Portland Maine Traditional Windjammer Sailing Tour


Free cancellation

A full refund will apply if you cancel more than a day before the activity start time.

Duration2 hours
Guide LanguageEnglish
Good To KnowE-voucher
196 reviews


Meet at the designated meeting location in Portland for this Casco Bay tall-ship cruise. Once you check in and board your historic windjammer boat, find a seat and relax. Remember you can also bring your own alcohol, drinks, and snacks, or a meal with you on board to enjoy during your time on the water. If you’d like to try and hoist the sails or be behind the ship’s wheel, let your guide know before you set sail.
As you cruise, your guide navigates the bay with ease, giving you great viewing points to take in the Maine Coast and Portland. Sightseeing highlights can include lighthouses, seals, and seabirds.
Your Casco Bay cruise lands back at the pier in Portland for drop-off after your experience ends.


See a perspective on Portland that most visitors miss
Enjoy the relaxing pace aboard a traditional, Maine-built windjammer
Bring your own snacks, refreshments, and alcoholic drinks
This family-friendly outing is suitable for kids and adults


Sail aboard Bagheera, Wendameen, or Timberwind for a two-hour cruise from Portland, Maine on Casco Bay. Sailing on our windjammers is the perfect way to experience the beauty of the Maine coast, complete with lighthouses, seals, seabirds and the rugged coastline
Pack a meal, bring your favorite wine or beer and sit back and relax as you slip through the cool waters of Maine. Or, if you feel inspired, join the crew to hoist the sails or take a turn at the ship's wheel. All ages are welcome! Whether you're nine years old or 99, sailing aboard our Maine schooners is a unique adventure. All of our wooden windjammers are listed on the National Register of Historic Places and were built in Maine. Certified by the U.S. Coast Guard, Bagheera was built in 1924 and can comfortably accommodate 35 guests.


Schooners are equipped with life jackets for adults and children
2 Hour Cruise


Food and Drink

Additional Information

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

Guide Languages

  • English

Cancellation Policy

  • A full refund will apply if you cancel more than a day before the activity start time.

  • No refund is possible if you cancel less than a day before the activity start time.