Portland, Maine: Sunset Windjammer Cruise Along the Coast

Planning a trip to Portland, Maine, and craving a memorable, authentic experience on the water? The Sunset Windjammer Cruise offers just that — a two-hour sail through Casco Bay aboard a beautifully restored historic schooner. At just $75 per person, it’s an affordable way to enjoy Maine’s rugged coastline, picturesque lighthouses, and the calming beauty of the bay as the sun dips below the horizon.

Two things we really appreciate about this cruise: first, the chance to help hoist the sails or even steer the boat, making it feel more like a hands-on adventure than a simple sightseeing trip. Second, the permit to bring your own picnic dinner, wine, or beer transforms this into a laid-back, personalized outing. The crew is friendly, knowledgeable, and happy to answer questions—though note, this isn’t a narrated tour, so you’ll want to bring your curiosity along.

A small caveat: some reviews mention uncomfortable seating or limited space to eat and relax. If you’re sensitive to seating comfort or planning to bring a large spread, you might want to prepare accordingly. However, if you’re looking for a peaceful, scenic escape with friends or family, this cruise fits the bill well.

This experience is perfect for those who enjoy outdoor activities, scenic views, and a relaxed pace. Families, couples, or groups celebrating special occasions will find it especially appealing — particularly if you love boats, the coast, or simply want to unwind with a stunning sunset and some fresh air.

Key Points

• Hands-on sailing: You can help hoist the sails or sit behind the wheel, adding an interactive element.
• Bring your own food and drinks: No included meals, but you’re welcome to pack a picnic or beverages.
• Beautiful scenery: Expect views of Portland’s coastline, lighthouses, seals, seabirds, and a memorable sunset.
• Historic vessels: Some boats are over 100 years old, and three are listed on the National Register of Historic Places.
• Casual, family-friendly vibe: It’s a laid-back cruise suitable for all ages, with a focus on relaxation and scenic beauty.
• Limited narration: The crew answers questions but does not provide formal commentary, so bring your curiosity and prepare to enjoy the moment.

You can check availability for your dates here:

Setting the Scene: Portland and Casco Bay

Once you arrive at the Maine State Pier, past Gate 5 of Casco Bay Cruise Lines, you’ll find a small dock house serving as your check-in point. Arriving about 30 minutes early allows you to get ready, meet your crew, and soak in the harbor atmosphere. The portside setting provides a natural gateway to Maine’s rugged coastline, dotted with historic lighthouses, rocky outcroppings, and the occasional seal surfacing nearby.

Casco Bay is renowned for its calm waters and scenic beauty, making it ideal for a sunset sail. As we’ve read in reviews, many travelers find the experience both relaxing and visually stunning, especially with the added magic of a Maine sunset.

The Vessels: Historic Schooners and Wooden Windjammers

The boats you’ll sail on are more than just vessels—they’re part of Maine’s maritime legacy. Some of these schooners are over a century old, with three listed on the National Register of Historic Places. Their craftsmanship and traditional design lend an authentic feel that adds a layer of historical charm to your cruise.

The crew will invite you to help with hoisting the sails or steering, giving a real sense of what life aboard these ships might have been like. This hands-on engagement isn’t a deep-dive into sailing mechanics but enough to make you appreciate the skill and effort it takes to command such a vessel.

What’s on the Itinerary?

Unlike many narrated tours, this cruise is intentionally straightforward: a two-hour sail meant for relaxation, taking in the coastline, wildlife, and sunset. The boat departs in the late afternoon or early evening, aligning perfectly with sunset watching.

As you cruise through Casco Bay, you’ll see iconic lighthouses, seabirds, and perhaps seals lounging on rocks or swimming nearby. The crew is eager to answer questions about the local sights, wildlife, and sailing tips, adding personal touches to the trip.

Most travelers mention that the actual route doesn’t extend far from Portland but offers ample time to enjoy the scenery and have a leisurely meal. Some reviews note that the boat doesn’t go as far as they expected; however, the focus remains on enjoying the bay’s tranquility and natural beauty.

Bringing Your Own Food and Drinks

One of the biggest perks is the freedom to pack your own picnic, soft drinks, or wine. We love the flexibility this offers—no need to buy expensive onboard meals, allowing for a personalized experience. Bring a blanket or jacket, especially if you’re sailing during cooler months or later in the evening, as some reviews suggest the temperature can drop as the sun sets.

While food isn’t provided, the crew is happy to help answer questions or share stories during the cruise, making your meal feel like part of the experience. For some, this adds a convivial, cozy element to an otherwise quiet cruise.

More Great Tours Nearby

The Crew and Atmosphere

Enthusiastic and knowledgeable, the crew members are often highlighted in reviews. They work seamlessly as a team, engaging with guests and sharing stories about their maritime careers and the ships’ histories. Captain Jonathon and his team have been praised for their friendliness and ability to make everyone feel comfortable—whether you’re helping hoist sails or simply relaxing on deck.

The atmosphere is casual—no need for formal dress or fuss—just bring your sense of adventure and a love for the coast. The small group size, usually limited to the boat’s capacity, ensures that everyone can participate and enjoy the surroundings.

Cost and Value

At $75 per person, the cruise is a solid value considering it includes not just the scenic sail but also the chance to actively participate in sailing a historic vessel. Reviews consistently mention that the experience is worth the price, especially for those who appreciate authentic, hands-on maritime activities.

However, some comment that since you bring your own food and drinks, the value might hinge on how much you enjoy a casual picnic on the water. For many, the combination of scenic beauty, historical vessels, and the sunset makes it a memorable outing worth every penny.

This cruise appeals to a wide range of travelers: families, couples, friends celebrating special occasions, or anyone who simply treasures scenic views and maritime history. It’s perfect if you want an activity that’s relaxing but also interactive, with plenty of chances to learn about Maine’s coastal heritage.

If you’re looking for a peaceful, scenic, and adaptable outing—one that lets you bring your own food and blend education with leisure—this cruise is a strong choice. However, if you’re sensitive to seating comfort or expecting a narrated tour, you might want to consider your preferences beforehand.

Final Thoughts

The Portland Sunset Windjammer Cruise offers a charming, authentic way to enjoy the natural beauty of Casco Bay. You’re transported to a different time aboard a historic schooner, with the added bonus of helping sail the boat and bringing your own picnic. It’s a laid-back, scenic experience that’s perfect for quiet reflection, family fun, or romantic sunset watching.

The crew’s friendliness, the vessel’s craftsmanship, and the stunning Maine scenery all combine to create a memorable outing. While it’s not a high-energy adventure, it’s a genuine slice of coastal life—something that leaves a lasting impression of Maine’s maritime spirit.

If you’re seeking an activity that combines history, nature, and personal involvement, this cruise deserves a spot on your Maine itinerary. Just remember to bring layers, snacks, and an appreciation for the simple pleasure of a sail on Casco Bay.

FAQs

Is this cruise suitable for children?
Yes, the cruise is family-friendly and offers a relaxed environment suitable for children of all ages, especially given its calm waters and engaging crew.

Can I bring alcohol onboard?
Absolutely, you can bring your own wine or beer to enjoy during the sail. Just remember to drink responsibly and be considerate of others.

How long is the cruise?
The cruise lasts about two hours, generally scheduled in the afternoon or evening to coincide with sunset.

Do I need sailing experience?
Not at all. The crew is happy to answer questions and involve you in sailing, but no prior experience is necessary.

What should I wear?
Dress casually and comfortably, with layers. A jacket or blanket is recommended for cooler evenings, especially when the sun sets.

Is there any included narration or guide?
No, this isn’t a narrated tour. The crew answers questions but mainly focuses on sailing and taking in the scenery.

You can check availability for your dates here: