Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

If you’re eyeing a unique way to explore Portland’s stunning coastline, this private lobster boat tour might just hit the mark. While we haven’t personally taken this exact trip, the glowing reviews and detailed descriptions paint a picture of a genuinely enjoyable experience. Think of it as a peaceful yet fascinating maritime adventure where you’re not just a spectator—you’re part of the scenery.

What makes this tour special are a couple of standout features. First, the opportunity to pass by four historic lighthouses offers some of the best photo ops around—perfect if you love snapping water views or lighthouse shots. Second, the knowledgeable captain and crew seem to strike a great balance between sharing insights and letting you soak in the scenery quietly. But it’s worth noting that some reviews mention a slight lack of narration, so if you’re craving an in-depth narration about each lighthouse and dock, you might want to keep expectations in check.

One thing to consider is the price point, which sits at around $380 for the entire boat—an average of about $63 per person if you’re a group of six. That’s not cheap, but given the private setting, the personalized experience, and the included drinks and amenities, many find it to be good value. Still, it’s worth considering whether a two-hour boat ride fits your budget and schedule, especially if you’re traveling with kids or looking for a more packed itinerary.

This tour definitely suits travelers who enjoy scenic boat rides, love maritime history, and want a flexible, private experience rather than a crowded tour. If you’re looking for a relaxing, intimate outing with stellar views and insightful commentary from a captain who knows the area well, this could be just what you need.

Key Points

• Private, intimate setting perfect for small groups or couples
• Passes by four iconic lighthouses, offering fantastic photo opportunities
• Learn about Maine’s maritime history from a friendly, knowledgeable captain
• Bring your own food and drinks on board—utensils and plates are provided
• Includes local beer or wine, plus soft drinks and bottled water
• Eco-friendly composting toilet adds to the comfort of the boat experience

Exploring the Details of the Tour

This two-hour private charter takes you out on the beautifully restored wooden lobster boat, MONHEGAN, into Casco Bay. From the start at Gilbert’s Chowder House, you’ll cruise through Portland’s harbor, passing by historic wharves and fortresses that tell stories of early American maritime hustle. The boat is designed for comfort and style—compact enough for intimacy but sturdy and beautiful, with a nostalgic wooden exterior that instantly transports you to Maine’s fishing roots.

The Itinerary in Depth

Boarding at Gilbert’s Chowder House:
You’ll meet your crew and captain here, get settled, and prepare for a relaxing ride that takes you past some of Portland’s most notable waterside sights. The harbor’s post-Revolutionary War period is evident in the stone fortresses, telling you that this area’s maritime importance goes way back. That initial stretch sets the tone for the scenic, historical feel of the trip.

Passing the First Lighthouse:
Your first lighthouse marks the entrance to Portland Harbor. It’s usually the first of four lighthouses you’ll see, and it provides an excellent chance for photos. The guide (or in some reviews, the crew) shares tidbits about its role in navigation and maritime safety, giving you a sense of the area’s nautical history.

Spring Point Light and Fort Preble:
Getting up close to Spring Point Light is a highlight. This lighthouse is backed by Fort Preble, a small but fascinating gun emplacement built to defend Portland’s harbor. The lighthouse itself isn’t open for tours, but its waterside view and historical context make it a worthwhile stop. The crew seem eager to share stories about how ships once navigated these waters and the importance of these defenses.

Maine’s Most Iconic Lighthouse – Portland Head Light:
This is the star of the show for many visitors. While you don’t go ashore, you spend time in the waters in front of Portland Head Light—one of the most renowned lighthouses in Maine. The views are spectacular, especially with good weather, and you’ll have plenty of time to take photos and chat about its history. One reviewer noted, “Seeing the lighthouse from the water was great,” and many agree that this perspective is unbeatable.

Ram Island Light:
On the opposite side of the harbor, Ram Island Light sits atop a rocky ledge. It appears to float at high tide, which makes for an interesting photo. The weathered look of the lighthouse adds a rugged charm, and the derelict pier leading to it hints at stories of abandoned maritime outposts. As one reviewer mentioned, climbing the outside ladder to the door is a bit of an adventure—definitely not a tour for anyone with mobility concerns.

Cruising Casco Bay’s Islands:
Casco Bay is famous for its rugged islands and charming harbors. The boat ride offers a panoramic view of tree-covered cliffs, small fishing communities, and places like Peaks Island and Cushing Island. The scenery here is one of the main reasons people love this tour, with reviewers repeatedly praising the vistas and the opportunity to see the islands from a unique perspective.

Fort Gorges:
A notable landmark visible from the water, Fort Gorges is a relic of 19th-century military engineering. While it was never used in active battle, it served as a storage facility during WWII. The scale and history of this fort make it a compelling sight, and many reviewers mention how impressive it looks from the boat.

Peaks Island and Cushing Island Views:
The trip ends with lovely views of Peaks Island’s quaint cottages and Cushing Island’s scenic cliffs. Peaks Island, with its small-town charm and history—once home to amusement parks—remains a peaceful retreat, especially in the fall when most seasonal residents have left.

What to Expect on the Experience

The boat itself is described as beautiful and comfortable. With a private booking for up to six guests, it’s an ideal setting for couples, families, or small groups who want their own slice of the Casco Bay scenery. The crew is praised for being friendly, knowledgeable, and eager to answer questions, but some reviews note that narration can be light at times. If you’re hoping for a super detailed history lesson, you might still enjoy it, but don’t expect full-on storytelling throughout.

Drinks and Snacks:
You’re encouraged to bring your own food and drinks, and utensils, plates, and glasses are provided. Many guests enjoy sipping on local Maine beers or wine, which are available on board. Soft drinks and bottled water cater to all ages and preferences. The inclusion of a composting toilet is a thoughtful touch that keeps the experience comfortable for everyone.

Timing and Duration:
At just about two hours, the cruise is an ideal length—long enough to see the key sights without feeling rushed. The experience is scheduled during daylight hours to maximize views, so plan accordingly.

Pricing and Value:
At roughly $380 for the whole boat, the cost might seem steep if you’re on a tight budget, but considering the exclusivity and personalized service, many find it worthwhile. The reviews consistently praise the experience as “fantastic” and “worth every penny,” especially when you factor in the private setting, drinks included, and the scenic, unhurried pace.

Who Will Love This Tour?

This private tour is perfect for those who appreciate a relaxed, scenic outing with a personal touch. It appeals to couples celebrating special occasions, small families, or friends wanting a memorable day on the water. If you’re someone who enjoys maritime history, stunning coastal views, and the comfort of a private boat, you’ll likely find this a highlight of your Portland trip.

People who prefer more narration or a guided storytelling experience may want to temper expectations—some reviews mention less commentary than expected. But if you enjoy the tranquility of being on the water, taking photos at your own pace, and enjoying a glass of wine while watching the scenery go by, this tour offers an excellent balance.

FAQs

Is this a private experience?
Yes, the tour is a private charter for up to six guests, so you’ll have the boat and crew all to yourselves.

What’s included in the price?
The price covers the boat, a licensed captain, all fees and taxes, bottled water, glassware, plates, utensils, and alcoholic beverages like local beer or wine. Soft drinks and soda are also available.

Can I bring my own food and drinks?
Absolutely. You’re encouraged to bring your own food and drinks, and the boat provides utensils, plates, and glasses for your convenience.

How long is the tour?
The cruise lasts about two hours, making it a perfect half-day activity that’s not overly long but still packed with sights.

Are there restroom facilities on board?
Yes, the boat has an eco-friendly composting toilet, which adds to the comfort for guests.

What sights will I see?
You’ll pass by four lighthouses, the Portland Head Light, Fort Gorges, Ram Island Light, and enjoy views of Casco Bay’s islands and cliffs.

Is this suitable for children?
While not explicitly stated, the boat’s private setting and duration make it suitable for most guests. Families with kids accustomed to boat rides should be fine, but always check with the provider for specific age recommendations.

What about weather cancellations?
If the weather isn’t suitable, the tour can be canceled or rescheduled. You’ll be offered a full refund if it’s canceled due to weather.

Final Thoughts

If you’re seeking a personalized, scenic, and relaxed way to see Portland’s waterside landmarks, this vintage lobster boat tour offers something special. The combination of stunning lighthouse views, expert guidance, and the chance to enjoy drinks on a beautifully restored boat makes it stand out. It’s well-suited for those who value quality over quantity and want their experience tailored rather than rushed.

While the price isn’t the lowest, the private setting, scenic stops, and friendly crew tend to justify the cost for many travelers. Whether celebrating a special occasion or simply looking to enjoy Portland from a different perspective, this cruise delivers a memorable day on Casco Bay.

In sum, this tour is best for travelers who appreciate scenic beauty, small-group intimacy, and maritime history, all enjoyed at a leisurely pace with good drinks and company. If that sounds like your kind of adventure, it’s likely to be worth every penny.