Ultimate Guide to Walking Tours in Portland, Maine in 2024

The 5 Best Walking Tours in Portland, Maine

Have you been wondering about walking tours in Portland, Maine? I’ve got you covered! These are the five best walking tours for exploring the history and food in downtown Portland.

Portland, Maine is a charming coastal town filled with a unique blend of historic allure and culinary delights. Whether you’re here to explore Portland’s famous lighthouses, pub crawl between the many breweries, stroll the historic cobblestone streets, or eat your way through the many distinctive restaurants, there’s bound to be a walking tour in Portland to guide you. 

I recently visited Portland, Maine for a little family trip. We went there for a concert at the Merrill Auditorium and stayed to explore Portland’s coastal charm. As a travel aficionado who loves to dive deep into the cultures of every place I visit, you can bet I did my research when it came to deciding on which walking tours we were going to do.

From historic tours to yummy food tours to self-paced audio guides, this blog will go over the best walking tours available in Portland, Maine. I’ll tell you what my favorite was and offer some advice based on what other travelers have experienced in the area. By the time you’re done reading, you’ll know exactly which tour in town is best for you.

So, without further ado, let’s get into it!

My Top 3 Picks: Walking Tours in Portland, Maine

Portland, Maine offers a wide variety of walking tours in town. I’ll dive into the five best-rated, but these three are my personal favorites.

⭐️⭐️⭐️⭐️⭐️

#1 Pick: A Walk Through Time Tour in Portland

✅ Historic Exploration

✅ Engaging Local Guide (who gives you snacks 😋)

✅ Intimate Group Experience

⭐️⭐️⭐️⭐️⭐️

#2 Pick: Portland’s World of Flavors Tour

✅ International Culinary Journey

✅ Educational and Entertaining

✅ Compact Flavorful Experience (with vegetarian options!!)

⭐️⭐️⭐️⭐️⭐️

#3 Pick: Audio Guided Walking Tour from Old Port of Portland, Maine

✅ Flexible Self-Paced Exploration

✅ Professionally Produced

✅ Entertaining Historical and Contemporary Stories

As you read further into this blog, I’ll outline more information about each of these tours to help you pick the right one for your trip.

Best Walking Tours in Portland, Maine

1. A Walk Through Time Tour in Portland

⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2-3 hours | ✅ Book it!

A Walk Through Time Tour will guide you through the heart of Portland, Maine. You’ll be led by an experienced local guide who tells you stories from the town’s thrilling history. 

This immersive walking tour is designed to unravel the layers of the city’s history. The tour takes you on a scenic exploration through the Old Port, downtown, and waterfront areas. This experience promises to be more than just a stroll; it’s an encounter with the historical essence of Portland.

Our tour guide was James, a Boston transplant who has lived in Portland for over 30 years. We had a total of nine people in our group (10 counting James), which was the perfect size for a more interactive and personalized exploration of Portland’s fascinating history. 

My family and I loved this tour for many reasons, including:

• Historic Exploration: We got an exclusive behind-the-scenes peek inside the historic Customs House. Other historic places this tour might take you could include the home of Hendry Wadsworth-Longfellow, the Eastern Cemetery, and the Abyssinian Church. 
• Engaging Local Guide: No one knows a town better than the locals. Since James had lived in Portland for more than half his life, he had more than enough historical secrets and local tips and tricks hidden up his sleeves.
• Intimate Group Experience: The tour is capped at 20 participants, but we only had nine. Our group size created the perfect environment for questions and discussions.

Overall, as historical enthusiasts, my family had a great time on this tour.

A Walk Through Time Tour in Portland Pros:

Every tour has its pros and cons. Let’s take a look at the pros of A Walk Through Time Tour in Portland.

• Immersive Historical Insights: The tour offers a comprehensive exploration of Portland’s history, covering significant landmarks and providing participants with a well-rounded understanding of the city’s past.
• Expert Guided Experience: The presence of a knowledgeable local guide who knows his stuff and is passionate about the experience enriches the tour, offering valuable insights and stories that go beyond basic historical facts.
• Snacks Included: Probably the best pro of them all is the fact that at the end of the tour, you get snacks! James brought us delicious cookies from a local bakery that were so good my mouth is watering now as I think about them. 😋

All in all, we had a great experience with this tour.

A Walk Through Time Tour in Portland Cons:

To make sure you have the full picture, let’s take a look at the cons of A Walk Through Time Tour in Portland. 

• Weather Dependency: Being a walking tour, the experience may be impacted by weather conditions, potentially affecting the overall enjoyment, especially during inclement weather.
• Physical Activity Level: Some participants may find the moderate physical activity involved in walking tours challenging, particularly individuals with mobility issues or those seeking a more leisurely experience.
• The Time Might Run Long: The website says the tour should last about 2 hours. But our tour was closer to three hours. While this might be a pro for many, it’s good to know in advance to plan a bit of a buffer between activities if you’ve got more on your Portland itinerary after this.

The cons of this tour are pretty standard when it comes to walking tours.

➡️ If you’d like to read my full review of this tour, including a description of the entire experience, click here. ⬅️

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2. Portland’s World of Flavors Tour

⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2.5-3 hours | ✅ Book it!

Portland, Maine is known for two things: lighthouses and food. Did you know that Portland ranks second in the US—coming in just after San Francisco—in terms of restaurants per capita?

Discover the vibrant culinary scene that defines Portland, Maine, with Portland’s World of Flavors Tour. This delectable journey promises to be more than just a walk; it’s a gastronomic exploration of hidden gems and great flavors that contribute to Portland’s cosmopolitan flair. 

Of all the walking tours in Portland, Maine, this walking tour is designed for those with an adventurous palate. This 2.5-3 hour walk through the historic Old Port and waterfront areas showcases a rich tapestry of tastes and ethnicities sourced from around the globe. On this tour, you’ll get the chance to taste cuisines from Japan, Turkey, Mexico, and India.

The Portland’s World of Flavors Tour includes:

• A Cosmopolitan Culinary Journey. This tour serves up a rich tapestry of flavors, allowing participants to experience the global influences that shape Portland’s culinary landscape.
• An Educational and Entertaining Experience. Gain insights into the food pathways and the personal journeys of restaurant owners as you savor locally sourced foods prepared with international recipes, customs, and spices. The tour is not just about eating but also about understanding the cultural narratives behind each culinary gem.
• An Adventurous Exploration. The tour caters to those with a big palate, offering a diverse punch of flavors that promises to be both exciting and memorable.

For foodies visiting Portland, this tour is a must.

Portland’s World of Flavors Tour Pros:

Here are the pros of the Portland’s World of Flavors Tour:

• Diverse Culinary Experience: Explore a variety of tastes and cuisines in a single downtown area on a tour that highlights the multicultural influences shaping Portland’s food scene.
• Local Expertise: Benefit from the knowledge of trained local guides who not only showcase the best culinary offerings but also provide cultural insights and stories, enhancing the overall educational and entertaining aspects of the tour.
• Hidden Gem Discovery: Uncover hidden culinary gems that may not be readily apparent or showcased on the front page of Google.
• Vegetarian Options Available: As a vegetarian myself, this got me excited. In a town known for its seafood, you wouldn’t expect to find a vegetarian-friendly food tour. But this one is! Just remember to call ahead to let the tour guides know.

This tour will show you the diverse, multicultural food scene that thrives in Portland.

Portland’s World of Flavors Tour Cons:

So, then, what are the downsides to Portland’s World of Flavors Tour?

• Dietary Restrictions: While the tour offers pescatarian and vegetarian menus, you have to call ahead to request these options. This may pose a limitation for those with spontaneous dining choices or last-minute plans. Also, vegan options may not be available.
• Duration: The 2.5-3 hour duration might be lengthy for individuals with time constraints or those seeking a shorter culinary experience.
• Weather Consideration: As an outdoor walking tour, weather conditions can impact the overall experience, potentially affecting the enjoyment of the culinary journey, especially during inclement weather.

While a perfect world would have food options available for every dietary need, that’s not always the case. Still, for those without strict food restrictions, Portland’s World of Flavors Tour is a top choice when it comes to exploring Portland’s culinary landscape.

3. Audio Guided Walking Tour from Old Port of Portland, Maine

⭐️ RATING: 4/5 Stars | ⏳ TOUR LENGTH: 1.5 hours | ✅ Book it!

While guided walking tours are great for meeting new people and asking questions to the local guide, you might prefer to travel self-paced on your own. I get that, which is why I’d like to recommend the Audio Guided Walking Tour from Old Port of Portland, Maine. 

This self-paced audio guide is professionally produced to provide high-quality education and entertainment. With this tour, you’ll discover the captivating tales woven into the fabric of Portland, Maine, as you step into the city’s historic streets. 

You’ll use your smartphone to access this guided adventure as it empowers you to explore at your own pace without sacrificing an immersive experience. The best part is, it never expires. So you can access this guide again and again, every time you visit this coastal town.

On this tour you’ll find:

• A Flexible Self-Paced Adventure: Enjoy the freedom to explore Portland’s historic streets at your own pace, enhancing the overall experience if you have varying schedules and preferences.
• Professionally Produced Narration: Immerse yourself in the stories of Portland with professionally produced narration and music.
• Comprehensive Exploration: Traverse significant landmarks, including cobblestone streets, Wharf Street, Henry Wadsworth Longfellow’s home, and stops on the underground railroad. Uncover the city’s diverse history, from tales of lighthouses and adventures to insights into prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, and colonial times.

This tour is a complete guide to the city of Portland.

Audio Guided Walking Tour from Old Port of Portland, Maine Pros:

Besides being a comprehensive guide, what other pros come with doing an audio tour over an in-person guided tour?

• It never expires. With this tour, you can revisit or continue the exploration over multiple sessions or visits.
• Location-Aware Guidance. Benefit from a step-by-step guide through the city’s streets, ensuring a seamless and stress-free exploration, even for those unfamiliar with the area.
• Inclusive Content. The tour covers a wide range of topics, providing a comprehensive overview of Portland’s history and cultural significance, making it suitable for both locals and visitors.

While some may still prefer a traditional guided tour, there are many reasons why an audio tour like this could be the better option for your trip.

Audio Guided Walking Tour from Old Port of Portland, Maine Cons:

Here are the downsides to purchasing an audio-guided tour:

• Limited Interaction: As a self-guided tour, the experience lacks direct interaction with a live guide, which some participants may miss for real-time engagement and the opportunity to ask questions.
• Device Dependency: A smartphone is required for this type of tour.

Unlike guided tours, the weather isn’t really a downside for a self-guided audio tour. Because, if you do experience adverse weather, you can rearrange your itinerary to do the tour earlier or later on your trip when you’re more likely to experience nice weather.

“This is a great intro to the city if you’re pressed for time or can’t commit to a guided tour. Informative and convenient.”  — dhaanstad, Oct 2023 (Read more reviews)

4. Donut Tasting Walking Tour in Portland’s Old Port

⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 1 hour 15 minutes | ✅ Book it!

Indulge in Sweet Delights on the Donut Tasting Walking Tour in Portland’s Old Port, Maine.

Satisfy your sweet tooth with this delectable adventure through the charming streets of Portland’s Old Port. This flavorful journey offers a unique taste of the Northeast as you follow your guide to discover some of the city’s best donuts. 

Designed for all ages, this tour takes you to three renowned downtown donut shops, providing the opportunity to savor six distinct samples.

On this tour, you’ll experience:

• Culinary Exploration: This tour allows participants to explore and appreciate the diverse flavors and styles of fried dough offered by Portland’s top donut shops.
• Historical Insight: Learn the fascinating legend of how the first-ever (modern-day) donut was created in Maine.
• Convenient Access: Enjoy the convenience of skipping the line at the renowned The Holy Donut shop. 

The tour is designed to be family-friendly, with accessibility for strollers and wheelchairs.

Donut Tasting Walking Tour in Portland’s Old Port Pros:

So what’s so great about the Donut Tasting Walking Tour in Portland’s Old Port (you know, besides getting to eat delicious donuts)?

• Diverse Donut Selection: The tour introduces participants to a variety of donut styles, from Maine Potato Donuts made with riced potatoes to Old World Style Cruellers and freshly made, gourmet, bite-sized donuts. 
• Local Favorites: Explore the sweet spots that locals love the most, gaining insider knowledge about the city’s beloved donut shops and their signature creations.
• Interactive Experience: Engage in an interactive and flavorful journey through the Old Port, offering the perfect blend of culinary exploration and historical storytelling.

If you’re a history buff with a sweet tooth then you will not want to miss this donut tour.

Donut Tasting Walking Tour in Portland’s Old Port Cons:

But when it comes to finding the right tour for your trip, it’s always good to look at the cons as well. Here are the downsides to the Donut Tasting Walking Tour:

• Limited Dietary Options: The tour may not cater to specific dietary restrictions or preferences, potentially limiting options for participants with special dietary needs. While some donut shops offer vegan donuts, it may not always be an option. Be sure to call ahead to the tour if you have questions about specific dietary preferences.
• Weather Dependency: As an outdoor walking tour, weather conditions can impact the overall enjoyment, especially during rainy weather. After all, no one likes a soggy donut.
• Additional Purchases: While samples are included, participants may feel tempted to purchase more donuts, leading to additional expenses.

All things considered, I still highly recommend the Donut Tasting Walking Tour in Portland’s Old Port.

“Loved the 3 donut stops! They were all very different and satisfied our sweet tooth for the day. We learned just the right amount of history to not be overwhelming.” — Savannah_H, Oct 2023 (Read more reviews)

5. Old Port Culinary Walking Tour from Portland

⭐️ RATING: 5/5 Stars | ⏳ TOUR LENGTH: 2-3 hours | ✅ Book it!

Considering that Portland is one of the biggest food hubs in the country, it makes sense that there’d be more than one top food tour available in the city. 

For food enthusiasts eager to uncover the culinary treasures of Portland’s historic Old Port, the guided Old Port Culinary Walking Tour is a superb choice. Led by an expert guide, this foodie journey invites participants to savor the very best of Portland, with stops at up to six different eateries providing enough tastings to replace a meal.

This tour provides:

• Culinary Exploration: The tour takes participants to five to six carefully selected eateries, allowing them to sample a diverse range of Maine-inspired cuisine.
• Local Insight: Benefit from the expertise of a knowledgeable guide who shares stories about Portland’s dynamic food scene.
• Intimate Tour Experience: Enjoy a more personalized and intimate tour setting with a maximum of 14 travelers. This ensures a more interactive and engaging experience, fostering a sense of camaraderie among participants.

While the Portland’s World of Flavors Tour is an excellent choice for those looking for international cuisine, the Old Port Culinary Walking Tour is perfect for those looking for more traditional Maine delights. 

Old Port Culinary Walking Tour from Portland Pros:

Here are the pros for the Old Port Culinary Walking tour from Portland:

• Diverse Culinary Offerings: From local favorites to hidden gems, participants can savor a broad spectrum of flavors.
• Expert Guidance: Participants are guided by a seasoned expert who not only leads them to the best food establishments but also shares insights into the cultural and historical significance of the Old Port, enhancing the overall tour experience.
• Meal Replacement Tastings: With enough tastings to replace a meal, you won’t have to worry about scheduling lunch into your packed itinerary.

If you’re a foodie in Portland, this tour is for you.

Old Port Culinary Walking Tour from Portland Cons:

Now, let’s dive into this tour’s cons.

• Weather Dependency: As an outdoor walking tour, the experience may be influenced by weather conditions. (FYI, if you hadn’t noticed already, this is a consistent con for every tour on this list since they all take place outside).
• Dietary Restrictions: While most of the restaurants will cater to gluten (not celiac), seafood, nut, and vegetarian sensitivities if you call ahead, the tour may not cater to vegan-specific needs.

If you’re someone who wants to find the local cuisine as recommended by people who actually live in Portland, this tour is for you.

“This food tour was fantastic. Portions were very generous—more than enough for a meal. Our guide, AJ, was super knowledgeable and charismatic. Great way to explore Portland and the food scene there.”  — Robin_G, Nov 2023 (Read more reviews)

FAQs About Portland, Maine Walking Tours

Now that we’ve covered the best tours in Portland, let’s go over a few frequently asked questions you should know before booking your trip.

Is Portland, Maine A Walkable City?

Yes, Portland, Maine is a highly walkable city, particularly in the downtown and Old Port areas. The compact layout, historic charm, and well-maintained sidewalks make it convenient for you to explore various neighborhoods on foot.

Are the walking tours suitable for all fitness levels?

Yes, most walking tours in Portland are designed to accommodate various fitness levels. However, it’s advisable to check the tour descriptions for any specific physical requirements. 

Keep in mind that most tours will require walking on Portland’s cobblestone streets and possibly stepping up small sets of stairs to enter buildings.

Can I join a walking tour if I’m traveling solo?

Absolutely! Walking tours are a fantastic way to explore solo. In fact, since many are structured to encourage interaction among participants, it’s a great opportunity to meet fellow travelers.

How long do the walking tours typically last?

Tour durations vary, but most walking tours in Portland range from 1.5 to 3 hours. Check the specific tour details for accurate timing.

What should I wear on a walking tour in Portland?

Layered clothing is advisable, given the potential weather changes in Maine. Comfortable walking shoes are a must, and it’s a good idea to bring a waterproof jacket, especially during the fall season.

Are the walking tours wheelchair accessible?

Accessibility varies among tours, and it’s recommended to check with the tour operator beforehand. While most of these tours are not wheelchair accessible, some tours may offer alternative arrangements or private options for those with mobility concerns.

Are walking tours pet-friendly? Can I bring my dog?

Policies differ between tours. For instance, the A Walk Through Time Tour in Portland allows dogs. However, the food tours on this list cannot legally allow your furry friend. 

If you’ve got a floofy traveling companion, it’s essential to check with the tour operator in advance regarding their specific pet policies.

What kind of historical information will be covered during the walking tours?

Expect a diverse range of historical content, including insights into Portland’s maritime history, notable landmarks, and cultural heritage. The specifics will depend on the chosen tour, though all of them will likely cover Portland’s pillar topics.

How far in advance should I book a walking tour?

Booking in advance is advisable, especially during peak travel seasons. Aim to secure your spot a few days ahead, and for popular tours, consider booking as early as possible.

Staying In Portland

Finding the ideal accommodation in Portland, Maine involves considering your mode of transportation and budget constraints. With Portland hotels ranking among the most expensive in the U.S., alternative options like Airbnb or VRBO may be more budget-friendly.

Cozy Airbnb Experience: Rustic Suite near Downtown Portland and Beaches

When my family and I visited Portland, we chose to stay in a vacation rental rather than braving the high prices of downtown Portland’s hotel scene. 

Nestled in Scarborough, the Rustic Suite offers a charming and comfortable stay hosted by Steven. The cozy studio apartment boasts a unique layout, featuring a master bed, an add-on room with a futon, and a loft area with twin beds. 

This pet-friendly retreat provided us with a comfortable home base just a 10-minute drive from downtown.

Recommended Hotels in Portland, Maine:

I’m all about customizing your travel experience to fit your needs. While some people love the vacation home experience, others prefer hotels or even hostels. 

Here are a few more recommended options on the best places to stay in Portland, Maine:

📍 Luxury: The Press Hotel

For a historic and luxurious experience, consider The Press Hotel. Housed in a century-old building, formerly the Portland Press Herald’s office, it’s now an independent luxury boutique hotel. 

Located in downtown Portland, this pet-friendly 4-star hotel offers refined rooms, distinctive features, and a rotating art gallery, ensuring an unforgettable stay.

📍 Mid-range: The West End Inn

Situated in the downtown area, The West End Inn offers mid-range lodging with convenient access to Portland attractions like the Victorian Mansion. 

Enhance your stay with a delectable breakfast menu and themed dinner nights, making it a charming and affordable option.

📍 Budget: Holiday Inn Portland-by the Bay

For a budget-friendly yet comfortable stay, the Holiday Inn Portland-by the Bay is a fantastic choice. Enjoy impressive views, hospitable staff, and valuable amenities, including parking and e-bikes, all while exploring the vibrant city.

📍 Hostel: Black Elephant Hostel

Embrace a budget-friendly and vibrant atmosphere at the Black Elephant Hostel, the first and only hostel in Portland, Maine. Created with the mission of uniting people and cultures, this colorful and funky hostel brings a unique hostel culture to this historic New England town.

Final Thoughts on Portland, Maine Walking Tours

In the enchanting coastal town of Portland, Maine, where history intertwines with a diverse culinary scene, walking tours are one of the best ways to explore this town’s vibrant essence. Having recently embarked on a family adventure to this charming destination, I meticulously researched and experienced the top-rated walking tours in Portland, Maine that promise a perfect blend of history, culture, and a foodie experience.

As you plan your visit to Portland, let this guide be your compass, navigating you through the captivating streets, delectable bites, and fascinating stories that define this coastal gem.

Additional Resources:

Taking a quick day or weekend trip over to Portland? Check out my full itinerary for what to do in Portland for a day.

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