Trolley at Portland Head Light. Photo Provided by Portland Discovery Land & Sea Tours
Boat at Portland Head Light. Photo Provided by Portland Discovery Land & Sea Tours
Boat Tour. Photo Credit: Bill Frappier
Lighthouse. Photo Provided by Portland Discovery Land & Sea Tours

Portland Discovery Land & Sea Tours

Offer a wide variety of sightseeing and charter transportation options by Land and Sea! Our friendly, attentive staff and nicely appointed trolleys and boats are sure to make your next outing a memorable one!

Travel Trade > Portland Discovery Land & Sea Tours

170 Commercial St
Portland, ME 04101

P. (207) 774-0808

About Us

2023 Season Runs: April 29 to October 29

We have a variety of charter packages designed to make your event a success! Our popular charters on land include city tours, dinner transfers, shuttle services, and weddings. By sea, we offer narrated cruises, Island Transportation, a Lobster Bake on the Bay and a Sunset Cocktail Cruise.

Trolley Charters: Go In Style… Go By Trolley!
Portland Discovery has a fleet of trolleys that are available for private charter. Trolleys are great for a wide variety of transportation events. Some of the charters we service are: Dinner Transfers, Shuttle Service, Group Tours, and Weddings.

Boat Charters:
The Islander and Bay View Lady are available to groups of all sizes for charters and functions. Corporate events, wedding rehearsal dinners, family reunions, birthdays, anniversaries, etc. are always more fun while cruising Casco Bay! All of our charters have a variety of catering, bar service, and entertainment options to suit practically any budget. Our boats are U.S. Coast Guard certified and can handle groups from 10-149!

Lobster Bakes on Casco Bay:
For a truly memorable experience, we offer full lobster bakes on board the Bay View Lady. Available in 2-3 hour blocks, come with us and enjoy Maine’s most treasured delicacy while cruising picturesque Casco Bay.

We are located at 170 Commercial Street in Portland, which is a small blue and white building marked “Long Wharf” on top. There are three kiosk windows and we are the middle window.