Sailing

All trips to Greece should end with a sunset cruise aboard a private boat in the sublime Santorini caldera, a mesmerizing mix of aquamarine waters, jagged volcanic islands, and the whitewashed houses on the island clinging precariously to the cliffs. Add the reddish/orange/pink orb of a sun melting into the sea, shading this scene with the full spectrum of color, paired with a glass of crisp Santorini wine, and you have a fitting ending to a memorable trip. It took me 25 years to return to Greece and I hope I don’t make that mistake again. In the meantime, I’ll certainly be selling the experience with passion to the members of ActiveTravels. I want to thank John Cagle at Heritage Tours for designing an ambitious itinerary. We packed a lot into a one-week trip.  

Last summer, I made the wise choice to sail on the Schooner Mary Day with my daughter, Melanie, before she left for her first year of college at Indiana University. We had a glorious trip dining on all the lobster we could stomach on a deserted island off the mid-Maine coast, spotting harbor porpoises, lonely lighthouses, and making new friends around the country as we hoisted sails and sucked in as much salty air as necessary. This comes on the heels of two memorable sails aboard the Grace Bailey with my dad and his wife Ginny. 

Sad to be leaving the Schooner Mary Day and heading back to civilization. I tried to convince Captain Barry to sail straight through Election Day but he had other commitments. The good news for you is that the Maine windjammer season runs all the way to mid-October. This year’s Camden Windjammer Festival takes place in the harbor on September 2nd and 3rd. Festivities include a parade of sail, live music, dancing, and fireworks. On Tuesday, September 13, the fleet gathers in Brooklin for a day of live music and tours at the WoodenBoat Sail-In. Also don’t forget the full moon sail over August 18th and the fall foliage sails in late September/early October. The windjammer Angelique is featuring a 4-night Wine and Foliage sail October 2-6. The schooner Ladona has a 4-day wine cruise with wine expert and consultant Michael Green August 26-30. Stephen Taber has a 6-day Photo & Lighthouse Cruise with photographer John Shipman September 4-10. With a 9-ship fleet, you’re bound to find a sail on a Maine Windjammer that fits your schedule. Take it from an expert, you won’t regret it. 

We wake up to blinding sunshine at Buck’s Harbor in South Brooksville, best known as the spot where children’s book author and illustrator Robert McCloskey (“Make Way for Ducklings,” “Blueberries for Sal”) summered. FDR would also stop here on his way to Campobello Island for a short ice cream break. We found some of those famous wild Maine blueberries in our pancakes that morning before hoisting the sails and setting a course for that hump atop Big Spruce Island. Each one of these Penobscot Bay harbors and islands has a legacy and Big Spruce Island is no different. This is the place where artist Fairfield Porter and his brother, photographer Eliot Porter, would spend their summers and there’s still a working artists’ community on the island today.

Aside from 11 year-old Mary Beth, who loved swimming and paddleboarding in the Atlantic, the highlight for most of us aboard the Schooner Mary Day was the first night lobster bake. Captain Barry anchored near a quiet beach with no other boats in sight and proceeded to row us over to the shore. The crew built a fire, then placed two massive pots brimming over with lobsters, corn on the cob, potatoes, onions, and a healthy top layer of seaweed. We swam and drank wine as the pots boiled, anticipating the feast. When ready, Captain Barry threw off the layer of seaweed and grabbed his tongs to place all the lobsters and fixins in a circular design. We each grabbed our lobster and plopped it on a tray, next to hot butter, corn, potatoes, and found a spot on the beach to dine. 

There’s a renewal of spirit as soon as we set sail on the Schooner Mary Day. The smell of wood mixes with the salty air as we glide out of that postcard-perfect Camden Harbor, gently crawling by the other historic schooners and yachts in the early morning fog. Goodbye mainland and the endless barrage of bad news, hello loons, anonymous pine-studded islands, and wide open water to bathe away all woes of modernity. I take deep gulps of the crisp air and breathe deeply.  

In 1936, an artist from rural Maine named Frank Swift had the wild and crazy idea of reinventing the American merchant sailing ship. Once essential in transporting lumber and granite along the Eastern Seaboard, fish from the Georges Banks, and fruit from the West Indies, these vessels were becoming obsolete by the 1930s. Swift knew full well that Maine’s 2500-mile stretch of jagged coastline, where long inlets form sheltered bays, was tailor-made for sailing. No other sport gives you the freedom to anchor in a pristine cove, hike on an untrammeled island, and sleep with a lighthouse beacon as your nightlight. So he went on a shopping spree, buying up old schooners with a vision offering travelers a new type of experience, windjamming. The business flourished and today there are now 9 ships in the Maine Windjammer Association fleet.

Sailors know the British Virgin Islands as legendary cruising grounds. Here, in places like Virgin Gorda, Peter’s Island, and Tortola, you’ll find sheltered marinas where you can dock or throw down your anchor, shopping, restaurants, and small hotels that are popular with yachters. Even better, you can sail to these various islands without going outside the reefs into the open ocean. But you won’t have to worry about navigational charts on Festiva Sailing Vacations 7-night night cruise around the BVIs, because a skipper comes with you. Their 45-foot Lagoon 450 catamarans, which sleeps 8 passengers in 4 guest cabins with private bathrooms, also comes with a chef and liquor to make this the ideal all-inclusive package. The weeklong jaunt starts in Tortola and includes snorkeling with sting rays in The Baths of Virgin Gorda, a stop at Cane Garden to listen to the steel band play at Stanley’s, and a night anchored off Norman Island, the treasure island author Robert Louis Stevenson made famous in his book. Cost of the trip starts at $3595 per couple, including meals, a berth onboard, and, of course, transportation. They still have one berth available on the March 19-26, April 9-16, and April 16-23 sailings. Please contact ActiveTravels and we’ll be happy to make the booking. 

For the first time in its 106-year history, Linekin Bay Resort will have new owners. I first visited the resort in 2012 with my family, penning a story for The Boston Globe after a memorable weekend. Located on one of the many inlets that form the landscape of midcoast Maine, Linekin Bay has one of the finest locales in New England to sail and sea kayak. Spend your day with the family boating, hiking with a naturalist, and swimming. Then dine communal style on Maine specialties like a lobster clambake and blueberry pie in the main lodge. The new owners, both local Mainers, have already begun to rehab the aging buildings, creating 14 new rooms in the new Linwood Lodge. They still aim to retain the rustic charm of this classic retreat, the only all-inclusive sailing resort in the Northeast.