CAMDEN — When it comes to work on sailing vessels, Tom Hollyday has done it all.

He has worked as a deck hand, cook, engineer, mate and captain, and he has a connection to Camden Harbor where he worked on various windjammers in the past.

Now Hollyday is the captain and owner of the Pilot Cutter Hesper, which has been based out of Portland for two years. In May, he and his partner, Pietra Brettkelly, are bringing the Hesper to Camden Harbor.

The Pilot Cutter Hesper is a 60-foot gaff-rigged West Country Cutter. Photo courtesy of Tom Hollyday

The Hesper is a 60-foot, 25-ton, gaff-rigged West Country Cutter. Hollyday said it is designed to cross oceans. In the United Kingdom, cutters of this kind would carry pilots out to the North Sea to meet with the large vessels and bring them in. Whoever was swiftest got the contract. The vessels would then be guided back by a single cabin boy, so Hollyday argues they are “kind” to sailors.

This one too has a small crew, just Hollyday and Brettkelly and their 9-year-old Nova Scotia Duck Tolling Retriever, Buddy.

The vessel’s owners are Tom Hollyday and Pietra Brettkelly. Photo courtesy of Tom Hollyday

Tom Hollyday and Buddy, a Nova Scotia Duck Tolling Retriever. Photo courtesy of Tom Hollyday

Hollyday said in this post-COVID era, customers want to get out on sailing cruises, but do not want to be exposed to strangers in close quarters. He said Hesper offers a curated sailing experience, with overnight trips around Penobscot Bay to the various islands, but private to just one party of up to six people.

These trips take people to Vinalhaven, Deer Isle, Stonington and Eggemoggin Reach.

Hollyday and Brettkelly prepare meals in the galley and on the campfire during island visits.

Hollyday said they had a good reception from the existing windjammers in Camden and noted his great respect for them. The couple are looking for property in the area with an eye to planting roots and they look forward to being a part of the community.

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A look at the interior. Photo courtesy of Tom Hollyday

The Pilot Cutter Hesper as seen from above. Photo courtesy of Tom Hollyday