Portland Tall Ship Cruise on Casco Bay: Sail Maine Schooners

Lighthouses, seals and the chance to steer a tall ship on Casco Bay

A two-hour sailing cruise on Casco Bay departing from Portland aboard one of three historic Maine schooners—Bagheera, Wendameen or Timberwind—where you can help raise the sails, take a turn at the wheel, or simply sit back and watch the Maine coast slip past. All three ships are wooden windjammers listed on the National Register of Historic Places, certified by the U.S. Coast Guard, and built in Maine. Life jackets are provided for all ages.

Step-by-step itinerary

Two-hour tall ship cruise on Casco Bay

• Board Bagheera, Wendameen, or Timberwind
• Sail along Maine coast and see lighthouses
• Observe seals and seabirds
• Relax with packed meal and drinks
• Optionally help crew hoist sails or steer

The Experience

You board one of three tall ships—Bagheera (built in 1924), Wendameen, or Timberwind—and spend two hours sailing Casco Bay. The route takes you past lighthouses, rocky shoreline and seals; seabirds wheel overhead. A live English-speaking guide is aboard. If you want to stay passive, you can bring a meal and your own wine or beer, find a spot on deck and watch the water. If you want to move, the crew will teach you to hoist the sails or let you take a turn steering the ship's wheel.

The ships are small enough to feel the sail work but large enough to hold 35 guests comfortably. All three are wooden vessels—not replicas—and their age and materials are part of what makes them work: they move differently through the water than modern boats, and the rigging and deck layout are the real thing. Bagheera, the oldest, was built in 1924. Everyone from nine years old to 99 can sail; there's no fitness requirement beyond being able to board and move around a working ship deck.

You can book the public cruise, which runs on a set schedule with other passengers, or reserve a private sailing for up to six people. Either way, life jackets are on hand for adults and children. Public transportation reaches the departure point in Portland, and the cruise itself is the activity—there are no additional stops or shore time built in.

What’s included

• Two-hour sailing cruise on one of three historic Maine schooners.
• life jackets for all ages.
• a live English-speaking guide.
• the option to help raise the sails or steer the ship.

Good to know

Easy physical levelPublic transport nearby

Operated by Wow A Tour

Is this one for you?Meet fellow sailors on a shared schooner cruise, or book privately to have the ship and your departure time entirely to yourselves.

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Top questions

What's the difference between the public cruise and the private option?

The public cruise runs on a fixed schedule and shares the schooner with other guests. The private cruise reserves the boat for your group of up to six people and lets you set the departure time together with the crew.

Can I really help sail the ship, or is that just something they say?

The crew teaches interested passengers how to hoist the sails and offers turns at the wheel during the two-hour sail. It's optional—you can participate as much or as little as you want, and many guests simply watch from deck.

What should I bring on the cruise?

Bring a meal and your own wine or beer if you want to eat aboard. Life jackets are provided. Wear layers and closed-toe shoes; the deck can be wet and the wind picks up on the water even on calm days.

How old do kids have to be to sail?

All ages are welcome aboard. Life jackets are available for children. The crew can advise on whether a very young child will be comfortable on a moving deck for two hours.

What will I see on Casco Bay?

The cruise passes lighthouses, the rugged Maine coastline, and rocky islands. Seals are common sightings, and seabirds are always present. The exact route depends on wind and weather, but the guide will point out landmarks and wildlife as you sail.

Are these real historic ships or modern replicas?

All three schooners—Bagheera, Wendameen and Timberwind—are original wooden tall ships built in Maine and listed on the National Register of Historic Places. Bagheera dates to 1924. They are certified by the U.S. Coast Guard and operate as working sailing vessels.