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FANTASY FEST – Key West, Florida – the best Halloween party on the planet! I was thrilled to attend my THIRD Fantasy Fest in 2022. One must be very “open-minded” to attend the week-long activities, as almost anything goes! It is always held the entire week leading up to Halloween, and it is an Adult party, not appropriate for children.

Be sure to reserve your hotel at least 7-9 months ahead of time to get a reservation at a great place (I recommend The Opal Resort on the Bay and The Southernmost House on the beach – both right off Duval (See Hotel section), and at least a 3-night minimum stay is suggested and often required for the Festival. Another favorite Hotel is the Best Western Hibiscus (good rates and free breakfast) located on Simonton Street, one block back from the ocean, and two blocks from Duval Street – the main drag of activities in Key West.

Check out the Key West Fantasy Fest website to see the full list of activities for the week, and prepare your costumes way ahead of time – because, yes, people dress to impress for these events! 

The Best parties require a ticket, and some sell out months ahead of time. Be sure to go to ALL Parties early – Some of my Favorite events for 2022 (and in the past years) are –

1) Playboy Bunny Pool Party – Southernmost House1400 Duval St, Key West.  Our FAVORITE Party! Get there early in your Best Bunny & Hef Outfits – as the line lasts for hours if you are late! Host & Owner Michael Hapner (Hef in the Pic) greeted us and welcomed us to his beautiful, historical mansion – the most luxurious B & B in Key West built in 1897.  Visited over the years by Thomas Edison who put the original electricity in the home, Al Capone, John F. Kennedy, Hemingway, Louis Armstrong, and Gloria Swanson, you too can enjoy this gorgeous property on the beach and at the Southernmost point on Duval St – that was graced by the rich and famous (see complete hotel write up under Hotel section).  This is an incredible party prepared by Hotel Manager Nina Powers who worked her magic preparing the property right after Hurricane Ian hit the property with outer bands. Join all the fun with Bunny dancers, an incredible DJ with the BEST dance music, and a Super Fun & Pretty party crowd! Held from12-5 pm.






2) Dantes Devil & Angel’s Pool Party; 951 Caroline St. The doors open at 11 am; get in line by 9:30 am to get a seat in the shade when you get in. We had great table service and enjoyed the scene that was attended by about 2,000! This is always such a cool party, held from 12-6 pm.

3)  Toga Party Night – Hosted at the infamous Sloppy Joe’s Bar on Duval Street; but you’ll see Togas all over all night long – so pack your best! Join all the parties, Sloppy Joe’s is packed, so get there early! Party starts at 8 pm; Free!

These are just a few samples – there are MANY other parties – about 5 a day during the full week of Fantasy Fest – I brought about 12 outfits with me, and we enjoyed dressing for each party. Pick your favorites, get your tickets early, and come enjoy the BEST Halloween Festival ever! There is a Huge Parade with tons of neon lights on Sat night – so be sure you stay to see that!

Philadelphia, PA:

HENRY DAVID BALL – downtown Philadelphia, PA Ok, this is the 2nd most fun Halloween party on the planet! : )  Hosted by Henry David of Philadelphia, and always held on Halloween night starting at 9 pm at the Sheraton Hotel Ballroom on 17th and Race, Philadelphia, this party has raised funds for HIV/AIDS awareness for over 40 years. The ticket price is $25 if in costume and $75 for those in street clothes – so obviously, hardly anyone is not dressed in a fantastic fantasy fare.

I have attended over 6 of these events, and am never disappointed by the great costumes and fun, friendly people. At midnight, there is a Parade of costumes for prizes, in several categories.Next Halloween, treat yourself by dressing trick for the party of over 1500 party-lovin people!

Boynton Beach, FL

PIRATE FEST – 100 Ocean Ave, Boynton Beach, FL 33436 – Hey Matie’s! Throw on your Best Pirate, Wench, or Mermaid outfit and come to this weekend event held Sat and Sunday, from 11 – 8 pm. Concerts, art booths, lots of food & drink, Pirate actors all over the place – it’s really a fun time when you get into the Halloween – Pirate Mentality! Come escape for a fun-filled day! Halloween weekend. 



NEW YORK CITY STREET FAIRS – New York, New York – located on different Avenues throughout the city of New York, this street fair is held every Saturday and Sunday from spring through fall – and stretches out for as long as 15 blocks or more. Vendors of every type, and the best values on so many items – be prepared to deal for the best prices. Held from 9 till 5, wear some comfortable shoes and stay all day.

Great deals on sunglasses, scarves, jewelry, arts and crafts, belts. socks, sheets, makeup, plants, and some yummy vendor food. Take a large shopping tote to collect all your goodies!on Sat


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