Casco Bay Cruise: Scenic Maine Coast Tour
5.0
19 Ratings
South Portland

Embark on a private boat charter for up to 5 guests and explore the scenic Casco Bay. Discover the beauty of Maine’s coast, visit charming islands, and enjoy delicious meals and cocktails at local hotspots. Choose from half-day tours with flexible itineraries and breathtaking sunset views.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Peaks Island - Experience tours of the Casco Bay islands and enjoy the stunning beauty of the Maine coastline.
  • Portland Head Light - Located in Cape Elizabeth, Maine, Portland Head Light is a historic lighthouse. Positioned on a headland at the entrance to the main shipping channel into Portland Harbor, it is part of Casco Bay in the Gulf of…
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What's Included
  • Towels, blankets, and cups provided on board
  • Complimentary water, plates, and ice available
What's Not Included
  • Food and beverages
Additional Information

Private Casco Bay Cruise – Accommodates Up to 5 Guests
Discover the stunning Maine coastline on a private 2-hour journey through the picturesque Casco Bay islands. This exclusive charter is ideal for small groups eager to uncover secluded coves, observe local wildlife, and enjoy the quintessential allure of the Maine shoreline.
Departures are available…

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Location
1 Spring Point Dr
Spring Point Drive
Look for our crew on the dock with blue shirts!
Cancellation Policy

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

Customer Ratings
5.0
(19 Ratings)
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Seaside26788445413
Jul 15, 2025
Sunset charter - Such a nice trip with Captain Kevin! Casco Bay is very beautiful. I’m glad that we booked a charter because it made our trip!!
Review provided by Tripadvisor
S4585ndangelar
Jun 13, 2025
Great experience!! - This 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.
Review provided by Tripadvisor
Franz_z
May 31, 2025
Beautiful afternoon on Casco Bay - We 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.
Review provided by Viator
Robert_w
Sep 29, 2024
Nice day on the water! - Very 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!
Review provided by Viator
Staceyt1981
Aug 17, 2024
Fantastic half day on a boat! - We 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!
Review provided by Tripadvisor
Connector32864828334
Aug 15, 2024
Beautiful, relaxed afternoon on the water - The 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.
Review provided by Tripadvisor
Flyer03239024641
Aug 13, 2024
Amazing Day With Captain Bosworth! - Calendar 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
Review provided by Tripadvisor
Marybetho280
Aug 12, 2024
Best charter - Great charter out in Casco Bay with Captain Boz. Beautiful boat, very comfortable with plenty of seating. Will definitely book again.
Review provided by Tripadvisor
T3642fbelizabethb
Aug 12, 2024
Relaxing, Fun Tour of Casco Bay - Can’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.
Review provided by Tripadvisor
Trail15709589254
Aug 12, 2024
Perfect Day on the Water - The 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!
Review provided by Tripadvisor
Check Availability
From $650
(Per Boat)
From $650 (Per Boat)
up to 5 guests
1 - Traveler
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Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).