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Spend two hours aboard a 1925 Alden schooner on Casco Bay, helping raise the sails or relaxing as lighthouses and islands slide past. This private charter from Portland offers hands-on sailing, close coastal views, and flexible food-and-drink options.
Spend two hours aboard a 1925 Alden schooner on Casco Bay, helping raise the sails or relaxing as lighthouses and islands slide past. This private charter from Portland offers hands-on sailing, close coastal views, and flexible food-and-drink options.
The schooner heels a little as the harbor loosens its hold and Casco Bay opens like a slate of moving coastline. Salt air pushes at your jacket, tucking gulls into your wake; islands cluster ahead, their rocky shoulders smoothed by ancient ice and tide.
Verified experiences and guided adventures in the surrounding area.
Operated by Wow A Tour · Portland, Maine
The schooner heels a little as the harbor loosens its hold and Casco Bay opens like a slate of moving coastline. Salt air pushes at your jacket, tucking gulls into your wake; islands cluster ahead, their rocky shoulders smoothed by ancient ice and tide.
This is Hearts Desire, a 1925 Alden-built 53-foot schooner based in Maine. The route threads past working lobster grounds, weathered sea houses and lighthouses that cut both warning and welcome into the headland—remnants of the region’s shipbuilding and fishing culture. Geologically, the bay is a glacially scoured archipelago; islands rise from bedrock and cobble shores where waves keep the line between land and sea sharp.
Local culture is maritime and plainspoken: captains trade weather tips over coffee in the Old Port, and island communities still mark seasonal rhythms by boat schedule. On a private two-hour charter you can help hoist canvas, take the wheel, or simply settle into the deck and watch forts and ledges slip by.
Practical notes: departures are from Fore Points Marina on Portland’s working waterfront; the cruise is two hours and suitable for most fitness levels. Life jackets are provided; alcohol and food are allowed aboard. Aim for morning light for calm water or late afternoon for warmer tones and dropping winds. Dress in layers, wear non-marking shoes, and bring sun protection and a refillable water bottle. If wind picks up, jackets and a steady hand at the rail make the difference between chilled and comfortable.
Whether steering for the first time or watching seals roll alongside, the trip pairs approachable seamanship with close-up coastal scenery—simple, social, and thoroughly marine.
Charters are arranged for your private group—typically up to six people, though confirm capacity with the operator when booking.
Yes; beer, wine and other alcoholic beverages are permitted and guests often bring snacks or small meals.
Yes; life jackets are provided and the cruise is suitable for a wide range of fitness levels, but boarding may require a short step from dock to vessel.
Trips may be cancelled for safety in poor weather—check cancellation policies and expect refunds if the operator cancels within the stated timeframe.
Wow A Tour operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
The schooner heels a little as the harbor loosens its hold and Casco Bay opens like a slate of moving coastline. Salt air pushes at your jacket, tucking gulls into your wake; islands cluster ahead, their rocky shoulders smoothed by ancient ice and tide.
The schooner heels a little as the harbor loosens its hold and Casco Bay opens like a slate of moving coastline. Salt air pushes at your jacket, tucking gulls into your wake; islands cluster ahead, their rocky shoulders smoothed by ancient ice and tide.
This is Hearts Desire, a 1925 Alden-built 53-foot schooner based in Maine. The route threads past working lobster grounds, weathered sea houses and lighthouses that cut both warning and welcome into the headland—remnants of the region’s shipbuilding and fishing culture. Geologically, the bay is a glacially scoured archipelago; islands rise from bedrock and cobble shores where waves keep the line between land and sea sharp.
Local culture is maritime and plainspoken: captains trade weather tips over coffee in the Old Port, and island communities still mark seasonal rhythms by boat schedule. On a private two-hour charter you can help hoist canvas, take the wheel, or simply settle into the deck and watch forts and ledges slip by.
Practical notes: departures are from Fore Points Marina on Portland’s working waterfront; the cruise is two hours and suitable for most fitness levels. Life jackets are provided; alcohol and food are allowed aboard. Aim for morning light for calm water or late afternoon for warmer tones and dropping winds. Dress in layers, wear non-marking shoes, and bring sun protection and a refillable water bottle. If wind picks up, jackets and a steady hand at the rail make the difference between chilled and comfortable.
Whether steering for the first time or watching seals roll alongside, the trip pairs approachable seamanship with close-up coastal scenery—simple, social, and thoroughly marine.