Florida Keys Activities!

"Keep up on Florida Keys Activities and Upcoming Events by subscribing to our "Rum Runner News"!

"The healthy being craves an occasional wildness, a jolt from normality, a sharpening of the edge of appetite, his own little festival of Saturnalia, a brief excursion from his way of life." - Robert Maclver

Quick Reference

Florida Keys Activities and Events

FLORIDA KEYS ACTIVITIES
Key Largo MM 118-90.7

November-December-January

December 07

Light Up Key Largo
Sponsored by the Key Largo Chamber of Commerce, loads of holiday events with live music, decor, food and drinks are designed to get you in the holiday mood, including the annual lighting of the tree event, between 6 and 9 p.m. at the Murray E. Nelson Govt. & Cultural Center, MM 102. Designed in concert with the celebratory events of the 100th anniversary of Henry Flagler's Over-Sea Railroad, the Key Largo community tree is to be decorated with railroad flair. Eggnog, caroling, holiday cookies and stocking stuffers are guaranteed to get everyone in the festive mood.
Contact: 800-822-1088
Email: info@keylargochamber.com

December 10

Key Largo Holiday Lighted Boat Parade
This year's theme: "Key Largo Imagination," and award-winning producer of "Avatar" and "Titanic," Jon Landau, has been named grand marshal. Blackwater Sound is to shimmer as decorated boats parade along the shoreline in celebration of the holiday season. The best viewing and libations are to be found at Sundowners, Senor Frijoles, the Marriott Key Largo Bay Resort and Caribbean Club, MM 103-104.
Contact: Call 305-394-3736

January 03

Orange Bowl Swimming Classic
Some of the best college swimmers - and perhaps future Olympians - in the country compete at Jacobs Aquatic Center, mile marker (MM) 99.6 oceanside, in a competition that is part of the celebration surrounding the annual Orange Bowl college football game in Miami. Spectators are invited to attend this free event and meet the swimmers and coaches. Warm-up is set for noon, meets are scheduled from 2 p.m. to 4 p.m.
Contact: 305- 453-7946

January 06 to January 08

16th Annual Key Largo Sailfish Challenge
Heralding the height of sailfish season, each year this boat tournament as part of the acclaimed Redbone@Large series is characterized by friendly but serious competition, professionalism and comaraderie among anglers who put their 20-pound test line skills to task. Up to four anglers per boat can register for the event, hosted at Sundowners, MM 104 bayside. Cash prizes and trophies await the first- through third-place teams. Entry fee for the first angler is $525, each additional angler is $475, and the fourth angler is no charge. Auctions and raffles are to highlight the event, whose proceeds benefit the Coral Shores High School band program.
Contact: Tammie Gurgiolo 305-240-9337
Email: fishnbully@msn.com

January 26 to January 27

Don Norris Silversmith Classes
Famed silversmith Don Norris will be coming to Key Largo to teach two intensive silversmithing courses. The first class is January 26th and 27th. The second class will be held on January 28th and 29th. The course will be 18 hours total. Each two day class will be held from 9am to 6pm (estimated time for the two day course). For more information and to secure your spot, call Josette at 786-619-0675.
Contact: 786-619-0675
Email: sales@josettedesigns.com

January 28 to January 29

Don Norris Silversmith Classes (2nd class)
Famed silversmith Don Norris will be coming to Key Largo to teach two intensive silversmithing courses. The first class is January 26th and 27th. The second class will be held on January 28th and 29th. The course will be 18 hours total. Each two day class will be held from 9am to 6pm (estimated time for the two day course). For more information and to secure your spot, call Josette at 786-619-0675.
Contact: 786-619-0675
Email: sales@josettedesigns.com

January 28 to January 29

3rd Annual Key Largo Stone Crab & Seafood Festival
A festival chock full of fresh stone crabs, conch, local seafood, music, entertainment and fun for the entire family, including a Conch Cook-Off, cooking demonstrations, a peel-and-eat shrimp eating contest, a "little mermaid" contest and a kids' play area with live fish aquarium & touch tank. Arts & craft vendors, Junkanoo band, magic shows, face painters, food, beverages and key lime pie.
Contact: 305-451-4502
Email: SeafoodFest@fkrm.com

January 31 to February 01

Poor Girls Sailfish Tournament
A large regional charity competition that typically draws more than 200 anglers, the challenge offers ten trophies, including first-, second- and third-place teams, grand champion and runner-up grand champion anglers, and the largest dolphin, kingfish and tuna. Entry fee is $95 per angler, including the kick-off party and awards banquet.
Contact: Sharon Mahoney Ellenwood 305-664-2012
Email: sharellen@netzero.net

December 31

New Year's Eve Fireworks on Blackwater Sound
The back bay is the setting for the annual New Year's Eve fireworks extravaganza hosted by Sundowners, Senor Frijoles, Cactus Jacks, Gus' Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Check website for upcoming details.
Contact: Robert Stoky 305-451-4502

FLORIDA KEYS ACTIVITIES
Islamorada MM 90.7-63

December 01 to December 04

48th Annual Islamorada Sailfish Tournament
The first leg of the triple-crown Florida Keys Gold Cup Championship Series - the Gold Cup limited to 25 boats - is characterized by high-flying sail action, conservation and sportsmanship. It’s also the only tournament in the Gold Cup series to offer a junior division for anglers age 16 and younger. Entry fee $600 for first angler, $500 for each additional angler. Junior angler $200. Unlimited anglers allowed per vessel.
Contact: Dianne Harbaugh 305-852-2102 or 305-664-4725
Email: ditournaments@aol.com

December 02

Florida Keys Holiday Festival
This extravaganza begins with a tree-lighting ceremony at Founders Park, MM 87. A holiday parade follows, featuring Santa, food, kids activity booths and live "on stage" performances with local kids dancing from Joyce Bennett School of Dance, the E.C.M.C. CAMP, and On Your Toes School of Dance. A mountain of snow is the favorite among mitten-clad munchkins.
Contact: 305-664-4503

December 02 to December 03

Pigeon Key Bicycle Ride & Campout
Enjoy a guided 50-mile ride; overnight stay at Pigeon Key in a historic bunk house, dinner, campfire and breakfast included. Starts and returns at the Key Largo Bike Tours & Adventures shop, at MM 91.9. Cost is $175 per person.
Contact: MARK TERRILL AT 305-395-1551

December 07 to December 08

Islamorada Fishing Club Captain’s Cup Sailfish Tournament
A winner-take-all prize of up to $30,000, along with the prestigious Captain's Cup, is to go to the top boat team - each team is allowed up to four anglers per boat. The guaranteed cash prize is based upon the number of boats registered for the one-day event; for a field of 15 registered boats the top payout is to be $20,000, for a field of 20 boats, payout increases to $25,000 and a full field of 30 registered boats ensures a grand prize of $30,000. The all-release tournament is limited to 30 boats. Entry fee $2,500 per boat for first two anglers; third angler is $300, fourth angler $200. Four social tickets are given per boat.
Contact: Dianne Harbaugh 305-852-2102 or 305-664-4725
Email: ditournaments@aol.com

December 09 to December 11

12th Annual Captain Don Gurgiolo Sailfish Classic
In the spirit of Captain Don Gurgiolo, who pioneered fishing today's offshore fishing techniques with light tackle and live ballyhoo, this boat tournament is part of the Redbone at Large series and awards the the winning title and trophy to the boat accumulating the most release points - anglers must use 12-pound test line. Attractive prizes are awarded, including an individual tagging trophy awarded for the most tagged sailfish. Entry fee $525 for the first angler, $495 for each additional angler on that vessel. Up to four anglers can fish per boat.
Contact: Tammie Gurgiolo 305-240-9337
Email: fishnbully@msn.com

December 15

Morada Way Arts & Cultural District presents: Third Thursday Art Walk
Showcasing the fine arts, music and culinary nuances of the Purple Isles, the Morada Way Arts & Cultural District features national and local artisans who are showcased in galleries at Morada Way between mile marker 81 and 82 - formerly named Industrial Road - as well as "culinary art" and live music from 6-10 p.m. In addition to individual artists, participating galleries include the Redbone Gallery, Gallery Morada, Pasta Pantaleo Signature Gallery and Bluewater Potters. Free admission. Art Walk is held the third Thursday of each month.
Contact: Daniela Woody 305-664-9100
Email: Daniela@MoradaWayArts.org

December 16 to December 18

47th Annual Islamorada Junior Sailfish Tournament
One weekend each year, anglers age 16 and younger can put lessons such as tying a bimini or rigging ballyhoo to use in the Islamorada Junior Sailfish Tournament, hosted by the OceanView Sports Bar & Grill, MM 84.5 bayside. Raffles, silent auction, cash prizes and more highlight the event. Entry fee is $100 per angler, with a maximum of six anglers allowed per boat. All anglers earn a tournament trophy. Proceeds benefit Monroe County Toys for Tots.
Contact: Tammie Gurgiolo 305-240-9337
Email: fishnbully@msn.com

December 17

Islamorada to Key West Bicycle Tour
Bicyclists, outdoor enthusiasts and history buffs have a unique opportunity to learn about the history of the Florida Keys while getting some exercise and sunshine. The 90-mile tour is $150 per person (which is a donation to local sports programs) and starts at 6 a.m. at the Coral Shores High School parking lot (MM 90). Rent or bring your own bike to meet the tour - vehicle support, break stations, lunch, time in Key West and ride back to Islamorada are included. This ride is limited to 6 riders. And remember to carry water and slather on the sunscreen ahead of time.
Contact: MARK TERRILL AT 305-395-1551

December 17

Pops in the Park presents: Tropical Christmas
Keys Community Concert Band presents an extra special holiday concert, to be held at Founders Park, mile marker 87 bayside. Starts at 4 p.m. All seats are outdoors, chairs and blankets recommended to bring.
Contact: Donna Heiner 305-853-7294
Email: keyscommunityconcertband@yahoo.com

December 31

New Year’s Eve Fireworks on the Beach
Fireworks on the beach are planned at Pierre's Restaurant and Morada Bay Beach Café, MM 81.6 bayside. Live music and cocktails are available for purchase to add to the celebration, but coolers are not allowed.
Contact: 305-664-8414

January 01

Village New Year’s Day Celebration
The annual 5k Run, Walk and Crawl is slated to start at 8 a.m. Jan. 1 at Founders Park, MM 87 bayside in Islamorada. For the less athletically minded, festivities follow with the 10 a.m. blessing of the fleet at Whale Harbor Bridge, MM 84 oceanside.
Contact: 305-853-1685

January 03 to March 27

Long Key Squares presents: Tuesday Round and Square Dancing
For residents and visitors who simply want to enjoy dancing, the nonprofit Long Key Squares continues a 30-year tradition, where square dance attire is not required ... but your attendance is desired! Held at Outdoor Resorts, mile marker 66, 65821 Overseas Highway, on Tuesday nights from 7-9:30 p.m. Cost is $5 per person. Lessons are also held for both beginners and plus dancers on Sundays from 2-4 p.m.
Contact: Joanne Prince 305-664-4060
Email: sylken-solutions@verizon.net

January 08 to January 09

Bartender’s Sailfish Open
A boat tournament among actively employed bartenders, this locals' favorite challenge offers trophy awards and bragging rights to winning bars. A hilarious yet competitive event.
Contact: Dianne Harbaugh 305-852-2102; 305-522-4868
Email: ditournaments@aol.com

January 11 to January 12

Islamorada SailFly
In this fly fishing, all-release sailfish boat team tournament, captains, mates or anglers can tease, but only the registered anglers can cast, hook and play the fish. Tournament rules are IGFA format. The invitational challenge is limited to 20 boats.
Contact: Sandy Moret 305- 664-5423
Email: sandy@floridakeysoutfitters.com

January 13 to January 15

NAMSA North American Championship & Tradewinds Midwinter OpenCat Nationals
The quiet beach at Founders Park, mile marker 87 bayside on Plantation Key, is to come alive with one of the largest winter sailing events in the U.S. as top catamaran sailors in the world arrive to race in the three-day event.
Contact: 305-451-3287
Email: rick@catsailor.com

January 14

Art Under The Oaks
Fine Art & Original Crafts, Self Guided Nature Walk, Specialty Food Booths, Children's Arts & Crafts, and raffle of items donated by the artists. San Pedro Church Gardens, 9 a.m. - 4 p.m., Mile Marker 89.5 on Plantation Key in Islamorada.
Contact: 305-664-5574

January 19

January 20 to January 22

Sailbone
Anglers vie to land as many sailfish and bonefish as they can in this new three-day backcountry and offshore competition.
Contact: Sharon Mahoney Ellenwood 305-393-6174
Email: sharellen@netzero.net

January 20 to January 22

Cheeca Lodge Presidential Sailfish Tournament
Now in its 22nd year, the tourney is a facet of the World Billfish Series and the second leg of the three-tournament Florida Keys Gold Cup Sailfish Championship. The event kicks off Jan. 20 with two days of 12-pound test, light tackle fishing Jan. 21-22 wrestling the high flyers.
Contact: Liz Hill 305-451-5094
Email: lizhillfirst@bellsouth.net

January 21

Keys Community Concert Band presents: Get on Board!
Florida Keys Community Concert Band presents its 2012 season at Islamorada Founders Park, Bayside, MM 87, Plantation Key. Performances are outdoors; no chairs provided. Starts at 4:00 p.m. Admission free for all concerts.
Contact: 305-853-7294
Email: heinerdonna@yahoo.com

January 21 to January 22

Islamorada Fine Art Expo
Enjoy this inaugural event, sponsored by the Morada Way Arts District. To be located at mile marker 81.5 to see local artists' work and learn the story behind the art. Expo is open 10 a.m. to 5 p.m. both days; Saturday from 5:30 p.m. to 7 p.m. Matecumbe Historical Trust presents local historian Irving Eyster, on the 100th anniversary of Henry Flagler's railroad. General admission is $5, no charge for children 12 or under, senior citizens (65 or older), active duty military personnel or disabled (wheelchair) attendees. Visit website for details and tickets.

January 23 to January 24

Al Flutie Over the Hill Rip-Off Sailfish Tournament
Entering its 23rd year, this event is still known to many anglers as "almost too much fun for old guys to handle." Locally called the Flutie, and as a donor or more than $400,000 to local and national charities, the tournament limits entry to anglers age 50 and over.
Contact: Gordon Ross at 305-852-3282, ext. 25
Email: ross4197@bellsouth.net.

January 25 to January 26

Islamorada Fishing Club Sailfish Tournament
Presented by the Islamorada Fishing Club, this final leg of the Florida Keys Gold Cup Series offers up to a $30,000 winner-take-all cash prize. The field is limited to 30 boats, so register early.
Contact: Islamorada Fishing Club 305-664-4735
Email: fishing@theislamoradafishinglclub.com

January 27 to January 28

22nd Annual Swamp Guides Fishing Tournament
All-release event offers fishing for bonefish, redfish and snook in the shallows of the Florida Keys and the saltwater fringes of the Everglades.
Contact: Terry or Rusty Albury at 305-664-5142
Email: talbury@aol.com

FLORIDA KEYS ACTIVITIES
Marathon MM 63-47

February 11th & 12th

Local's Art Show in Marathon
Don't Forget about the Local's Art show in Marathon this Saturday & Sunday! Many local Artist from Islamorada and the surrounding Islands will be taking part in this year's Pigeon Poop Show, as many Conchs around here know it. Come see some familiar faces and meet some new ones at this show with free parking and free admission! 10-5pm, Winn-Dixie / Marathon Parking Lot MM 50.2.

October 26 to December 22

Holiday Photos with Santini (or another dolphin) at Dolphin Research Center
Guests who participate in our Meet the Dolphin program have the option of posing for a holiday photo with the dolphin! Trainers will offer holiday themed props and guests are welcome to bring their own Santa hats, reindeer antlers, and other accessories. Meet the Dolphin is $25 per person plus the cost of general admission. High-resolution photos taken by DRC's talented photographers will be available on disk for $15 for one person, $30 for two-six people in the same shot. Maximum group size of six people! Meet the Dolphin, with Holidays Photos, is offered several times a day on a walk-in basis until December 22. Dolphin Research Center is located at mile marker 59, along the Overseas Highway, Grassy Key. Open 9 a.m. to 4:30 p.m. daily.
Contact: 305-289-1121

November 10 to December 03

Marathon Community Theater presents: Sleeping Indoors
Jim Holt's play showcases the rifts between the haves and the have-nots with humor and insight, and affords a glimpse of the true holiday spirit. Anyone purchasing two tickets to a play on any Thursday, other than opening night, will receive $5 off the price of the two tickets. Both tickets must be purchased and paid for in one transaction. This offer is not valid with any other discounts. Visit website for showtimes and ticket prices.
Contact: 305-743-0994
Email: gm@marathontheater.org

December 04

Annual Tree Lighting Celebration
An early evening event, from 4-7 p.m. at the parking area outside Fishermens Community Hospital, helps gather the Marathon community to light the tree atop the hospital. Holiday entertainment includes a "special guest" appearance, raffles, kids activities, jazz and tap dancers, music and cookies and punch.
Contact: 305-743-5533

December 10

Boot Key Harbor Lighted Christmas Boat Parade
A middle Keys holiday kick-off event for 15 years; watch as dinghies, mega-yachts and anything in between turn the harbor into a sparkling procession along the parade route. Best viewing sites include Lazy Days South, Marathon Marina, Sombrero Dockside Lounge and Burdine's Waterfront. Starts at 5 p.m. Contact: Greg 305-849-0285
Email: CapnGreg@BootKeyHarbor.com

December 11

Key Colony Beach Lighted Boat Parade
Christmas lights on outriggers and displays on boat decks are part of the beautiful festivities during the Key Colony Beach Boat Parade, set to begin at the 7th Street canal. The parade route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the area behind city hall. Open to the public, any and all boats are welcome to enter.
Contact: 305-743-7214

December 17

Marathon Community Theater presents: Christmas Concert
Two shows are slated to ring in the holiday cheer, at 5 p.m. and 8 p.m. Tickets are $5 for adults, $2 for children. Visit website for ticket details.
Contact: 305-743-0994
Email: gm@marathontheater.org

January 05 to January 28

Marathon Community Theater presents: The Dixie Swim Club
Five southern women, all friends since their college swim team days, gather every year for a long weekend, sans husbands or kids. This comedy follows the directions their lives takes them, and that true friendship lasts forever. Performances are Thurs - Sat evenings, at 8 p.m. Anyone purchasing two tickets to a play on any Thursday, other than opening night, will receive $5 off the price of the two tickets. Both tickets must be purchased and paid for in one transaction. This offer is not valid with any other discounts. Visit website for more information and tickets.
Contact: 305-743-0994
Email: gm@marathontheater.org

January 05 to January 28

"Tropical Impressions" Group Art Show
Eight local artists are to present their tropically-themed, original works for view and purchase in the main gallery of The Marathon Community Theater (MM 49.5, oceanside) during the production of "The Dixie Swim Club." Art Show opens Jan. 5-28, and a meet-the-artists opening reception is Sunday, Jan. 8 from 5-7 p.m. with hors d'oeuvres and cash bar. Viewing is before curtain and during intermissions each Thursday, Friday and Saturday evening, as well as a 3 p.m. matinee on Sunday, Jan. 15, and from 11 a.m. to 2 p.m. each Thur, Fri, Sat & Sun with an artist there to welcome viewers. The ever-popular art raffle tickets are also to be available. Art viewings in the gallery are open to the public!
Contact: 305-743-0994
Email: juliejoyce2@yahoo.com

January 14

Flagler Centennial Event: Free, Family Fun Day at Historic Pigeon Key
Continuous ferry and catamaran rides to the island are available, in addition to any visitor wanting to walk or bicycle over the Old Seven Mile Bridge to see an unrivaled view of the island and waters surrounding it. Attendees can also come to the island in a personal boat, limited dock space is available. Tour Pigeon Key's museum, historic buildings and grounds - snorkel, bring a chair or blanket for a picnic and relax for the day. Historical reenactments, period games and demonstrations for children of all ages - enjoy sing-alongs and square dancing! A touch tank for kids, live music and entertainment are scheduled all day, between 10 a.m. and 4 p.m. Regular fare such as hamburgers and hot dogs, in addition to 1900s-era foodie favorites are to be served.
Email: Rietttt@aol.com

January 15

Free Admission at Crane Point - Flagler Centennial Celebration
See the Flagler train exhibit, and pack a picnic and bring a blanket to participate in a family-oriented concert that features music of the Henry Flagler era. Concert starts at 5 p.m. Free admission applies all day.
Contact: 305-743-3900

January 16

Florida Keys Concert Association presents: Guy Lombardo's Royal Canadians
Enjoy "the sweetest music this side of heaven," for a night of big band, tributes and nostalgia. Tickets are $30 on sale at 6 p.m., doors open at 7 p.m. and showtime is 7:30 p.m. Performances at San Pablo Church, 550 122nd Street, Marathon. Seasonal tickets are available for $85 General Admission and $150 Preferred Seating, see website for details.
Contact: Lynda Berrigan 305-743-4687

January 22

Marathon Community Theater Welcomes Henry Flagler Back to the Keys
Paul J. Jellinek, who has been active in theatre for more than 40 years, is to recreate Henry Flagler in a one-man show with two acts, revealing the fascinating story of the man who started it all with the creation of the Florida East Coast Railway. This theatrical event is in tandem with the Flagler Centennial Celebration events throughout the Florida Keys. Showtimes are 3 p.m. and 8 p.m.
Contact: 305-743-0994

January 23

Florida Keys Concert Association presents: Trio Solisti
Hailed "the most exciting piano trio in America," Trio Solisti is comprised of three brilliant instrumentalists - violinist Maria Bachmann, cellist Alexis Pia Gerlach and pianist Jon Klibonoff. Their soulful and passionate performances are marked by soloistic virtuosity, electric energy, seamless ensemble playing and thrilling abandon. Tickets $30, purchased at the door. Seasonal tickets available for $85 general admission and $150 preferred seating; visit website for details. Performance takes place at the San Pablo Catholic Church of Marathon, 550 122nd St. Doors open 7 p.m., showtime 7:30 p.m.
Contact: Lynda Berrigan 305-743-4687

January 28

January Jamboree!
It's expected to be a smorgasbord of tropical plants, "used treasures," a plant raffle, even baked goods and honey! Attendees can find Keys and South Florida natives, bamboo, palms, heliconias, orchids and unusual, rare tropicals. Open from 8:30 a.m. to 3 p.m. at Marathon Garden Club, MM50; pastries available at 9 a.m., lunch available at 11:30 a.m.
Contact: 305-743-4971

FLORIDA KEYS ACTIVITIES
Big Pine and the Lower Keys MM 47-4

December 04

Lower Keys Chamber Million Dollar Golf Tournament
The annual tournament is offering a million dollar specialty shot, a $10,000 hole-in-one shot and a 60-foot putt specialty shot that pays out $5,000 cash. The tournament is to be held at the Key West Golf Club, with a shotgun start at 7:30 a.m., as a four person scramble format using one-half the combined handicaps. First Place is $1,000; Second Place $500; Third Place $300 and Fourth Place will win $200. Contact the Chamber for details and applications.
Contact: 305-872-2411
Email: executivedirector@lowerkeyschamber.com

December 10

Big Pine & The Lower Keys Island Art Festival
Highlights of this holiday event include live music by local entertainers, food, exhibits and booths featuring locally produced arts and crafts. Festivities traditionally take place on the grounds of the Lower Keys Chamber of Commerce, MM 31 oceanside.
Contact: 305-872-2411
Email: executivedirector@lowerkeyschamber.com

December 17

Lower Keys Lighted Boat Parade
All boats are welcome to enter the parade including deep-sea cruisers, dinghies, kayaks and canoes. Santa and Mrs. Claus are expected to arrive and hand out candy to the kids. The best recommended viewing is from Pine Channel Causeway or Parrotdise Waterfront Bar & Grille, 183 Barry Ave. on Little Torch Key. Parade begins at 7 p.m.
Contact: Steve 305-923-5370
Email: bigpinenews@aol.com

December 18

Christmas on the Farm 2011
Kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public.
Contact: Jeanne Selander 305-293-7300

FLORIDA KEYS ACTIVITIES
Key West MM 4-0

November 23 to December 31

Key West 'Bight' Before Christmas Holiday Celebration
The harbor walk along the Historic Seaport at the Key West Bight, stretching from Greene Street to Grinnell Street, is to be festively lit from rooftops to the sea for the holiday season. Celebrate with holiday events, browse at unique island shops and galleries, and relax at waterfront restaurants and watering holes. Part of the Key West "Bight" Before Christmas Holiday Celebration, the festivities are presented by the Key West Bight Preservation Association.

November 24 to December 04

Pirates in Paradise 2011
Historic Key West and Fort Taylor transform into a pirates' stronghold with over 150 pirate entertainers during the 12th annual celebration. Tall ships, sea battles, arts and crafts, pirate sails, a living history encampment and nonstop entertainment!
Contact: 305-296-9694

December 03

Key West Holiday Parade
The island city shows its holiday spirit with this annual hometown parade, set to start at 7 p.m. Featuring marching groups and motorized and nonmotorized floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. Starting at Truman Avenue and White Street, it proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street.
Contact: 305-809-3881

December 03

Key West Triathlon (TRIKW)
The second annual Olympic Distance and Sprint Triathlon event returns to Key West! A full-day Expo from 11 a.m. to 6 p.m. is planned for Dec. 2 at the Casa Marina Resort; race is scheduled Saturday morning, Dec. 3. Limited to 1,200 participants. Visit web site for details and registration.
Contact: 305-294-0693

December 03

Key West Model Railroad Show
Presented by the Key West Model Railroad Club, enjoy this free, family-friendly event. Open from 9 a.m. to 5 p.m. at the Doubletree Resort, the young at heart and kids of all ages can view model trains, collectibles, antiques & historical railroad items. Highlights of this year's event include the Locomotive Drag Races, as visitors pit their locomotives against one another on a specially created 24-foot mutli-scale race track.
Contact: Skip Fleet 305-586-7768
Email: keywesttrainman@aol.com

December 09

Historic Lighted Inn Tours
Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns, including the Mermaid & The Alligator, 729 Truman Ave.; Cypress House, 601 Caroline St.; Artist House on Fleming, 1016 Fleming St.; Rose Lane Villas, 522-524 Rose Lane; Wicker Guesthouse, 913 Duval St., and Tropical Inn, 812 Duval St. Participants can visit the inns on their own each evening or in conjunction with a holiday trolley tour presented by CityView Trolley Tours. Tickets are $25 per person for the tour itself or $40 per person with the trolley tour.
Contact: 305-295-1334

December 09

Keys Chorale 2011 Holiday Concert
The Keys Chorale at Florida Keys Community College, under the direction of Dean Walters, presents its annual holiday concert featuring seasonal favorites from around the world. Highlights include a featured selection of "Gloria" by Antonio Vivaldi, accompanied by a small instrumental ensemble. Tickets for Friday night are $30 for reserved seating and $20 for general admission. Staged at the Tennessee Williams Theatre, 5901 College Road.
Contact: 305-296-1520

December 10

Schooner Wharf Bar 21st Annual Lighted Boat Parade
Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Before the boat parade, at 6 p.m., the Gerald Adams Elementary School Steel Your Heart Band will welcome spectators with songs of the season. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport.
Contact: 305-292-3302

December 11

Southernmost Christmas Tree Celebration
Holiday revelers enjoy free conch chowder, then board Conch Tour Trains to proceed to the continental United States' Southernmost Point to set up the southernmost Christmas tree at sunset overlooking the Atlantic Ocean. The event is an annual community thank-you party presented by the Monroe Association for ReMARCable Citizens. The fun starts at 1401 Seminary St.
Contact: 305-294-9526

December 13 to January 14

Red Barn Theatre presents: Forbidden Broadway
This Off-Broadway satirical musical smartly spoofs show tunes, plots and characters of popular Broadway musicals with snappy lyrics and fabulous costumes. Forbidden Broadway has been seen in more than 200 U.S. cities, and now arrives in the southernmost city! Visit website for show times and tickets.
Contact: 305-296-9911
Email: info@redbarntheatre.com

December 17

Historic Lighted Inn Tours
Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns, featuring Westwinds, 914 Eaton St.; Artist House, 534 Eaton St.; Cypress House; Villas Key West, 512 Angela St., and Avalon, 1317 Duval St. Participants can visit the inns on their own each evening or in conjunction with a holiday trolley tour presented by CityView Trolley Tours. Tickets are $25 per person for the tour itself or $40 per person with the trolley tour.
Contact: Contact: 305-295-1334

December 17 to December 18

Holiday Music on the Harbor Walk of Lights
Enjoy traditional Christmas music under the stars on the Key West Harbor Walk of Lights. Classical violin and Celtic fiddle compositions of favorite holiday tunes are to be performed by "Violins in Motion" from Fort Lauderdale, consisting of talented 4- to 18-year-old South Florida and international students, all self-funded. The event is free, but donations will be accepted for the fight against childhood diabetes. From 6-8 p.m. each evening.

December 20 to January 14

Waterfront Playhouse presents: August -- Osage County
It's August in Oklahoma. A father is missing, a mother is in the grip of addiction, a marriage is unraveling and lies are being exposed. You are cordially invited to one bitch of a family reunion. This raucous dark comedy transforms one family gathering into an evening filled with sex, secrets, and really inappropriate behavior. One of the most lauded plays of the decade, August: Osage County is a can't-miss, hilarious and stinging look at the American family. Showtime 7:30 p.m.
Contact: Box Office 305-294-5015
Email: Box_Office@waterfrontplayhouse.org

December 27 to December 31

Florida Keys Art Guild, Art Festival
A free art festival to be held at Bayview Park, enjoyable for the whole family. Dozens of artists from around the country join local artisans to display their work, ranging from fine jewelry, sculpture, paintings and photography as well as fine crafts. Open from 10 a.m. to 5 p.m. daily.
Contact: Joey Smith 305-897-9098 home
Email: sarasotajoe2000@yahoo.com

December 27 to December 28

52nd Annual Key West House & Garden Tours
Tour a series of elegant and unique homes of Key West decorated for the holidays! 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
Email: tickets@oirf.org

December 29 to December 30

Key West Pops Orchestra presents: Joseph and the Amazing Technicolor Dreamcoat
Andrew Lloyd Webber and Tim Rice's production stars Marc Crow as the boy who makes his fame and fortune with his gift for interpreting dreams; also featuring Nulita Loder as The Narrator. The concert features an all-Key West cast with the orchestra conducted by Pops maestro, Vincent Zito. Show starts at 7:30 p.m. at St. Paul's Episcopal Church, 401 Duval Street.
Contact: 305-296-6059
Email: info@keywestpops.org

December 31

Florida Keys New Year's Eve Celebrations
The Southernmost City celebrates with a conch shell drop at Sloppy Joe's Bar, 201 Duval St.; a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St.; and a pirate wench descending from a tall ship mast in the island city's Historic Seaport.
Contact: (305) 296-2388, (305) 293-9800;(305) 292-3302

December 13 to January 14

January 01

Gay Key West Trolley Tour
Enjoy a fabulous tour of Key West...with a twist. A gay twist that is! Get a unique tour of Key West and learn about our colorful history that includes the famous and the infamous. Departs from the City Hall Parking Lot, located on the corner of Angela and Simonton. Tickets $25. Can be purchased ONLINE or at the trolley, our G&L Visitor Center (located at 513 Truman), and many of our distinguished gay and lesbian guest houses.

January 02

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)
Email: pewtar@bellsouth.net

January 05 to January 08

30th Annual Key West Literary Seminar
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 06 to January 07

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!
Email: Carrie Meng carrie@ragnarrelay.com

January 15 to January 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 18 to January 28

Red Barn Theatre presents: Red
Red is a searing portrait of the master abstract expressionist Mark Rothko and his young assistant. Ambition and vulnerability go hand in hand as Rothko tries to create his crowing achievement that could also become his undoing. Visit website for show times and tickets.
Contact: 305-296-9911
Email: info@redbarntheatre.com

January 20

Waterfront Playhouse presents: Dancin’ Man -- Denis Hyland In Concert
Key West's own dancing man (and singer, actor, comedian) is to present a one-night concert featuring the inimitable stylings of Mr. Hyland. Showtime 8 p.m.
Contact: Box Office 305-294-5015
Email: Box_Office@waterfrontplayhouse.org

January 20 to January 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 20 to January 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
Email: lee@murraymarine.com

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. Tickets are to be available for purchase at the Flaglerkeys100 site. Cost per person: $100, includes one hour of 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. More details to follow, check website for updates.

January 22

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 22

Key West Half Marathon Run
The annual Key West Half Marathon takes place on a flat, fast 13.1-mile half-marathon course through Key West's Old Town and scenic waterfront area. Entry fee $45, $50 day of race.
Contact: Barbara Wright 305-296-7182
Email: bwpromo3@bellsouth.net

January 22

The Key West Pops Orchestra presents: Obbligato
A concert of opera arias, scenes and ensembles featuring singers and instrumental soloists. The singers will include returning soprano Victoria Atwater and her husband, tenor Bruce Reed. The instrumental soloists are to feature Pops concert-master Geremy Miller and cellist Steve Sigurdson, among others. The full-sized concert orchestra will be led by Vincent Zito and the program will include music of Handel, Mozart, Rossini and Verdi. Tickets available online at www.keystix.com starting Oct. 31, 2011. Show starts at 7:30 p.m. at Tennessee Williams Theater.
Contact: 305-296-6059
Email: info@keywestpops.org

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 to January 29

Third Annual Key West Dulcimer Festival
Attendees can take workshops in hammered and mountain dulcimer, guitar, steel drums, pennywhistle, banjo, autoharp and other instruments from a stellar performing and instructing staff. The four-day festival is to be held at Hurricane Hole Marina, MM 4.5 oceanside.

January 26 to January 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
Email: info@keywestfoodandwinefestival.com

January 28 to January 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
Email: kwartctr@earthlink.net

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.
Email: mckeefund@aol.com

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

January 29

Waterfront Playhouse presents: Annual Winter Wonderland Gala
Waterfront Playhouse's Annual Winter Wonderland Gala is a must-attend event. This sparking event-of-the-year includes a fabulous dinner by Key West's Iron Chefs, drinks, silent auction and surprise performances.
Contact: Box Office 305-294-5015
Email: Box_Office@waterfrontplayhouse.org

January 31 to February 18

Waterfront Playhouse presents: Dead Man’s Cell Phone
In a quiet cafe a cell phone rings. And rings. The stranger at the next table has had enough. She confronts the owner of the cell phone, but, well ... he's dead. She begins to answer his calls and suddenly finds herself enmeshed in his life and family. Unfortunately, the dead guy has quite a number of shady loose ends. This comic fantasy traces one woman's accidental quest to make a few people feel just a little bit better about themselves. Showtime 8 p.m.
Contact: Box Office 305-294-5015
Email: Box_Office@waterfrontplayhouse.org

FLORIDA KEYS ACTIVITIES
Florida Keys

January 12 to January 22

Paddle Florida presents: Florida Keys Challenge
Join a once-in-a-lifetime paddling experience! This 115-plus mile adventure from John Pennekamp State Park arrives at Key West on the 100th anniversary of the grand opening of the Key West Railroad. Sign up for any day of paddling or for a group of days, only $90/day or $800 for the entire trip - meals included. Visit website for complete details.
Contact: Bill Richards 352-377-8342
Email: bill@paddleflorida.org

Florida Keys Events for February and March, 2012
Coming Soon!

Add Your Event to Our Calendar!

Thanks for visiting our Florida Keys Activities Guide!

From Florida Keys Activities to the Florida Keys Guide!