Rum runner fans rejoice at O'Leary's reopening

By Dana Kampa
| 3:30 p.m. May 5, 2025

Arts + Entertainment
Eat + Drink

Greg Corvelle, regional director of food and beverage for O'Leary's Tiki Bar & Grill, joked the restaurant should have sold tickets for the many patrons who gathered along the waterside of Sarasota Bay to see a boat wrecked on the dock by the monstrous winds of Hurricane Milton get hauled away.

By coincidence, removal day fell on O'Leary's official reopening after the storms. The watering hole opened its doors at 11 a.m. on Friday, heralding a new chapter in its history since the first grand opening in the 1980s.

The bayside restaurant has idyllic views of Sarasota Bay from its sandy shore, and Lana Jackson, general manager for the past five years, shared how she focused on expanding and fortifying the restaurant for the future.

Friday marked the day O'Leary's Tiki Bar & Grill bid farewell to the boat washed up on its dock and celebrated its reopening.

Builders made notable structural improvements. From the sealed glass walls designed to keep out floodwaters to the Tiki bar support beams cemented into place, the rebuilt restaurant isn't going anywhere anytime soon.

However, Jackson said she is glad they could still maintain the easygoing, breezy aesthetic of the establishment.

There are also some customer-facing improvements they made Jackson thinks visitors will enjoy, like the new on-tap beers, which replaced the restaurant's ice cream offerings.

Permitting was a main factor in the timeline for the reopening, but Jackson said she is pleased with what they've been able to accomplish in the downtime.

"This has been a long time coming," she said.

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Corvelle said the restaurant didn't even know for certain that it could go ahead with its planned opening until the day before. They needed the city to do one final make sure everything was ready to roll.

Among the opening day attendees were Sarasota residents Larry and Susan Siebl. While enjoying a rum runner and Mai Tai and the shade from the sunshine above, they welcomed back one of their favorite go-to spots in the city, especially for breakfast.

"We walk here quite a bit, so we've been monitoring it," Susan said. "We like it a lot because it's a casual vibe with fun people."

Corvelle said he looks forward to welcoming familiar and new faces, and if he could make a recommendation to anyone, it would be the "Rachel" sandwich with a side of mozzarella sticks. But he said it's tough to go wrong when enjoying a meal at one of the best places on Sarasota's coast.

Sarasota residents Larry and Susan Siebl were fans of O'Leary's Tiki Bar & Grill before hurricanes Milton and Helene, and they were thrilled to join staff in celebrating the official reopening on Friday.

T.J. McKenna tends bar at the official reopening of O'Leary's Tiki Bar & Grill on Friday.

Patrons of O'Leary's Tiki Bar & Grill coincidentally got front-row seats to bid farewell to a wrecked boat brought on by last year's hurricanes.

General manager Lana Jackson shares a smile with the newly refurbished and strengthened O'Leary's Tiki Bar & Grill at her back.

Perks of the new renovation include the addition of on-tap brews for the bayside bar.

Customers at O'Leary's Tiki Bar & Grill can look forward to some pending additions, including a larger outside bar.

Ron Rigot, attending the grand reopening of O'Leary's Tiki Bar & Grill with wife Audrey, gives his stamp of approval for bartender T.J. McKenna's rendition of a piña colada.

Opposite the bar, O'Leary's-branded gear greets guests returning to the Sarasota establishment.

Outdoor picnic benches quickly began to fill up at the grand reopening of O'Leary's Tiki Bar & Grill.

Removal crews busted out the heavy machinery to remove a wrecked boat, one of the last physical reminders of the damage caused by hurricanes Milton and Helene.

Onlookers lined the beach to watch the boat removal.

author

Dana Kampa

Dana Kampa is the Longboat Key neighbors reporter for the Observer. She first ventured into journalism in her home state of Wisconsin, going on to report community stories everywhere from the snowy mountains of Washington State to the sunny shores of the Caribbean. She has been a writer and photographer for more than a decade, covering what matters most to readers.