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  • Writer's pictureLisa Codianne Fowler

Celebrating on a Sailboat is a (Key) Breeze!

Current and former owners of Key Sailing reunite

Happy people on sailboat
Sailing reunion with Jan holding the key to the city of Sarasota

It was a dark and cloudy morning. The skies were menacing. Yet, today was to be a special afternoon at sea, and my husband and I were delighted to be included in the celebration. Every year for the last 14 years, Jan and Tim Solomon of Key Sailing reunite with original owners Tom and Sally Reed for a festive sail.

On this day, both captains Tim and Tom predicted the conditions would be ideal during our allotted time on the water, regardless of the turbulence on land. But based on the weather at the moment, I lacked confidence that the trip would take place. I should have known better.

Here comes the sun

Just as we arrived at Marina Jack, the rain came to a sudden halt, the sun broke through, and the winds picked up. Turns out the passing morning downpour left us with stellar conditions for a picture-perfect sail. Once underway, Tim and Tom took turns at the helm, Tom steering with his feet – just like he used to when we sailed with him, Sally, and their seafaring dog Abby, many years ago.

Tom steering boat with his feet
Tom is Keybreezing with the classic foot drive move as Tim raises the mainsail

The guys quipped back and forth, joking about each other’s sailing skills and changes to the boat since Tim and Jan took over. Though it had been a few years since Tom captained a yacht, he seemed comfortable and adept at managing the 41' Morgan. "It's like riding a bicycle," he said.

Tim serenaded us with his guitar, and we sang boomer favorites. His repertoire is wide and varied, and even includes a boatload of melodic Spanish hymns.

Tom and Sally brought their lovely teenaged granddaughter, Hattie. Tim gave her a sailing lesson under the shade of the Bimini, after which she sunbathed on comfy cushions at the bow. We glided through Sarasota's mellow waters, with waves gently lapping against the hull, and playful dolphins leaping alongside.

The frosting on the cookie

Just when we thought it couldn't get any sweeter, Jan brought out decorative fresh-baked cookies from Publix that read "Your boat is my boat" and "My boat is your boat" in honor of the couples' reunion.


Fresh-baked cookies from Publix
Fresh-baked cookies from Publix

She brought out the Key to the City, presented the girls with bouquets of brightly colored roses, and, as she does for all of her guests, she served us mouthwatering fine chocolates. Jan presented one last treat when we arrived back at the marina… a delightful docking song she performs at the end of every trip.

The Solomon “Sailing Home” story

Jan is a local girl from 1960, whose hometown roots include 60 years of offering official prayers along with her family at our Bayfront ceremonies, including Jan’s original dedication for the iconic statue which marks the end of WWII. She was asked to return for prayer to commemorate the 75th anniversary of VJ Day. The monument of the “sailor and nurse” is slated to be removed and replaced by a roundabout and, in an ironic twist of fate, may just end up in the bayfront park named in honor of Jan's father, Chaplain Hamel, if the official recommendation of the Sarasota County Veterans Commission is approved by the city commissioners this fall.

Tim is a U.S. Coast Guard Master Captain and a licensed and ordained minister. He grew up overseas as a “Missionary Kid,” but learned to sail with Jan in 1975 at Sarasota High School. Tim and Jan were married in 1977 by both fathers, and together with their young children, they set off to change the world. Their global great adventures have taken them to more than 30 countries on five continents, and, as Jan quips, “It seems the world has followed us home.”


Sails up against Sarasota skyline
Sails up against Sarasota skyline

The company

Key Sailing is the longest-running sailboat charter in the history of Sarasota and Manatee Counties, with the ONLY sailing yacht (41’) in our city, and the ONLY company in our history hosting guests as a couple sailing at the helm together! It comes as no surprise that this relaxing, educational, and historical attraction has been recognized with multiple awards and the Trip Advisor Five Star Hall of Fame! Founded by Tom and Sally, it is now 24 years in operation. Previously frequent guests, The Solomons are now in their 14th year of operation, with Jan as the owner and Tim as captain.

Ready, set, sail!

Key Sailing currently only accepts private charter requests so that you will be sailing with your own family and friends. For details, directions, pricing, FAQ, and About Us pages, visit www.siestakeysailing.com. Call or text 941-346-7245 for the quickest response, 24/7.

Already sailed on Key Breeze? Catch up by writing: siestakeysailing@gmail.com

Want to help others? Key Sailing supports www.hopefleet.org


Reprinted from Siesta Sand newspaper, September 2020 issue


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