Sunset & Scenic Private Boat Tour of Portland & Casco Bay
Overview
Available languages
2 hours
Mobile ticket
Private Casco Bay Cruise – Up to 5 Guests
Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline.
Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.
Additional Info
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
What To Expect
Peaks Island
Tours of Casco bay islands and all the beauty the Maine coast has to offer.
Portland Head Light
Portland Head Light is a historic lighthouse in Cape Elizabeth, Maine. The light station sits on a headland at the entrance of the primary shipping channel into Portland Harbor, which is within Casco Bay in the Gulf of Maine. Completed in 1791, it is the oldest lighthouse in Maine.
Options
Sunset & Scenic Private Boat Tour of Portland & Casco Bay
What‘s Included
On board we have towels, blankets, waters, plates, ice, and cups.
Food and beverages
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
19 reviews
Total reviews and rating from Viator & Tripadvisor
Sunset charter
Seaside26788445413,Jul 15, 2025
- Review from Tripadvisor
5.00Such a nice trip with Captain Kevin! Casco Bay is very beautiful. I’m glad that we booked a charter because it made our trip!!
Great experience!!
S4585NDangelar,Jun 13, 2025
- Review from Tripadvisor
5.00This was an absolutely perfect trip. Our captains, Kevin and Sarah were excellent tour guides. They had a wealth of knowledge of the area. We voted around numerous islands that were just breathtaking.
Beautiful afternoon on Casco Bay
Franz Z,May 31, 2025
- Review from Viator
5.00We had a fun afternoon seeing the islands of Casco Bay. Kevin and Sarah provided a fun, relaxed time and expertly showed us many scenic views. Near the end, we visited a great restaurant for food and drinks then ended the trip right at dusk when the light turned golden.
Nice day on the water!
Robert W,Sep 29, 2024
- Review from Viator
5.00Very nice day seeing the calendar islands with Captain Kevin. Tailored the tour based on our interests, very accommodating. Clean ship with comfortable seating and the extras, such as blankets, hats etc. were available. I would do this trip again!
Fantastic half day on a boat!
StaceyT1981,Aug 17, 2024
- Review from Tripadvisor
5.00We had an absolutely fantastic half day experience with Captain Kevin and his mate John. While the usual route for a scenic tour was interrupted due to a swimming event, Captain Kevin took us around several of the islands and Fort Williams, we were able to see some dolphins, and pulled up to a beautiful island inn where they allowed us to quickly moor and run ashore for a view from the inn. Both captain and mate knew the islands and the waters well, and were a wealth of information. We'd absolutely recommend this activity to anyone wanting to explore the islands and enjoy time on a boat!
Beautiful, relaxed afternoon on the water
Connector32864828334,Aug 15, 2024
- Review from Tripadvisor
5.00The crew is relaxed and easy going but knowledgeable and reassuring. Captain Kev, born and raised Mainer, has years of experience navigating Casco Bay. By judging the weather, Kev will know where the best spot for the day will be. Lovely day out on the water.
Amazing Day With Captain Bosworth!
Flyer03239024641,Aug 13, 2024
- Review from Tripadvisor
5.00Calendar Island Charters is amazing!! Captain Bos took my group and I around the harbor for a few hours and we were not disappointed. We stopped by Portland Head Light, Diamond Cove, Cow Island, and Seal Rock for some unbelievable sightseeing. Bos was incredibly knowledgeable and kind. We felt super safe on the water, and the boat was so comfortable for all of us! If you’re looking for a fun day on the water, look no further than Calendar Island Charters
Best charter
marybetho280,Aug 12, 2024
- Review from Tripadvisor
5.00Great charter out in Casco Bay with Captain Boz. Beautiful boat, very comfortable with plenty of seating. Will definitely book again.
Relaxing, Fun Tour of Casco Bay
T3642FBelizabethb,Aug 12, 2024
- Review from Tripadvisor
5.00Can’t think of a better or more engaging captain than Boz to show my family around Casco Bay. Boz knows the area like the back of his hand, and is an excellent and entertaining tour guide. If you want to see and get to know the islands of Casco Bay from the water - feel comfortable and welcomed by the Captain, look no farther than Calendar Island Tours.
Perfect Day on the Water
Trail15709589254,Aug 12, 2024
- Review from Tripadvisor
5.00The entire experience was amazing! Captain Boz was the perfect “Mainah” to spend the day on the water with! He took us to spots where you could really take in the beautiful Maine coast. I will definitely be coming back again!
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Operated by Calendar Island Charters