TakeMe2 Lincolnville, Maine!

Go Sailing!

What’s the best way to experience Maine? Hands-down, it’s on the water, especially with the wide variety of sailing options available in and around Lincolnville. From day sailing on a windjamming schooner to week-long chartered adventures, you’ll find everything you need to bring out the real seafarer in you.

Maine Windjammer Cruises

P.O. Box 617, Camden, Maine 04843

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Captain Ray Williamson will show you the way on Penobscot Bay – or so they say. Ray and his Windjammer crews have been setting the course for Mainers and tourists since he purchased the business in 1986. Originally established in 1936, Maine Windjammer Cruises is the registered trademark for the first and oldest fleet of historic vessels in America. Today, it’s a small, family-run business that prides itself on continuing the tradition of offering the best oceangoing experience for visitors who want to experience an authentic Maine adventure.

The schooners

Before we dive into the many types of cruises you can take, let’s first introduce you to these magnificent boats – starting with the Grace Bailey and the Mercantile. Recognized as National Landmarks, these authentic turn-of-the-century coastal cargo schooners sail with no inboard power. They still rely on wind and canvas, just like they did hundreds of years ago.

Grace Bailey

Offering 5-day and weekend cruises

She is a beauty. The Grace Bailey was originally built in 1882 and lovingly restored with her historic integrity preserved in 1990. The restoration included the addition of amenities that maximized guest comfort. As the finest example of a 19th century coaster afloat today, this flagship boat is a popular choice for some authentic windjamming. And she has some stories to tell with a history that includes the West Indies fruit trade and the time she carried Maine granite to New York City to help build Grand Central Station.

At 123 feet overall, 81 feet on deck, the Grace Bailey can accommodate 29 passengers in magnificent comfort. Guests will enjoy the restored interior, beautifully finished with hand carved wood paneling, that even features a piano. There are 12 private double cabins; some containing either a double bed or two single beds and a window or porthole for light and ventilation. There are two private single cabins with two Pullman beds and one double cabin with a private head. There are four heads below decks, one in each passenger area. And, there is a fresh hot water shower below decks.


Offering 3-day and 4-day cruises

The Mercantile has earned the reputation as the "prettiest coaster on the bay." She was built in 1916 and restored in 1989. At 115 feet overall (80 feet on deck), she can accommodate 29 passengers. Designed as a shoal-draft vessel, she was able to take on and discharge cargo in places that deeper draft vessels couldn't get to. This is why she is still able to explore secluded ports today.

There are 14 double cabins (with full standing headroom and a porthole for light and ventilation) with options for double or twin beds. There is one private single cabin and three heads below decks and passenger areas. Finally, guests can enjoy a warm and spacious main cabin, galley, dining area, and a hot fresh shower below decks.


If you are looking for a traditional Windjammer experience but want the feel of a private yacht - with more privacy than bigger boats, the Mistress is your match. This specialty boat is the "princess" of their fleet. She is a blend of a traditional schooner and private yacht. While she is rigged in the same traditional manner as their other schooners, the mistress has inward power and modern accommodations below decks.

She was built in 1960 and restored in 1992. At a much smaller size than the other boats, the mistress is 60 feet overall (46 feet on deck) and accommodates only six lucky passengers and a crew of two. There are two cabins each with a double bed; one cabin has two bunks. Each cabin contains a private head and sink. Aboard the ship, you will sail the waters with a personable and professional captain and mate-cook. The meals are delicious.

Unless it’s chartered, young children should not be on this boat. Although, this is likely not a problem since many people reserve this boat for a romantic getaway or special adventure!

A new schooner cruise in Lincolnville!


Summertime schooner reservations*:

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*Bookings for the shorter trips may also be made at the kiosk on Lincolnville Beach if space is available

Maine Windjammer Cruises just added the 53-foot pinky schooner, Summertime, to its fleet in June 2014. As a new addition to the team, the Summertime will sail on several daily trips from Lincolnville Beach.

Pinky schooner seems like an awfully cute name, doesn't it? It’s actually derived from the term “pinked,” which is an upturned stern. It originated in Europe in the 1600s. Before the Revolutionary War, the pinky was used in New England's fishing fleet. It continued its use through the turn of the 20th century. The pinky Summertime was built in 1986 using traditional methods at the hands of George Allen, Bill Brown, and many volunteers in Brooklin, Maine.

So, why did she join the group? Simply, many Maine tourists want an abbreviated way to enjoy sailing.

In a recent Bangor Daily News article, Capt. Ray said: “With the Summertime, we’ll be able to offer passengers two new options. Every season, we meet hundreds of vacationers who want to experience the beauty of our unspoiled coastline and islands from the water. But some of them can’t spare the time for a two-, three-, four-, or five-night cruise on the Grace Bailey, Mercantile, or Mistress. By bringing the Summertime into the fleet, we’ll be able to give them the opportunity to get out on Penobscot Bay and enjoy a taste of traditional sailing for a couple of hours or an overnight.”

On the Summertime, guests can choose from a variety of amazing options: picnic lunch sail, afternoon sightseeing sail, happy hour cruises, and overnight cruises that include a lobster dinner and a delicious breakfast. She can accommodate up to 18 passengers on day sails and up to seven passengers for one-night cruises.

Overnight passengers on the Summertime won't need to rough it. There are three private double cabins that have six-and-one-half-foot-long bunks, crisp sheets, and warm blankets for cooler nights. There are private washstands and a warm water shower. Also luxurious? The meals - straight from the wood burning stove on the Summertime. At breakfast, you can start the day with things like pancakes, fresh blueberry muffins, or eggs. At lunch, you can enjoy delicious soup with a freshly baked biscuit. And at the end of the day, after a long afternoon on the water, you can enjoy a family-style dinner of seafood, pasta, or chicken - with available options for vegetarian entrées and special dietary needs.

Other new Windjammer additions

Summertime isn't the only rookie on the fleet; Maine Windjammer Cruises just added Sally, too. Built in 1941 in East Boothbay, this 27-foot classic wooden lobster boat is back home in the Maine waters after a complete restoration by the famous International Yacht Restoration School in Newport, Rhode Island. She will carry guests to Warren Island State Park for lobster picnics, and will be used as a launch when needed.

The last piece of news? Maine Windjammer Cruises is introducing new Farm-to-Galley specialty cruises; they’ll be offered three times this summer. This incorporates local foods and using products made from recycled materials. It's good to be green here on the blue water.

Schedules and logistics

If you're planning to take the Summertime in Lincolnville, head to the Lincolnville Beach Town Dock next to the Islesboro Ferry Dock. You should always plan to arrive about 15 minutes before your scheduled boarding time. Parking is available.

Since there are so MANY options for these cruises, your itinerary is totally up to you. Whether you want to take a short two-hour cruise or book five nights on one of these beautiful schooners, you can customize your trip.

For all schedules, pricing, reservations, special events, and specific details about your trip, visit the Maine Windjammer Cruises website, email them, or give them a call.

Crewed Sail Boat Charters

If you want to charter your sailing trip, Penobscot Bay is the perfect place to do it. The three mainland Midcoast Maine harbors (Rockland, Rockport, and Camden) are home to plenty of charter companies that offer crewed, bareboat, sail, and power of just about any size vessel – whether you want a runabout to a super yacht.

Look to Maine’s boat yards and talented builders; they'll often offer certain bolts for charter. Some are “brokerage boats” in which the owners are more than happy to have them working as they're waiting for sale. If you want a Yacht, check out the up-to-date database on Yacht World Charters – searchable by Penobscot Bay.

Charters are usually contracted on a weekly basis, but it all depends on the operator. You might even be able to find daily charters if you look hard enough.

When should you charter your cruise? The sailing season runs from July to September – and you should plan for foggy conditions. Locals often say that September is the best time to set sail with its warm days and cool nights.

Remember, if you need some provisions (fuel, water, other marine services) stop off in the coastal towns like Rockland, Rockport, and Camden that cater to this. You can also enjoy a great meal at one of the many famous restaurants in these coastal spots.

Here are a few popular charter destinations:

Pulpit Harbor on North Haven Island: This well protected harbor is an easy and straightforward sail from the Rockland Breakwater.

Carver’s Harbor, North Haven: Want some mystery in your sail? Head here. Granite quarries (used back in the day when this used to be a booming industry in Midcoast Maine) are abandoned. They now are swimming holes with scattered granite tailings; it’s certainly worth exploring!

Matinicus: About twelve nautical miles south of Carvers Harbor, Matinicus is a pretty popular destination. It is Maine’s outermost island with a year-round population.

And here are a couple companies that can help get you to these destinations:

Bonnie Lynn

401.835.3367 or 3368

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If you are in Islesboro, Maine, and want to book an exclusive cruise from there – check out Bonnie Lynn; the homeport is right in this small island town.

Bonnie Lynn can accommodate up to six overnight passengers, and up to eight if it’s a family group. Since this is an exclusive booking, you tell them what the itinerary should be. Their charters have lasted between a few hours to three months, carrying guests ages 2 to 92. Call them directly for more information and reservations.

Makana Tours

Camden, Maine 04843


With a variety of charter options (full day, overnight, two-day, week long, etc.), you can enjoy all of Penobscot Bay with their skilled and knowledgeable team. If you pick the right tour, you’ll be ending your nights with fresh Maine Lobster and a glass of wine!

Visit their website for available options, company details, and pricing. For reservations and specific inquiries, best to give them a call.

Sailing Maine’s ocean waters is a one-of-a-kind-experience

Don’t pass up this incredible opportunity to experience Maine the way mariners have for years during your trip to Lincolnville. Since these boating adventures are so popular with limited space availability, it’s a good idea to reserve your ocean going experience as soon as you lock down your vacation dates.

One thing is for sure; sailing on Maine’s waters will exceed your grandest expectations. Truthfully, there are no words or cleverly crafted phrases adequate enough to describe this one-of-a-kind-experience.