The Grace Bailey is an elegant gem of a schooner, and as the winds pick up just past the Rockland Breakwater Lighthouse, her sails ripple, and it’s like we are flying across Penobscot Bay, racing the seagulls. Brian and I lean back against the yellow pine deck as we head toward North Haven Island with its craggy inlets and harbors. Built in 1882 in Patchogue, New York, as a “long hauler” of produce, lumber, and granite up and down the eastern seaboard to the West Indies, this “old girl” was designated as a National Historic Landmark in 1991.

There’s something mesmerizing about watching dotted islands on either side of the vessel and feeling the push of current, roll of tide, as the Grace Bailey glides past Pulpit Rock and the summer cottages along Mackerel Point. A private plane circles down to a landing strip by Webster Head and my imagination spins tales of storied histories of those who live or have lived “on island” for generations, farming, fishing, and eventually “summering.”

“I’m going to grab my guitar,” Brian tells me, as he ducks down the steep companion way ladder to our berth, or bunk room, below deck. He’s stuffed his instrument underneath his bunk while my top bunk has a bungie-strapped laundry line drying our bathing suits from a morning dip after breakfast. Tight quarters make for creative sleeping, and all of us passengers laugh and share tales of adjustments “down below” before we sprawl, as a community of sailors, on deck. Meals are abundant and seem to flow from one delectable selection to another: homemade blueberry muffins, raspberry pastries, eggs Florentine, thick cut bacon turns into kale/pomegranate/crushed tomato salads, fish chowders, Moroccan rice salads, fluffy chocolate chip cookies, and then fills with afternoon appetizers like freshly made egg rolls, slabs of smoked salmon, artistic charcuterie boards with vegetable “flowers”, local Maine cheeses, house made crackers. Chef Ian is a taste bud magician.

“Save me some cookies,” Brian adds, as he sits with his newfound friends from the folk band, Golden Oak.

We’re on a four-day music-themed sail and luckily, the talented sibling-fronted Golden Oak is on deck, keeping us all spellbound with their rich harmonies, and powerful nature-inspired lyricism. The lead singer, Lena, and I have already jumped off the bow, and we have plans to swim after the lobster bake tomorrow on an “unnamed island.” The whole band is open and ready for singalongs and sharing time with everyone.

We curve between Oak and Burnt Islands as the skies darken and the captain informs us that he’s finding a protected cove for the evening. Soon we are nestled deep inside Banks Cove. Two people on a long reach of beach wave at us. They’re excited to see the flapping masks being lowered by the whole group of us, as we call out to “hand the sails” while the crew is flaking the thick pleats to the boom. The anchor is “let go” and we are set for the evening.

Lanterns are lit. Cocktails are poured and shared, and Golden Oak harmonizes their songs to the breeze, the sounds of distant buoys, the creaking of the wooden hull. Dinner is served under tarps as light rain adds a calming patter. Sizzling platters of farm-raised beef, grilled vegetables, butter glazed potatoes, and huge slabs of pie make for culinary excitement until the couple on the beach lights fireworks to brighten the dimming evening sky.

Sleep comes easily as we are rocked to slumber. Brian and I wake up early for sunrise coffee and blueberry scones as the sky turns pink to gold to lightening blue. A seal pops its head up in greeting as the quiet cove holds a hush. Others soon join, most of us in flannel pajamas and slippers. We spend the day searching for the “perfect beach,” roaming the reaches near Deer Isle, Little Deer Isle, and finally, into the coves surrounded by Little Hen, Big Hen, and Penobscot Islands off Vinalhaven. A white sandy curve of beach is discovered, and we find our resting place for that afternoon/evening before the promised lobster bake at sunset. We take turns loading up into the dingy and off we go to the beach for swimming, exploring the rocky coastline, and watching the preparations of lobster steamed in seaweed, corn roasted in husks. After dinner, Golden Oak leads us in rounds of sea shanty songs on the beach and continues onward that evening to a full-out concert on the lantern-lit deck underneath a star-filled sky and full moon. One word: magical.

The last morning is filled with morning coffee and conversation as we sit on the deck with warm pastries. We have all become fast friends; musicians, crew, fellow “bunksters” as we’ve been calling ourselves, and there were tons of hugs as we sail past Thayer Point, Goose Rocks Lighthouse, and along the Fox Island Thoroughfare. We hit some wind and the mainsail fills, and as we zip back to Rockland Harbor, we hold onto the time left before shore. Schooner

Grace Bailey. www.sailgracebailey.com. Come for the cuisine, camaraderie, and classic schooner charm on themed sails from Rockland Harbor, Maine. Lobster bakes on small Maine islands set the tone for swimming and sunsets.