Your private charter sets sail from Portland’s Old Port, the historic heart of Maine’s largest city. This vibrant waterfront district blends 19th-century brick warehouses, cobblestone streets, and working fishing piers with boutique shops, acclaimed restaurants, and lively pubs. Just steps from our dock, it’s where modern Portland meets its salty roots. For large private groups—corporate gatherings, weddings, reunions, or celebrations of any kind—the Old Port offers the perfect blend of charm and convenience. It’s not just a meeting location; it’s a built-in prelude to your Casco Bay experience. As you board one of our classic wooden vessels, the buzz of the city fades and the beauty of the bay unfolds—starting your private cruise with both energy and elegance.

Bug Light Park

Officially named Portland Breakwater Light, Bug Light is a charming, cast-iron lighthouse that marks the entrance to Portland Harbor. Though small in stature, its elegant Greek Revival design and striking white tower make it one of the most photographed beacons in Maine. As the first of four iconic lighthouses typically seen on our cruises, Bug Light offers a postcard-perfect moment right at the start of your journey. For large private groups—whether you’re here for a celebration, corporate outing, or just a memorable day on the water—this scenic highlight sets the tone for the rest of your experience aboard our beautifully restored wooden vessels. With the Portland skyline behind you and open bay ahead, it’s a breathtaking introduction to Casco Bay’s maritime charm.