Top 7 Historical & Heritage Tours in Portland, Maine (ME)

February 6, 2022 Jasper Kershner

From ornate mansions to ocean views, this charming city - the largest in Maine - will enchant you. Saunter down the brick sidewalks and cobblestone streets of the revitalized Old Port District, where you can browse through bookstores, explore craft shops and eat to your heart's content. Visit the Portland Head Light, which dates back to 1791, and is the oldest lighthouse still in continuous use in the U.S. The great poet Henry Wadsworth Longfellow is the city's native son, and you can visit his childhood home, the Wadsworth-Longfellow House. With kids in hand, enjoy the highly interactive Children's Museum of Maine. And then go next door to the calmer Portland Museum of Art, a small, but eclectic museum with Impressionist works, Maine landscapes by Homer and Wyeth and other collections. Land or sea is an option here, so if you're tired of the street life, take one of the popular scenic cruises or whale watches, or hop on a ferry to the islands in Casco Bay. At the end of the day, and without kids in hand, unwind and rest your tired feet at one of the city's brewpubs.
Restaurants in Portland

1. 2 Hour Private Portland, Maine Lighthouse Tour

320 Fore St, Portland, ME 04101, USA Portland Explorer
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5.0 based on 2 reviews

Visitors to Portland can easily miss some of Maine's most stunning sights. Avoid the headache of arranging your own transportation, or renting a car, on this guided tour of Portland's must-see sights. Enjoy a personalized experience on the tour with a local Mainer and lobsterman! We have the tour outlined but the time and stops can easily be adjusted to meet the requests of your group. Tour downtown Portland, visit three lighthouses, including Portland Head Light. See Portland's top sights, and working waterfront, with a local lobsterman. Visit Commercial Street, the Old Port District, and 3 lighthouses!

Inclusions: Air-conditioned vehicle, Private transportation, Umbrella to use if it rains during the tour. , TV display with photos and video of tour stops and history of Portland

Exclusions: Gratuities

Reviewed By tippsieq

We had THE best tour ever and our tour guides Eric and Mario made the experience the best. It felt like hanging out with friends with them. The tour exceeded our expectation and everyone should check it out. We didn’t want it to end! Support this family run business and her an opportunity to see the beautiful lighthouses and learn about some really great history! Thank you for making such a special day for a group of lifelong friends who were celebrating 35+ years of friendship, a future bride and health and even better day!

2. The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

96 Commercial St, Portland, ME 04101, USA The Real Portland Tour
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5.0 based on 362 reviews

Welcome to my hometown! Hop aboard for an authentic 90 minute sightseeing tour of Portland and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, ME. Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows! As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor. This is The Real Portland Tour! Check my website for a complete listing of tour days, times, and availability.

Inclusions: Air-conditioned vehicle, Knowledgeable, entertaining guide with 20 years experience giving tours of his hometown of Portland.

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Reviewed By hennes6606

We really enjoyed the tour. It was very informational and entertaining. We made trips back to multiple of the locations visited on the tour.

3. Around The Peninsula Bike Tour

The Portland Encyclepedia, 6 Commercial St, Portland, ME 04101, USA Summer Feet Cycling - Day Tours
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4.8 based on 13 reviews

Discover the rich history and stunning architecture of the Portland peninsula. Only 3.5 miles long and 3/4 miles wide the Portland peninsula is packed full of food, history and culture. This 2.5-hour tour will show you the best of the peninsula.

Inclusions: Use of bicycle, helmet, Snacks, Guide

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Reviewed By Lauren R

We had a fantastic tour with Summer Feet in Portland! Visited 4 lighthouses with a stop for lunch. Our guide (Tom) was great - super knowledgeable about the area and very personable! Would definitely recommend!

4. Portland, Maine Lighthouse Tour

320 Fore St, Portland, ME 04101, USA Portland Explorer
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4.8 based on 202 reviews

We are always adding new tour times to accommodate travelers, please call us directly to inquire if you do not see your preferred time listed! Whether this is your first visit or you've lived in Portland for years, you’ll explore the Greater Portland area from a new perspective. Travel through downtown Portland with a local lobsterman and hear about the working waterfront, commercial fishing industry and more! Next, visit 3 lighthouses and spend about 40 minutes walking around and taking pictures at historic Portland Head Light. 2 more photo stops are included on the tour at Spring Point Head Light and Bug Light. Transportation provided in a temperature controlled 12 passenger Ford Transit. Your guide provides tips for dining and activities during your stay in Portland, Maine. Call us directly for information on booking a custom or charter service tour!

Inclusions: Umbrella to use if needed, Air-conditioned vehicle, TV display with photos and video of tour stops and history of Portland

Exclusions: Gratuity not included

Reviewed By ClassifiedOne

Overall had a good tour. I'm a history buff when it comes to city's and towns and this tour definitely provided me with known and unknown facts. Eric was personable and knowledgeable about the history of the lighthouses and Maine itself. If you're looking for a scenic tour this is for you.

5. Vintage Fire Truck Sightseeing Tour of Portland Maine

180 Commercial St, Portland, ME 04101, USA Portland Fire Engine Co
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4.8 based on 281 reviews

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable guide helps relive Portland’s colorful history from a local’s perspective. See lighthouses, Civil War forts, city parks and buildings, interesting stories and a multimedia experience packed with historic images of Maine. This is one family-friendly tour you should not miss out on!

Inclusions: Driver/guide, Tour

Exclusions: Food and beverages, Gratuities (suggested)

Reviewed By rangerswife02

Nice little piece of Portland history. Great guide he was very knowledgeable and engaging with guests. Fire truck ride was fun and they do warn you about bumpy roads.!

6. Portland: Old Port "Seafood Lovers" Lunch Tour

1 Union Wharf, Portland, ME 04101, USA Maine Foodie Tours
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4.8 based on 5 reviews

Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , view lobster boats often unloading their catch and visit Old Port and waterfront district destinations for a progressive, iconic Maine lunch. - This walking tour is appx. 1 - 1.5 miles visiting local favorites with plenty of food, and food for thought - lots of time for Q/A. - There's always a whole lobster roll, a New England clam or seafood chowder, local craft beer (or soda) plus a whoopie pie or other Maine sweet, and a surprise seafood taste or two along the way. This is our most “classic heritage” Maine experience with a bit of modern flare.

Inclusions: Guided walking tour of the Old Port, Enjoy a fresh picked lobster roll, New England or seafood chowder, Maine craft beer or soda and more, VIP gift

Exclusions: Gratuity to your tour guide

Reviewed By rkblanch

We loved the food and Timothy was an excellent, knowledgeable guide with the perfect mix of food and historical information! What a great way to see the Old Port area and try some awesome food!

7. A Walk Through Time Tour in Portland

1 Union Wharf, Portland, ME 04101, USA Maine Foodie Tours
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4.8 based on 119 reviews

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.

Inclusions: Two hour - closer to two and a quarter duration, You will be treated to a sweet treat at the end of the tour.

Exclusions: Your tip to your guide is not included. The suggested gratuity is 20%.

Reviewed By rkblanch

We loved the food and Timothy was an excellent, knowledgeable guide with the perfect mix of food and historical information! What a great way to see the Old Port area and try some awesome food!

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