The Keys are offering a variety of activities this Holdiay Season. Looking for the perfect Florida Keys Vacation Rental - you’ve got them here at Florida Gulf Vacation.
And once you arrive at your destination get out and enjoy both the warm winter sun and the many activities going on this month in tht Florida Keys!
Key Largo / November 27 to December 06
Key Players presents: “Don’t Hug Me” With its over-the-top songs and crazy characters, this wintertime Minnesota love story with singin’ and stuff will leave you laughing until the spring thaw. Tickets $25 sold at the door. Murray Nelson Govt. & Cultural Center, 8 p.m. curtain, Sunday 1 p.m. matinee.
Contact: (305) 453-0997
Key West / November 29 to December 06
Pirates in Paradise 2009 Historic Key West and Fort Taylor transform into a pirates’ stronghold with over 150 pirate entertainers. Tall ships, sea battles, arts and crafts, pirate sails, a living history encampment and nonstop entertainment!
Contact: (305) 296-9694
Islamorada / November 29 to December 05
Hobie Wave Race Week at Founders Park Come see the quick and light Hobie Wave catamarans as racers navigate triangle courses set around buoys. Race officials estimate at least 15 exciting races, bayside off the beach at Founders Park (MM 87). Call or visit Web site for details.
Contact: Rick White 305-451-3287
Email: rick@catsailor.com
Islamorada / December 01 to January 31
Florida Keys Gold Cup Sailfish Championship Anglers are to pursue sailfish, the most plentiful billfish in the waters off the Keys, in a series of competitions.
Contact: (305) 852-2102
Email: ditournaments@aol.com
Key West / December 01 to January 31
A Very Merry 1940s Christmas at the White House! See a collection of a number of WW II and 1940s Christmas decorations that bring holiday cheer to the LWH reflecting that period. Also on display is the Presidential Christmas Card collection of cards sent by the Presidents and First Ladies to staff and supporters. Admission tickets $15, discounts for seniors and children. Visit web site for details.
Contact: (305) 294-9911
Key West / December 02
South Duval Gallery & Cafe Neighborhood “HOWL” The quiet upper Duval neighborhood of small unique shops and cozy bars and lavish restaurants opens their doors for the full moon. Between Truman and United Streets, open 7 to 10 p.m. with food & drink specials, music, hospitality, arts and entertainment.
Contact: Judi Bradford
Email: (305) 304-4190
Key West / December 02 to January 02
Red Barn Theatre presents: “A Christmas Survival Guide” A Christmas Survival Guide is a jazzy “Santa’s Bag of Songs” which includes beautiful holiday classics that sometimes take an unexpected twist like “The Reindeer Boogie,” and “Sleigh Ride Gone Awry.” Featuring musical arrangements from many genres, this fast-paced and sometimes poignant show pulls from gospel, carols, secular and jazz styles. Showtime 8 p.m. Ask about group discounts!
Contact: 305-296-9911
Marathon / December 02
Crane Point presents: Moonlight Cocktails From 6-9 p.m., enjoy tropical cocktails, gourmet hors d’oeuvres, music by the Jim-Bob Jazz Combo and live entertainment from Josh Glisam-Fire Dancer. Contribution $25, tickets on sale at Crane Point, D’Asign Source, Food for Thought Bookstore, Marathon Chamber of Commerce and at the door the night of the event.
Contact: (305) 743-3900
Islamorada / December 03 to December 06
Islamorada Sailfish Tournament This competition is the first leg of the triple-crown Florida Keys Gold Cup Championship Series. The tournament is one of the oldest in the Florida Keys.
Contact: Dianne Harbaugh at (305) 852-2102
Email: ditournaments@aol.com
Marathon / December 03 to December 05
Marathon Community Theater presents: Incorruptible Who would have thought the Dark Ages could be so much fun? A fast-paced, laugh-a-minute look at how we humans willingly twist our convictions to rationalize our bad behavior.
Contact: (305) 743-0408
Key West / December 04 to December 05
FKCC Keys Chorale Holiday Concerts This annual event will feature the Magnificat by Monteverdi, and Laud to the Nativity by Respighi. The second half of the concert will feature holiday favorites for the entire family. Showtime 8 p.m. Friday, tickets $30 reserved, $20 general admission. Saturday 2 p.m. matinee, tickets $20 general admission. Children under 12 free with paying adult for both shows, at Tennessee Williams Theatre.
Contact: (305) 295-7676
Islamorada / December 04
Florida Keys Holiday Festival This extravaganza begins with a tree-lighting ceremony at Founders Park, MM 87. A holiday parade follows, featuring Santa, and continues with a holiday gift bazaar and silent auction of ornaments decorated by local artists.
Contact: (305) 664-4503
Big Pine & the Lower Keys / December 04
Artists In Paradise Presents Walk on Winn Dixie Stroll through stores and galleries for a fall night of art and live music, from 7 to 9 p.m.. Enjoy wine, beverages munchies and music.
Contact: (305) 872-1828
Islamorada / December 05 to December 06
A Lignumvitae Christmas It’s the late 19th century at the historic Matheson House from 9 a.m. to 3 p.m. Handmade trimmings and homemade treats are to be on hand for visitors. Take the short boat ride to Lignumvitae Key from Robbie’s, mile marker 77.5 bayside.
Contact: (305) 664-2540; 664-9814
Big Pine & the Lower Keys / December 05
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
Key West / December 05
Key West Holiday Parade Local leaders, civic clubs and churches share their holiday spirit by parading through historic Key West.
Contact: (305) 809-3700
Big Pine & the Lower Keys / December 06
Lower Keys Chamber Golf Tournament Amateur golfers are to compete for cash prizes, including $25,000 for a hole-in-one, at the Key West Golf Club. Shotgun 7:30 a.m., four-person scramble format, $100 per person. Call Lower Keys Chamber of Commerce for details.
Contact: (305) 872-2411
Email: executivedirector@lowerkeyschamber.com
Islamorada / December 09 to December 10
Islamorada Fishing Club Captain’s Cup Sailfish Tournament Anglers compete for a winner-take-all $25,000 jackpot for catching and releasing sailfish.
Contact: The Islamorada Fishing Club at (305) 664-4735
Email: fishing@theislamoradafishingclub.com
Islamorada / December 11 to December 13
Don Gurgiolo Sailfish Classic This all-release tournament offers the ever-popular ugly sport coat award in honor of Captain Don.
Contact: Tammie Gurgiolo (305) 852-9337
Email: fishnbully@msn.com
Key West / December 11 to December 12
Historic Lighted Inn Tours Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns. The tours include creative offerings by local chefs, artists, writers and performers.
Contact: (305) 295-1334
Key Largo / December 11 to December 13
Key Largo Christmas Pageant A cast and crew of over 50 people present a powerful musical drama about the real meaning of Show times are Fri/Sat 7 p.m., Sun. 10 a.m. & 6 p.m. FREE admission. Coral Shores Performing Arts Center, MM 90.
Contact: (305) 451-1642
Key West / December 12
Key West Lighted Boat Parade Decorated and lighted boats cruise through Key West Harbor and the waters of the Historic Seaport. The Gerald Adams Elementary School Steel Your Heart Band kicks off the festivities at 6:00 pm with a set of holiday tunes and standards on stage at Schooner Wharf, followed by the high energy Robert Douglas Band with Raven Cooper. Sponsored by Schooner Wharf Bar.
Contact: (305) 292-3302
Marathon / December 12
Crane Point presents: Holiday in the Hammock From 11 a.m. to – 3 p.m., families will delight in a day of fun activities in anticipation of the holidays! Have your picture taken with Santa, share lunch, visit the Elves’ workshop, listen and sign along to carols with the Stanley Switlik School chorus, as well as face painting, Barbles the Clown, tree decorating and games and prizes. Admission $5 per person (children under six free).
Contact: (305) 743-3900
Key Largo / December 12
Keys Community Concert Band presents: Holiday Melodies An extra special holiday concert, to be held at Key Largo Community Park, mile marker 99.6 oceanside. 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
Key Largo / December 12
Holiday Boat Parade Blackwater Sound will 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) 451-4502
Marathon / December 13
Stand Up for Animals Holiday Mutt Strut Bring your own or borrow a shelter mutt (purebreds okay, too) to join the strut. Costumes and pictures with the Grinch! Strutters are asked to get pledges to raise funds for Stand Up for Animals. Start location to be announced.
Contact: (305) 743-3779
Marathon / December 13
Key Colony 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. Open to all boats, 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.
Contact: (305) 743-7214
Islamorada / December 16
History of Diving Museum presents: Dive Safety A free program about new insights and fresh perspectives, from Alex Brylske, Ph.D. Immerse yourself in the fun! Starts at 7 p.m.
Contact: (305) 664-9737
Email: info@DivingMuseum.org
Key West / December 17 to January 09
Waterfront Playhouse presents: Twelve Angry Men Twelve jurors. Twelve walks of life. And only two ways to rule: Guilty or Not Guilty. When a 16-year-old boy is accused of murdering his father, his fate is left in the hands of a dozen men. What seems like an open-and-shut case becomes a twisted puzzle as evidence is revealed and prejudices are exposed. Showtime 8 p.m.
Contact: (305) 294-5015
Islamorada / December 18 to December 20
Islamorada Junior Sailfish Tournament Anglers through age 16 are to target sailfish for trophies.
Contact: Tammie Gurgiolo (305) 852-9337
Email: fishnbully@msn.com
Key West / December 18 to December 19
Historic Lighted Inn Tours Discover the history and holiday spirit of Key West by touring beautifully decorated historic inns. The tours include creative offerings by local chefs, artists, writers and performers.
Contact: Contact: (305) 295-1334
Key Largo / December 19
The Arts Foundation presents: CocoNutcracker The fourth annual production of The CocoNutcracker is presented to visitors and the community at the Coral Shores Performing Arts Center, with two shows at 2 p.m. and 7 p.m. The cast is all local dance students and admission is free.
Email: nina@joycebennettdance.com
Marathon / December 19
Free Christmas Concert Presented by and held at the Marathon Community Theatre; free for the public. Showtime 5 p.m.
Contact: Call 743-0408 for details.
Big Pine & the Lower Keys / December 19
Lower Keys Lighted Boat Parade If it floats, decorate it and join in the fun! Cruisers, dinghies, deep sea, kayak or canoes are welcome. Candy for the kids, Santa and Mrs. Claus to be there as well! Show starts at 7 p.m., view from the Pine Channel Causeway or Parrotdise Waterfront. Sponsored in part by Big Pine & Lower Keys Rotary Club.
Contact: Holly (305) 872-0106, (305) 879-6824
Islamorada / December 19
Keys Community Concert Band presents: Musical Holidays Concert Florida Keys Community Concert Band presents their annual holiday performance at Founders Park, MM 87 bayside, at 4:00 p.m. Performance is outdoors; no chairs provided. Free admission.
Contact: (305) 853-7294
Email: heinerdonna@yahoo.com
Key West / December 29 to December 30
50th 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
Key West / December 30
Key West Pops Orchestra presents: Home For the Holidays Alumni vocal and instrumental soloists are set to return to the Pops for this 7:30 p.m. performance at St. Paul’s Episcopal Church, 401 Duval Street; including Clinton Curtis, Daniel Curtis, Ralph Garcia, Stephanie Leone, Lina Robles, Carmen Rodriguez and Joe Lowe. Tickets $20, students & military $15, kids under 12 free.
Contact: (305) 296-6059
Email: info@keywestpops.org
Key West / December 31
Key West 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. Call (305) 296-2388, (305) 293-9800 and (305) 292-3302.
Key Largo / 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.
Contact: (305) 451-4502
For the perfect 
