Fantasy Fest in Key West - Schedule of Events
Key West, FL -Here’s the schedule of events…so far. Please keep checking back for updates, we’ll do our best to keep you informed. If in doubt, email us at events@tripsmarter.com and we’ll find out what you don't know…or something like that!
This year, Key West celebrates 30 years of Fantasy Fest with even more fantastical fun shared as usual by more than 70,000 costumed partygoers from all over the world. This year's theme, "Pirates, Pundits and Political Party Animals"; is right in synch with the nation's political fervor and is expected to be every bit as zany!
Fantasy Fest 2008 promises to have it all! Parades, costume contests, street parties, and much more! Can't wait for Fantasy Fest 2008? Check out our Fantasy Fest Photo Gallery for tons of great photos from previous years!
Friday, October 17
Royal Coronation Ball
Meet Key West's Royal Family and vote for the King and Queen of Fantasy Fest 2008; a benefit for AIDS Help, Inc.; 6- 10 pm; Suggested donation $5
Goombay
Tastes, sights and sounds of the Caribbean in Bahama Village, located at Duval and Petronia streets. The lively street party continues Saturday! Noon - midnight; FREE
Saturday, October 18
Goombay
The party continues in Bahama Village! Noon - midnight; FREE
Monday, October 20
Dungeons & Dragons
A leather fetish party that's definitely not for the timid or shy!; 801 Bourbon Bar;(305)293-9800; 9 pm
Tuesday, October 21
Reddy Ice Fantasy Facade Competition
Festively decorated homes and
businesses compete for cold cash! To enter, call 305-296-5334
Finnegan's Wake Green Party
Come celebrate the ultimate Irish party!
Party in Plaid
Swing into Fantasy Fest at legendary Capt. Tony's Saloon! Explore your fantasies in naughty or nice plaid attire. Meet new friends, enjoy live music and rum specials all night long; www.capttonyssaloon.com;428 Greene St.; 9pm.
Free Official Fantasy Fest Poster Signing Party
Meet the artist of this year's poster! Crowne Plaza La Concha Hotel; 5 pm; posters for sale.
26th Annual
Headdress Ball
A gala where headdresses are the stars of the show; Prizes for Best Headdress: (costumes not judged) $1,000 first; $300 second; $200 third; 8pm; General Admission $30; Tables VIP for 4-$300 or for 4- $250; www.keystix.com or 305-296-1520.
Wednesday, October 22
Celebrity Look-a-like Contest
Imitators of the famous and fabled vie for cash and prizes; Crowne Plaza La Concha Hotel. Contestant sign up 8 pm; FREE to watch; FREE to enter.
1st Annual Dancapalooza
The newest competition and chance to win big $$$! Dancers of all ages are encouraged to compete. Dancers are judged on creativity, style and costume. Prizes for individuals, pairs and teams. Party start at 8:00 pm; Beachside Resort 3841 N. Roosevelt Blvd; For registration and ticket information call 305-296-8100; General Admission $20
Homemade Bikini Contest & Beach Party
Hog's Breath Saloon proudly presents the 21st Annual Fantasy Fest Homemade Bikini Contest and Beach Party. Details of the contest are at www.hogsbreath.com; 400 Front St.; 305- 296-4222; 10 pm.
Club Zu Sponsored Fantasy Fest Party
Leather and Lace will be the theme of the night. Sexy and Sensual vibes will fill the air. Wear the appropriate attire and drink for free from 8pm to 10pm; 422 Applerouth Ln.; www.clubzu.com; 305-295-2498
Pet Masquerade & Parade
A magical carousel of frisky pets and playful owners delightfully disguised and ready to frolic for fame and fortune; Location TBA
Thursday, October 23
Pretenders in Paradise
The legendary costume competition with $10,000
in cash and prizes! Combining extraordinary creative genius and performing energy,
this year's event promises to by eye popping entertainment; Pier House Resort & Caribbean
Spa, beachside; www.pierhouse.com;
8pm.
Cowboy Bill's 2nd Annual Git-R-Wet T-Shirt Contest
Catch the hottest ladies competing for $1,500 in cash prizes in this over-the- top competition. Contestants model the finest in creative cotton wet t- shirt apparel. DJ Bill Hoebee MC's all the wild festivities. See the action live at www.CowboyBillsKW.com 610 1/2 Duval St.; 10 pm; 295-8219; VIP seating available, Door Charge.
Pajama and Lingerie Party
The hottest Playboy model in the world, Kristy Morgan from the reality TV show "Tila Tequila,"encourages you to dress sexy for this skimpy affair. Enter the $700 Hugh Hefner and Marilyn Monroe look-a-like contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out. Purchase advance VIP tickets online at www.keystix.com; Mangoes; 700 Duval Street; 305-304-1188; 10 pm.
Sloppy Joe's 25th Annual Toga Party
"Still The Best Ancient Roman Party In Town!" To enter contest, contestants must be dressed in toga and are encouraged to dress in Fantasy Fest theme “Pirates, Pundits and Political Party Animals.” Three divisions: Groups/Couples $500 first place; Men’s $250 first place; and Women’s first place $250. Free to enter contest; registration at 8:00 pm and contest begins at 9:30 pm; Door charge; www.sloppyjoes.com; 201 Duval St.
Dante's 2nd Annual "Halos & Horns" Pool Party & Wet T-Shirt Contest
Whether you wear the halo of an ANGEL or prefer devilish HORNS, GET WET & WILD @ Dante’s for a chance to win BIG $$$! Free body painting, Live Music, Great Giveaways, Fantastic food and drink specials & our one of a kind stage in the CENTER of the POOL! The party starts at 1:00pm & goes till 6:00, pole dancing starts at 4:30; Dante’s Restaurant & Raw Bar; 951 Caroline St, next to the ferry terminal; 305-293-5123; keywest.com
Friday, October 24
Fairvilla Megastore Masquerade March
Join the crowd as they
parade through Old Town with music and noisemakers; thirst quenchers provided
at selected guesthouses. Begins at the Key West Cemetary Frances Street entrance;
revelers can join the mad march anywhere along the two routes; 5pm; All welcome;
sponsored by Fairvilla Megastore; www.fairvilla.com.
Annual Street Fair
Duval Street's mile-long extravaganza
features arts and crafts, food vendors, lively libations and costumed frivolity;
Duval St. from Noon to 10 pm; FREE
Wyland Galleries "Fantasy of Art" Extravaganza
Discover new artisitic fantasies by America's leading masters of ocean, surrealistic and dreamscape art. Celebrate Fantasy Fest's exuberant creative spirit at Wyland's 623 and 102 Duval St. galleries; 6-10 pm; 305- 292-4998 or 305-294-5240; www.wylandkeywest.com.
Pimp and Ho Party
America's #1 movie star, Ron Jeremy, invites you to come fulfill your fantasy at this exotic dance party. Enter the $700 Mr. Pimp and Ms. Ho costume contest, plus enjoy guest D.J.'s live. This event is guaranteed to sell out. Purchase advance VIP tickets online at www.keystix.com; Redfish Bluefish; 407 Front Street; 305-304-1188; 10 pm.
Rum Barrel's 2nd Annual Pirate Bash
Dress and DRINK LIKE A PIRATE at the Rum Barrel! Key West"s resident pirate and rum experts --- Pirate Soul Museum and Rum Barrel Restaurant & Bar --- team up to throw the most outrageous Pirates Bash in the world! More than $1500 in cash prizes for the best pirate and wench costumes, great music on the rooftop stage, and awesome rum specials. More info at RumBarrel.com or (305) 292-7862. Piratical inspiration at PirateSoul.com.; 9pm.
Presidents, Politicians and Public Affairs
Calling all "presidents, politicians and participants of their public affairs" to exercise your right to participate in the Southernmost Hotel in the USA 13th Annual Costume Contest, a pre-event to the half-way party of the Masquarade March! The most "theme oriented" costumes have the opportunity to win airline tickets, hotel stays and more!Grand Prize: 5 night stay at Southernmost Hotel and 2 round trip tickets on Southwest Airlines; $300 Cash ; 4-6 pm; www.southernmostresorts.com; Southernmost Hotel; 1319 Duval St.
8th Annual Living Art Airbrush Expo
Contestants will use the human form as a living canvas for artistic expression in competition for more than $1,500; drink specials and live entertainment; Sunset Pier at Ocean Key Resort; Painting and Partying Start at Sunset; judging begins at 9 pm; 305-295-7045.
Monster's Ball
Sea serpents, mermaids and other bizarre creatures of the deep! What lurks below and who's dancing on the reef? Dive into this annual costume party and explore some surreal fantasies and some-too-real fantasies that should perhaps remain submerged! Green Parrot Bar; 10 pm.
Saturday, October 25
Captain Morgan Fantasy Fest Parade
Join 70,000 exuberant partygoers
as this year's parade rolls down Duval Street. Featuring glittering floats, marching
bands and dancing groups, it doesn't get any wilder than this! Parade route includes
Whitehead, Front and Duval Streets; www.captainmorgan.com
Bourbon Street Pub - Tea in the Street
An afternoon street party starting at noon giving you a Taste of New Orleans decadence in Old Town Key West. Booze, Beads and Boys. Live entertainment and much more at the biggest street dance party of Fantasy Fest; 724 Duval St.
Duval Street Promenade
Sassy entertainers, enticing food and spirited
libations tempt costumed merrymakers as they party from the Gulf to the Atlantic;
Noon - 10:30 pm.
Sunday, October 26
"The Fat Lady Sings" Tea Dance
As the saying goes, "It ain"t over 'til the fat lady sings." Everyone will be at La Te Da from 4:00 pm to 9:00 pm for the last official event of Fantasy Fest 2008. DJ Junior provides the music for the last hoorah while local celebrity Sushi passes out free jello shots and beads. La Te Da Hotel, Restaurant, Cabaret and Bars; 1125 Duval Street; 305-296-6706; www.LaTeDa.com; FREE ADMISSION
Grog and Frog! With the Pirates of the Sanctuary Brunch
Ahoy Matey! Set sail and join the Pirates of the Sanctuary for some delicious “Grog & Frog". So round up your Captain and Crew and make your way to the shores of the Hyatt Key West Resort and Spa or face the perils of Davy Jones" Locker! Ahhhrrrrrrr! Enjoy the great fortune of complimentary mimosas and unlimited champagne $37.50 plus tax per Pirate and Pirates 12 and under half fare; Reservations suggested; Hyatt 601 Front Street; 11 AM - 3 PM; 305-809- 4000
Official Big Pecker Wine Tasting
Stop by MM 28.5 on your way out of town for a free wine tasting of Big Pecker Wine; the Official Wine Sponsor of Fantasy Fest 2008; 11 am to 11 pm; Parrotdise Waterfront Bar & Grille; 183 Barry Ave., Little Torch Key; 305- 872-9989; www.parrotdisewaterfront.com
Children's Day
A family event featuring food, games, arts and crafts and a costume contest for children. Bayview Park at Truman Ave. and Eisenhower Dr.; 305-292-8912 
