Maine Under Sail: Coastal Towns of Penobscot Bay - August 7, 2019 - Atlas Obscura Trips


Maine Under Sail: Coastal Towns of Penobscot Bay

This summer, explore the offshore townships of Maine the old-fashioned way—under sail. At 3,478 miles, Maine’s coastline is longer than California’s, and its northernmost stretches are best seen from the water.

We’ll spend five days living and traveling aboard a pair of classic schooners, complete with cozy bunks, handcrafted styling, and an experienced crew. Along the way, we’ll visit local communities and discover the wonders and oddities that make up this beautiful, remote corner of the world.

This trip is best for people who are...

  • Curious about Maine’s hidden corners, nautical history, and local traditions.
  • Comfortable with life aboard a boat: It doesn’t take extraordinary strength or ability to move safely around a schooner, but you should feel confident climbing up and down a ladder and moving about as the boat leans over while in motion, as well as sleeping in a bunk in a shared cabin.
  • Eager to make the most of each day—when you’re exploring an uninhabited island, meeting a knot-tying aficionado, and digging into a local lobster bake, you’ve got to cover a lot of ground.

Maine’s Penobscot Bay region boasts one of the most beautiful coastlines in North America. Led by our two seasoned captains, we’ll sail up to islands with working fishing fleets and meet the dynamic individuals who call these places home. When we’re not relaxing aboard, we’ll be exploring a boatbuilding school, meeting with a marine researcher, and learning the legends of ghost ships. We’ll buy the best lobster in the world right from our boats, grab a morning coffee at the local general store, and take long afternoon swims in clean, cool waters.

This trip is limited to a small group of 12 travelers.


  • Sunrise and sunset aboard a classic schooner: Wake up and go to sleep right on the water, with breakfast and dinner often cooked onboard—this is your front-row seat to the most beautiful scenery that Maine has to offer.
  • Experienced captains and chefs: While aboard, you’ll be looked after by a talented crew who’ve sailed all over the world.
  • Fresh fare and local explorations: Sample Maine’s freshest lobsters, berries, and other freshly harvested delights. You’ll also have the opportunity to meet boatmakers, marine scientists, and local fishermen.


Our group will be staying aboard two classic wooden vessels, the schooner Alamar and the brigantine Actress, both over 70 years old. Alamar is 45 feet long, while Actress is 75 feet long. The cost per passenger is $240 more aboard the Actress, since her interior is more spacious. However, keep in mind that the cabins and berths aboard both boats will be snug.

Each boat holds six guests plus two to three crew members. The sleeping quarters are steeped in sailing tradition, meaning that they are comfortable but compact; each guest will have a bunk in a shared cabin, and shared access to a bathroom equipped with a manual pump marine toilet. Showers can be taken on deck with water heated from the sun. 

Sailing on traditionally rigged boats along the coast of Maine is a bit like traveling back in time. Over the course of the trip, you’ll have the opportunity to handle sails and take the helm, learning  a traditional skill that still survives on these historic vessels. Each boat also has a small library for those who’d like to read more about the area’s local history, nature, and folklore.


Liz Monahon, Captain
Liz began sailing on the Hudson River when she was eight and immediately fell in love. She soon moved to the Maine coast where she started her education in coastal cruising after obtaining her own boat. Between then and now, Liz has worked at Morris Yachts as a rigger and cruised from Barcelona to London in a 79-foot trimaran, Earthrace (made famous by the TV show Whale Wars as the Ady Gil). She began her captaining career on a privately owned lobster yacht and has gone on to do deliveries up and down the U.S. East Coast on an array of vessels. In the summer months she manages the waterfront of The Northeast Harbor Fleet Yacht Club, maintaining the club’s boats and providing private sailing lessons in her free time. She lives aboard her 25-foot sailboat and is a USCG certified captain.

Hans Vierthaler, Journey Operations & Captain
Captain Hans Vierthaler has been sailing, teaching, and working on boats for 35 years and has had his USCG Captain’s license for 25 years. He previously owned and operated Abigail, a 39-foot Alden ketch, which he used as a sail training vessel. He teaches coastal cruising courses at The WoodenBoat School, and operates a charter business with his schooner Actress out of Belfast, Maine. He knows all the best spots and events happening in and around the rich cruising grounds of Penobscot Bay, loves meeting new people, and looks forward to sharing the experience of sailing.

Day 1
All Aboard
  • We'll meet at 10 a.m. on the main pier in Rockland, Maine. After introductions to your crew and fellow passengers, we'll all transfer our belongings to the boats and take some time to get settled.
  • Before setting sail, we'll hop back out and make a short visit to a true hidden gem: the nearby Owls Head Transportation Museum, originally founded in 1974. Every plane, automobile, and bicycle in this collection is kept in working order, with regular demonstrations to the public.
  • From there, it's time for our maiden voyage: a short sail across West Penobscot Bay to the Island of North Haven, where we'll tuck into the cozy pulpit harbor.
  • This evening, we'll buy fresh oysters directly from the island's local oyster farms to enjoy aboard, and raise a glass to the start of an exciting journey.
Day 2
Eggemoggin Reach & WoodenBoat School
  • Today, we'll wake up to our first morning on deck and enjoy breakfast on the water.
  • Then we'll traverse the eastern side of Penobscot Bay toward the legendary Eggemoggin Reach—the channel between Deer Isle and the coastline. Along the way, we'll sail under the Deer Isle Bridge, a suspension span that replaced the ill-fated Tacoma Narrows Bridge, which collapsed shortly after opening.
  • Our destination is the WoodenBoat School, where students learn the old ways of boatbuilding on a beautiful campus overlooking the Eggemoggin Reach. We'll be treated to a special tour focused on  traditional boatbuilding techniques that are still being taught today.
  • Afterward, we'll visit a legendary private nautical library, then end the day with a hearty lobster bake along the waterfront.
Day 3
Buckle Island & Nervous Nellie’s
  • We'll wake early this morning and enjoy breakfast aboard as we sail to Buckle Island for lunch and a chance to go swimming. Buckle is an uninhabited island that’s nonetheless been deeply influenced by visitors—its wooded areas are full of  unusual art installations. We'll be sure to leave time to explore some of Buckle’s more whimsical trails.
  • After lunch, we'll sail on to Deer Island. In the small town of Stonington, we'll get to meet a world-famous knot-tying professional and check out Nervous Nellie's Jams and Jellies, a charming spot decorated with original sculptures created by Peter Beerits, who also lives on the grounds. Beerits’s artworks are an eclectic hodgepodge of styles made from wood, metal, and glass, all repurposed from old farm equipment and other found materials. Needless to say, we'll also sample some jams and jellies.
  • We'll have dinner ashore at the Aragosta Restaurant in town before returning to the boat for a cozy night's sleep.
Day 4
Lobsters, Lobsters & More Lobsters
  • Today, we'll explore the lobstering community of Vinalhaven, learning about the commercial fisheries here and getting a taste of real island life—both its beauty and its hardships. If we're lucky, we'll get to meet some locals who were born into the lobster trade and who can tell us its dirtiest secrets and most harrowing stories.
  • After an afternoon venture, we'll anchor around the corner from town in the Greens Island Reach and dig into a home-cooked meal on the boat. 
  • After dinner, perhaps we'll share a tale or two of the various ghost ships said to haunt the Maine coast, prominently featured in both nautical literature and first-hand accounts.


Day 5
Marine Science & Departure
  • Today is our last on the water. In the morning, we'll drop anchor and go ashore at Hurricane Island. Formally a granite quarry, and later an Outward Bound school, this island is now a center for science, leadership, and marine research.
  • If we haven't been able to cross paths with her yet, we'll rendezvous with the legendary Kipp Quimby of Isle Au Haut to talk about her business collecting some of the more unusual specimens living underwater on the Maine coast. You'll get some hands-on time with her catch of the day and the opportunity to touch and feel some of the odder things she harvests. If there's something strange under the ocean in these parts, chances are that Kipp has made its acquaintance. Come with any and all questions you have about the fascinating cold-water seabed in the Gulf of Maine.
  • We'll pull into the dock in Rockland before sunset and disembark. We'll say our farewells and from here, return to our respective land-bound vessels.
  • Until the next adventure!
The Fine Print


  • The services of two experienced boat captains.
  • Four breakfasts, four lunches, three dinners, and additional snacks aboard, all prepared by your private chefs.
  • All activities and events as mentioned in the itinerary.
  • Accommodations on board: Each passenger has their own individual twin-sized berth.
  • Marina fees, dockage, and moorings for overnight anchorages, as well as boat-related incidentals.
  • A great group of fellow Atlas Obscura fans, excited to explore all that Maine's waterways have to offer.


You should plan to arrive by 10 a.m. on Wednesday, August 7 at the main pier in Rockland, Maine. The trip will end back in Rockland around 6 p.m. on Sunday, August 11. Travelers are responsible for getting to and from Rockland. Portland International Jetport (PWM) is the nearest major airport and is a two-hour drive from Rockland. Rockland has several car rental companies including Enterprise, Budget, and Avis, if you’d like to arrange two one-way rentals.


August in Maine is usually the most pleasant month for sailing. Daytime temperatures reach up to around 80°F, dropping to the low 60s in the evenings, while humidity can reach 75 percent. The water is warmer than early summer and there is less fog. You can expect some amount of rain during the week.


Keep in mind that life aboard a boat is fairly active. You should feel confident climbing up and down a ladder, as well as moving about as the ship leans over while in motion. You can also expect to walk between 2 to 3 miles per day, often on rocky coastline and dirt paths.

You should also feel comfortable on and around water. Since these are bigger boats, life jackets are not mandatory unless the weather gets choppy. If you feel more comfortable in a life jacket, you are more than welcome to wear one.


Itineraries are subject to change. We expect to do everything listed in the itinerary, though the order may be rearranged based on weather and other local conditions.


The total cost per person is $2,320 or $2,560, depending on whether you reserve a berth aboard the schooner Alamar or the brigantine Actress. A $500 deposit is required to hold your space. This deposit is nonrefundable after three days. The final payment of will be due by May 9, 2019. All reservations will be final after this date and subject to our cancellation policy. By submitting your deposit, you agree to our Terms & Conditions.


  • Transport to and from Rockland, Maine.
  • Tips for your crew; it is customary in the industry to tip the crew 10 to 15 percent. Crew members split the tips evenly.
  • One or two dinners on land, and alcoholic drinks.
  • Travel insurance (recommended).

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