Private Casco Bay Sails

Custom Sailing Adventures on Casco Bay

4-Hour Sails

Afternoon or Sunset Sails

All of our sailing trip include snacks, soft drinks, water, and a signature drink of the day - featuring in season local ingredients and spirits. (These can be tailored to your needs).  

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The four-hour sail is a perfect way to spend the afternoon or enjoy the sun setting over the picturesque Portland skyline.  

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Trip starts at $475 for up to 6 passengers, and can be modified to include expanded dining options, tailored drop-off, or other special considerations.  

Full-Day Sails

All-Day Customized Sails

All of our sails include snacks, soft drinks, water, and a signature drink of the day - featuring in-season local ingredients and spirits. (These can be tailored to your needs).  

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A full-day sail allows you to experience all of Casco Bay, and let's you dictate the type of adventure you will have.  Sailing to lunch at Dolphin Marina, Chebeague Island, or to just explore Maine's iconic rocky coastline and scenic lighthouses.  The chances of spotting whales and porpoises increase as we get outside Casco Bay.  

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Trip starts at $875 for up to 6 passengers, and can be modified to include expanded dining options, tailored drop-of, or other special considerations.  

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Add-Ons

Inspiration for Customizing Your Trip

You are in fantastic hands with Captain Paul Leddy - who can tailor every trip to meet your needs.  

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Let us know if you'd like - 

• Pick-up or drop-off at a special location

• A lobster bake on board 

• A Maine beach cookout

• Overnight at Sebasco Resort

• An elopement cruise, engagement photos, or special wedding transportation