Private Sunset Charter on a Vintage Lobster Boat with Drinks

Imagine cruising through Casco Bay aboard a charming vintage lobster boat, watching the sun dip toward the horizon with a cold drink in hand. That’s the kind of experience this private sunset charter offers—an authentic, relaxed way to enjoy Maine’s rugged coastline. From the moment we learned about it, we found two things especially appealing: the cozy, vintage boat setting and the opportunity to sip beer or wine while soaking in spectacular views.

On the flip side, you’ll want to consider that this is a two-hour outing, which might feel brief if you’re eager to linger longer over the scenery. But if your aim is a romantic, photo-worthy evening with personalized service, this tour hits the mark. It’s best suited for couples, small groups, or anyone craving a more intimate look at Portland’s maritime charm—perfect for celebrating a special occasion or simply savoring the sunset.

Key Points

• Private, intimate experience with a knowledgeable captain-guide
• Stunning lighthouse views and historic forts from the water
• Drinks available for purchase onboard, including local beers and wine
• Eco-friendly on-board restroom adds comfort
• Well-rated, highly recommended by past guests
• Ideal for romantic outings or small groups seeking authentic maritime views

The Private Sunset Charter on a Vintage Lobster Boat offers a unique way to see Portland and Casco Bay. This is not your typical sightseeing cruise. Instead, it’s a tailored, small-group voyage that emphasizes comfort, natural beauty, and local history. The boat itself is described as spotless and beautiful, with a vintage charm that adds to the overall experience. It’s a classic Maine boat, rebuilt for comfort and style, giving you that authentic maritime feel.

The tour, offered by Casco Bay Custom Charters, is designed for just up to 6 guests at a flat rate, making it perfect for an intimate experience. The boat’s size means you won’t be jostled by large crowds, and the crew’s professionalism and friendliness shine through in the reviews. Past travelers rave about the knowledgeable guides—they’re enthusiastic without being overwhelming, eager to share stories and answer questions about the sights.

The Itinerary in Detail

The cruise begins at Gilberts Chowder House on Commercial Street, a convenient starting point in Portland’s Old Port district. From there, the boat glides into Casco Bay, revealing some of Maine’s most iconic sights.

Each stop on the tour is thoughtfully chosen:

Spring Point Light & Fort Preble

This first stop brings you close to Spring Point Light and Fort Preble, which played a role in Portland’s harbor defenses. The lighthouse once stood on an unconnected rock, guiding ships safely past shallow ledges. Past guests note the history and maritime significance of these sites, and many enjoy snapping photos of the lighthouse with Portland’s skyline in the background.

The First of Four Lighthouses

The cruise then moves to the smallest lighthouse, which often attracts kite flyers and sometimes even a floating purple octopus kite if the wind’s right. It’s a quirky highlight and offers a playful contrast to the historical sites. Some reviews mention the fun of watching kite-flyers and appreciating the lighthouse’s charm from the water.

Bug Light & the Liberty Ship Statue

Next up is Bug Light, a distinctive Portland lighthouse known for its unique design. Nearby stands a Liberty Ship statue, honoring the vessels built here during WWII. One reviewer highlighted the significance of the area, mentioning the fascination with maritime history and the story of the Liberty Ships.

Portland Head Light

No water-based tour in Portland is complete without viewing Portland Head Light, Maine’s oldest lighthouse. Built in 1791 and commissioned by George Washington, it’s a symbol of Maine’s maritime heritage. From the water, it’s even more breathtaking — a perfect photo backdrop. A guest commented, “seeing this iconic lighthouse from the water makes it even more impressive.”

Fort Gorges

The stone fortress of Fort Gorges is a commanding presence in Casco Bay. Though never used for battle, it’s a significant military relic and a favorite photo spot. The guide typically explains its strategic importance and how it served during WWII as a storage site.

Scenic Views of Cushing Island & Peaks Island

Finally, the cruise offers views of Cushing Island’s cliffs and Peaks Island, a quiet community with a fascinating history. Once home to amusement parks and bustling with summer visitors, Peaks Island now offers peaceful streets and cozy cottages. From the boat, you see this island’s charm—verdant trees, small beaches, and a laid-back vibe.

What’s Included & What’s Not

The tour’s all about comfort and personalized service. Included are licensed captains, bottled water, a cooler, glassware, plates, and utensils, plus a restroom on board—a thoughtful touch that makes the two-hour experience more comfortable. You can purchase craft beer, hard seltzers, and wine onboard, making it easy to toast the sunset. Soft drinks are also available for those who prefer non-alcoholic options.

It’s a private charter for up to six guests, which means you won’t be sharing your experience with strangers. The flat rate makes this a good value, especially considering the personalized feel and the all-inclusive approach.

Not included are parking fees in Portland’s Old Port and gratuities, which are customary but not mandatory. The meeting point is conveniently located at Gilbert’s Chowder House, just a short walk from the city center.

The Experience in Practice

The reviews consistently highlight the comfortable, clean boat and the informative, friendly guides. One guest said, “The guides answered all our questions and showed us the lighthouses and wildlife,” which underscores how much the guides add to the overall value.

The timing—around two hours—strikes a good balance. It provides enough time to see the highlights of Casco Bay without feeling rushed. Past travelers appreciated the sunset timing for its photogenic quality and the peaceful atmosphere.

Cost-wise, the $407.40 per person might seem steep at first glance, but considering it’s a private, all-inclusive experience with drinks and a knowledgeable guide, many reviews affirm it’s well worth the price. It’s more than just a boat ride; it’s a curated, memorable slice of Maine’s coastal life.

Who Will Love This Tour?

This cruise is perfect for couples celebrating special occasions, small family groups, or friends who want a private, relaxed experience. It’s especially suited for those interested in lighthouses, maritime history, and scenic photography. If you enjoy a mix of nature, history, and a touch of luxury with drinks and comfort, this tour will satisfy.

This private vintage lobster boat sunset cruise offers a truly authentic Maine experience. You’ll glide past historic lighthouses, explore military relics, and enjoy stunning ocean views—all while sipping local drinks in a cozy setting. The guides’ knowledge and friendly approach help make it feel like an outing with friends rather than a tourist trap.

The value, considering the exclusivity and intimacy of the experience, stands out. It’s about more than sightseeing; it’s about making memories in a setting that feels exclusive but accessible. The tour’s relaxed pace and focus on comfort make it especially appealing for those looking to unwind and take in the natural beauty of Casco Bay.

If you’re seeking a peaceful, scenic, and personal way to experience Portland’s coastline, this cruise hits the right notes. It’s a charming, well-reviewed option that’s likely to be a highlight of any trip to Maine.

How long is the cruise?
The experience lasts approximately two hours, providing ample time to see major sights and enjoy the sunset.

What is included in the price?
Your ticket covers a private charter with a licensed captain, bottled water, drinks for purchase (beer, wine, seltzers), a cooler with glassware, plates, utensils, and access to the restroom on board.

Can I bring my own drinks?
No, but you can purchase craft beer, hard seltzers, and wine onboard. Soft drinks are also available.

Is this experience suitable for children?
Most travelers can participate, and the boat has a composting toilet for comfort. However, the tour is designed as a romantic/private outing, so families should consider whether the two-hour cruise suits their needs.

What are the meeting details?
The cruise begins at Gilbert’s Chowder House, 92 Commercial St, Portland. It’s a central location close to Portland’s Old Port.

What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. The tour is weather-dependent, and poor weather may lead to rescheduling or a complete refund.

In essence, this sunset lobster boat tour is a delightful way to experience Portland’s maritime charm in an intimate, relaxed setting. Whether celebrating something special or simply wanting a peaceful break on the water, it promises memorable views, friendly guides, and a touch of luxury—without the crowds.