Truman Waterfront. 
  • Dance-a-thon - The Sheriff’s Office Relay for Life team “Jailhouse Rock” will be holding a dance-a-thon on Saturday, March 24, from 8 a.m. to 1 p.m. at the White Street Pier. A number of local dance instructors will be there. Have a terrific time and get your weekend exercise session in, while raising money for a great cause.
  • Hippie Workshop - Hear Ye, Hear Ye 2nd Annual Open House from 10 am until who knows when! Artists in Fine Woodworking, Sculptors, Painters, Artful Skateboards, Clocks & Mixed Media Artists All One-Of-A-Kind Works! 6991 Shrimp Road Just past Bernstein Park on Left.
March 24-25
  • Shakespeare Auditions – Key West Fringe is holding auditions for its “Shakespeare in School” project, bringing live performances of Shakespeare to a number of middle and high schools throughout the Keys in mid-May. They are looking for two women in their 20s to 30s and two men in their 30s or 40s, plus one actor any age. Auditions are Saturday, March 24, from 3:30 to 5:30 p.m. and Sunday, March 25, from 10 a.m. to 1 p.m. At the MLK Community Center at 300 Catherine St. or by appointment. For further information or to make an appointment, contact Tammy Shanley at 612-386-7426.
March 25
  • 17th Annual Hospitality Open Golf Tournament - One of the longest running golf tournaments in the Florida Keys, the event supports scholarships for Florida Keys students in the hospitality and culinary fields of study. Just $100 per player includes greens fees at Key West Golf Club, goodie bag, food (Breakfast and Lunch), drinks, hot dog stand, Mimosas and Bloody Mary’s and much more! Team up with 4 of your friends or sign up individually! The event sells out quickly! Contact: (305) 296-4959
  • 10th Annual Willie Wonka Chocolate Fest - from 11 a.m. to 3 p.m. March 25 at the Southernmost House, 1400 Duval St. The Cancer Foundation of the Florida Keys depends on contributions — monetary and in-kind — for the event. Homemade or store-bought chocolate treats are requested, such as cakes, cookies, candies, doughnuts and cupcakes, for the enjoyment of hundreds of people. The chocolate fountain needs an array of goodies to dip, including strawberries, bananas, and pretzels.To contribute or become a sponsor for the festival, call Doria Goodrich at 305- 293-7104. The Cancer Foundation nonprofit helps local cancer patients undergoing treatment.
  • WomanKind Croquet Tournament – This is the 7th annual show of skill, held on the lawn at the Edward P Knight Thompson Island Estate from 10 am to 5 pm. For information call 305-294-4004.
  • Wine Favorites – Noble Wine Estates and Grand Vin present A premium private tasting of small-production wines from around the world, rated in the 90′s by the major trade publications (Wine Advocate, Wine Spectator, Wine Enthusiast, Wine & Spirits, Gambero Rosso etc.) $36 per person, limited to 26 people; CALL 305-296-1020 FOR RESERVATIONS 
  • Save Our Pines Potluck –  1:00pm… To celebrate the 4th anniversary of Save Our Pines and its successful campaign to stop the destruction of our wonderful shade Australian pine trees, we invite all our friends and supporters to a potluck picnic at the tables under the pines. Bring a dish you would like to share with others and enjoy what others would like to share with you. Napkins, utensils and water will be provided by Blue Heaven and Salute! restaurants. In order to enable us to continue the work necessary to maintain the health and safety of the pines at Fort Zach, we need to raise funds. Each surviving pine has been identified with a circular, numbered medallion. For a nominal contribution, individual pines may be “adopted” by those interested in the trees continued survival. Proceeds go to support ongoing monitoring and the advocacy work of Save Our Pines. Save Our Pines will be happy to arrange adoptions at the picnic. Please plan to come and enjoy the fine beach, wonderful food, refreshing sea breezes, pleasant company, and the shade offered by the canopy of the marvelous pine trees. 
  • Animal Farm Easter - The annual “Easter on the Farm” will take place from 1 to 3 p.m. Sunday at the Monroe County Sheriff’s Office Animal Farm, underneath the Sheriff’s Office on College Road, Stock Island.
    The family-friendly event is free and offers something for everyone. The Easter bunny will hide eggs and take pictures with the kids. An egg hunt will start at 1 p.m. sharp. There will also be face-painting, arts and crafts and visits with all the animals. Email beckyherrin@keysso.net.
March 29
  • ENCORE at Lucky Street - A reception from 6 to 8 p.m. spotlights many of the artists that make Lucky Street the gallery that sets the bar. Rebecca Bennett, Helen Colley and Claudia Richards will all be on hand to talk about their new works on exhibit. Works by John Martini will return, and Michael Haykin, Roberta Marks and Susan Sugar will have selections from their newest work displayed. The exciting and vibrant new pieces by Michel delGado will expand perceived boundaries. Come and join us to explore the creations of Lucky Street artists, and enjoy music outside, snacks and wine. Contact: Lucky Street 305-294-3973
March 31
  • Reef Relief Celebrates 25 Years - Started in 1987, Reef Relief rings in 25 years of coral conservation and dedication to improving the coral reef ecosystem of the Florida Keys. From 6-10 p.m. at Salute on the Beach, tickets are $15 in advance, $20 at the door. Special musical guest Howard Livingston and the Mile Marker 24 Band are to provide entertainment. Proceeds benefit Reef Relief Programs. Contact: 305-294-3100
April 2012

April 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

April 17-21

  • World Sailfish Championship - With a guaranteed top prize of $100,000, the prestigious sailfish challenge draws top teams and benefits the Don Shula Foundation for Breast Cancer Research, Camp Boggy Creek for youngsters with chronic and life-threatening illnesses, and other national and local charities. Contact: Chris King 727-631-0072.

April 20-29

  • 30th Annual Conch Republic Independence Celebration - With activities ranging from wacky bed race to a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys. Contact: 305-296-0213.

April 23

  • 17th Annual Taste of Key West - Scores of area restaurants present mouthwatering samples of their cuisine to benefit AIDS Help Inc. The culinary celebration takes place at the Truman Waterfront overlooking Key West Harbor. Contact: 305-296-6196.

May 2012

May 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

May 2-6

  • Key West Songwriters’ Festival - The 17th-annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. Contact: Charlie Bauer 305-304-0814.

May 4-13

  • Waterfront Playhouse presents: Key West Mystery Fest - The Key West Mystery Fest is a 10-day festival of mysteries and mystery-related events highlighted by the world premiere of Home Exchange and will include a Clue Dinner Party (a progressive dinner based on the Clue board game), a Classic Mystery Movie Night at the Tropic Cinema, Mystery-themed “Behind the Scenes” at the Waterfront Playhouse, a “Monk Night” at the Tropic Cinema with Andy Breckman (creator of Monk) and Hy Conrad (writer/producer of Monk), a Mystery Writers Panel Discussion and Book Signing, a Mystery Short Story Contest and many other mystery activities. Contact: Box Office 305-294-5015.

May 6

  • Waterfront Playhouse presents: Clue, The Dinner - Will it be Miss Scarlet or Professor Plum? Come dressed as a suspect from the popular board game Clue and win a prize for solving who killed Mr. Boddy at this progressive dinner. Part of the Key West MysteryFest. Event time 7 p.m. Contact: Box Office 305-294-5015.

May 8

  • Waterfront Playhouse presents: Behind the Scenes - Get a free backstage tour of the Waterfront Playhouse with Artistic Director (Danny Weathers) and Technical Director (Michael Boyer). See the magic that happens “behind the scenes.” Wine and light hors d’oeuvres served. Admission is free but reservations are required. Event time 6 p.m. Contact: Terri Wilson 305-394-4106.

May 10-13

  • Key West Paddleboard Classic - During this ocean paddleboard race, participants will enjoy a challenging 12-mile course over crystal blue waters, circling Key West through scenic mangroves, passing by the Historic Seaport district and more. The race begins and ends on Smathers Beach. Contact: 305-797-1174.
May 18 – 29
  • 10th Annual Harry S. Truman Legacy Symposium - Key West’s political history is highlighted in panel discussions, a reception and tours of the Little White House where Truman spent many working vacations during his presidency. Contact: 305-294-9911 
May 26
  • 11th Annual Yamaha Dolphin Masters Invitational - Headquartered at Key West’s Historic Seaport, competitors vie for first-place honors and more than $13,000 awaits the angler scoring the highest total combined weight of three dolphin catches. Other prizes include four-night tropical fishing vacation for four, among many more. The tournament is open to all anglers, entry fee is $750 per boat. There is no limit on the number of boats that can register. Contact: John Stuempfig 305-304-7674

June 2012

June 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

June 6-10

  • Key West Pride - Key West shows its Pride every day, and this is your chance to be a part of the celebration! his five day celebration includes a film festival, dance parties, drag shows, bike tours, clothing-optional pool parties, water excursions, a street fair, Pride Pageants, and a ‘Pride in Our Community’ Parade down Duval Street. Contact: 800-535-7797; 305-294-4603.

June 7-10

  • Third Annual Key West Bacchanalia - A food and wine event with a twist – join Keys celebrity chefs as they face off in culinary competition with a great cause in mind. Benefits support the Darrell Gwynn Foundation. Visit site for details, schedules and tickets. Contact: Aga and James Hilferty 305-766-3356.

June 16

  • The Original FKCC Swim Around Key West and Swim Meet - Sponsored by the Bone Island Masters Club, this USMS-sanctioned event is a 12.5 mile swim clockwise around the island of Key West. Age groups 18 through 65 and older can register. Visit Web site for details. Contact: Lori Bosco 305-809-3562.

June 22-24

  • Key West Gator Club Dolphin Derby - A grand prize of $5,000 cash is to be awarded the boat team with the largest aggregate weight in dolphin during the derby’s two fishing days, with teams allowed to enter one qualifying fish each day. Second- and third-place teams will earn $2,500 and $1,000, respectively. Individual anglers can compete for trophies, prizes and cash totaling more than $20,000 in the tournament’s divisions for male, female and junior participants. Contact: John Stuempfig 305-304-7674.

July 2012

July 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

July 15-18

  • Del Brown Permit Tournament - 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. 
July 17-22
  • Hemingway Days - The 32nd celebration of the legendary author’s work and lifestyle features literary readings, a theatrical premiere, short story competition, fishing tournament, Sloppy Joe’s Look-Alike Contest and a pre-birthday “party” commemorating Ernest’s July 21st birthday. Contact: (305) 296-2388 (Look-Alike); 294-0320 (literary)

July 18-21

  • Drambuie Key West Marlin Tournament - Anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. Held in conjunction with Key West’s annual Hemingway Days, the event awards $25,000 to the first-place team. Teams can enter one fun fish (dolphin, tuna, wahoo or released sailfish) per day to add to their point total. Contact: Jane Greene 305-292-2710.

July 19-21

  • 32nd Annual Sloppy Joe’s “Papa” Hemingway Look-Alike Contest -This annual contest takes place at Sloppy Joe’s Bar, 201 Duval St., where Ernest Hemingway often enjoyed cocktails with cohorts. The event attracts look-alike contestants from around the United States and international locales to vie for the title of “Papa,” and is a highlight of the annual Hemingway Days celebration of the legendary author’s literary prowess and colorful lifestyle. 

August 2012

August 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

August 10 – 12

  • Key West Lobsterfest 2012

    Key West Lobsterfest 2012

    Key West Lobsterfest 2012!- It’s a celebration of our favorite crustacean! Make plans now for the 16th annual Key West Lobsterfest August 10, 11 & 12, 2012. Events include the Duval Crawl on Friday Night, a Street Fair and Free Concert Saturday, and a spectacular brunch on Sunday.  Saturday’s Street Fair features lobster-inspired culinary creations ranging from appetizers to full dinners with traditional trimmings. Twenty local restaurants and over one hundred arts and craft vendors are expected to participate. The festive feast will take place in the 100 through 500 blocks of Key West’s famed Duval Street. A free concert featuring local and regional bands is scheduled to enhance lobster-lovers’ appreciation of the day, beginning at 1 p.m. and continuing until 11 p.m. Lobsterfest celebrates the bounty of the Florida Keys lobster season that runs from August 6 to March 31. All lobster to be served at the event will be caught by Keys lobster fishermen.  Known as spiny lobsters, the clawless crustaceans found in Keys waters offer sweet and tender meat. Lobster often is served steamed with drawn butter, in creamy bisque, or cold in savory salads. As well as showcasing the sweet and flavorful Florida lobster, Lobsterfest benefits a scholarship fund for Key West High School students. For more information about the Key West Lobsterfest, visit www.KeyWestLobsterfest.com

August 16-29

  • Tropical Heat - Tropical Heat offers four days of All Male-All Adult fever-pitch revelry on the island whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Contact: 305-294-4603; 800-535-7797.

August 30 – September 3

  • Third Annual Key West Brewfest - More than 50 different kinds of beers and micro-brews are on tap at this second annual “tasty” event, that benefits Key West Sunrise Rotary Club of the Conch Republic. Beer tastings, food and musical rhythms round out the weekend activities. Contact: 800-354-4455.

September 2012

September 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

September 1 – September 3

  • Third Annual Key West Brewfest - More than 50 different kinds of beers and micro-brews are on tap at this second annual “tasty” event, that benefits Key West Sunrise Rotary Club of the Conch Republic. Beer tastings, food and musical rhythms round out the weekend activities. Contact: 800-354-4455.

September 7-9

  • Robert James Sales S.L.A.M. Celebrity Tournament - In the first of three tournaments in the annual Redbone Celebrity Tournament Series, also called The Trilogy, anglers target tarpon, permit and bonefish to achieve the coveted “flats grand slam.” The event raises funds for the fight against cystic fibrosis. Contact: Gary or Susan Ellis at 305-664-2002.

October 2012

October 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

October 19-28

  • 33rd Annual Fantasy Fest - An outrageous, 10-day celebration featuring costume competitions, promenades, street fairs and a grand parade with marching groups and lavish floats. Contact: 305-296-1817.

October 23

  • 30th Annual Headdress Ball - This “over the top” contest includes an extravagant show with lots of Key West razzle dazzle, and is a competition “head and shoulders” above the rest with contestants judged from the shoulders up! Major cash prizes. Contact: Rebecca Tomlinson at 305-294-4603.

November 2012

November 1 – November 30

  • Key West Fishing Tournament - More than 40 species of fish are targeted during these months, with divisions for men, women, junior anglers (ages 10 to 14) and Pee Wees (under 10 years old). In a March kickoff event, anglers target 15 species and $5,000 in cash prizes is split between the top anglers. 

November 4-11

  • Key West World Championship Race - High-speed offshore powerboats race in Key West Harbor and surrounding waters to continue Key West’s longstanding tradition in this 31st annual challenge, known internationally as the Indianapolis 500 of powerboat racing. Contact: 305-296-6166.

November 21 – December 31

  • Key West “Bight’ Before Christmas” Holiday Celebration - Live holiday music, games for the kids, holiday cheer and a chance for photos with Santa highlight this event along the historic harbor walk linking colorful seaport restaurants, bars and businesses at the Key West Bight. Created as a gift to the community, the gala is produced by the Key West Bight Preservation Association and tenants of the Key West Bight. Contact: 305-304-2633.

December 2012

December 1-31

  • Key West “Bight’ Before Christmas” Holiday Celebration - Live holiday music, games for the kids, holiday cheer and a chance for photos with Santa highlight this event along the historic harbor walk linking colorful seaport restaurants, bars and businesses at the Key West Bight. Created as a gift to the community, the gala is produced by the Key West Bight Preservation Association and tenants of the Key West Bight. Contact: 305-304-2633.

December 31

  • Key West New Year’s Eve Celebrations - Events take place at Sloppy Joe’s, Bourbon Street Pub, and the Historic Seaport.

For more information about things to do and see in our island city, go to our Key West Web Site.

And for restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at www.gotothekeys.com.

Island Genn – Your Key West Concierge