Festivals and Events
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| Key West Festivals and Events |
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| Key West is famous... for staging many fabulous and unique world-famous festivals and special events throughout the year that make for Key West vacations that are exciting and memorable. Here we provide you with a selection of some of the more popular events and major festivals that many of our vacation rental guests plan around their Key West vacations. Our guests know that choosing a vacation rental property from Vacation Homes of Key West provides them with the most authentic, comfortable, convenient, and generally the most affordable accommodation from which to enjoy their favorite Key West festivals and events year after year. Due to the demand for our vacation rentals, we encourage you to reserve your Vacation Homes of Key West property for your Key West vacations well in advance for the most popular festivals and events. | |
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| JANUARY 2008 | |
| International Yacht Race Week (Jan 12 – 19) |
This has become one of the most important and premier sailing yacht races in the world with world class competitors. www.Premiere-Racing.com Contact: (781) 639-9545 Email: KWinfo@Premiere-Racing.com |
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| Sculpture Key West (Jan 20 to April 19) |
Opens at West Martello Museum – and then expands to Fort Zachary Taylor on February 24. An amazing annual contemporary outdoor art exhibit. www.sculpturekeywest.com Contact: (305) 295-3800 Email: info@sculpturekeywest.com |
| FEBRUARY 2008 | |
| Civil War Heritage Festival (Feb 7 to 10) |
Fort Zachary Taylor. Civil War scenes are staged and re-enacted by actors in full Civil War costume. Tour the Fort and learn about our islands’ past. www.fortzacharytaylor.com Contact: (305) 292-6850 |
| Key West Garden Tours (Feb 9 – 10) 11:00 am – 3:00 pm |
Start at Nancy Forrester’s Secret Garden at One Free School Lane (off 500 block of Simonton St., Key West). www.greensong.org Contact: (305) 294-0015 Email: nancy@nancyforrester.com Then tour private homes and gardens participating in the tours. www.oirf.org Contact: (305) 294-9501 |
| Key West Boat Show & Nautical Market (Feb 29 to March 2) |
Truman Waterfront. New boats from leading boat dealers in the Florida Keys. Live music. www.keywestboatshow.com Contact: (305) 393-6099 |
| MARCH 2008 | |
| 48th Annual House and Garden Tours (March 14 – 15) |
Contact the Old Island Restoration Foundation. www.oirf.org Contact: (305) 294-9501 |
| Hot Havana Nights (March 8) |
Party in the Key West Tropical Forest and Botanical Garden, from 7 pm to 11 pm. Live music featuring Miami’s Havana Soul, Cuban art, silent auction, and Cuban cuisine. Call for tickets. www.keywestbotanicalgarden.org Contact: (305) 296-1504 Email: kwbgs@bellsouth.net |
| Key West Fishing Tournament (March 14 -16) |
Kick-off for annual seasonal-long tournament. Prizes and awards for best catches. www.keywestfishingtournament.com Contact: (305) 295-6601; (800) 970-9056 Email: director@keywestfishingtournament.com |
| APRIL 2008 | |
| World Sailfish Championship (April 15 -19) |
Fish in the day and fun filled evenings of food, drink and entertainments. www.worldsailfish.com Contact: (305) 395-3474; (727) 631-0072 Email: lemmole@worldsailfish.com |
| Conch Republic Independence Celebration (April 18 - 27th) |
Celebrate the spirit of the Conch Republic with a commemoration of its founding in response to a U.S. Border Patrol roadblock that stopped traffic in and out of the Florida Keys on April 23, 1982. www.conchrepublic.com Contact: (305) 294-2298 Email: conchcept@aol.com |
| 13th Annual Taste of Key West (April 21) |
Truman Waterfront. A culinary celebration that includes booths of many of Key West’s presenting delectable samples of their best cuisine to benefit AIDS Help, Inc. www.aidshelp.cc Contact: (305) 296-6196 |
| Key West Songwriters’ Festival (April 30 - May 4) |
13th-annual showcase featuring some of America’s foremost performing and upcoming songwriters. Concerts in intimate casual settings throughout the island of Key West. Presented by Hog's Breath Saloon, 400 Front St., Key West. www.hogsbreath.com Contact: (305) 296-4222 |
| MAY 2008 | |
| Harry S. Truman Legacy Symposium (May 16 - 17) |
“Harry Truman and Immigration.” The political history of Key West is addressed in panel discussions. Tour The Little White House (located in Truman Annex) where President Harry Truman worked and recreated while he was in office as President of the United States. www.trumanlittlewhitehouse.com Contact: (305) 294-9911 |
| Yamaha Dolphin Masters Invitational (May 31) |
Experienced offshore captains compete for big prize money in dolphin fish tournament. Contact: (305) 304-7674 Email: wave.whacker@hotmail.com |
| JUNE 2008 | |
| PrideFest Key West (June 7 -15) |
A festival honoring the Key West concept of “One Human Family” that embraces and honors diversity, openness and freedom in the little island city that is recognized as one of the world's top gay and lesbian vacation destinations. www.pridefestkeywest.com Contact: (305) 292-3223 |
| Southernmost Swordfish Tournament (June 14 – 15) |
Overnight swordfish challenge that is part of the season-long Key West Fishing Tournament. www.keywestfishingtournament.com Contact: (305) 295-6601; (800) 970-9056 Email: director@keywestfishingtournament.com |
| JULY 2008 | |
| Conch Republic Ladies' Dolphin Tournament (July 05) |
Women who love to fish are invited to complete to catch dolphin fish for cash prizes. Contact: (305) 304-7674 Email: wave.whacker@hotmail.com |
| Hemingway Days (July 15 – 20) |
This will be the 28th celebration of the legendary Ernest Hemmingway’s work and lifestyle in Key West and Cuba. It features literary readings, short story competition, fishing tournament and Sloppy Joe’s Ernest Hemmingway Look-Alike Contest. (literary events) Be sure to visit the Hemmingway Museum where he lived. www.hemingwayhome.com Contact: (305) 296-2388 (Look-Alike Contest); (305) 294-0320 |
| AUGUST 2008 | |
| Lobsterfest (August 8 – 10) |
Street fair celebrating Florida lobster with live music and delicious lobster. Live bands start a 1:00 pm and go until 11:00 pm. www.keywestlobsterfest.com Contact: (305) 849-2706 Email: erik@keywestwalkingtours.com |
| SEPTEMBER 2008 | |
| Woman Fest (Sept 4 – 9) |
Social activities staged at various locations around the island of Key West. This is the 22nd legendary event for women! Activities include pool parties, dances women only sunset sails and dolphin watching. www.womenfest.com |
| 36th Annual Key West Poker Run (Sept 19 – 21) |
From Miami to Key West. www.petersonskeywestpokerrun.com Contact: Matt Cochran (305) 295-3286. |
| OCTOBER 2008 | |
| Goombay Festival (Oct 17 – 18) |
Annual authentic Caribbean island style street fair in Key West’s unique Bahama Village. Some of the streets are closed for pedestrian traffic only. Local island food, art, music and entertainment. Local’s favorite event to meet in the street. Find the center of the festival around Petronia and Thomas Streets near Blue Heaven Restaurant at 729 Thomas St. www.goombay-keywest.org |
| Fantasy Fest (Oct 17 – 26) |
This is the 30th annual festival. The theme for 2008 is “Pirates, Pundits, and Political Animals.” Fantasy Fest is festival with entertaining costume events and contests each night that culminates with main event adult entertainment parade on Saturday night October 25. Events leading up to the parade include a variety of events that are staged in various locations around the island. Some events such as the Pet Masquerade can include the family but for the most part this is an adult event. www.fantasyfest.net |
| NOVEMBER 2008 | |
| Parrot Heads in Paradise (Oct 30 – Nov 7) |
17th Annual Convention Meeting of the Minds. Jimmy Buffet fans meet in Key West every year for the “Meeting of the Minds”; “Bar Stools and Beach Chairs” is the theme for 2008. To attend you must be a member in good standing of a Parrot Head Club. There are over 200 chapters in the US, Australia, Canada and Europe, including the Virtual Parrot Head Club. www.phip.com/MOTM.asp |
| Super Power Boat Races (Nov 2 – 9) |
Super Boat International presents the biggest, fastest boats in the world. www.superboat.com Contact: (305) 296-6166 |
| Pirates in Paradise (Nov 29 – Dec 7) |
A gathering of pirates, pirate lovers, and those who love the pirate lore. Costumes, parades, staged events. A fun filled gathering full of costumed pirates and pirate performers. Events are staged throughout Old Town Key West. Contact: (305)296-9694 Email: info@piratesinparadise.com |
| DECEMBER 2008 | |
| Holiday Parade (Dec 6) |
The City of Key West closes down Truman Ave. and hosts the annual locals Holiday Parade. Truly an authentic and charming small-town holiday celebration for everyone in the family. Watch the local paper in December for details; “The Key West Citizen.” www.tripsmarter.com Contact: (305) 809-3881 |
| Lighted Boat Parade (Dec 13) |
Hosted by the Schooner Wharf Bar – 202 William St. Historic Seaport. A beautiful lighted parade in Key West Harbor mostly of local boats from the Florida Keys and Key West that are creatively decorated with bright lights and animated holiday themes. Live music and food surrounds the event on the waterfront. An authentic Key West maritime tradition enjoyed by locals and visitors from all over the world. www.schoonerwharf.com Contact: Sherry (305)-292-3302. |
| New Years Eve (Dec 31) |
World Famous Dropping of ‘The Conch Shell’ at Sloppy Joes Bar at 201 Duval St. Watch the six foot Queen Conch Shell drop with synchronicity as the clock strikes mid-night to giant six foot tall bottles of champagne. www.sloppyjoes.com Contact: (305) 294-8759 |
For more events, you may want to visit the Key West Chamber of Commerce web site. www.keywestchamber.org |
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