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Key West Time
August 13th
5:10pm · 86°F

Happy New Years from VHKW!

What is it about dropping things from the sky at mid-night to ring in the New Year, and then lighting up the sky with fireworks? New York City is the best known, of course, for the dropping of the crystal ball in Times Square. But did you know that the tiny island of Key West, Florida, the southernmost City in the United States, has three of the most outrageous 'sky dropping' rituals you can imagine?

Key West is an exotic island, only two miles by four miles, with a diverse culture that's as quirky and creative as it gets. It's also known for over-the-top parties, and New Year's Eve is one of the best times ever. Here are three of the most thrilling choices: The descent of a giant red high heel shoe holding the exotic drag queen, Miss Sushi, in the 800 block of Upper Duval Street. Crews from CNN are on hand to feature this event to the world; The dropping of a super-size "Conch Shell" in the 200 block of Duval Street; and the lowering of a glamorous pirate wench from a tall schooner's mast in the island's Historic Seaport. Crowds swarm at all of the come-as-you-are events and are garbed in everything from formal attire to bathing suits. The following poem captures the essence of the wondrous New Years Eve night in Old Town Key West.

T'was the night before New Years, when all through the house,
Not a creature was sleeping, not even my spouse?
The champagne was set on the table with care,
In hopes 'Father Time' would soon be there.

Our friends were all dressed in their very best threads,
While visions of fireworks danced in their heads.
And Papa in his boxers, and I in my wrap,
Had just settled our brains for a pre-party nap.

When down in Old Town there arose such a clatter,
I sprang from the bed to see what was the matter.
I jumped on my bike and I rode like a flash,
Straight down Duval Street, I made a mad dash.

The moon on the lanes led most of the way,
For I'd lost my bike-light that very same day.
What suddenly appeared to my eyes on the scene,
But a giant red high heel, and saucy drag queen?

With Anderson Cooper, so lively and Gucci,
I knew in a moment it must be Miss Sushi.
More rapid than eagles her coursers they came,
All the 801 girls, as she called them by name!

"Now Josie! now, Kylie! now, Elle and Cassy!
On, Majon! On, Marilyn! You're all looking so classy!
To the top of the balcony! To the top of the wall!
Now get ready everyone! The shoe's gonna fall!"

As palm fronds that before a hurricane fly,
I jumped back on my bike and looked to the sky.
Much to my wonderment just down Duval,
A giant Conch Shell was strung high on the wall!

It appeared to be twinkling upon the roof-top,
At the strike of midnight it was scheduled to drop!
As I drew in my head, and was turning around,
The crowds were all swarming in downtown Old Town.

I jumped back on my bike and rode toward the wharf,
To take in the schooners and grab a quick quart.
When off in the distance I heard even more clamor,
Way up in the yard-arms was a wench with glamour?

Her eyes-how they twinkled! her smile how merry!
Her cheeks were like roses, her hair like a fairy!
Her beautiful mouth was drawn up like a bow,
And her perfect teeth were white as the snow.

The schooners back-stay she held tight in one hand,
With a sword in the other, she pointed at a rock band.
She had a glistening corset and a fine feathered cap,
Fishnet stockings and boots to bat!

She was gorgeous and happy and giggling at us all,
And I realized that she too, would take the midnight fall!
A wink of her eye and a twist of his head,
Soon gave me to know I had nothing to dread.

I sprang back on my bike, to the wench sent my best,
With visions of stuff dropping from skies in Key West,
Toward my house I rode back in the dark starry night,
Happy New Years to all, and to all a good-night."

-Poem written by Cindy Rhoades.


That's is, 2016 is drawing to a close and it’s time to ring in the New Year! If you’re lucky enough to be celebrating in our Southernmost City, the weather promises to be excellent. There are several popular venues around the island offering unique ways to celebrate the New Year "Key West Style.” Here are a few favorites and some information on how to catch these great happenings on the last night of 2016. The most popular events draw large crowds, so plan to arrive early to find your spot.

  1. The Conch Drop at Sloppy Joe's Bar - The show takes place on top of Sloppy Joe’s Bar, where a giant conch shell is lowered from the flat roof. An internationally famous Key West tradition for over 20 years, the best viewing spot is on the street at the intersection of Duval & Greene Streets. More Info Here.

  2. 'Diva Sushi' Red Shoe Drop on the 700 Block of Duval St. - For 16 years, Diva "Sushi" (aka Gary Marion) has taken center stage on New Year’s Eve when she's lowered in a giant red hi-heeled shoe from a 2nd story balcony. This is another internationally known event that takes place on Duval Street at the end of the 700 block. More Info Here.

  3. Pirate Wench Drop at the Schooner Wharf Bar - This one-of-a-kind world famous bar is fondly called "a last little piece of paradise," and rings in the New Year with a pirate flare. A few minutes before midnight, local favorite Evalena Worthington, co-owner of the Schooner Wharf Bar, will once again dramatically descend the 75 ft. mast of the Schooner Adirondack III, against the back-drop of lighted countdown numbers. Overlooking the Key West Seaport, this is a delightfully mesmerizing nautical themed alternative to the Duval Street bustle on the night of New Year’s Eve. More Info Here.

If none of these spectacles are your style this year, many popular Key West restaurants and smaller clubs have tables available for reservation for a more low-key setting to celebrate. Here are a few suggestions that are on or close to Duval Street:

Nine One Five:

915 Duval. (305) 296-0669
Created by owner Stuart Kemp, this fine European style tapas restaurant is a several-time winner of the James Beard Foundation Award for culinary excellence in New York. Located in a gorgeously renovated Victorian house with minimalist elegant interior, this is a great place to 'see-and-be-seen' on the town. The creative chef offers an eclectic variety of tapas, and full fare of gourmet food and fine wine selection to choose from. Everything is delicious. Dining inside or outside on the porches the overlook Upper Duval St. Great retro-design club room upstairs overlooking Duval St., 'Point 5', can be rented for private events. Excellent service. Friendly attentive staff.

Louie's Backyard and the Afterdeck Bar:

700 Waddell St. (305) 294-1061 -
Two of the best places on the island at the same location. Louie's Backyard restaurant is housed in a perfectly renovated Greek Revival Victorian Key West home that is on the National Register of Historic Places. Executive Chef Doug Shook offers award winning fine international and Caribbean Cuisine with a specialty in locally caught fish. The Afterdeck is on the expansive ocean deck in the back yard with a rare view and intimate feel of the ocean. Sunset, moonrise, and star gazing experiences are unsurpassed.

La Trattoria:

524 Duval Street. (305) 296-1075 -
Fine Italian dining. Wonderful food and excellent atmosphere feels a little like being in Italy. A perfect place for a special night out to celebrate. Everything is delicious. Great wine selection. Street side dining room and bar with great view of Duval St. It adjoins Virgilio's bar in the back on Appelrouth Lane, a local's favorite music venue and outstanding chocolate martinis.

Smokin’Tuna Saloon:
4 Charles Street. (Small lane off Duval St.) (305)517-6350 –
If you like the Key West tradition of 'dropping things from up high' on New Year’s Eve, one of Key West's newest bars & restaurants does something very unique when ... ta da ... ‘The Tuna Drops at Midnight,’ and everyone toasts with champagne. There’s a $10. cover charge for this fun event that includes your first drink. Smokin’ Tuna gets rave reviews from locals and visitors alike for great live music, fantastic fresh seafood & raw bar.


917 Duval St. (305) 295-0111 -
For the morning after, we love Martin's for a decadent gourmet Sunday brunch. The variety of choices on the menu for gourmet eggs benedict is impressive. They're also well known for their Bellini cocktails, and they offer delicious German specialty dishes and fabulous French toast. Martin's has a very chic island-cosmopolitan flare with both inside and outside with a view of Duval St. plus intimate garden dining in the back. Open for breakfast, lunch, and dinner.

Now you have some of our favorite things to do in Key West to ring in the New Year. Happy New Year from all the staff at Vacation Homes of Key West (VHKW). Have fun, and please play safe! See you in 2017.

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