Private Sunset Charter on a Vintage Lobster Boat in Portland booking from $407.40

Private Sunset Charter on a Vintage Lobster Boat

Overview

Leave the crowds behind and step aboard a vintage Maine Lobster Boat for a private 2-hour sightseeing and lighthouse viewing charter, ending with a breathtaking Maine sunset.

We’ll navigate through the islands of Casco Bay, passing by Portland’s most iconic coastal sights, including historic 19th-century forts, lighthouses, and the stunning Maine coastline.

This experience is perfect for families and small groups, offering a completely private and personalized tour just for you.

First round of alcoholic drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the view!

City: Portland

Sat 21 Jun

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Starting at $407.40

Make a reservation

Sat 21 Jun

Starting at $407.40

Make a reservation

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What's Included

Licensed Captain

Private Charter for up to 6 guests (cost is a flat rate)

Enjoy a local Portland, Maine beer or a glass of wine on us!

Bottled water

All Fees and Taxes

Local Guide

Restroom on board

Additional Info

Infants and small children can ride in a pram or stroller
Service animals allowed
Suitable for all physical fitness levels

What To Expect

Casco Bay

With over 200 islands that are home to both tiny coastal fishing towns and Maine's largest city, Casco Bay is vibrant, scenic, and a great way to experience Maine's incredible beauty, world-class cuisine, and wonderful boating opportunities.

Spring Point Ledge Lighthouse

Get up close to Spring Point Light and nearby Fort Preble, a small gun emplacement built as a part of Portland's Harbor Defenses. In the early years, the lighthouse was not connected to the mainland by the granite breakwater that exists today, and ships that went on the wrong side of the lighthouse went aground on shallow ledge.

Bug Light Park

This is the smallest and first of four lighthouses we will encounter on our cruise through Casco Bay. On windy days, keep an eye out for gatherings of expert kite flyers and their colorful kites. Sometimes there's even a giant purple octopus floating lazily in the breeze! Just around the corner from Bug Light is a statue of the bow of a Liberty Ship. Many ships were constructed here during WWII, including the S.S. Jeremiah O'Brien, which is a popular tourist attraction in San Francisco and one of the only surviving Liberty Ships.

Portland Head Light

See Portland Head Light, Maine's oldest and most iconic lighthouse, from the water. Commissioned by George Washington and constructed starting in 1791, this lighthouse has been an important navigational beacon and local landmark for more than 2 centuries. The lighthouse has withstood hurricanes and global conflicts. German U-boats sunk a US Navy ship just 15 miles off the Head Light in the waning days of WWII.

Fort Gorges

As the most conspicuous stone fortress protecting Portland Harbor, Fort Gorges is a landmark visible from much of Casco Bay, which is exactly why it was built on this rocky outcropping a short distance from Peaks and Little Diamond Islands and the mainland itself. The fort could fire more than a dozen cannons on attackers coming from any possible sea route, but was never used in active battle. Technological advancements in artillery during the Civil War rendered it too vulnerable to be useful. The fort did serve as a storage facility for the army during World War II, when underwater mines, electromagnetic sensing cables, and other systems were used to help protect Portland and Casco Bay from German attack. Remember, Portland was home to a large shipyard during WWII and was the start of a pipeline that supplies oil to Montreal and eastern Canada, so the region was of high strategic importance even in more modern conflicts.

Peaks Island

See some of the most incredibleEnjoy fantastic views of the scenic cliffs on Cushing Island and the tree-lined streets and quaint cottages of Peaks Island. Once home to several amusement parks that were served by direct steamer routes from New York, Peaks is now a quiet island neighborhood that is technically part of the City of Portland but has a small-town feel all its own. By the time the fall colors are in full view, most seasonal residents have returned to their usual homes, and Peaks is home to just a couple hundred hearty year round souls who must take a ferry or water taxi to get to the mainland.

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Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (37)

Jae S

Aug 2017

Our charter was at the end of July 2017, a group of four including myself. Our pick-up point was the Water Taxi pick-up/drop-off, which is located right behind the big, red buoy in the Bell Buoy Park and next to the Casco Bay Terminal parking garage off Commercial St. The pickup point is shared by different water taxi boats, with lots of customers, so you might be a bit anxious waiting for the right boat. But just look for the ship's name MONHEGAN, and ignore the rest!

The Monhegan arrived as expected, and on time. The pilot John? and the guide Matthew warmly welcomed us onboard with helping hands, and provided us with comfortable, dry seating. Excellent! Matthew sat down with us with a map and gave us an overview of our trip, which was great. I really appreciated the personal attention from our guide, who actively gave us information and insights on the different locations we were passing by lighthouses, big ships, various sights around us.

Upon entering open waters outside the harbor, the boat got caught up for a few minutes in rough waters. I started to get queazy, and let the crew know. Matthew made a snap decision to skip the open waters, and head back towards the islands for calmer cruising. He offered me cold seltzer water to see if it'd help, and also asked John to drive the boat to avoid rolling as much as possible I felt he made a noticeable effort to do so. All of this was helpful in my seasickness going away, and I was able to enjoy the rest of the charter without further problems.

In lieu of the open waters, we stayed longer around the islands. This gave us a chance to tour the summer homes on the islands, as well as to look for ospreys and bald eagles. We were lucky enough to find 2 bald eagles sitting by their nest. On the way back, we also encountered a group of seals perched on a tiny rock island! And all the while, we had an amazing sunset and very colorful clouds all the overcast gray had magically disappeared once we cast off. What exuberance!

Some tips for this trip:

1 Park at Casco Bay Terminal Parking Garage, which is right next to the pick-up/drop-off point. If that garage is full, park at DiMillo's Restaurant parking lot open to public it's the next closest lot available. Prices are about the same. Just forget about street parking on the opposite side of Commercial St -- it's impossible to find a spot.

For those that might experience sea-sickness, 2 Eat well before the cruise, and 3 take a dose of Dramamine when you eat. And though there are lots of restaurants on Commercial St, they are pretty much all packed solid, so do leave plenty of time for it.

4 Bring a light jacket or sweater, because it will get chilly heading back into the harbor, even in the dead of summer. That's Maine for you!

5 Sunglasses are a must.

Conclusion:

The tour description says folks could bring their own food and drinks, but I found it to be nearly impossible to eat, not only because I was a little seasick but that there was no time to focus on food. We were relatively busy listening to the guide and looking at different sights, that it would have been difficult or very impractical to have a meal.

About the Monhegan: The boat was clean and orderly, and the engine running quietly and smoothly. Matthew made sure we were seated comfortably in dry seats 3 to a bench at the rear of the boat, plus 1 folding chair. The Monhegan does have clear plastics that can be rolled down and zipped together tight to keep out the winds. Matthew did exactly that on one side of the boat while heading back in. Engine fumes are directed away completely so you won't smell anything that might make you sick if you're sensitive to exhaust fumes. No complaints at all, the boat was impeccable!

This trip was memorable, and it's sure to become a part of our family lore and storytelling. The skies turned out absolutely beautiful that evening, and we were enthralled by the whole experience. Although we rolled a little in the rough waves in that one instance, I felt the pilot and the guide took firm measures to keep the rest of our trip a success. The personal attention and detailed guiding are very much appreciated, my hats off to Matthew! And for the effort on John's part to keep the ride as smooth as possible, thanks! If one had the option to request specific individuals on the charter cruise, I'd say, request Matthew and John most definitely! This rates as one of the most memorable boat outings of my life, and I wholeheartedly recommend this to anyone visiting Portland, Maine.

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Private Sunset Charter on a Vintage Lobster Boat

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