Maine
Sightseeing Walking Tours

Enter your dates to find available activities

Our most recommended Maine Sightseeing Walking Tours

Portland Maine: Tour in Vintage Fire Engine

1. Portland Maine: Tour in Vintage Fire Engine

Enjoy seeing Portland in an unforgettable way. Hop on board a vintage fire truck with onboard multimedia system, including a large, flat-screen LED TV. Experience Portland in a unique and fun way with this local-led tour aboard a classic fire engine. Explore the city’s peninsula as you drive along the cobble-stoned streets. Enjoy great views of lighthouses, civil war forts, and the historic architecture that make up the wonderful Maine city. Enjoy a 50-minute tour narrated by local guides who love sharing their knowledge of Portland Maine. Get to know the vibrant neighborhoods of this city by the sea from high up on your truck.

Portland: Old Port Culinary Walking Tour

2. Portland: Old Port Culinary Walking Tour

Enjoy this experience that showcases the culinary culture of Portland, Maine comprised of talented food and beverage artisans, from bakers and brewers to confectioners, chefs, and more. Visit the spots the locals enjoy visiting on a daily basis. Join a friendly and engaging tour guide as they take you to several Old Port and neighboring artisanal shops, restaurants, and pubs where you’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages. You will have the opportunity to meet and greet culinary artisans along the way, learn what inspires them and how they got their start with a lively narration from your guide. Along the way, your guide will dish about the colorful, social, and culinary history unique to the “Port City” with lots of additional recommendations on how to dine and imbibe. You are sure to leave full of delicious food and local history. This experience actively works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues. While tours vary, your foodie experience may include, fresh-picked lobster, from-scratch confections, locally-sourced temaki (raw fish) roll, Maine seafood “chowdah”, iconic Maine craft beer, Maine honeywine, and dark chocolate truffles made with Aroostook County potatoes.

Kennebunkport, Maine : Lunchtime Culinary Walking Tour

3. Kennebunkport, Maine : Lunchtime Culinary Walking Tour

Discover the area that has been home to those who make their living on the sea for centuries. Visit a popular destination for visitors who love history, beautiful beaches, and plentiful outdoor activities. Explore the culinary scene that In recent years is attracting visitors with nationally renowned chefs, gourmet catering companies, craft brewers, and award-winning food artisans. This tour takes a leisurely half-mile walk from Dock Square across the bridge into the lower village as you taste all along the way what it means to be from Maine.  You will visit with shop keepers and food artisans, taste chowders, lobsters, and more, all regionally sourced and created by local talent. A friendly and knowledgeable guide will take you to several venues to sip, taste, and learn about Maine’s culinary history and vibrant food scene. This experience actively works with gluten (not celiac), seafood, nut, and vegetarian dietary preferences and sensitivities to the best of our ability. Guests may pick and choose their participation for any further food issues.  While tours vary, your foodie experience may include, Satellite donuts, fresh lobster right off the boat, Maine clam or fish “Chowdah”, craft-brewed ales or fruit sodas, Maine honey wines, the original Maine whoopie pie, freshly roasted coffees with local roaster and macaroons, and a visit to a summer stand for ice cream.

Portland, Maine: 2-Hour Guided History Tour

4. Portland, Maine: 2-Hour Guided History Tour

Meet your local guide, a history lover who will bring the stories and facts from Portland’s past alive throughout the tour. Starting on Commercial Street, walk through the cobble stone streets of the historic Old Port, downtown, and waterfront areas.  Some of the locations that may be featured as part of the tour include the lobster statue, the home of Henry Wadsworth-Longfellow, the Eastern cemetery, the Abyssinian Church, and more. Your tour will finish on a sweet note with a local treat.

Bar Harbor, Maine: Culinary Walking Tour with Tastings

5. Bar Harbor, Maine: Culinary Walking Tour with Tastings

Immerse yourself in Bar Harbor's culinary scene during this 3-hour guided walking tour. Savor an array of local flavors at various stops along the tour, while learning about the local history from your local guide. As you sample the fare at the various stops, the establishment owners will reveal the history behind their industry and what goes into making their specialties. This tour is a fairly short walk around the Village Green and the beautiful harbor, with plenty of food stops for lunch.

Portland, Maine: Hidden Histories Downtown Walking Tour

6. Portland, Maine: Hidden Histories Downtown Walking Tour

Discover Portland's hidden histories on a guided walking tour of the Old Port, downtown, and the working waterfront. Marvel at images of the past and at the colorful storytelling your guide shares with you to make the past come alive. Hear stories only a local knows about the city's sights, streets, and buildings. Explore the Old Port, Portland's major public buildings, and the working waterfront, winding through intimate cobblestone streets along the way. See the city's charming red-brick buildings, its waterfront filled with seafood restaurants and sea views, and more. Learn fascinating anecdotes and facts about Portland, sharing them with friends down the line to show your newly-gained local knowledge. End your tour in a waterfront park, about a 5-minute walk from where you started, surrounded by boutiques, restaurants, and other activity opportunities to continue your own discovery of the city.

Kennebunkport: 2-Hour Historical Walking Tour

7. Kennebunkport: 2-Hour Historical Walking Tour

Step into the quiet neighborhoods of the first residents during this 2-hour guided walking tour through the historic district of Kennebunkport, Maine. Learn from your local guide about the interesting history of the town as well as amusing anecdotes from the days of being a flourishing shipbuilding town. The tour begins at the Dock Square and will immediately take you back in time to the thriving shipbuilding days of Kennebunkport, Maine. Stroll along Maine Street and weave your way through side streets, seeing the homes of the shipbuilders and merchants of the late 18th and early 19th centuries. Your expert guide will tell you the fascinating history, fun stories, and interesting facts of the area. Learn how “Poor Arundel” as it was known in 1743, become one of the wealthiest towns in Maine by 1810 and what happened at the Customs House during the shipbuilding era in the 1800s.  The tour ends back at Union Square, bringing you full circle. A local treat will be provided to sweeten the rest of your day in Kennebunkport.

Portland: Old Port Seafood Lovers Tour

8. Portland: Old Port Seafood Lovers Tour

Explore Portland’s vibrant working waterfront to view lobster boats often unloading their catch, learn about the historic wharves and their relationship to the sea. Visit a mix of Old Port and waterfront district destinations, and sometimes a locale or two on the fringes, for a progressive lunch. Servings vary from dine-in and to go from restaurants, pubs, markets, and artisanal shops. Learn about the life of lobsters dwelling on the ocean floor and hear about how hardy lobstermen and women haul in their catch year-round, rain, snow, and shine.

Boothbay Harbor: 3-Hour Foodie Walking Tour

9. Boothbay Harbor: 3-Hour Foodie Walking Tour

Taste your way through Boothbay Harbor, Maine during this 3-hour culinary walking tour. You’ll learn about the history of Boothbay, its harbor, and lobstering and fishing industries. You will also discover the harbor's award-winning aquaculture and sustainability practices.  Begin your tour with a Prosecco toast as you set off on a mile-long adventure. As you walk along the harbor, you will make stops at a selection of restaurants, bakeries, and gourmet shops, tasting the local seasonal flavors. Enjoy items such as local cheeses, lobster specialties and local oysters.  This is a great way to start your visit to Boothbay, as you will also receive recommendations from your guide for all sorts of activities to enjoy during your time here.

Boston: Kennebunkport Day Trip with Optional Lobster Tour

10. Boston: Kennebunkport Day Trip with Optional Lobster Tour

Admire both the New England Coast and the state of Maine on this semi-private, fully-narrated day trip from Boston. Start with a prearranged pickup from your hotel. Once aboard, begin your journey to Kennebunkport, Maine. Make some photo stops at some scenic locations along the coast of New England, including a 1-hour stop in the historical town of Portsmouth, New Hampshire, and the Nubble Lighthouse in York, Maine. Once in Kennebunkport, enjoy some time to explore this popular summer vacation retreat and do some shopping.  Add a lobster tour to your day trip to enjoy a quick visit to Walkers Point where former President Bush has a summer vacation home. After spending the day cherishing Maine’s coastal culture, sit back and relax on the ride back to your Boston hotel.

Frequently asked questions about Maine Sightseeing Walking Tours

What are other things to do than Sightseeing Walking Tours that are worth visiting in Maine?

The other unmissable things to do in Maine are:

Which Maine Sightseeing Walking Tours are taking additional COVID-19 precautions?

Other Sightseeing Options in Maine

Want to discover all there is to do in Maine? Click here for a full list.

What people are saying about Maine

We had an absolutely wonderful walking tour with Ross. If you are visiting Portland or live in Portland and have out of town visitors don't miss this most informative, fun, and pleasant tour. Portland has such rich history and Ross won't disappoint as he shares interesting facts, fun stories, and some "behind the scenes" tidbits. Ross is also helpful with restaurant suggestions and other sites to see, both in Portland and other nearby Maine locations. Thanks Ross for a great tour!

We had a fantastic experience with Dugan as our guide. He was friendly and enthusiastic and had the facts at his fingertips. He had a compelling story to tell and was sensitive to contemporary issues still existing today. Overall, he added to our enjoyment of Portland, Maine and enriched our visit to the city. We loved it and talk about it to other people back home.

We enjoyed a sunny day and the city tour and information. Feel like we can drive around more on our own and find more interesting spots in Portland. Thank you!

This was one of the best tours we’ve ever been on!! Paul and Mike were friendly, informative and showed us all the highlights of Portland. It was EXCELLENT!!!

Great tour. Tour guide who also owns the company was very informative; kept the tour entertaining. Covered alot in 2 hours and time went by fast.