The 61st annual Windjammer Days will take place Sunday, June 25 through Saturday, July 1, 2023. This year the Friends of Windjammer Days is celebrating our rich population of Maritime Explorers. Those featured have traveled extensively on different bodies of waters either for work, pleasure or both.

Nowadays Herb and Doris Smith live a relatively quiet life since they have retired to their self/built log home. Among other pastimes, Doris now kayaks and Herb pens books and sails on the Appledore Child, but their lives over the past several decades have been anything but quiet.

Herb and Doris first came to Boothbay Harbor in 1974 when they sailed the Appledore I, a 49-foot schooner Herb had just built. They planned to sail from Portsmouth to Rockland but were hit by a big squall by Sequin Island and were nearly knocked down so they decided to pull into to the nearest port which was Boothbay Harbor. They fell in love with Boothbay Harbor and soon started a day chartering business out of the Spruce Point Inn. Herb had previously worked as a cinematographer on an icebreaker that sailed to Antarctica and Greenland so he did not hesitate to sail to the Caribbean that winter and many winters after that where Doris and Herb again ran day charters.

In 1978, they launched their second vessel called the Appledore II, a 65-foot schooner which they helped build with the Gamage Shipyard in South Bristol, Maine. The Appledore II sailed around the world via the Panama Canal. The trip lasted a year and a half and visited 50 ports of call ending up at Portsmouth, New Hampshire in May of 1980.

After that voyage, the Smiths moved to Littleton, New Hampshire where they tried to live a “normal” life but found it wasn’t for them. They soon were building their third schooner, Appledore III. She was launched in Newburyport, Massachusetts and made her way to Boothbay Harbor where they were given permission to dock in front of the Fisherman’s Wharf Inn and charter out of the hotel. That summer Herb also began planning another trip around the world in the Appledore III. This time they followed a different path through the straits of Magellan which allowed them to visit more out of the way islands. This voyage was completed in Boothbay Harbor in May of 1986.

Next Herb had a 65-foot steel replica of the Appledore II built in Florida for the purpose of traveling around the five great capes of the world with his whole family which now included three children. The new Appledore IV first ran charters along with the Appledore III out of Fisherman’s Wharf in the summer of 1988 and in the fall of 1988 it set sail on the longer voyage. Upon reaching Bermuda, Herb decided it was more prudent to spend the winter in the Caribbean. After chartering her again over the summer of 1989 in Boothbay Harbor, they decided to sell the Appledore IV.

The Appledore IV was built as a 56-foot replica of the Appledore III. The plan was again to sail around the five capes. At the last minute Herb decided he just couldn’t do it knowing that his son was looking forward to his first year of high school and the chance to play football. The rest of the family was in agreement. After being chartered for a couple of summers, the Appledore IV was sold, but Herb was able to continue to manage it until the new owner decided to put it up for sale.

At this point boat-less, Herb and Doris starting building a wooden boat which was launched in 1999 as the Eastwind. That winter Herb and Doris, accompanied by their daughters, sailed to the Caribbean. This was the last “big sail.” The Eastwind was sold to their son Tom who ran her out of Boothbay Harbor for 14 years until being sold this past year.

Asked whether they ever dream of sailing again, Herb responded, “Yes, I’m leaving this summer on the Appledore Child. I’ll be sailing around the islands of Boothbay Harbor.” Doris says that she may accompany him though it may be just paddling alongside him in her kayak.