A captain who has answered his calling

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With some prominent family history at his disposal, Matt Reid is a natural storyteller at the helm of his Siesta sunset cruise

By Jane Bartnett

On a late spring evening, Capt. Matthew Reid stood on the deck of CB’s Saltwater Outfitters on Stickney Point Road. With a distinctly southern drawl, he greeted his passengers and welcomed them aboard the 30-foot tour boat that would take them out to enjoy one of Siesta Key’s famous sunsets.
“This vessel can carry up to 19 passengers, but we’re only nine tonight so we all have plenty of room for dancing,” he said with a laugh.
Then he introduced his first mate and wife, Janna Reid.
As he got behind the wheel of the High Tide Tiki Tours boat, owned by Parasail Siesta, the captain eased the boat out of the slip and into the Intracoastal Waterway. The three-hour journey began.
With the sun dipping ever so slightly in the sky, a golden haze covered the Siesta Key waterfront homes. Reid ramped up the music. His passengers smiled, chatted and laughed.
“When we start a cruise,” he said, “we fit the music to the passengers.” Starting off with a distinctly upbeat country tune, he gave everyone a preview of where the boat would travel and what sights they would see. A family from Ottawa, Canada, were aboard with three teenage girls, along with a 20-something couple from Austin, Texas. All were new to Siesta Key.
“How ‘bout we have some dancing?” said the captain.
“Great music, love it,” said the dad as his wife got up to dance.
“You’ve got it,” Reid said encouragingly. “Hey, I’ve had a 90-year-old lady dancing on this boat. C’mon y’all!” The mood was set.
Even a pod of dolphins came near the boat to play. “We’re gonna have a great cruise tonight,” proclaimed the captain.

Capt. Matthew Reid at the wheel during one of his sunset tours along Siesta Key. (photo by Jane Bartnett)

Being out on the waters of Siesta Key comes naturally to the Sarasota native who spent his childhood on boats, discovering the area’s islands and waterways. He traces his family roots back seven generations to 1858, noting it played an important role in the region’s history.
“My great-grandfather Sam Sweeting was Mr. Ringling’s personal fishing captain and he once escorted John Ringling and a visiting prince from Syria on a fishing trip,” said Reid, referring to the legendary Sarasota entrepreneur and circus founder. In 1925, Time Magazine named Ringling one of the wealthiest men in America.
“My grandfather knew this coast all the way to the Bahamas. He ran a fishing boat business out of Marina Jack for 45 years.” Reid said wistfully.
A generation before that, in the early 1900s, Reid’s great-great grandfather served as Bertha Palmer’s head rancher and managed the 37,000 acres belonging to the Chicago millionaire businesswoman and philanthropist. “That land,” Reid said, “is now Myakka State Park.”
As an adult, Reid has taken his place back on the water, following in the footsteps of family members who came before him. Few can say that they know the secrets of the islands and the waterways that surround Siesta Key better than Reid. “About five years ago, I took my first U.S. Coast Guard license test to get my captain’s license. It’s a challenging test,” he recalled.
No stranger to challenges, Reid spent his early adult years in the U.S. Army. After returning to Sarasota, he went into the construction and masonry business but the water kept calling him back.

Reid awaits a departure from Stickney Point. (photo by Jane Bartnett)

For Reid, spending each day watching the sun set over Siesta Key is about as close to paradise as it can get. Creating truly memorable experiences for Siesta Key visitors has become his new life mission. “True southern hospitality has been lost in this area,” he said thoughtfully. “We’re trying to bring back that flair.”
A knowledgeable tour guide as well as a skilled captain, Reid offers details on the homes along the shoreline, tidbits about how dolphins teach their newborn babies to breathe, the life of manatees, and details on the many bird species that call this area home.
As he brought the vessel into an area filled with mangroves, he announced that we had arrived in the “Siesta Key Bayou,” an area behind Skiers’ Island, heading toward the North Bridge. “That’s not the official name, but that’s what I call it,” he said as the passengers laughed. The pontoon boat’s low draft, Reid explained, allows travel into shallow areas.
As the sky turned into spectacular shades of red and pink and yellow, Reid slowed the boat and everyone took pictures. As darkness fell and the sky darkened, the time had come to return to shore. “This was a good night, y’all,” said the captain.
To book a High Tide Tiki sunset, morning or afternoon tour, visit parasailsiesta.com/pontoon-boat or call (941) 260-1566.

First mate Janna Reid photographs a couple visiting from Texas. (photo by Jane Bartnett)
Jane Bartnett
Author: Jane Bartnett

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