
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks
Traveler rating
4.9/5
Based on 73 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Sightseeing Charter on a Vintage Lobster Boat with Drinks worth booking?
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks is a 2-hour experience in Portland, United States, from $380 per person. It scores 67 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 73 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 67 / 100
- Rating
- 4.9/5 (73)
- Duration
- 2 hours
- From
- $380 per person
100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline. Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome! First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!
What you get
About this experience
100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we cruise through the islands of Casco Bay, passing four iconic lighthouses, historic 19th-century forts, and the stunning Maine coastline. Charters depart from Portland’s Old Port and are perfect for families and small groups. Each charter is completely private for up to 6 guests, and all ages are welcome! First round of drinks included – Enjoy a local Portland, Maine beer or a glass of wine as you take in the breathtaking views!
What's included
Included
- Licensed Captain
- Alcoholic beverages
- Private Charter for up to 6 guests (cost is a flat rate)
- Bottled water
- All Fees and Taxes
- Local Guide
- On-board restrooms
- Carbonated beverages
- Cooler, glassware, plates, & utensils for guest use
Not included
- Parking in Portland's Old Port
- Gratuity for your Guide
What you'll see and do
Portland
Board M/V MONHEGAN, a beautifully restored wooden lobster boat, and make yourself at home as you cruise through Portland's Harbor, past wharves dating to the period just after the Revolutionary War. At one point, Portland was one of the busiest harbors in the early decades of the United States, a fact attested to by the incredible stone fortresses protecting the harbor.
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Bug Light Park
Marking the entrance to Portland Harbor, this small lighthouse is typically the first of four lighthouses we see on our sightseeing excursions aboard our vintage wooden boats.
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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.
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Portland Head Light
See Maine's most iconic lighthouse from the water. Weather and sea conditions permitting, we spend time in the waters in front of the lighthouse for photos and discussion about the history of the lighthouse. We do not go ashore or tour the lighthouse. Lighthouse is not open for tours as it is still an active navigational beacon.
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Ram Island Ledge Light
Marking the opposite side of the harbor channel from Portland Head Light, Ram Island Light sits atop a rocky ledge and at high tide appears to be floating and completely unattached to land. Whereas Portland Head Light has its stately keeper's house and beautiful white washed sides, Ram Island Light is weathered and gray almost inaccessible, with a now-derelict pier leading to a ladder that requires one to climb up 30 feet on the outside of the lighthouse before you get to the door.
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Casco Bay
Casco Bay is world-renown for its rugged islands, protected waters, and fantastic scenery. Cruise past some of the bay's 200+ islands boasting tree-covered rocky cliffs, small fishing communities, and cute harbors.
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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.
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Peaks Island
Enjoy 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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Where it starts and ends
Meeting point
Portland
Meet at the back of the parking lot between Gilbert’s Chowder House and Dry Dock in Portland’s Old Port. Arrive 20 mins early to find parking. Wait at the top of the boat ramp next to Boone’s Fish House & The Porthole deck. Your deckhand will meet you at the ramp just before tour time
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Meet at the back of the parking lot between Gilbert’s Chowder House and Dry Dock in Portland’s Old Port. Arrive 20 mins early to find parking. Wait at the top of the boat ramp next to Boone’s Fish House & The Porthole deck. Your deckhand will meet you at the ramp just before tour time
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- Casco Bay Custom Charters, LLC
Know before you go
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 73 traveler reviews. Written by us, not quoted from reviewers.
The guide
4 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Small groups
4 mentionsThe group size is repeatedly described as intimate rather than packed.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
73 verified traveler reviews for Private Sightseeing Charter on a Vintage Lobster Boat with Drinks. Ratings and reviews provided by Viator and Tripadvisor.
Dogs friendly company
Today, Tuesday 09/15, turned out to be our lucky day. While it wasn’t our first time visiting Portland, Maine, it was our very first sailing experience with Casco Bay Custom Charters and what a wonderful experience it was! There are many charter companies in Portland, but we chose Casco Bay Custom Charters because they offer a variety of unique charter experiences, including dog-friendly trips. As proud owners of three Portuguese Water Dogs (PWDs), that was a huge deciding factor for us. This time, however, we only brought two of our dogs. Our oldest dog absolutely loves swimming and dock diving, and we were concerned he might jump off the boat the moment he saw open water. He has done it twice before! As soon as he gets near water, his excitement takes over, so we decided it was best to leave him comfortably behind at our vacation cottage in Georgetown. From the moment we arrived, the service was outstanding. Lauren meet us at the parking and lead us to the ship in the dock where Captain Zack welcomes us and ensured that our trip was both relaxing and informative. Drawing on his extensive experience navigating Casco Bay, Captain Zack skillfully guided us through the many islands surrounding Portland. He handled the boat so smoothly that we barely noticed the waves created by other vessels. His expertise and confidence on the water made the entire journey comfortable and enjoyable. Lauren complemented the experience perfectly by sharing fascinating information about the islands, the area’s rich history, and the route we were taking. She answered every question professionally and thoroughly, providing insights that reflected both her deep local knowledge and her passion for the region. The combination of excellent seamanship, outstanding customer service, and genuine hospitality made this charter a memorable experience for both the three of us and our dogs. If you’re looking for a unique and enjoyable way to explore Portland from the water especially if you’re traveling with dogs, we highly recommend Casco Bay Custom Charters. And one final note: the maximum rating may be 5 stars, but if we had the choice, we would happily give Casco Bay Custom Charters, Captain Zack, and Lauren 8 stars. They truly exceeded our expectations and made our day on the water unforgettable. Thank you, Captain Zack and Lauren, for an unforgettable day on the water. We look forward to sailing with you again!
via Tripadvisor
Outstanding!
We could not have asked for a more perfect private sunset cruise! Damien was our Chef, Maria our hostess, and Nick, our captain! The boat was pristine and super comfortable and yes, we did get amazingly perfect weather! Chef Damien outdid himself with the food selection as we left it to him! Highly recommend this adventure for couples and or small groups
via Tripadvisor
Perfect experience!
Our experience with Casco Bay Custom Charters was awesome! Our daughter and son-in-law booked a private boat trip aboard the Monhegan for the four of us for our anniversary. Best! Gift! Ever! Our two-hour cruise was piloted by Captain Nick whose seamanship is unquestionable. He knew when to slow down for a special sighting (like a gray seal!) and how to navigate the “retired” lobster boat through waves and wakes to minimize potential seasickness. (We were fine!) First Mate Lauren was terrific. She acted as our tour guide and was super-personable and extremely knowledgeable and informative without being the least bit boring. Quite the contrary! She was interesting, engaging, open to questions, and very easy to talk to. The boat itself was immaculately clean. Passengers could order food or bring their own. Alcohol could not be brought onboard, but a complimentary first drink was offered with the option to purchase more. We brought our own little makeshift charcuterie. Lauren provided all the serving ware, utensils, napkins, etc. Captain Nick and First Mate Lauren gave us a perfect 2 hour cruise on the Monhegan. We saw a lot, learned a lot, enjoyed one another’s company, and just had an absolutely wonderful time! Kudos!
via Tripadvisor
Quintessential Portland ME on the Water!
Hands down one of the best highlights of our trip! The vintage lobster boat was super comfortable, and the route captured quintessential Maine beauty. Our guide was top-notch, sharing all the history and local info you could ask for. Highly recommend this private sightseeing charter to everyone—10/10!
via Viator
Had a lovely relaxing...
Had a lovely relaxing trip on a gorgeous day! Crew was great and we got to see the beauty of Portland from the sea.
via Viator
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $380 to $760
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 26
- Verdict
- Solid Choice
Who runs this experience
Operated by Casco Bay Custom Charters, LLC, who run 3 experiences we rank across 1 city, with an average Outty Ranking of 57.0.
See everything Casco Bay Custom Charters, LLC runsWhy this scores 67
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Sightseeing Charter on a Vintage Lobster Boat with Drinks: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Portland.
How much does Private Sightseeing Charter on a Vintage Lobster Boat with Drinks cost?
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Prices start at $380 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Portland usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Sightseeing Charter on a Vintage Lobster Boat with Drinks take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Portland is not rushed.
Is Private Sightseeing Charter on a Vintage Lobster Boat with Drinks worth it?
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It holds an Outty Ranking of 67 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 73 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Portland, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Sightseeing Charter on a Vintage Lobster Boat with Drinks suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Around 26 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Portland can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Portland and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Private Sightseeing Charter on a Vintage Lobster Boat with Drinks start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Portland within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Portland?
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Portland sells lighthouse and lobster-boat tours in Casco Bay, Old Port food and brewery walks, seal and puffin cruises, and fall foliage runs up the Maine coast. On Outty we rank every Portland experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local, Portland, Maine: Hidden Histories Guided Walking Tour, A Walk Through Time Tour in Portland. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Portland?
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June to October, with peak foliage in early October. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Portland?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Included: Licensed Captain; Alcoholic beverages; Private Charter for up to 6 guests (cost is a flat rate); Bottled water; and All Fees and Taxes. Not included: Parking in Portland's Old Port; and Gratuity for your Guide. Always check the voucher for the final list before you travel.
Where is the meeting point for Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Meet at the back of the parking lot between Gilbert’s Chowder House and Dry Dock in Portland’s Old Port. Arrive 20 mins early to find parking. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Private Sightseeing Charter on a Vintage Lobster Boat with Drinks offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
What happens to Private Sightseeing Charter on a Vintage Lobster Boat with Drinks if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Private Sightseeing Charter on a Vintage Lobster Boat with Drinks?
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Across 73 reviews averaging 4.9 out of 5, recurring themes include the guide, knowledge and storytelling, small groups. Travelers single out the guide as the reason the experience works.
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