Portland Maine: Sunset Windjammer Cruise & Casco Bay Lighthouses★★★★★★★★★★4.72 (183)2hYou board a working wooden schooner and sail Casco Bay for two hours, passing lighthouses, seals, and the 1858 Fort Gorges while Portland's fishing wharves slip behind you. Bring your own food and wine, ask the crew what you want to know, and let the sails do the work. No narration, no schedule—just the water and the boat.Is it for me?Right for anyone wanting to be on the water without a guided tour script—you get the boat, the sails, the lighthouses and seals, and two hours of quiet time with a drink and a meal. The boat works for all ages and fitness levels, though expect to be outside on deck the whole time.fromUS$ 77View ›
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Portland Sunset Harbor Cruise & Local Craft Beer★★★★★★★★★★4.65 (115)1h 30mYou board the Elizabeth Grace at Portland's harbor, cruise past Maine's oldest lighthouse and a 19th-century island fort while sipping included local craft beer, watch for seals in Casco Bay, and take in the sunset from the water before the city's nighttime skyline lights up. The whole thing takes 1.5 hours, small groups stay under control, and you're back on land before dark.Is it for me?Book this if you want the Maine sunset and the lighthouses without arranging your own boat—the fixed departure time and included drink mean you show up, board, and the rest happens on schedule.fromUS$ 89View ›
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Portland Maine: Lighthouse Cruise & Casco Bay with Wine★★★★★★★★★★4.52 (99)1h 30mYou board Ruth at the Portland waterfront and spend ninety minutes drifting past five lighthouses, Fort Gorges, and the working islands of Casco Bay while seals and seabirds move around you. Bring your own picnic and wine. The boat does the work; you just sit there and let the 1935 wooden hull carry you through water that's been doing this since before the lighthouses were built.Is it for me?Right for families and groups who want to see Maine's lighthouses without a guided narrative — just a slow boat, salt water, and time to talk or sit quiet. The ninety minutes is short enough for restless kids but long enough to actually feel like you've left the city.fromUS$ 64View ›