We make every effort to honor individual preferences and enjoy designing tours with our guests' desires in mind. The following information details just a few of the sailing tours we offer:

Our most popular trip is the half-day sail, which runs about three to three-and-a-half hours. During a typical half-day trip in Southwest Harbor you will sail past Bear Island Lighthouse, around the Cranberry Islands, and possibly out to Baker Island Light! On a Bar Harbor tour you will cruise the famous Porcupine Islands, witness spectacular summer "cottages," and head out to Egg Rock Light where the local seal population makes its home. This trip provides the perfect amount of time to get the feel of sailing a traditional boat on the coast of Maine. Wildlife is easily spotted and there is plenty of opportunity to haul the sails and take a turn at the wheel. 3-3 1/2 hrs
There is nothing like a sunset as seen from the sea. From Southwest Harbor, witness the most famous sunset over Mount Desert Island while we sail past the rock-bound coast of Bear Island, where a lighthouse originally built in 1838 towers above. Enjoy a bottle of wine and appetizers while the sun slips behind the Western Mountains of Acadia. From Bar Harbor, we'll sail among the Porcupine Islands as the sun sets over Cadillac Mountain.
2 to 6 hr trips
The perfect trip for families with young children--or simply those looking for a relaxing morning on the water. In Southwest Harbor, this trip will take you out around Bear Island Lighthouse and through the mouth of Somes Sound. In Bar Harbor we'll leave the harbor and head out to famous Egg Rock Light, where the seal-sighting opportunities are endless. A perfect way to enjoy Acadia! 2 to 6 hr trips
Bear Island Light in Southwest Harbor was originally built in 1838. It is now part of Acadia National Park...
Taking you beyond the shelter of the Cranberry Islands and well off the coast of Southwest Harbor, this trip is for the adventurous sailor who wants a taste of ocean sailing. Baker Island was first settled by William and Hannah Gilley during the War of 1812, and in 1828, a lighthouse was built. In the 1960's, the lighthouse was automated and the island became part of Acadia National Park. Definitely an "off the beaten path" destination that few visitors to Acadia ever experience, the Baker Island sail will reward the adventurer with excellent views of the Atlantic Ocean and the mountains of Acadia National Park. If you would like to make landfall, Baker's walking trails allow for a rare look at the unique history of this outer island where you can explore the old cemetery, lighthouse, and houses ashore. 4 to 6 hr trips
This trip will leave you captivated by the maritime history of the Acadia region. Take a step back in time and sail to the Cranberry Islands, which were first settled around the time of the American Revolution. Observe a scenic lighthouse on Bear Island and an inhabited 100 year-old osprey nest as we sail past Sutton Island, which was purchased from the Abenaki Indians in 1755 by Eben Sutton for just two quarts of rum! Explore local museums and learn about island life during a time when commerce depended on islands and sailing vessels, not roads and autos. We'll stop off at the island if you'd like; you can witness a busy working pier where fishermen unload their lobster catch, artists display their pottery craft and watercolors, and a local restaurant welcomes you for an incredible lunch or dinner. Narrow roads, a working waterfront, and an intimate community offer a unique respite away from the crowds. A great trip even without ideal sailing conditions; if the wind is slack, the fog rolls in, or the kids are restless, the Cranberry Islands tour offers a flexible full-day combination of an ocean and island experience. 3 to 6 hr trips
Somes Sound is the only fjord on the east coast of the United States and is only a short sail from Southwest Harbor. Carved by a glacier some ten thousand years ago this deep, narrow channel is bound by granite cliffs and makes for a dramatic geological canvas. It is also an excellent habitat for birds and marine mammals as well, making this sail a favorite among naturalists. Your Captain has a bachelor's degree in Geology so bring a few questions about how a fjord is formed! 2 to 4 hr trips
Our Lobster-Bake trip brings together great food and a fantastic view. In Southwest Harbor, guests dine on Downeast-style steamed lobster, salad, corn, and blueberry pie while enjoying incredible scenery from the famous Valley Cove area in Somes Sound; in Bar Harbor, you'll sail and dine among Acadia's renowned Porcupine Islands. We offer the Lobster-Bake Cruise during private charters and suggest that the trip be at least four hours to accommodate sailing and dining time. Lobster-Bake cruises are priced as private charters with an additional cost of $25-$35 per person, depending on specific menu selections. You are welcome to bring along beer and wine; we have a full galley and plenty of ice-box space on board. 3-6 hr trips
Learning to sail is not as hard as you think! Our instructional trips teach the basics of sailing, covering vocabulary, techniques, and good seamanship. Have a unique experience learning the ropes of a traditional vessel and sail the boat in your first lesson. Couples and families are encouraged to learn together. Navigation and charts of Bar Harbor and Southwest Harbor will be covered if you wish. 2-6 hr trips
We'll take you and your companion to one of the quiet coves near Southwest Harbor or Bar Harbor to spend the night afloat--sure to be the most memorable evening of your vacation. After a steamed lobster dinner and a great bottle of wine served on deck, gentle waves will lull you to sleep in your private cabin, where a large overhead hatch affords an extraordinary view of the stars right from your bunk. Our guests' cabin is trimmed in varnished mahogany and teak hardwoods with traditional gimballed oil-lanterns and a wardrobe. Your cabin will be comfortably fitted out with down pillows, 100% cotton sheets, fleece blankets, towels, electric fans and reading lamps. There is a marine toilet on board. In the morning we will serve you a Downeast-style breakfast including fresh locally-roasted coffee, blueberry pancakes or grilled blueberry muffins, locally-baked bagels and fresh spreads, fruits and juices. We steam back to the marina by 9am, where hot showers (Southwest Harbor location only) in newly renovated bathrooms are available. OVERNIGHT
As sailors and kayakers we might be biased, but we remain convinced that there is no better place to witness the diverse wildlife of the Acadia region than from the sea. With your registered Maine Guide on board, each trip offers a fantastic opportunity to observe and learn about the marine mammals and birds that inhabit coastal Bar Harbor and Southwest Harbor. Bring a camera and binoculars if you like; we do have binoculars on board which you are welcome to use.
From the deck of a boat powered by the wind, you have an excellent opportunity to witness harbor seals, gray seals, harbor porpoise, and even the occasional Minke whale! Bald eagles, osprey, black guillemots (a relative of the Atlantic Puffin), cormorants, and terns are among some of the birds commonly seen during our trips. Our Bar Harbor and Southwest Harbor tours offer excellent wildlife viewing opportunities. From the 100 year-old osprey nest on the Southwest Harbor tours to the largest Eagles nest in the area on the Bar Harbor tours, and the low-tide ledges covered with seals in both locations, watching wildlife from the deck of a sailboat is truly amazing.
One of the many highlights for bird enthusiasts
is the osprey nest on Sutton Island; it is one of the
oldest nests in the area, and has been inhabited
for over one hundred years.
The Friendship Sloop is graceful and distinctive, easily recognized by its bowsprit, gaff-rigged mainsail, and elliptical stern. Like many traditional boats on the coast of Maine, the Friendship Sloop is a product of an era gone by, the working days of sail. Along the coast of Southwest Harbor and Bar Harbor in the late-1800's Friendship Sloops were a common sight as they were the favored boat for lobstering and fishing. The evolution of the sloops' design met the needs of Maine fishermen, as seaworthiness and maneuverability were important along the rock bound waters peppered with islands and shoals. A large cockpit, low water line and broad beam made her roomy and stable for fishermen to haul traps over her gunwales while the large sail area got her home quickly.
Our sloops are outfitted for your comfort, with Maine's maritime history in mind. We are the only charter available where you can have the traditional-boat sailing experience coupled with yacht quality amenities. You'll enjoy cushioned seating, varnished teak and mahogany hardwoods, polished brass hardware, and full accommodations (including a galley, restroom, and icebox) below-decks.
With the advent of the internal combustion engine aboard boats, the Friendship Sloop was nearly forgotten in the wake of technology. Fortunately, her beautiful lines and sea-kindly nature kept the design alive among pleasure sailors, a rare occurrence among working boats. Now, over a hundred years later, the Friendship Sloop is still sailing. In fact, their popularity is evident by the organization called the Friendship Sloop Society which keeps tabs on as many sloops as it can find and allows owners of the sloops to get together every year for races and celebration.
Karl is a USCG-licensed captain who grew up sailing on the coast of Maine. After studying abroad in New Zealand, he earned a Geology degree at Colorado College and then thru-hiked the Appalachian Trail. Missing the ocean, he returned home to Maine to work in the Windjammer industry in Camden, where he began working toward his USCG Master's license by serving as a deckhand aboard a turn-of-the-century wooden schooner sailing from Maine to the Caribbean. Since then he has logged thousands of bluewater miles by delivering private yachts between the Caribbean and the east coast.
After graduating from St. Michael's College in Vermont, Kristen earned her Maine Guide's License in Sea Kayaking and Recreation. She has led single and multi-day excursions in Bar Harbor, Southwest Harbor, and in the Virgin Islands and has been teaching visitors about the history and wildlife of Acadia National Park since 1998. During the off-season Kristen works as a deckhand on offshore sailing deliveries between the East Coast and the Caribbean. She recently thru-hiked the Long Trail in Vermont, and when she is not on the water, she has worked as an archaeologist, a yacht manager, and a public relations official.
Kristen and Karl met while working as deckhands aboard the Schooner Roseway, which was sailing from Maine to the Caribbean. Upon arriving in the Virgin Islands, they were offered jobs working as archaeologist interns in St. John, where a pre-Columbian Taino site was being excavated. After the internships ended at different times, they met again and raced in the Antigua Classic Yacht Regatta before sailing back to the states where they worked on a schooner sailing out of Southwest Harbor. They have sailed together extensively on charter yachts, offshore deliveries, and on their own boats, here in Maine and in the Caribbean. During the past few winters, they have rebuilt a Bristol 27 which they live aboard and sail in the Virgin Islands.
Kristen and Karl were married at the Asticou Inn on September 10, 2004. In November, 2004, they purchased a Southwest Harbor-built Jarvis Newman Friendship Sloop and are currently shaping the mast from a donated spruce tree. The "new" sloop will allow Downeast Friendship Sloop Charters to operate from two locations: Great Harbor Marina in Southwest Harbor, and the Harborside Hotel and Marina in Bar Harbor.