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Tiki-themed ‘Tipsy Skipper’ hoping to open downtown Ocala lounge this winter

The Tipsy Skipper is hoping to open the doors on its new tiki-themed lounge in downtown Ocala later this year.

The new business, which is located next door to the Marion Theatre at 48 S Magnolia Avenue, recently announced via Facebook that they were planning on opening their doors in “early-mid November,” indicating that they would “announce a grand opening date” when finalized.

The Tipsy Skipper in Ocala, Florida
The Tipsy Skipper has plans to open soon in downtown Ocala, Florida

In an email to, the business says that although they are still hoping to open in November, it is “seeming more like December.”

The Tipsy Skipper bills itself as a “1950’s boutique, tiki-themed lounge” that will feature a rotating selection of cocktails, juices, and “secret menu items hidden throughout the town.” The interior is filled with tropical decorations and the tiki bar’s logo, which was designed by local tattoo artist Adam Roof, features a hula dancer with an island backdrop.

The Tipsy Skipper Logo - Adam Roof
The Tipsy Skipper logo was created by local tattoo artist Adam Roof

Just before this year’s Ocala Arts Festival, the business installed new windows, and earlier this fall, they shared a sneak peak photo of the interior.

The Tipsy Skipper
The Tipsy Skipper shared this image on their Facebook earlier this fall

Regardless, the restaurant joins a growing list of businesses that have opened in downtown Ocala in just the past six months, including Big Hammock Brewery which opened its doors in May, and Bank Street Patio Bar and The Black Sheep on Broadway, which started serving customers in early October.

Later this year, The Mellow Mushroom, a popular pizza restaurant chain that serves creative pizzas in a setting filled with funky art and decorations, has plans to open a location in the building formerly housed by Brothers’ Keeper Thrift Store.

For more information on the opening of the new tiki lounge, visit The Tipsy Skipper website.

Do you have plans to try the new tiki lounge? What other types of businesses would you like to see open in downtown Ocala and throughout the rest of the city? Share your opinions with us in a comment below, a letter to the editor, or by visiting us on Facebook, Instagram, or Twitter.

Photos in Ocala, Florida

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