Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

A Private Wooden Boat Tour of Casco Bay: The ideal way to explore Portland’s coastline

Imagine cruising along Casco Bay in a charming, classic wooden vessel, with just your friends or family onboard. For $680, you get a two-hour private charter designed for groups of up to 15 guests. Departing from Portland’s vibrant Old Port, this tailored experience takes you past iconic lighthouses, historic forts, and rugged coastlines. It’s a chance to enjoy an authentic Maine seafaring adventure in style—without the crowds of public cruises.

What we particularly love about this experience is its personalized atmosphere—you’re not just another passenger on a large boat, but the entire vessel is yours. That means you can bring your own food, sip local beers or wines, and truly relax while soaking up stunning views. Another highlight? The opportunity to spot harbor seals, seabirds, and other wildlife, making it more than just a sightseeing cruise—it’s a genuine nature encounter.

A possible consideration is that this is a two-hour tour, so if you’re eager to explore the bay thoroughly or want a more extended experience, you might find it a bit brief. Also, parking in Portland’s Old Port isn’t included, so plan for that. This tour suits groups of friends, families, or special occasion parties who want a relaxed, intimate maritime adventure with the freedom to customize their voyage.

Key Points

• Exclusive Private Experience: The entire wooden vessel is yours, perfect for personalized adventures.
• Iconic Landmarks: Pass by Portland Head Light, Bug Light, Fort Gorges, and more.
• Wildlife Opportunities: Spot harbor seals, seabirds, and other local creatures.
• Bring Your Own Food: Enjoy snacks or meals onboard, with glasses, plates, and utensils provided.
• Beverages for Purchase: Local craft beer and wine available to buy during the cruise.
• Flexible and Relaxed: No crowded public tours—ideal for special occasions or intimate outings.

An in-depth look at the Casco Bay private boat experience

Starting point and setting the scene

The adventure begins at Gilberts Chowder House in Portland’s historic Old Port. This lively waterfront district brims with 19th-century brick warehouses, cobblestone streets, and a bustling fishing harbor atmosphere. From here, you’ll board the Marie L, a classic wooden boat that exudes nautical charm and invites a sense of stepping back in time. This setting immediately sets the tone for a relaxed, authentic Maine experience.

The captain and local guide onboard are there to enrich your journey, providing insights into the sights and the area’s maritime history. The group size of up to 15 people makes for an intimate trip, where everyone can enjoy the scenery and ask questions.

The itinerary: a tour packed with iconic sights and local charm

The route is flexible, but typical stops include some of the most beloved spots in Casco Bay:

Portland Head Light: This lighthouse is arguably the most photographed in the U.S., perched dramatically atop rugged rocks in Fort Williams Park. We loved the way the boat approaches it, offering a unique perspective that’s hard to get from land. The guide might share stories about its history, making it more than just a pretty picture.

Bug Light: Officially Portland Breakwater Light, this small cast-iron lighthouse is a charming sight. Its Greek Revival design and bright white paint make it a striking feature on the water. It’s an excellent photo op, and you might appreciate the relaxed pace as you drift nearby.

Spring Point Ledge Lighthouse: One of the rare sparkplug-style lighthouses you can get close to by boat. Built in 1897, it served as a vital warning for ships entering Portland Harbor. Seeing it up close offers a tangible connection to Maine’s maritime past—and the chance to shoot some memorable photos.

Ram Island Ledge Light: Sitting atop a rocky outcrop surrounded by swirling tides, this lighthouse provides a dramatic contrast to the others. It’s a reminder of the challenging navigation in Casco Bay, and the guide often points out the swirling currents and natural beauty surrounding it.

Fort Gorges: Built in the 1850s, this stone fortress is one of Casco Bay’s most impressive relics. We loved the way the boat approaches the fortress, giving a sense of its commanding presence. The guide may share stories about its role in defending Portland during past conflicts.

Peaks Island: The largest island in Casco Bay, about a 15-minute ferry ride from Portland. Its quiet residential streets and scenic charm make it a favorite. While the boat doesn’t dock here, the views of the island from the water are spectacular. This stop offers a glimpse into life on Maine’s islands, and some may opt for a future visit ashore.

Fort Scammel: Tucked into House Island, this fortification from 1808 offers a glimpse into Maine’s military history. Its strategic role during the Civil War might come up in storytelling, adding depth to the sightseeing.

What makes the experience special

One of the biggest draws is the personalized attention. Unlike crowded public cruises, your group receives the full attention of the captain and guide, making it easy to ask questions or request specific sights. The two-hour duration strikes a good balance—long enough to see multiple landmarks without feeling rushed.

Another plus is the boat’s comfort and charm. The Marie L’s classic wooden design creates a cozy, nostalgic atmosphere that enhances the maritime feeling. It’s also eco-friendly, equipped with a composting toilet, so you don’t need to worry about facilities onboard.

The onboard offerings and flexibility

While the tour doesn’t include food or drinks, you’re welcome to bring your own snacks and meals. All plates, glasses, and utensils are provided, making it easy to set up a picnic-style spread. Beverages like local craft beer and wine can be purchased onboard, adding a relaxed convivial vibe.

The pricing of $680 per group (up to 15 people) offers good value considering the exclusivity. You’re paying for the whole vessel, which makes it cost-effective for small groups seeking a private experience. The fee includes all taxes and fees, so there are no surprises.

The practicalities

Meeting at Gilberts Chowder House is convenient, and the boat departs and returns to the same spot. Parking isn’t included, so plan ahead if you’re driving. The tour operates in most weather conditions, but poor weather might lead to cancellations with a full refund or rescheduling.

The duration is roughly 2 hours, making it ideal for a half-day activity. It’s suitable for most travelers, including families, couples celebrating special occasions, or friends wanting an authentic Maine experience.

Authenticity and value

This tour stands out because it offers more than just sightseeing. It’s a chance to experience Casco Bay’s beauty intimately, with the flexibility to customize your time on the water. Given the reviews and the detailed itinerary, it’s clear that the focus on personalized service, stunning vistas, and wildlife viewing truly makes this experience memorable.

Who should consider this tour?

If you’re looking for a relaxed, intimate, and authentic Maine seafaring experience, this private wooden boat tour is a fantastic choice. It’s especially suitable for small groups celebrating a special occasion, nature lovers eager to spot wildlife, or travelers wanting a personalized way to explore Portland’s coast. It’s also perfect if you prefer avoiding large, crowded tours and want the flexibility to bring your own food and beverages.

FAQs

Is this a private tour?
Yes, this is a fully private charter for your group of up to 15 people, making for a personalized experience without strangers onboard.

How long is the tour?
The experience lasts approximately 2 hours, giving ample time to see multiple landmarks and enjoy the scenery without feeling rushed.

Can I bring my own food and drinks?
Yes, you’re welcome to bring your own food and snacks. Glassware, plates, and utensils are provided. Beverages like beer and wine can be purchased onboard.

What landmarks will we see?
You’ll cruise past Portland Head Light, Bug Light, Fort Gorges, Spring Point Ledge Lighthouse, Ram Island Ledge Light, and more. The exact route can be flexible.

Is parking included?
No, parking in Portland’s Old Port is not included. Plan accordingly, especially if arriving by car.

What happens in bad weather?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.

Final thoughts

This private wooden boat cruise offers a wonderfully authentic and personalized way to experience Casco Bay. It balances comfort, scenery, and wildlife watching in a way that larger tours simply can’t match. The opportunity to customize your journey—bringing your own snacks, enjoying local drinks, and avoiding crowds—makes it an appealing choice for small groups seeking a relaxed yet immersive outing.

Whether celebrating a special occasion or just craving a peaceful day on the water, this tour provides a genuine taste of Maine’s maritime charm. It’s a fantastic way to create memories with loved ones while soaking in the rugged beauty and historic sights of Casco Bay.

For those who value authenticity, intimacy, and scenic beauty—and don’t mind a bit of nautical charm—this private boat tour is a real winner. It’s a great investment in a memorable Maine experience that you’ll fondly remember long after your trip ends.