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Portland Maine Driving Tours

Portland Maine Driving Tours

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Walking Tours

You can learn from local experts about Maine's history and culture by taking a guided walking tour. Experienced guides will lead you to the best sights and tastes you might not have discovered otherwise.

Walking Tours

In Maine's largest city, you can learn about maritime history and enjoy modern dining and shopping. You'll find a variety of walking tours to help you explore the cobblestone streets of the city's Old Port, tour mansions from the early 1800s, and visit a burial site for colonists, seafarers and soldiers. You can find great views of Portland's harbor, Casco Bay and the Fore River from the old neighborhoods on the Eastern and Western Promenades. You can also climb to the top of the Portland Observatory, the only remaining maritime signal tower in the country.

And check out the Portland Freedom Trail, a self-guided walking tour of Underground Railroad sites throughout the city.

Maine Day Ventures offers a variety of walking tours in Portland, Bar Harbor, Kennebunkport, Rockland, Biddeford and Boothbay Harbor – from historic strolls to waterfront walks.

In York, learn about Colonial York, one of the nation’s oldest communities, on a variety of historic walk tours from the Old York Historical Society.

Food Tours

Maine Day Ventures also offers culinary walking tours of Portland, Kennebunkport, Boothbay Harbor and Bar Harbor where you will enjoy samples of local fare. Maine’s rich maritime history lends itself to the character of the food. These tours reveal the flavorful past of these cities through the cuisine. Dine at dozens of award-winning eateries and sample a variety of Maine specialties, from seafood and cheeses to blueberries and whoopee pies at the Old Port. Maine has the fourth-highest concentration of microbreweries, and if you're a beer connoisseur you will enjoy tasting the many hand-crafted beers and ales found in Old Port brewpubs.

Haunted Walking Tours

You can explore "haunted" Portland by taking a nighttime tour to learn about the Old Port's ghosts and witches with  Wicked Walking Tours. You can enjoy more ghostly history on tours of the village of York and the Jameson Tavern in Freeport. In Bar Harbor, join one of the country’s best ghost tours or a Monsters by Moonlight tour.

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