In the waters off Provincetown, Massachusetts, the cutter Bloodhound cruises the pristine, blue waters in the painting of the same name by Derek Macara. Long Point Lighthouse and a small beach cottage sit on the otherwise empty shoreline. Boldly-stroked cirrus and cumulus clouds in the bright blue sky suggest gentle wind and ideal sailing conditions.

Originally built in 1874 for the Scottish Marquess of Ailsa, Bloodhound was a 70-foot cutter designed by William Fife II. The Bloodhound in Macara’s painting is a replica built in the 1990s in Del Rey, California. Bloodhound was once a racing vessel, but now with a 22-foot retractable bowsprit and 3,500 square feet of sail, she is a cruising vessel. Owned by Hindu Charters in Provincetown, she regularly carries 34 passengers on short cruises around the Cape.

Macara, 36, was raised in Provincetown, as were many generations of his family. He grew up sailing and was exposed to respected maritime artists from a young age. He attended the Cape Cod School of Art in that city and has never lacked for inspiration. While endless scenes of beauty surround him daily, Macara works mostly from photographs.

“Most of them are photos I’ve taken or a combination of several different photos that I’ve taken,” he says. He has taken hundreds of photos of Bloodhound over the years, as she is often seen cruising the local waters.

Growing up in an “artist community,” as Macara puts it, helped him see painting as a tangible career choice. Before picking up painting as a full-time profession, Macara worked a family job on a dragger and as a scallop fisherman, raking in all sorts of marine life. Out on the water, he was constantly surrounded by stunning seascapes and realized that his true calling was painting. He has been painting professionally for six years with no plans to stop.

“I feel really lucky that I can do something that I enjoy for a living,” he says. “So I’m probably going to do it as long as I can.” 

This article was originally published in the September 2023 issue.