Portland Schooner Co.

"Set sail with Portland Schooner Co. for a 2-hour cruise on an early-20th-century wooden schooner hand-built in Maine." - Sophie Friedman

"Boarding one of these three schooners, all of which are on the National Register of Historic Places, is a terrific and different way to see Portland. It's also fantastic for kicking back while discovering how beautiful Casco Bay is, with fresh, salty air all around you. For anyone who appreciates the above (as long as your stomach doesn't do flips on the water), consider a sail with Portland Schooner Co. your one-and-done mode of exploration." - Alexandra Hall

"Zoom out. What’s the big picture here? Portland Schooner Co. uses three vessels: The Bagheera, The Wendameen, and The Timberwind, all of which are listed on the National Register of Historic Places. The stunningly beautiful windjammers hold between 35 and 45 guests and were all built in Maine. And while the boats themselves don't feel crowded once you're on them for the two-hour sail, tickets should definitely be bought in advance. Tell us about your fellow tourees. Friend groups and couples from neighboring cities and on vacations from Virginia, L.A. , and Europe. The experience is far more of a relaxing sail than a verbal tour—the incredibly friendly and helpful sailing crew will often point out significant attractions as they go by and has even been known to let guests steer. Guests on our ride seemed more than happy to relax and enjoy the sail. How are the guides, then? The boats' crews could not be nicer to guests, or more enthusiastic about sailing and being out on the water. They clearly know the waters of Casco Bay and are expert sailors. Anything you’ll be remembering weeks or months or years from now? The sail itself is the show here. It's a glorious rush of natural scenery mixed with a salty breeze and soul-warming sun. Guests—including strangers—talk easily among each other, sharing stories from home and enjoying the coastline's sights, which include lighthouses and marine life like seals and seabirds. So: Who will enjoy this most? It's a terrific way to see Portland from a different perspective, and to relax and take a deep breathe of sea air while discovering how beautiful Casco Bay is. It's great for anyone who appreciates any of that, but it is not great for those with stomachs that are particularly sensitive to seasickness. Though the boats stay within the calm waters of the bay, those prone to queasiness will be risking two hours of unhappiness." - Alexandra Hall