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Key West & Fantasy Fest Every Halloween Week


Key West & Fantasy Fest Every Halloween Week

Key West, especially during Fantasy Fest, is called "Mardi Gras on Steroids"  as the Conch Republic do it "their way".

The 39th Annual Adventure and Rendezvous in Paradise at Fantasy Fest in Key West, Florida is set for October 19-28, 2018—-& the theme is "Oh, the games we play"

I know I can’t wait for the 39th Annual Fantasy Fest—in and around Capt. Tony’s Saloon, Kelly’s, Sloppy Joes, Duval Street…..and in and out of costumes and bodypaint!


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Location: Key West, Florida, USA
Members: 9
Latest Activity: Oct 14, 2018

Tips for 1st timers to Fantasy Fest in Key West, Florida every October during Halloween week

Hello and get ready to enter the world of Fantasy Fest in Key West , Florida which I have often referred to as "Mardi Gras on Steroids".

Also, a question I get all the time are requests to help find accomodations and I have used <a href="" rel="nofollow"></a>; for several years for places to stay. Just ask for Susie and tell her Ann The TravelSlut referred you.

I also think you should be informed before you go as either a FF veteran or 1st timer to FF about some tips that may make your experience more fun.

In addition, while in Key West, learn about the nightly meets by various groups and learn where the best parties are for each night as many are announced only on the day of the party.

The TravelSlut® 's Top Tips for First Time Fantasy Fest attendees

You are in for a treat both for the Fantasy Fest event itself and for Key West which is a great, eclectic island-city in itself.

While I've only been 14 times to FF since 1999 (and 30+ times to Key West), I have learned a few things through personal experience or from the experience of others: (in no particular order):

Clothing/Shoes/Weather Gear: Key West is a walking town especially on and around Duval Street so comfortable, soled shoes or sandals are a must. Don't walk downtown in barefeet as the streets are likely to have either debris or glass, etc. that could cut your feet. Also, in the heat, both streets and sidewalks heat up tremendously and you don't want to either burn your feet or have to do an emergency purchase of shoes/sandals from a downtown vendor unless absolutely necessary. Consider having a lightweight/foldable rain poncho for those occasional showers to protect bodypaint or costumes.

Toiletries & Medical Supplies: Essentials (especially if you plan do to a "Duval Crawl" include: Aleve/Tylenol, antacids, Pepto-Bismol, and or special hangover OTC meds. Also have available at your hotel/B&B some insect repellent, sunscreen & aloe vera gel or know where the nearest source of these items can be found.

Camping/Beach/Outdoor Gear: If you plan to do the beaches, bring a blanket and or chair and some sort of sun protection. The sun is brutal on skin not normally exposed to this heat and UV's at this latitude. A beach or gear bag works also for carrying around Key West even at night while in costume.

Transportation: During high season or any major event, parking can be almost non-existent near Duval Street even if you have a reservation at Bed & Breakfast, motel or hotel. Don't even think about parking in a resident's zone unless you have specific permission or blocking a driveway or access point as the fine and/or tow bill will be huge.

There are parking garages, meters and some free side-street parking but again, Key West during Fantasy Fest parking will be both expensive and extremely limited. This is especially true for Fantasy Fest week when Key West's island population swells from 26,000+ to well over 50,000+.

Be cautious driving on the one-way street & the narrow streets where the Conch Train operates. Watch out for bicycles, pedalcabs, small (silent) electric vehicles, mopeds and of course, pedestrians. Open drinking and walking occurs 24/7 so be careful in all regards with driving and/or walking.

Key West, while small & compact in size, has some streets that are both very narrow and have obscured sidewalks/driveways so watch your step--especially at night. Some walkways are not level, are obstructed, or even have debris of some type.

Be extremely careful driving as pedestrians (sometimes intoxicated, sometimes jaywalking) will walk right out in front of you from previously hidden or obscured areas.

Be wary on the streets for bicylists and people riding scooters/mopeds that may not be careful in operating them. Finally, it is easy to be distracted while looking at the people and sites of Key West so concentrate on driving.

Key West also has a "Conch Train" that operates on both main and side streets so be sure to give it leeway and right of way as it is a very long train.

Coming into Key West's "new town" at the north end of the island there can be a culture shock after driving the previous 50 miles or so. Key West is modern and developed and always seems to have ongoing renovations/construction. Be cautious of traffic controls, traffic workers, and slow-downs. Don't be in a hurry. Remember, you are on "Island Time" now and the 26,000+ full time residents will appreciate patience as will your additional fellow 50,000+ Fantasy Fest revelers.

Traveling along Highway US 1 (aka North Roosevelt Blvd. and at mid-town, Truman Avenue), you will start to see the signs of the Fantasy Fest celebration as many people decorate their homes and businesses in the colors or theme of the event.

2018's theme is “Oh the Games we Play" and is the 39th Anniversary of Fantasy Fest and this year runs from Friday, Oct. 19 to Sunday, Oct. 28 with the big parade on Saturday, Oct. 27 basically culminating the week of Halloween-type fun.

Key West during Fantasy Fest is definitely not for the timid or shy and small children should not be downtown after dark (or at all if possible). Bodypaint, nudity and skimpy, sexy/see through clothing rules day and night and is very prevalent especially in the Fantasy Zone on Duval Street!

Nightly costume themes, both official and unofficial, can be found on the main Fantasy Fest website of <a href="" rel="nofollow"></a>;.

You really should consider costumes for every night for the most interactions and best-fun participation--and expect to be photographed/videotaped in all public areas.

The official events and activities of FF can be found here: <a href="" rel="nofollow"></a>; Refer to this for a comprehensive list of activity/party options.

Other unofficial events, parties and activities occur regularly around Key West and some are even spontaneous so ask veteran Fantasyfesters for the latest updates. And here are all the 2018 Krewe de Krazy Life events, parties and activities (thanks to ER):

Friday - Mad Hatter Party at Capt. Tony's 8pm
Saturday - Little Black Dress at Capt. Tony's 8pm
Sunday - Meet and Greet At The Sunset Tiki Bar at the Galleon 1pm
Sunday - Pirate Party at Capt. Tony's 8pm
Monday - Rubberball at Capt. Tony's 8pm
Tuesday - Tie Dye Tripping Tutu Scooter Krawl 12:45pm
Walkers meet at Lucy's Retired Surfers Bar & Restaurant
Scooters meet at HogFish Bar & Grill on Stock Island
Tuesday - Party in Plaid at Capt. Tony's 8pm
Wednesday - ABC Costume contest at Sandbar Sports Grill at 1pm
Wednesday - Capt. Tony's Journey Thru Time at Capt. Tony's 8pm
Thursday - Charity Raffle Bar Krawl Starting at Capt. Tony's at noon
Thursday - Pretty in Pink Party at Capt. Tony's 8pm
Friday - Masquerade March "Doing Time" meets at Susie's house at 4:30pm
Friday - Tripping to the 60's Krewe Private Party at The Oriole Club 8pm
Saturday - Decorate Float at the annex at noon
Saturday - Fantasy Fest Parade Capt. Tony's Time Travellers starts at 7pm.

So you can start planning your costumes.
All our events are free to attend except for the Friday Private krewe party and the Saturday Parade.
More info will be posted on the website soon.
Tickets will go on Sale August 1st.

Here are some of my favorite parties with the Krewe de Krazy Life that I have experienced since 1999. Nightly gatherings 7 pm-??? occur at Capt. Tony's Saloon.

1st SATURDAY NIGHT-- Little Black Dress Night at Capt. Tony's Saloon. Anything goes but keep it PG on the streets as there are still many tourists and residents prepping for FF and unaware of the quasi-clothing-optional nature of FF. Save the risque fun for the bars and clubs and use common sense to cover up on the street.

SUNDAY NIGHT--Pirate, Wench and Booty Night with the earlybirds of Fantasy Fest getting warmed up at various venues around town and Capt. Tony's has been the place to be the past few years to the point that police have shut down Greene Street south of Duval Street to accomodate the overflow.

MONDAY NIGHT-- Fetish Night features all those in leather, vinyl, rubber and all types of Fetish and Fantasy wear up to and including bodypaint (which is acceptable any night). It's not uncommon to see 100's (if not 1,000's) of people dressed in leather or latex or some variation for this various parties.Many others parties exist in non-sanctioned venues. Again, Capt. Tony's has a special celebration in their Dungeon side room called Capt. Tony's Rubber Fetish Ball.

Also, MONDAY is Leather & Fetish costume theme night@ Kelly's Kinky Karnival at Kelly's Caribbean Bar & Grill restaurant. I've attended this leather-fetish party @ Kelly's for several years and this is definitely NOT the place for anyone shy, timid or shocked easily as you will just about everything and anything..

Plan to be amazed at what you see, hear or even experience on the streets, in the bars and at the private parties. The costumes and actions of the crowds are often awesome and amazing Some of the photos in my Flickr Group and some of the videos in my YouTube videos only reveal a small aspect of happenings..

TUESDAY NIGHT--features the Plaid Party @ Capt. Tony's Saloon and in addition to the other parties throughout Key West. Crowded parties are the norm especially as the week goes on.

WEDNESDAY NIGHT--features Red Night @ Fogerty's & elsewhere on Duval Street and the crowds really start to arrive. Usually Duval Street is blocked off to allow only pedestrian traffic late at night and a long section of Duval is labeled the "Fantasy Zone" where open containers of beer, wine or alcohol are permitted and are served from bars and vendors. I often try to use street vendors that use a portion of their proceeds for local charities.

All the while these official events are occurring, many bars and saloons feature their own party theme and of course, thousands of people flock into the streets and sidewalks of Duval where people-watching takes on a new level.

THURSDAY NIGHT--features Toga Night @ Sloppy Joes & everywhere else and there are thousands of togas and variations of them everywhere in Key West. After all, togas are relevant to party times and are easy to make or buy, and they feel great!

Again, Duval Street becomes an event in itself with thousands of people costumed and as many taking photos or just people watching and cruiseship passengers that happen to be in port during the week sure get an eyeful.

The remainder of the festival has many events both FRIDAY and SATURDAY NIGHTS with Friday's highlight being the Duval Street Fair, Masquerade March and Pimp N Ho party while Saturday night features a Bourbon Street Tea Dance, Bodypaint Contest @ the Green Parrot and Captain Morgan Fantasy Fest parade where 70,000 onlookers and 50+ or more floats are all part of the celebration's pending conclusion down Duval Street on Saturday Night.

SUNDAY NIGHT: the town almost returns to "normal" and has a children's day at a local park and a conclusion somewhere that focuses on "it's not over until the fat lady sings".

The drive back home or the flight back home is always a challenge. Between hangovers, crowds, and general dismay about returning to reality, leaving Key West and Fantasy Fest can be tough except for the knowledge that the next Fantasy Fest is less than 360 days away!

Now, for some important DO's AND DON'T's of Fantasy Fest:

Don't wear a mask you can't drink in or see out of.

Don't choose a costume you can't use the bathroom in.

Don't wear shoes you can't walk in.

Do dress sexier than you thought you might initially (but no nudity in public and if walking from residential areas, consider a cover-up for modesty purposes).

Do make sure you have a place to stay before you get too drunk and find yourself under a tree or on a sidewalk.

Do realize that the shape and size of your breasts/penis will not change with spray paint.

Don't wear your thong with your leg in the wrong hole.

Do trim your private areas within the limits of your costume ...please.

Do donate your leftover items to locals who want to enjoy Fantasy Fest as much as the rest of us but often just make room for us.

Don't flash the cops. Not cool, not legal.

Don't ask the cops to flash you. Really not cool.

Do understand that just because you are near-naked doesn't mean that others will accept your choice of costume.

Don't go out carrying valuable items that you are likely to lose if/when you get drunk--- such as a purse wallet, expensive jewelry or your spouse.

Do wrap your money in plastic or a ziplock first if you have nothing to carry it in but your bikini bottoms or sweaty shorts.

Do know that unoccupied bathrooms will be scarce all week

Don't verbally abuse anyone---ever!; Everyone is there to have a good, laid back time.

Don't be in a hurry---remember you are on (overcrowded) island time

Don't step in front of moving parade floats to pick up candy or beads.

Do be aware that if you take Henrietta home with you may wake up with Henry.

Do take pictures but be polite, patient, and asking 1st if it is OK to take a photo will usually result in a yes answer and you will get a nicer, posed shot or two. Also, have your camera ready to shoot FIRST before you ask.

Do exercise some tact and courtesy with the folks working in the bars and cafes. They may be there working their days off for your enjoyment. Drinks take time to create and be served as so meals.

Don't tip in beads - service workers don't want or need beads--- tip with cash please.

Don't ask the female servers to show you their boobs--there are thousands of women on Duval Street dying to show you all that they've got.

Don't try to touch, kiss, etc service workers or Fantasy Fest workers or other costumed Fantasyfesters..

Do carry some info or business card of your hotel/B&B address so someone can help get you home if you need help late at night should you be too intoxicated.

Don't be afraid to dress up. Have an outrageously fun time and tip big.

And for those that can't make Fantasy Fest either this year or next year here is an option--------------

The 13th Annual Reunion-Rendezvous of FantasyFesters and KrewedeKrazyLifers will occur June 16-23, 2019 at the wickedly-wild, renovated Hedonism II resort in Jamaica where we will again enjoy theme nights like Fetish, PimpNHo, Plaid/Schoolgirl, Pirate/Wench and Toga, costumes, plus 24/7all-you-can eat and drink, a nude day cruise and twice-daily complimentary nude snorkeling & scuba,, and all in a cashless, clothing optional-nude environment where you don't even tip because everything is included in one low, group rate. More info: with 6,800 members and 3,800 photos.

Daily updates of Fantasy Fest and my other travels:

All my Fantasy Fest videos are here:

In the meantime, take care, travel safe and have safe fun!
NOTE: I MAY miss my 15th Fantasy Fest this October as I return from Australia sometime in late October.

Ann, The TravelSlut :-)
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Comment by Ann, TS on October 14, 2018 at 6:12am

Update:  I am still traveling in New Zealand as of October 13 and will be in Sydney, Australia on business until at least October 24 so I will miss my 15th Fantasy Fest unfortunately.

But, fortunately there is still the lucky 13th Annual Krewe de Krazy Life group trip June 15-22, 2019 for a Fantasy Fest-Caribbean style available to me and all singles and couples for more fun in the sun and special delights at night both in and out of costumes and clothes at Hedonism resort in Jamaica.

Email me for details, rates and availability:


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