Portland Sailing

Explore sailing adventures in Portland, Maine. Enjoy windjammer cruises, private charters, and sunset sails along Casco Bay. Book your maritime experience today!

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2 Hour Private Morning Charter on Heart's Desire in Casco Bay

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built i

From $550.00 USD

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard He

★ 5.0 (2)

From $675.00 USD

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with li

★ 4.7 (271)

From $69.00 USD

Casco Bay Morning Windjammer Sail

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, c

★ 4.9 (40)

From $61.00 USD

Casco Bay Sailing Escape: Half Day Custom Boat Charter

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run s

From $199.00 USD

Casco Bay: Private Afternoon Charter on Heart's Desire

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten

★ 4.0 (1)

From $650.00 USD

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink on the water. C

★ 5.0 (2)

From $185.00 USD

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make y

★ 4.6 (243)

From $101.66 USD

Portland Tall Ship Private Charter on Casco Bay

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the

From $1,071.13 USD

Private Half Day Sailing Charter in Portland Maine

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience a

★ 5.0 (1)

From $475.00 USD

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine the perfect way to experience the beauty of the rugged coastline, complete with ligh

★ 4.7 (201)

From $77.00 USD