Portland Maine: Sunset Windjammer Cruise & Casco Bay Lighthouses

Two Hours Under Canvas, Past Granite Forts & Working Docks

You 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.

Step-by-step itinerary

Windjammer cruise along Portland coast

• Board historic Maine schooner
• Sail through pristine Casco Bay
• Enjoy rugged coastline views
• Spot lighthouses and seals
• Observe Portland skyline and waterfront
• View massive granite Fort Gorges

The experience

The boat is already moving when you step aboard. The crew has the sails up and you're slipping into Casco Bay before you've found your spot on deck. It's a two-hour windjammer cruise on one of Maine's historic wooden schooners, the kind built right here in Portland and old enough to be on the National Register. You're not getting narration or a script. The crew answers questions if you ask, but mostly you're just sailing. Lighthouses come into view, seals surface near the hull, and Fort Gorges (those massive granite blocks stacked from 1858 to 1864) rises up from the water like something that's been there longer than the country itself.

The working waterfront slides past as you move through the bay. Fishing boats are still tied up or heading out, the wharves busy with the kind of local business that's been running the same way for generations. You can bring your own meal, your own wine or beer, and just sit with it while the water moves under you. The whole thing takes two hours, which is long enough to feel like you've actually left, but short enough that you're back on the dock before the light goes completely soft. Life jackets are there if you need them (kids and adults both), and the boat works for everyone from nine years old to ninety-nine.

The schooner itself is part of it. These aren't replicas or modern boats dressed up to look old. They're the real thing, built in Maine, wooden hulls and canvas sails doing what they've always done. You're not touring Casco Bay. You're sailing it the way people have for a long time. The crew knows the water, knows where the seals hang out, knows the history of the granite fort. If you want to ask, they'll tell you. If you want to sit quiet and watch the skyline of Portland fade behind you, that works too.

What’s included

• Your two-hour cruise includes a spot on one of Maine's historic wooden schooners, life jackets for all ages, and access to the boat's deck as you sail through Casco Bay.
• You bring your own food, wine, or beer.
• An environmentally friendly marine composting toilet is onboard.
• The crew is available to answer questions about the lighthouses, seals, Fort Gorges, and Portland's working waterfront, but there is no formal narration or guided tour.

Before you book

Days and timesThursday to SaturdayDeparts at 16:00Last departure this season: 31 Oct

Book up toStart time

AgesAdult (13 and older) · Child (under 13)

GroupUp to 45

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyPublic transport nearby

Operated by Portland Schooner Co.

Is this one for you?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.

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Top questions

Can children come?

Yes. Ticket types: Child (under 13).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How long is the cruise?

Two hours on the water.

Can I bring food and drinks?

Yes. Pack your own meal and bring wine or beer if you want.

Is there a guide or narration?

No narration. The crew is there to answer questions if you have them.

Are life jackets provided?

Yes, for both adults and children.

What will I see?

Lighthouses, seals, Fort Gorges (a granite military fort from 1858–1864), and Portland's working waterfront with fishing boats and local wharves.

Are the boats really historic?

Yes. All the windjammers are wooden schooners built in Maine. Three are on the National Register of Historic Places.

What if the weather is bad?

Check with the operator about their weather policy before booking.