Fantasy FestNot for the faint-hearted, this wildly outrageous, world-renowned event which takes place from Friday, October 20 – 29, celebrates over four decades of fun and debauchery. This year’s theme: “Uniforms & Unicorns—200 Years of Sailing into Fantasy.” is sure to stir your creative juices. For late-breaking news, hit up fantasyfest.com. Have fun and be safe!

FRIDAY, OCTOBER 20
Noon-Midnight Goombay Festival
Historic Bahama Village, Petronia St., FREE!

3 – 6 pm Goombay Jam in the Courtyard
Rams Head Southernmost, Historic Bahama Village, Petronia St., FREE!

4 – 7 pm Pink Pool Party
Pink drink specials, pizza specials, silent auction & more. The Marker Key West, 200 Williams St. 305-501-5193, FREE!

8 pm The Rocky Horror Show
That sweet transvestite and his motley crew are back for the Time Warp.
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

SATURDAY, OCTOBER 21
Noon-Midnight Goombay Festival
Historic Bahama Village, Petronia St., FREE!

Noon – 4 pm Prohibition Pool Party
Gates Hotel, 3424 N Roosevelt Blvd. 305-320-0930

3 – 6 pm Goombay Jam in the Courtyard
Rams Head Southernmost, Historic Bahama Village, Petronia St., FREE!

7 – 9 pm The Arena Rock Show
Ocean Key House Sunset Pier, Zero Duval. 305-492-2307. FREE!

7 pm 8th Annual Smallest Parade in the Universe
Workbench-size parade floats that celebrate the theme of this year’s Fest (Cult Classics and Cartoon Chaos). The 18″ floats are auctioned off during a mini-parade down a replica of Duval Street. Takes place at The Studios of Key West, 533 Eaton St. Info 305-296-0458; tskw.org.

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

In this Sunday, Oct. 22, 2017, photo provided by the Florida Keys News Bureau, bicycle riders roll during the Fantasy Fest Zombie Bike Ride Sunday, Oct. 22, 2017, in Key West, Fla. The ride, which attracted thousands of locals, was one of the many events set for the island city's 10-day Fantasy Fest costuming and masking celebration that continues through Sunday, Oct. 29. FOR EDITORIAL USE ONLY SUNDAY, OCTOBER 22
11 am – 2 pm Post Goombay Bloody Mary Brunch
Rams Head Southernmost, Historic Bahama Village, Petronia St. $

2 – 6 pm Zombie Bike Ride
Starts at Fort East Martello, 3501 S Roosevelt Blvd. zombiebikeride.com

6 pm ZombieFest Official After Party
Coffee Butler Amphitheater, 21 E Quay Rd.

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

MONDAY, OCTOBER 23
Noon – 4 pm Duck, Duck Booze Pool Party
Perry Hotel, 7001 Shrimp Rd, Stock Island. 305-296-1717. FREE!

4 – 8 pm Fantasy Beard Contest
All genders! General Horseplay, 423 Caroline St. 305-741-7599.

5:30pm, 9pm & 11pm Beatles Tribute Concert
Green Parrot Bar, 601 Whitehead St. 305-294-6133. $

5:30 – 8:30 pm Hog Roast & Beach Party
Southernmost Beach Cafe,1405 Duval St. Info:305-295-6550. $

6:30 pm Martini Monday
Virgilio’s, 524 Duval St. 305-296-1075.

8 pm Pirates of the Conch Republic:
The Search for Bodacious Booty – A Burlesque Parody, Key West Theater, 512 Eaton St. 305-294-4004. $

8 pm – 1 am Kinky Carnival
First Flight Brewery, 301 Whitehead St. 305-293-8484. $

8 pm Comic Book Cape-ers Party
Sloppy Joe’s Bar. 305-294-5717.

10pm – 4 am Tops or Bottoms Underwear Party
Men only. Island House Resort, 1129 Fleming St. 305-294-6284. $

TUESDAY, OCTOBER 24
11 am – 5 pm 5th of July Party
Dante’s Restaurant & Raw Bar, 951 Caroline St. 305-293-5123.

2 – 5 pm Pirates & Parrot Heads Pool Party
Margaritaville Beach House, 2001 S Roosevelt Blvd. 786-751-4190.

2:30 – 4:30 pm 3rd Annual Fantasy Fest Bar Crawl
Kicks off from the Conch Republic Seafood Co, 631 Green St. 305-292-9994. $

3 – 5 pm Fantasy Fest Poster Signing Party
La Concha Hotel, 430 Duval St. 305-296-2991

5:30 – 6:30 pm Tutu Tuesday Pre Party
General Horseplay Complex, 423 Caroline St. 305-741-7599.

7 pm – 4 am Cocktails for Animal Tails Benefit
Rick’s Complex, 202 Duval St. 305-294-4857. $

7 pm Tutu Tuesday Dance Party
Aqua Complex, 711 Duval St. 305-294-0555.

8 pm Pirates of the Conch Republic:
The Search for Bodacious Booty – A Burlesque Parody, Key West Theater, 512 Eaton St. 305-294-4004. $

8 pm Party in Plaid
Capt. Tony’s, 428 Greene St. 305-294-1838. FREE!

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

10pm “Who Dat” Party
Green Parrot Bar, 601 Whitehead St. 305-294-6133

Fantasy FestWEDNESDAY, OCTOBER 25
11 am Slumber Party
Sloppy Joe’s, 201 Duval St. 305-294-5717.

Noon – 3 pm Living on the Edge Pool Party
Oceans Edge Resort & Marina, 5950 Peninsular Ave, Stock Island. 877-935-0862.

5 – 8 pm Humpday Pool Party
Men only. Island House Resort, 1129 Fleming St. 305-294-6284. $

6pm – ??? Luau Party
Margaritaville Cafe, 500 Duval St. 305-292-1435

6:30 pm Pet Masquerade & Parade
Truman Waterfront Amphitheater, 21 East Quay Rd. Petmasquerade@hotmail.com.

7 pm WHARFSTOCK
Schooner Wharf Bar, 202 William St. 305-292-3302; schoonerwharf.com. FREE!

8 pm Homemade Bikini Contest
Smokin’ Tuna Saloon, 4 Charles St. 305-517-6350. FREE!

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

8 pm Pirates of the Conch Republic:
The Search for Bodacious Booty – A Burlesque Parody, Key West Theater, 512 Eaton St. Info 305-294-4004. $

9 pm – 1am Lucy’s Blue Party
Lucy’s Retired Surfers Bar, 221 Duval St. 305-922-2616

9 pm Luv2Glow Party
Mary Ellen’s Bar, 420 Appelrouth Lane. 305-916-5816. $

10 pm – 4 am Desire Male Fetish Party
Bourbon St Pub, 724 Duval St. 305-293-9800. $

10 pm – 2 am Party Like A Rock Star Costume Party
KAYA Backyard Bar, 618 Duval St. 305-395-0213. FREE!

Fantasy FestTHURSDAY, OCTOBER 26
11 am – 1 pm Naughty Bike Ride
Registration Pre-Party, 803 Duval Parking Lot. keystix.com. $

11am – 2 am Annual 80’s Party
Irish Kevin’s, 211 Duval St. 305-292-1262. $

Noon – 6 pm Halos & Horns Pool Party & Wet T-Shirt Contest
Dante’s Restaurant, 951 Caroline St. 305-293-5123. $

6:30 – 10:30 pm Glittery Disco-Themed Party
La Concha Hotel, 430 Duval St. 305-396-2991.

7 pm Rock the TaTas Contest
Benefits “Making Strides Against Breast Cancer.” Hanks Hair of the Dog Saloon, 409 Caroline St. 305-509-7758.

8 pm 40th Annual Headdress Ball
Truman Waterfront Park, 21 E Quay Rd. 305-294-4603; gaykeywestfl.com. keystix.com.

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

8 pm Pirates of the Conch Republic:
The Search for Bodacious Booty – A Burlesque Parody, Key West Theater, 512 Eaton St. Info 305-294-4004. $

9 pm Pink Party
Fat Tuesday, 305 Duval St. 305-296-9373.

10 pm – 4 am Exposed
Bourbon St Pub, 724 Duval St. 305-293-9800. $

Fantasy FestFRIDAY, OCTOBER 27
10 am – 5 pm Fantasy Market Truman Waterfront Park, 21 E Quay Rd. FREE!

10 pm – 2 am Island Vibes Reggae Night
KAYA Backyard Bar, 618 Duval St. 305-395-0213.

Noon – 5 pm Bowties & Birthday Suits
Men only. Island House Resort, 1129 Fleming St. 305-294-6284.

Noon Tea In The Street & Pool Party
Bourbon Street, 724/801 Duval St. 305-293-9800. FREE!

Noon – 5 pm Beach Bunny Pool Party Bash
Southernmost Hotel, 1400 Duval St. 305-296-3141.

Noon – Midnight Block Party
San Carlos Institute, 516 Duval St. 305-294-3887.

4 – 6 pm Red Elvises Pool Party
The Marker Resort, 200 Williams St. 305-501-5193. FREE!

5:30 pm Masquerade March
Begins at the Key West Cemetery Frances St. entrance. FREE!

7 pm Living Art Airbrush Expo
Sunset Pier, Zero Duval 305-295-7047. FREE!

7:30 pm Masquerade March After Party
Green Parrot, 601 Whitehead St. 305-294-6133.

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

8 pm Pirates of the Conch Republic:
The Search for Bodacious Booty – A Burlesque Parody, Key West Theater, 512 Eaton St. 305-294-4004. $

8 pm – 4 am Kinky Couples Only Party
801 Bourbon Bar, 801 Duval St. Tickets: 786-886-4766.

10:30 pm Rock-N-Roll Fantasy & Costume Contest
RockHouse Live, 135 Duval St. 305-440-3263. $

SATURDAY, OCTOBER 28
10 pm – 2 am Under the Sea – Live Like a Pirate Costume Party
KAYA Backyard Bar, 618 Duval St. 305-395-0213.

Noon – 5pm Pool Party
Clothing optional. New Orleans House, 724 Duval St. 305-294-9800.

Noon – Midnight Block Party
San Carlos Institute, 516 Duval St. 305-294-3887.

3 – 6 pm BBQ & Rock N’ Roll Party
Southernmost Beach Resort, 506 South St. 800-354-4455. FREE!

6 pm VIP Parade Balcony Bash
Bourbon Street, 724/801 Duval St. Tickets: 305-293-9800; keystix.com.

6 pm Parade Viewing Party
Hard Rock Cafe, 313 Duval St. Tickets: 305-293-0230.

7 pm Fantasy Fest® Parade
It doesn’t get any wilder than this! Duval St. FREE!

8 pm – 4 am Kinky Couples Only Party
801 Bourbon Bar, 801 Duval St. Tickets: 786-886-4766

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

SUNDAY, October 29
Noon – 5 pm Children’s Day
Bay View Park, Truman Ave at Eisenhower Dr. 305-292-8912. FREE!

Noon – 5 pm After Church Pool Party
Men only. Island House Resort, 1129 Fleming St. 305-294-6284.

1 – 4 pm Hangover Rehab Pool Party
Southernmost Beach Resort, 506 South St. 800-354-4455. FREE!

2 – 5 pm Reggae Rehab Pool Party
The Marker Key West Harbor Resort, 200 William St. 305-501-5193.FREE!

4 – 8 pm “The Fat Lady Sings” Tea Dance
La Te Da, 1125 Duval St. 305-296-6706. $

6 pm Fantasy Fest Close-Out Concert
Sunset Pier, Zero Duval St.305-809-8072.

8 pm The Rocky Horror Show
Waterfront Playhouse, 310 Wall St. 305-294-5015; waterfrontplayhouse.org.

And that’s a wrap, folks! For event details, hit up fantasyfest.com.

Archives

Categories

cruise direct
orbitz
cruise critic
travelocity
orlando vacation
extended stay
expedia
Dolphin Reaserch Ad
Aqua D blog ad