15 Best Casco Bay Cruises In Portland

Casco Bay Cruises, Cruises & Boat Tours, Evening Experiences, Portland, Private, Tour Reviews, Tours

Sunset & Scenic Private Boat Tour of Portland & Casco Bay

/ June 6, 2026

1.Sunset & Scenic Private Boat Tour of Portland & Casco Bay

A private 2-hour sunset boat tour around Portland and Casco Bay, with Portland Head Light and island views, plus blankets and waters on board.

Casco Bay Morning Windjammer Sail

/ June 6, 2026

2.Casco Bay Morning Windjammer Sail

A 2-hour morning windjammer sail on Casco Bay from Portland, Maine. See lighthouses and Fort Gorges. Bring snacks and enjoy.

★ 5.0

“Had such a great time on the Casco Bay Morning Windjammer sail! The breeze was perfect, the views were beautiful, and the crew was super chill and friendly. It’s a really relaxing way to spend the morning in Portland. Oh, and definitely bring your own drinks and snacks if you want — makes it even…”

18 reviewsFrom $59.00by Portland Schooner Co.

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Casco Bay Cruises, Cruises & Boat Tours, Portland, Private, Tour Reviews

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

/ June 10, 2026

3.Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Private 2-hour lobster boat cruise in Portland for fall foliage, lighthouses, forts, and local beer or wine included.

★ 4.5

“Great way to see the beautiful fall scenery, we brought lunch from Luke’s and the crew provided the drinks!”

11 reviews2 hours (approx.)From $380.10by Casco Bay Custom Charters, LLC

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Casco Bay Cruises, Cruises & Boat Tours, Portland, Portland City & Sightseeing Tours, Tour Reviews, Tours

Sightseeing Boat Tour in Portland’s Casco Bay Bird’s Eye Maine

/ June 9, 2026

4.Sightseeing Boat Tour in Portland’s Casco Bay Bird’s Eye Maine

Private 2-hour Casco Bay boat tour in Portland with Fort Gorges, multiple lighthouses, possible Ram Island, and seal sightings.

★ 5.0

“Captain Matt did a fantastic job showing us the coast of Maine! We had such a a great time seeing a bunch of Portland's lighthouses, as well as Fort Gorges. We thoroughly enjoyed our time on the water with his fun trivia and expertise, and would highly recommend his tour around the waters of Maine!”

11 reviews2 hours (approx.)by Matthew Ayres

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Canoes & Kayaks, Casco Bay Cruises, Portland, Tour Reviews, Tours

Sea Kayak to an Island Tour in Casco Bay

/ June 11, 2026

5.Sea Kayak to an Island Tour in Casco Bay

Sea kayak from Mere Point to a Casco Bay island for wildlife spotting and homemade hot muffins, led by a small guided group.

★ 5.0

“This was a very fun experience. Alice started off the tour with explaining how to kayaks, such as boarding and rowing to keep you at ease. During the whole trip, she pointed out birds, we even saw an Osprey and their nests. We landed an a small cove where she explained the shells that were…”

8 reviews3 hours (approx.)From $89.00by Alices Awesome Adventures, LLC.

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Casco Bay Cruises