Portland, Maine: Coastal Windjammer Sailing Cruise

This review explores a delightful two-hour sailing adventure in Portland, Maine, operated by Portland Schooner Co. The experience promises a peaceful cruise on authentic windjammers like Bagheera, Wendameen, or Timberwind, gliding through Casco Bay. With a high rating of 4.7 out of 5 based on 42 reviews, it’s clear travelers find this tour both enjoyable and memorable.

What makes this sailing cruise truly appealing is its ability to combine scenic beauty with a taste of Maine’s maritime craftsmanship. We particularly love the chance to see Portland from a totally different perspective—standing on a classic wooden schooner, feeling the wind, and spotting lighthouses, seals, and seabirds along the way. The relaxed pace and authentic vessel offer an experience that’s both educational and fun for all ages.

A potential consideration is that the tour is entirely BYO food and drinks, which means you’ll need to pack your own picnic or beverages if you want to sip wine or beer during the cruise. While this allows for personalized snacks and drinks, it’s one more thing to organize. This cruise suits families, couples, or groups of friends who enjoy outdoor adventures and scenic marine environments but don’t mind bringing their own refreshments.

This windjammer sailing in Casco Bay is perfect for those looking to slow down, enjoy nature, and soak up Portland’s coastal charm in a relaxed and authentic setting. If you appreciate maritime history, wildlife, and stunning views, this is a route you’ll want to consider.

Key Points

• Authentic Wooden Vessels: Sail on historic windjammers listed on the National Register of Historic Places, offering a genuine maritime experience.
• Scenic Views: Experience Portland and Casco Bay from a unique vantage point, watching lighthouses, seals, and seabirds in their natural habitat.
• Relaxing Atmosphere: The two-hour cruise offers a peaceful, laid-back outing suitable for all ages, with friendly crews like Shawn, who are both knowledgeable and personable.
• Bring Your Own Food & Drinks: The tour doesn’t include food or beverages, so packing a picnic, wine, or beer is necessary—making it customizable.
• Educational & Fun: Besides sightseeing, expect interesting commentary from guides about the area and its maritime history, which adds depth to the experience.
• Excellent Value: At $67 per person, this cruise provides a memorable, hands-on maritime adventure without breaking the bank.

An In-Depth Look at the Portland Windjammer Cruise

The Experience and What You’ll Love

We love the relaxed vibe of this two-hour cruise. It’s less about ticking off landmarks and more about enjoying the coast’s natural beauty and tranquil waters. As you set sail from 56 Commercial St, the starting point is conveniently located at the Maine State Pier, with straightforward check-in. Boarding a classic wooden schooner like Bagheera, Wendameen, or Timberwind feels like stepping back in time—these vessels are true pieces of Maine’s maritime heritage.

During the cruise, you’ll glide past iconic lighthouses—an absolute highlight for many reviewers—offering fantastic photo opportunities. Seals are often spotted lounging on rocks or popping their heads up near the boat, which delights wildlife lovers. Birdwatchers will also appreciate the seabird activity, adding lively elements to the scenery.

The crew, led by experienced skippers such as Shawn, receives high praise for their friendliness and knowledge. One reviewer mentioned Shawn’s enthusiasm for sharing local stories and maritime history, making the trip both entertaining and educational. The crew’s attentiveness ensures everyone feels safe and engaged, whether you’re a seasoned sailor or trying it for the first time.

The Itinerary Breakdown

Starting at 56 Commercial St, the journey begins with calm waters as the crew prepares the schooner for departure. Once under sail, the focus is on enjoying the ride—feeling the wind in your hair, listening to the creaking of the wooden frame, and taking in the expansive views of the coastline.

The core of the tour is the Casco Bay sailing segment, which lasts around two hours. During this time, you’ll drift by striking lighthouses, watch seals swim nearby, and observe seabirds in flight. The pace is slow enough for photographs and conversation, making it ideal for families or couples seeking a peaceful escape.

Returning to the dock at 56 Commercial St, you’ll arrive refreshed and with plenty of memorable snapshots. The whole experience is designed to be easy, with no complicated logistics—just show up, bring your snacks, and relax.

What Reviewers Say

Multiple guests appreciated the crew’s friendliness and the boat’s charm. One shared that Shawn and his team “were great,” with the captain being “very knowledgeable” about the area’s history. Another review mentioned, “It was a brilliant day, a good group, and it could not have been a better experience,” highlighting the convivial atmosphere.

The weather can make or break the trip. One reviewer pointed out that an October sail was especially relaxing, adding that “a hot chocolate or two would have topped it off,” implying cooler days might benefit from warmer drinks. Still, with proper planning, most find the experience quite comfortable and enjoyable.

Practical Details and Value

At $67 per person, this cruise offers a reasonable price for a memorable maritime adventure. Since food and drinks are not included, you can bring your own soft drinks, wine, or even a picnic dinner. This flexibility allows you to tailor your experience—whether you prefer a light snack or a full meal as you cruise.

The tour duration of 2 hours is ideal for fitting into a busy day without feeling rushed. It’s perfect for those wanting a brief yet immersive coastal experience. Group size tends to be moderate, ensuring a more personalized vibe, and the crew’s attentiveness adds value to the trip.

The onboard amenities include a marine composting toilet, making the trip more environmentally friendly—a detail appreciated by eco-conscious travelers.

Who Is This Tour Best Suited For?

This cruise is especially well-suited for travelers who value authentic maritime experiences and scenic, leisurely outings. It appeals to families eager for a safe, fun activity, couples looking for a romantic escape, or groups of friends wanting a relaxed day on the water. If you enjoy wildlife watching, stunning coastal views, and a touch of history, you’ll find plenty to love here.

However, those seeking an all-inclusive experience with snacks and beverages included might find it more suitable to bring their own. Also, if you’re sensitive to cooler weather, consider packing an extra layer—October sailings have been described as “chilly,” though still pleasant with the right clothing.

FAQ

Is the cruise suitable for children?
Yes, the cruise is family-friendly and fun for all ages. The relaxed pace and scenic wildlife sightings make it a great outing for kids.

Do I need to bring my own food and drinks?
Yes, food and drinks are not included, so you should bring your own picnic, soft drinks, wine, or beer if you want to enjoy beverages during the trip.

What should I wear?
Dress comfortably and consider layers, especially if sailing in cooler months. Since the trip is mostly outdoors, bring sunglasses, sunscreen, and a hat for sun protection.

How long is the cruise?
The sailing itself lasts approximately 2 hours, but plan for additional time for check-in and boarding at 56 Commercial St.

Are there any environmental considerations?
Yes, the boat has an environmentally friendly marine composting toilet, which supports eco-conscious tourism.

Is there a minimum or maximum group size?
While not explicitly stated, the reviews suggest a comfortable group size that allows for personal attention from the crew, likely moderate to small.

Final Thoughts

The Portland Windjammer Sailing Cruise offers a genuine taste of Maine’s maritime heritage and coastal beauty. Its combination of historic vessels, peaceful waters, and friendly crew makes it a standout experience for those wanting to connect with nature and history in a relaxed setting. At a reasonable price point, it’s a fantastic way to spend a couple of hours soaking in the scenery, spotting wildlife, and enjoying a bit of the seafaring lifestyle.

If you’re looking for an authentic, scenic, and flexible outdoor activity that suits families, couples, or groups of friends, this cruise is definitely worth considering. Just remember to pack your preferred snacks and drinks, dress appropriately for the weather, and prepare for a memorable voyage along Casco Bay.

In summary, this windjammer cruise is best for travelers who seek a peaceful, scenic escape with a taste of maritime history. It’s perfect if you value authentic experiences and appreciate the natural beauty of Portland’s coastline, all while enjoying the comfort of being aboard a beautifully maintained historic vessel. Whether you’re a wildlife enthusiast or simply wanting to unwind on the water, you’ll find plenty to love here.