Skip to primary navigation Skip to content Skip to footer


Back to Blog

Which Portland, Maine Trolley Tour Should You Take?

a passenger bus that is parked on the side of a train

If you are mapping out your first trip to Portland, Maine, you may be overwhelmed with the number of destinations there are to see. While this is arguably a good thing, logistics often prevent you from being able to visit all the sights on your list. After all, when you factor in driving time, finding parking spots, and navigating directions through unfamiliar roads, you could end up spending more time in your car than visiting a Maine landmark! Fortunately, with Portland Discovery Land and Sea Tours, you can visit the most beautiful (and historically significant) places in Portland without the logistical headaches. As Portland’s #1 sightseeing tour company, we offer tours to fit every guest.

Portland Discovery Land and Sea Tours is well known in the industry for our commitment to 100% customer satisfaction and for our Certificate of Excellence from Trip Advisor. Our trolleys meet exceptionally high standards, are fully updated and impeccably clean. We have comfortable open-air seating with unobstructed views and a top-notch sound system that makes the narration crystal clear.

On one of our most popular tours, the Portland City & Lighthouse Tour by trolley, our guests enjoy a 105 minute fully narrated tour of Portland’s diverse history and architecture. This trolley tour also visits the Portland Headlight, an icon of the Maine coast. This lighthouse has been standing tall and helping vessels find safe passage since it was first lit on January 10, 1791. The Portland Headlight is also visible from our Lighthouse Lovers Cruise. Another option for those who don’t have a lot of time to spend but who wish to get a taste of what our little city has to offer is the 60 minute Peek at Portland tour . This fully narrated trolley tour of the Portland peninsula explores Portland’s rich history and explores highlights that include The Portland Observatory, The Longfellow House, and Victoria Mansion.

Portland Headlight is adjacent to the historic Fort Williams Park, a fort that was once used during World War II to protect the Cape Elizabeth shoreline and contribute to Harbor Defense in Portland. While the fort was closed and deactivated on June 30, 1963, the 90-acre park is now home to residents and tourists alike for recreational activities. In addition to seeing the Portland Headlight up close (with plenty of time for pictures), our Portland, Maine trolley tour also brings our guests to these other unique destinations:

The Old Port

You can’t visit Portland without a proper introduction to the Old Port district. Recognized for its authentic cobblestone streets, comfy taverns, and working waterfront, this unique dockside community is known for its foodie restaurants and eclectic shopping opportunities. There are countless places to eat, satisfying every craving from Maine lobsters and Maine whoopie pies to escargot and filet mignon.

The Victoria Mansion

This famous mansion (also known as the Morse-Libby House) was built between 1858 and 1860 as a summer home for Ruggles Sylvester Morse, a Maine native who made his fortune as the proprietor of luxury hotels in New Orleans. Henry Austin, a famous New Haven, Connecticut-based architect, built this home. True to his style, the Victoria Mansion is recognized as one of the most prominent (and important) examples of the Italian villa style within our American domestic architecture. Gustave Herter, a famous interior designer and furniture maker, designed the interiors of the Mansion. Today, ninety percent of the Mansion’s original furnishings still remain intact.

The Wadsworth–Longfellow House

Housing three generations of a family that made important contributions to the political, literary, and cultural life of New England, this house is an important stop on the trolley tour. One of the most famous men in this family, if not all of

America, poet Henry Wadsworth Longfellow (1807–1882), grew up here. Almost all of the artifacts and household items found on the property are original to the Wadsworth and Longfellow families. Longfellow Garden is located behind the home, and its beautiful landscaped grounds and paths are open to the public in seasonal weather.

Booking Your Portland, Maine Trolley Tour Today

For your convenience you may book your reservation online. If you have a very important event, like a wedding, corporate event, or another private group function, consider a trolley charter for your transportation or shuttle service needs. Please contact us if we can help you coordinate this service; it’s one of the best ways to travel in Portland.

When you travel with us, our tour guides will be happy to help you maximize your Maine experience by giving you the “insider scoop” on all the best places to dine and shop in Portland. Portland is a city that’s meant to be fully enjoyed and Portland Discovery Land and Sea Tours can make that happen for you! We invite you to be our guest – and experience the best Portland has to offer for yourself

  • Posted in: