Afternoon Windjammer Cruise Along the Coast of Portland Maine

If you’re looking for a laid-back way to enjoy Portland’s scenic shoreline, the Afternoon Windjammer Cruise with Portland Schooner Co. might just be what you need. This two-hour sailing adventure offers a peaceful escape on one of Maine’s historic schooners — perfect if you want a taste of maritime life without the fuss of a narrated tour.

What we really like about this experience is how relaxed it feels. You can bring your own snacks and drinks—think wine, beer, or a picnic—and simply sit back while the crew navigates the waters. Plus, it’s a great way to see Portland’s rugged coastline, lighthouse islands, and maybe even catch sight of seals and seabirds.

One thing to keep in mind is that this isn’t a guided or narrated trip — it’s more about the experience of being on a boat, soaking in the views, and chatting with friendly crew members if you’re curious. It’s best suited for those who enjoy a calm, scenic ride rather than a structured tour with detailed commentary. Overall, if you’re after a peaceful, scenic outing that’s flexible and informal, this cruise is worth considering.

Key Points

• Relaxing two-hour sail perfect for unwinding and soaking in views
• Bring your own food and drinks for a personalized experience
• All ages welcome, including families, with a friendly crew ready to chat
• Beautiful scenery of Portland’s coast, lighthouses, seals, and seabirds
• Historical schooners, three of which are listed on the National Register of Historic Places
• No narration included, so curiosity about sights is encouraged to prompt questions

What the Experience is Like

This cruise is about enjoying the ride rather than learning minute details about every landmark. The crew is friendly and responsive, happy to answer questions about the harbor sights—so if you’re interested in the area, don’t be shy about asking. The schooner itself is a beautiful piece of Maine maritime history, giving you a real sense of what sailing was like centuries ago.

The 2-hour duration is just right: long enough to relax and take in the scenery without feeling drained or restless. The boat is well-maintained, with life jackets provided for safety. The crew is described as professional, friendly, and knowledgeable, making the journey smooth and pleasant.

Several reviews highlight how peaceful and enjoyable the sail is, with “perfect weather,” “gorgeous scenery,” and “friendly staff” making it a memorable outing. One reviewer even mentioned how their first time on a sailboat was a “very beautiful boat” experience, emphasizing the calming nature of the ride.

The Itinerary in Detail

The tour primarily involves sailing along Portland’s rugged coastline, where you’ll see iconic lighthouses and possibly seals lounging on nearby rocks or swimming alongside the boat. The focus isn’t on stopping at sights but rather passing by them in a way that highlights their natural beauty.

While the main activity is floating peacefully through Casco Bay, the crew occasionally help with sail handling, which can be a fun interaction for those interested in the maritime craft. If wind conditions permit, you’ll feel the thrill of actual sailing, but if winds are light, the crew might use the boat’s motor to keep the cruise on schedule. One reviewer mentioned this as a minor point but still found the experience thoroughly enjoyable.

You’ll find that the scenery from the boat is stunning, with views of Portland’s coastline, islands, and the open water. The quiet and calm waters make for a smooth ride, ideal if you’re prone to seasickness or just want a relaxing day on the water.

What You Can Expect on Board

You’ll meet at 56 Commercial St, a central location in Portland, easily accessible and near public transport. The meeting process is straightforward, and the tour ends back at the same location, making logistics simple.

Once aboard, you’ll be given a life jacket, but beyond that, there’s no formal guide or narration. This means you’re encouraged to ask questions if you’re curious about anything during the trip, which many reviews praise as a highlight. The crew‘s friendliness and knowledge make this easy and enjoyable.

Since you’re welcome to bring your own food and beverages, you can pack a picnic, snacks, and drinks, turning this into your own personalized outing. Just remember, the price is $67 per person, which many consider a fair deal given the length and the unique experience on a historic schooner.

Analyzing the Value

At $67, this cruise offers a leisurely way to experience Portland’s coastline without breaking the bank. It’s a value-for-money experience because you’re getting a scenic, boat-only adventure with no hard sell or extras expected. The chance to sit back, enjoy your own meals and drinks, and soak in the scenery makes it feel like a personalized day out on the water.

Plus, the small group size—maximum 45 travelers—ensures a more intimate experience, avoiding overcrowding. The reviews consistently note how friendly and accommodating the crew is, which adds to the overall value.

Who This Tour Is Perfect For

This cruise is ideal for families with kids who want a safe, calm adventure or for couples and friends looking for a relaxed escape. It suits those interested in nature, photography, or simply enjoying a peaceful day on the water. It’s also great if you’re curious about sailing but don’t want a long or complicated lesson — just a serene sail in beautiful surroundings.

However, if you’re seeking detailed historical stories or a narrated tour, you might find this too quiet. Also, since the sailing depends on weather conditions, it’s best to book on a day with a good forecast, especially if you’re eager for wind-powered sailing rather than motoring.

Final Thoughts

The Afternoon Windjammer Cruise offers a genuinely relaxing and scenic experience for anyone wanting to enjoy Portland’s coastal beauty at a gentle pace. The historic schooners, combined with the friendly crew and freedom to bring your own food and drinks, create a casual, enjoyable outing.

While it might not be the best choice if you want detailed commentary or a more active adventure, it excels as a peaceful, picturesque escape. For those who love being on the water, soaking in views, and enjoying a laid-back vibe, this sail checks a lot of boxes.

If you’re in Portland and craving a quiet, beautiful boat ride—especially with good weather—you’ll likely come away feeling refreshed and grateful for the experience. Just remember, booking early and checking the weather forecast will help ensure your trip goes smoothly.

FAQ

Can I bring my own food and drinks?
Yes, you’re welcome to bring your own snacks, wine, beer, or other beverages to enjoy during the sail.

Is this tour suitable for children?
All ages are welcome, making it a family-friendly option, especially if everyone enjoys calm waters and scenic views.

How long is the cruise?
The cruise lasts approximately two hours, offering plenty of time to relax and take in the scenery without feeling rushed.

What should I wear?
Dress comfortably and consider layers, especially if the weather is cooler or windier on the water.

Are there any narration or guided commentary?
No, this is a non-narrated tour. The crew is happy to answer questions if you’re curious about what you see.

What happens if the weather isn’t good?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or full refund.

Is the boat accessible by public transportation?
Yes, the starting point at 56 Commercial St is near public transit options.

Can I book last minute?
Yes, but it’s advisable to book in advance, especially during peak times, as the tour can sell out and has a limited group size.

If you’re after a peaceful, scenic, and flexible sailing experience in Portland, this Windjammer Cruise offers just that. It’s a low-key way to enjoy Maine’s stunning coast, with the bonus of historic vessels and friendly crew making the journey special.