“Call me Ishmael” in Search of a Maine Windjammer Cruise

By David Currier -


My love of the coast of Maine and its windjammers began in 1968 when I worked at Ocean Point Inn in the Boothbay Harbor area. Our front desk manager was being courted by a crew member from the Victory Chimes. Once a week, this sleek three-masted schooner arrived at our dock to pick up its “VIP” passenger for the ship’s sunset cruise. My imagination went on its own search for Moby Dick or other nautical experiences at the sight of this magnificent ship sailing toward the horizon of Boothbay Harbor.

With the arrival of the earliest settlers, Maine played an integral part in expansion of the colonies and the new nation. In 1691, British soldiers blazed towering Maine pine trees, reserving them for masts in the Royal Navy. (One of these trees with the king’s mark was recently discovered still growing near OxBow. It was preserved, un-harvested, by the J.D. Irving Company.)  Shipbuilding became a major industry, and several villages remain famous for their craftsmanship. A shipping industry prospered, and at one time Belfast, Maine was home to more sea captains than any other American city.

The sweeping hull design of the 19th-century working-class schooners, along with the lines of their gracefully crafted sails, and the freedom offered to escape mainland life’s predictability embody many travelers’ concepts of independence, relaxation and adventure – components of a fulfilling vacation.

Space that now serves as ‘staterooms’, galleys, heads (toilets) and lounges was once filled with Maine granite (destined for buildings like New York’s Cathedral of St. John the Divine and Lincoln’s tomb), lumber, dried/salted fish, cotton and rum. The windjammers’ utilitarian status and importance was transformed with the advent of trains, and then paved highways and 18-wheelers. But thanks to some ‘old salts’ who had foresight coupled with nostalgia, many of these windjammers were preserved and restored to offer an unparalleled passenger sailing experience.

The Maine coast is guarded by many lighthouses.

From Kittery to Eastport, 250 miles as the cormorant flies, historic fortresses like Ft. Knox, Ft. Edgecombe, and Ft. Popham, along with nearly 60 lighthouses offered security to Maine coast seafarers and residents. Peninsulas of granite run from U.S. 1 into the Atlantic, creating 3500 miles of shoreline and over 3000 islands to explore; places with intriguing names like Dagger Island, The Porcupines, The Graves and Chickawaukie Pond.

There are 13 ships in Maine Windjammer Association’s fleet. We chose the Grace Bailey because of her status as a National Historic Landmark, and the dates we selected included musical entertainment. Other specialty Maine windjammer cruises include wine tasting, wellness, races, art and photography, kids and family, and even knitters’ cruises.

Sailing schedules frequently require passengers to board ship in the afternoon and make sail the following morning. Your first evening is free to shop, sightsee and dine locally. Rockland, Rockport, and Camden, the three harbors used by the Maine Windjammer Association, each prepare your senses for your windjammer adventure.

Camden Harbor in the evening.

The Grace Bailey sails from Camden Harbor, a seacoast village unspoiled by throngs of tourists, yet busy enough to offer fine art galleries, exquisite dining, and stores for wine, clothing or incidentals that you may realize you need (and have room for!). Two cases of refreshing wines or beer may be adequate!

At 5:30 p.m., we boarded and “unpacked” simply by pushing our two duffels under our bunk-berths. The August afternoon sunlight had a golden tinge that accentuated the colors and shadows of the many boats in Camden Harbor. We scrambled around Grace Bailey’s deck, the wharf, and then the town’s boardwalk, photographing everything in sight.

After a beer at Cappy’s Chowder House bar, with local fishermen whose Down East accents made us think we’d just met “Bert and I”, we feasted on fresh Maine scallops and clams and more Shipyard Ale. At 9:00 p.m., we were back on deck, meeting new friends and sizing-up our accommodations.

Introductory, laughter-filled conversations were limited to what we had in common – small ‘staterooms’, locating the three shared heads and one shower, and mastering the manual foot-pumping techniques required to make each function properly.

At eleven-bells, per Captain Ray’s orders, voices were lowered, good-nights were exchanged, and we descended our respective ladders for our first night aboard.

Kim Kisner, our head cook, started work at 4:00 a.m., building a fire in the wood-burning, black, cast-iron kitchen stove in the galley – nothing electric or gas on this 1882 landmark. Even the water for the shower is heated by the wood fire. (Don’t plan showers before 7:00 a.m. as your water may be very cold. Besides, the shower pump resounds through the ship like a cat coughing up a hairball and you’d wake other passengers – though most of us were early risers.) At sea, dawn’s ephemeral qualities should not be missed.

During each of her 16-hour workdays, Kim prepared three “boat-made” meals for 34 souls, all from scratch, including fresh baked yeast breads and typical Yankee brown bread – no Eggo waffles or Duncan Hines here!

Your on-deck breakfast before the “he-man sailor’s” breakfast.

The galley and mess are one room, the largest on board, though most meals other than full breakfast are served on deck. A 6:00 a.m. wake-up breakfast of fresh fruits, muffins and coffee is served on deck with a vase of fresh flowers from local gardens. Full breakfast follows at 8:00.

Changing from day to day, the menus may include French toast, blueberry pancakes, bacon or sausage, orange juice and brewed coffee. Lunch and dinner are equally as fresh including baked stuffed halibut, lasagna, baked chicken, New England baked beans, fresh salads, strawberry shortcake, and gingerbread.

A special captain’s BBQ of steak, chicken and ribs is offered one evening, and we also took the “lifeboat” and yawl to a deserted island cove for a dinner of lobster and corn-on-the-cob (which we all helped cook).

Lobster Bake Corn on Cob Wine Beer S'mores

The crew artfully serves cooked lobsters and corn.

This was accompanied by wines and beers brought by the passengers. Then dinner followed by s’mores that you make yourself. You won’t go hungry!

Windjammer cruises feature opportunities for volunteers to operate the vessel – raising and lowering the massive anchor, hoisting and furling the sails, steering between shoals and islands while the captain further plots the day’s routing, and even the mundane dish washing brigade. If winds or weather change suddenly, there’s a sense of obligation for able-bodied passengers to assist.

Winds were light on our first day out. Our journey was powered by a motorized yawl that quietly ushered Grace Bailey over the calm waters. However, as we sailed between two small islands to less protected seas, the sails filled with air and pushed us to Swan’s Island where we sought shelter from predicted evening thunderstorms – which never materialized.

That night at anchor in Burnt Coat Harbor, the captain from the Mercantile moored next to our Grace Bailey, jumped to our deck, guitar in hand, and performed with our troupe. The impromptu trio entertained passengers on both vessels. Favorite sing-along songs included a creative version of Drunken Sailor.

Weather was hot and sunny, cold and sunny and windy, rainy with fog and then sunshine – but we enjoyed them all. In addition to Burnt Coat Harbor, we anchored in Mullen Cove on North Haven Island, Buck’s Harbor back on the mainland, and Pulpit Harbor on the opposite side of North Haven. Friendships grew, and passengers dropped their corporate images. At the last two stops, nearly everyone (crew included) dove overboard for a refreshing swim. Several couples took a romantic row along the shore.

Each day, our ears were treated to the mournful pulse of foghorns, screeching herring gulls, calls of lonely loons, and clanging harbor buoy bells.

Each passing island and peaceful cove presented views like Goose Rocks, Hockamock Head or Curtis Island lighthouses; lobster pounds built on wobbly stilts, necklaced with colorful buoys, thrusting themselves out over the sea as if to challenge its ferocity, its control of fishermen’s lives.

Bald eagles soared over craggy islands and ospreys nested atop navigational posts; inquisitive harbor seals and porpoises surfaced nearby; magnificent private mansions and simple colonial cottages or salt-farm houses were sprinkled across fields of wild blueberries.

Sunrise, sunset, ocean surface reflections or pea-soup fog, the pungent smell of mud-flats and Victorian perfume given off by heirloom roses each ruffled senses dulled by day-job routines.

As our Grace Bailey sailed into home berth back in Camden Harbor, passengers carried their dunnage topside. Moods were subdued; somehow refined by their experience of the basic life of an ‘old salt’.

It’s difficult for me to imagine that one is not positively changed, à la Thoreau, by several days of simple life at sea. A windjammer cruise is truly one of a kind, and Maine Windjammer Association epitomizes the state’s slogan “Maine – The way life should be.” Back in Texas, I’m humming a 1970’s favorite by Christopher Cross:

It’s not far back to sanity;
At least it’s not for me.
And when the wind is right
You can sail away and find serenity.
The canvas can do miracles,
Just you wait and see.
Believe me.

Personal Dunnage for Windjammer Cruises

What to Expect

  • Windjammer life has no black-tie dinners or dancing with the captain
  • Your clothing will be wrinkled; so will everybody else’s!
  • Captain will inform you of the area of your cruise, but actual harbors are dictated by the winds
  • No tax-free ports-of-call in Maine and not much shopping in the fishing villages.  Obtain necessities before departure. But the village of Freeport is “outlet central”.
  • Rooms are Spartan, “quaint” – meaning very, very small. Floor-space may not exceed five square feet! Massive wood beams supporting the deck bump heads.
  • No room service
  • Don’t expect cellphone service at sea



Think “minimalist”! Ask, “What’s the least I need to survive?” Storage space is next-to-nil. 3 or 5 days, your needs are similar. Plan to ‘recycle’ your wardrobe.

Bring –

  • Duffel bag. Samsonite roll-aboard will not fit under berths, the only storage space, no matter how hard you kick! If you must, use hardside luggage traveling; transfer items to duffle bags before boarding ship.
  • Toothbrush and non-electric razor, lip balm, sunscreen, insect repellant, hat and sunglasses
  • Thin beach towel that dries faster after use and can be discarded after cruise. (Alas, value at your dollar store!)
  • Batteries and memory cards for cameras. (In five-days, I used seven batteries.) Remember, no electricity for recharging.
  • Medications in a zip-lock bag protect them from moisture.
  • Supply your own alcohol, wine and cokes. There’s lots of time to socialize, and you’ll enjoy great food. For five days, two of us drank a case of wine. Coolers with ice provided. Difficult to obtain en route.


Bring (Maybe) –

  • Sleeping bag to sleep on deck – many people do
  • Flashlight. Not much room for reading in dimly lit cabins. Use it to find lost socks under your berth.
  • Motion sickness pills. Take one a day to make yourself (and shipmates) more comfortable. Rough seas are rare. However, once it hits, motion sickness is difficult to overcome.
  • Collapsible camping chair for sitting on deck
  • Bottled water. Drinking water provided, but may have a wooden cask taste.
  • Musical instrument for evening entertainment
  • Binoculars
  • Reading material
  • iPod, whatever – headphones required unless you want to walk the plank


And Not –

Leave luxuries home

  • Calvin Klein or Versace scents (attract mosquitoes), mascara, blush. The outdoor-windblown look is “in”.
  • Bathrobes are for Princess Cruises or princesses cruising
  • Electric appliances that are not battery operated


How to Get There

Coastal Maine is served by airports in Rockland, Portland, Augusta, and Bangor. Boston is a four hour drive – except a Boston commute may be much longer on weekends and holidays. The primary highway, U.S. Route 1, can be a nightmare at Wiscasset. Friday inbound and Sunday outbound traffic frequently jams U.S. 1. Augusta, Bangor and Rockland airports permit you to avoid many traffic jams.

Children (Very important)

Each windjammer sets a minimum age for children. Details available on the website.

Photographs by David Currier.