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

Maine Under Sail: Coastal Towns of Penobscot Bay

from $2,320 USD per person for 5 days, 4 nights
  • Max Group Size: 12
  • Moderate
  • On the Water

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.

  • Sunrise and sunset aboard a classic schooner
  • Experienced captains and chefs
  • Fresh fare and local explorations


Itineraries and daily schedules are subject to change. We expect to do everything listed in the itinerary, though the order may be rearranged based on weather or other local conditions.
Sailing Collective
In Partnership with Sailing Collective

Additional Info

Arrival & Departure

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.

Activity Level

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.


Our group will be staying aboard a classic wooden vessel, the schooner Actress. Actress is 45 feet long and 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.

Dates and Prices

Aug 07–11, 2019
Single Berth: Schooner Actress
$2,320 USD per person
The total cost of this trip is $2,320. A $500 deposit is required to hold your space. The deposit is non-refundable after three days. The final payment of $1,820 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 the trip's Terms & Conditions. 
  • 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.
  • 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).

Trip FAQ

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.