Tips for 1st time attendees to October's Fantasy Fest in Key West, Florida

Key West Travel Blog

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The TravelSl_t Top Ideas for First Time Fantasy Fest attendees

You are in for a treat both for the Fantasy Fest event itself and for Key West.

While I've only been 9 times, I have learned a few things through personal experience or 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 up 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.

Toiletries & Medical Supplies: Essentials if you plan do to the "Duval Crawl" include: aspirin, Tylenol, antacids, Pepto-Bismol, and Chaser Plus.
You should also have available at your hotel or B&B at least some insect repellent, sunscreen & aloe vera gel.

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 at this latitude.

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

There are parking garages, meters and some free side-street parking but again, if there is something going on in Key West (which seems to be most every weekend), then parking may be both expensive and limited.

Be cautious driving on the one-way streets, the narrow streets and the streets where the conch train operates. Watch out for bicycles, pedalcabs, small electric vehicles and of course, pedestrians.

Key West is small and compact in size and some streets are both narrow and have obscured sidewalks or side paths so watch your step--especially at night.

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

Be careful on the streets of bicylists and people riding scooters or Vespa's that may not be used to operating them. It is easy to be distracted while looking and at the sites of Key West.

Key West also has a "conch "train that operates on both main and side streets-be sure to give it leeway as it is long in length.

Coming into Key West's "new town" at the north end of the island, is a culture shock after driving the previous 50 miles or so. Key West is modern and developed and fully recovered from 2005's devastating Hurricane Wilma but ongoing renovations and construction of new condo units continue. Be cautious of traffic controls, traffic workers, and slow-downs. Don't be in a hurry.

Traveling along Highway US 1 (now called 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.

2009's theme is: " Villains, Vixens and Vampires" from Oct. 23 to Nov. 1

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 clothing (or lack thereof) rules!

Nightly themes include: (and you should really consider costumes for every night)

Monday night-- features a "Dungeons & Dragons" Leather-Fetish Party @ the 801 Bourbon St. Bar. It's not uncommon to see dozens if not hundreds of people dressed in leather or latex or some variation for this party or the many others featured in non-sanctioned venues. Also Monday is Leather & Fetish @ Kelly's Kinky Karnival at Kelly's Caribbean. (Personally, I've attended the leather-fetish party @ Kelly's Caribbean Bar & Grill for several years and this is definitely not the place for anyone shy or timid).

I am sure that many of the people in attendance both on the streets and in the bars and private parties are amazed at the costumes and antics of the crowds. Words cannot describe here what you might see so you will have to use your imagination. My photos only scratch the surface.

Tuesday night--features Plaid Nite & bodypaint @ Capt. Tony's Saloon

Tuesday night has several parties throughout Key West and this is good as it keeps crowds down & separated so you don't feel so crowded & congregated.

Remember, depending on the statistics used, Key West grows from a small town of 25,000 to almost 100,000 for Fantasy Fest as crowds are estimated to be from 50,000-75,000 and most are primarily situated in an area on a one-mile section of town called Duval Street.

Tuesday nights festivities included everything from an 80's Flash Back Dance Party at Fat Tuesday's to a Headdress Ball, a concert, there is a free poster signing party and Capt. Tony's Saloon highlights the evening with its "Party in Plaid" event. I can usually be found spending my evening here.

Wednesday night--features Red Night @ Fogerty's & elsewhere on Duval Street

Wednesday night the crowds really start to arrive and Duval Street is blocked off to allow only pedestrian traffic late at night.

There is a two block long section of Duval which is labeled the "Fantasy Zone" where open containers of beer, wine or alcohol are permitted and flow freely from bars and vendors. I often try to use vendors that use a portion of their proceeds for local charities.

The theme for the night is "Red" and Fogerty's & Flying Monkey's Bar is the place to be-- although other events are also fun including:

Pet Masquerade & Parade at the Westin Key West resort (daytime)
Celebrity Look-a-Like contest @ La Concha
Cheeseburger's Feeling Lucky Luau
Rock till you hit Bear Bottom Party @ Bear Bottom Beach Club
Beach Party @ Hog's Breath Saloon with world famous Homemade Bikini Contest

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

Thursday nights theme is Toga 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!

Fantasy Fest features several events throughout old town including Nightmares in Dreamland; Pretenders in Paradise costume contest (where the prize money is $10,000) at the Pier House Resort & Caribbean Spa; Monsters Ball at the Green Parrot Bar and of course, the famous (Hemingway used to hang out here) Sloppy Joes 26th annual Toga Party with a $1,000 cash prize.

Again, Duval Street becomes an event in itself with thousands of people costumed and as many taking photos or just watching.

Cruiseship passengers that happen to be in port for the week sure get an eyeful.

The remainder of the festival has many events both Friday and Saturday night 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 Parrotdise Bar & Grill Happy Hangover Party on Little Torch Key and a conclusion somewhere that focuses on "it's over when 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 is tough except for the knowledge that the next Fest is less than 360 days away!

Now, for some important Do's and Dont's of Fantasy Fest:
(and thanks to the person that created this list where ever you are)

Don't wear a mask you can't drink in.

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.

Do make sure you have a place to stay before you get too drunk.

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 pubic hair 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.

Don't ask the cops to flash you.

Do understand that just because you are naked doesn't mean that others find you

Don't go out carrying valuable items that you are likely to lose 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 consider getting a personal catheter for parade night as unoccupied bathrooms will be scarce (just joking)

Don't verbally abuse anyone before stepping inside a porta-potty as the result could be disastrous and gross.

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 lots of pictures but use a disposable camera if you are prone to losing them. And asking 1st if it is OK to take a photo will usually mean yes and you will get a nicer, posed shot or two.

Do exercise a little tact and courtesy with the folks working in the bars through the festivities. They are there working days off for your enjoyment.

Don't tip in beads - they 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 stick your tongue down the bartender's throat unless of course he wants you to (just joking, again)

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

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

Ann, The TravelSl_t  :-)
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photo by: X_Drive