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Boat Charter in Portland, Maine

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Have a Memorable Experience in the Beautiful Portland, Maine!

Portland Discovery Land and Sea Tours is pleased to 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!


From our fleet of classic trolleys to our three boats, our team here at Portland Discovery is here for your wedding charter needs, perfect for making your big day memorable. From welcome drinks and rehearsal dinners, while sailing Casco Bay to transporting guests in style between the ceremony, your venue, and even back to their accommodations at the end of the night, we cater to all your transportation needs with elegance. Our versatile fleet ensures a magical setting, whether on land or water, turning your Maine wedding celebrations into lasting memories.

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Trolley Charters

Go In Style… Go By Trolley!

Portland Discovery has a fleet of classically styled trolleys that are available for private charter. Comfortable, spacious and safe, our trolleys have helped make many weddings, rehearsal dinners and other events memorable and fun! Each trolley can accommodate up to 30 people. Trolleys are great for a wide variety of transportation events such as; dinner transfers, shuttle service, group tours, weddings and rehearsal dinners.

Boat Charters

Harbor Queen, Islander and Bay View Lady are available to groups of all sizes for charters and functions.

Company parties, corporate events, weddings, 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 10-140!

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Meet the Fleet

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Islander 1


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Islander 2


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Islander 3


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Charter Inquiry

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For pricing and availability:

For a truly memorable experience, privately charter Bay View Lady for a group lobster bake. Available in two and three hour blocks, come with us and enjoy Maine’s most treasured delicacy while cruising picturesque Casco Bay.

Traditional New England Lobster Bake on the Bay View Lady Includes 2-3 hours of cruising around beautiful Casco Bay and a Lobster Dinner on board.

  • Fresh Garden Salad
  • New England Seafood Chowder
  • 1 1/4 lb. Steamed Lobster
  • Lemon Herb Roasted Chicken or Veggie Burger or Avocado & Cheddar Wrap
  • Baked Potato, Corn on the Cob, Rolls & Butter
  • Maine Wild Blueberry Pie

For pricing and availability:

Please note this is a specialty private charter option and we do not currently offer a dinner cruise to the public.