Afternoon Windjammer Cruise: Casco Bay Sailing in Portland

Wooden schooners built in Maine, three on the National Register of Historic Places.

An afternoon windjammer sail on Casco Bay in Portland, Maine, where you board a historic wooden schooner and spend two hours under sail past lighthouses, seals, and seabirds. The crew is there to answer questions about what you're seeing, but this is not a narrated tour—you set the pace by how much you want to engage. Life jackets are provided; you bring your own food and drink.

Step-by-step itinerary

Afternoon Windjammer Cruise on Casco Bay

• Board historic Maine schooner
• Sail along rugged coastline
• View lighthouses and seals
• Relax and enjoy the scenery

The Experience

The boat leaves Portland for Casco Bay, and the two-hour sail takes you through waters lined with lighthouses and rocky points where seals haul out. You'll see seabirds working the bay and the rugged Maine coastline that makes this stretch of water distinctive. The schooner itself is the draw—all three of the fleet's wooden windjammers were built in Maine, and three are listed on the National Register of Historic Places, so you're sailing on a piece of maritime history, not a modern replica.

Pack a meal or grab something before you board, bring wine or beer if you want it, and settle in for the afternoon. The crew doesn't narrate the sail, so there's no script or schedule of facts—instead, you watch the water, feel the boat move under sail, and ask the captain or crew about anything you're curious about. All ages sail together; infants and small children can ride in a stroller or pram, and specialized infant seats are available if you need one.

Life jackets are provided. Public transportation options are nearby if you're getting to the dock without a car. The sail works for anyone, regardless of fitness level—you're sitting or standing on deck, not climbing or exerting yourself.

What’s included

• Life jackets.
• two hours on the water under sail in Casco Bay.
• access to a historic Maine-built schooner.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by Portland Schooner Co.

Is this one for you?You're sailing an actual historic schooner through Casco Bay's lighthouses and seals—the crew answers questions, but the experience centers on the vessel, water, and coastline.

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Top questions

What will I see sailing through Casco Bay?

Casco Bay's rugged coastline passes lighthouses, seals hauled out on rocks, and seabirds. The two-hour sail stays in the bay waters off Portland, so you're seeing the working harbor and natural features of this stretch of Maine coast.

Is there a guide or narration on the windjammer?

The captain and crew are happy to answer any questions you have about the sights and the boat, but this is not a narrated tour. You decide how much you want to learn as you sail.

Can I bring food and drinks aboard?

Yes—pack a meal and bring your favorite wine or beer. Food and drink are not provided, but you're welcome to bring your own and enjoy them on deck.

Are the schooners really historic?

All three wooden windjammers in the fleet were built in Maine, and three of them are listed on the National Register of Historic Places. You're sailing on working historic vessels, not reproductions.

Can I bring young children or infants?

All ages are welcome. Infants and small children can ride in a pram or stroller, and specialized infant seats are available if you need one.