In case you missed the January Mainebiz article, for the first time since summer 1974 in Boothbay Harbor, there will not be a schooner owned by Herb and Doris Smith or their son and daughter-in-law, Tom and Jennifer. Eastwind was built by Herb and Doris and launched in 1999. Tom and Jennifer bought Eastwind 14 years ago and the Lazy Jack two years ago. They sold both boats to Schooner Explorations of Maine, LLC – Paul McGrail, Sean Rowley and Rod Veal – Dec. 15, 2022.

The trio were no strangers to the Smith-built Appledores; they already owned the Appledore II that had been sailing out of Camden since John and Jane McKean bought her from the Smiths in 1988. There is also the Appledore Star, which has been sailing out of Key West for decades.

McGrail, Rowley and Veal’s Sebago Watersports began partnering with the McKeans in 2003 when they would bring Appledore II down to the Sunshine State for the winter.

While Rowley was in Maine to see the ships a few weeks back, he said the Eastwind is the “perfect boat.”

“Everything Herb and Doris learned building boats over all those years they put into Eastwind,” Rowley said. “She has laminated frames, brass riveting … She’s perfect.”

Nineteen-year-old Rowley learned a thing or two about shipbuilding before meeting McGrail during the three years he worked for Frank Luke at the Luke boatyard in East Boothbay. He went on to build catamarans with McGrail for Sebago Watersports.

“When Tom’s (Smith) lawyer called us to say the boats were for sale we said we want them,” Rowley recalled. “We are so excited. Our goal is to improve where needed to keep up with the times. Eastwind will be at Hodgdon for some cosmetics, but it is in incredible condition. It looks like a 4-year-old boat, but is really 24 years old. Apple Jack will be at Paul E. Luke’s getting new floor timbers and forward planks; paint will be removed and reapplied. We are passionate about our boats.”

When Rowley was about 13, he saw the Apple Jack sailing past the island he and his father had sailed to. “I said I’m going to own that boat someday.” 

Local boat builder Tony Finocchiaro of Boothbay is Schooner Explorations of Maine’s shipwright. “I’ve known Tony for years – and I love Bet,” said Rowley. “Tony’s a very skilled wooden boat shipwright. There isn’t anything he can’t fix.”

Rowley said Eastwind will never be renamed. Lazy Jack was renamed Apple Jack largely as an homage to the Smiths and their five Appledores – plus, the company already had the Appledore Star. 

This season, both ships will take passengers on three-day sails and one sunset cruise, with Veal and Rowley as captains. Eastwind will begin the season in Camden May 16. When Appledore II returns from her winter port in Key West, Eastwind will return to Boothbay Harbor and join Apple Jack for the 2023 season.

Both ships will have alcoholic beverages available, a historical narrator will be on board; and passengers will be encouraged to help hoist the sails and take photos of themselves at the helm.

Locals will sail for half price. Rowley said the aim is to get all the year-rounders out for some fun.

“Paul and Rod and I are the stewards of these boats. It’s our job to take care of them, love them, maintain them ... they will go on under us,” said Rowley. “We are very excited about this season.”