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Maine Sailing trips & boat tours

Our most recommended Maine Sailing trips & boat tours

Penobscot Bay: Historic Schooner Day Sailing Trip

1. Penobscot Bay: Historic Schooner Day Sailing Trip

Experience one of the top things to do in Camden sailing along Maine's magnificent rocky coastline. Climb aboard the elegant Appledore II, a historic schooner. Feel like an adventurer from the 19th-century while enjoying state-of-the-art accommodations onboard a modern windjammer. Stroll along the wide decks as you take in the sights without needing to duck beneath the rigging. With a capacity of only 49 passengers, there is abundant seating to make yourself comfortable for this intimate sailing trip. Enjoy the chance to sail your own wooden ship as the crew welcomes your participation. Offer to help raise the sails and take a turn at the wheel of this hard-working, seaworthy schooner. Ask your crew about the history of the boat which has sailed around the world, docking at many harbors along the way. Twice a year, she still sails the Eastern seaboard between her 2 home ports of Camden, Maine and Key West, Florida.  Start the tour by departing from Bayview Landing and heading out of Camden Harbor. Discover why Camden is often called the jewel of the Maine coast as you sail past the impressive lighthouse, Curtis Island Light, dating from 1836, and into Penobscot Bay. Considered to be one of the top cruising bays in the world, Penobscot Bay will amaze you with its uninhabited islands, wildlife, and views of Camden Hills and other coastal mountains dropping off into the sea. During the tour, look along the shore for Mount Battie, historic inns, and elegant summer mansions of the rich and famous with their million dollar yachts. Watch lobstermen hauling in their traps. On a typical day, you may see porpoises playing in the water, ospreys, eagles hunting for fish, and even the occasional whale. Watch for seals sunning themselves on rocks and cute guillernots (cousins of the puffin), with their bright red feet, wobbling as they walk along the rocky shoreline. Quench your thirst with cocktails, beer, wine and soft drinks, all available for purchase during your sailing cruise. As Camden Harbor comes back into view, relax and feel the wind sweep through your hair as your memorable sailing ship cruise draws to a close.

Portland: Schooner Tall Ship Cruise on Casco Bay

2. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Camden: Sunset Sailing Cruise Aboard Appledore II

3. Camden: Sunset Sailing Cruise Aboard Appledore II

Board the Appledore II in Bayview Landing in Camden, and enjoy a 2-hour sunset cruise. Admire the beautiful harbor, framed by mountains, and appreciate the views from the wide decks. Help to raise the sails, take a turn at the wheel, and experience captaining a traditional wooden ship. Cruise past Curtis Island Light and into Penobscot Bay. Sail along the rugged coastline, take in the majestic mountains, and look out for local wildlife such as seals, porpoises, and eagles. Cocktails, beer, wine, and soft drinks are available for purchase as you enjoy the sunset over Mount Battie.

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What people are saying about Maine

Overall rating

4.5 / 5

based on 6 reviews

Definitely not a sailor so when the boat tilts it’s a bit disconcerting until you realize that’s what sailing is supposed to be. We apparently had real good wind on our trip so got to go out past where most end up. Very cool activity, got to see three lighthouses, some very cool houses along the coast and the rugged coast line without the drone of an engine. Captain and the other crew were knowledgeable and very cool, a nice peaceful adventure, definitely worth it in my book

This was the perfect way to end our Maine trip. Staff was friendly and knowledgeable and the boat itself was stunning. Learned A lot of history about the boat. My partner and I Loved every minute of it . Take advantage of the byob.

Was great but got charge for two people- only order for myself! Need a refund. Everything else was excellent!

Very relaxing! Lots of nice views! The crew is knowledgeable and funny!

Great sailboat rode around Casco Bay! Beautiful. Wonderful crew!