Top Portland Bike Tours

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Stop in downtown Portland, and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland's history since 1632. Some of the locations we may feature on your tour include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern Cemetery, the Abyssinian Church, the U.S. Customs House and more. ***Tour duration is two "ish" hours, based on guest engagement and pace of the group. Planning on 2.5 hours for arriving early to check-in and make it back to your vehicle post tour is recommended.

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 your visit to Portland live long in the memory.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses and natural feature, and you're welcome to bring food and beverages, even the adult kind, on board.

Our 3-Hour tour leaves at 11:30 am and follows the scenic South Portland Greenbelt Pathway to three local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble. Next, the tour will pass by Willard Beach before arriving at the final stop, the famous Portland Head Light located at Fort Williams Park in Cape Elizabeth. It is recommended that patrons bring a lunch or we can assist in purchasing lunch from a local food truck that serves Lobster Rolls.