Portland Sightseeing Cruises

Explore Portland's scenic waterways with sightseeing cruises. Enjoy sunset sails, lighthouse views, private charters, and group boat tours on Casco Bay.

No tours match these filters.

Large Group Private Wooden Boat Sightseeing & Lighthouse Charter

Crowded public cruises make it harder for groups to enjoy Casco Bay together. From Portland's Old Port, charter a classic wooden boat for up to 16 guests, wit

★ 4.8 (8)

From $850.00 USD

Maine Fall Foliage Private Lobster Boat Cruise with Local Drinks

Experience COLORFUL Maine on this 2-hour sightseeing tour, where you’ll take in the vibrant fall foliage and the best coastal sights in the Portland area. It do

★ 4.6 (11)

From $380.10 USD

Portland Tall Ship Cruise on Casco Bay

What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make y

★ 4.6 (245)

From $100.60 USD

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

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

★ 4.9 (73)

From $380.10 USD

Private Sunset Charter on a Vintage Lobster Boat with Drinks

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

★ 5.0 (45)

From $407.40 USD

Small Group Sunset Lighthouse Boat Cruise With Local Drinks

Board the Elizabeth Grace to cruise around Portland Harbor while sipping local craft beer. This 1.5-hour harbor cruise will take you out into Casco Bay. Keep yo

★ 4.7 (128)

From $89.00 USD