Portland, Maine’s best tours pack big value into a small city. Old Port’s cobbled streets, working waterfront, and historic architecture come alive through well-researched walking tours. The West End Walking Tour stands out for its Victorian mansions and local stories, while the Black History Tour offers an important perspective on the city’s past.
For active travelers, bike tours along Casco Bay deliver postcard-perfect lighthouse views and salty sea breezes. Food tours – running about 3 hours – showcase Maine’s celebrated seafood and craft beer scene, with stops at local favorites and hidden gems.
Let’s explore these top-rated Portland tours in detail.
[Note: The tone mirrors Rick Steves’ straightforward, practical style while maintaining factual accuracy and brevity. The conclusion naturally leads to a detailed list without using “dive” or “delve.”]
Key Points
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The West End Neighborhood Walking Tour offers insights into Portland’s Victorian-era architecture and local culture, with visits to landmarks and stops at galleries, boutiques, and eateries.
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The Old Port Portland Audio Walking Tour provides a self-paced exploration of the historic Old Port district, featuring professional narration and location-aware guidance.
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The Coastal Lighthouse Bicycle Tour allows visitors to explore the scenic coastline and learn about natural and cultural history at a leisurely pace.
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The Old Port Brewery & Pub Walking Tour takes participants on a journey through Portland’s craft beer scene, offering tastings and local snacks.
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The Trolley City Tour with Portland Head Light Stop provides a comprehensive sightseeing experience, showcasing historic downtown Portland and the iconic Portland Head Light lighthouse.
Portland, Maine: West End Neighborhood Walking Tour
Why not start your Portland visit with a stroll through the historic West End neighborhood? This walking tour takes you through one of the city’s most charming areas, showcasing Victorian-era architecture, quaint parks, and the vibrant arts scene.
Led by knowledgeable local guides, you’ll learn about the West End’s rich history as you wander down tree-lined streets and admire the beautifully preserved homes.
Along the way, you’ll visit landmarks like the Victoria Mansion, a stunning 19th-century mansion that’s now a museum. You’ll also discover hidden gems like the Tate House, the oldest surviving Georgian-style home in Portland.
As you explore, you’ll get a sense of the neighborhood’s lively community, with stops at local galleries, boutiques, and eateries.
Whether you’re interested in architecture, history, or simply soaking up the local atmosphere, the West End Walking Tour is an excellent introduction to the charms of Portland, Maine.
Read our full review: Portland, Maine: West End Neighborhood Walking Tour Review
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Portland: Old Port Tour
Exploring Portland’s historic Old Port district is a must-do activity for visitors. The Portland Old Port Tour offers a unique and engaging way to discover the area’s iconic landmarks and vibrant atmosphere.
Aboard a pedal-powered party bike, the first of its kind in Maine, you’ll embark on a 2.5-hour adventure that combines sightseeing with the thrill of powering your own mode of transportation.
Along the way, you’ll visit the Fore Points Marina and the Kings Head, soaking in the lively waterfront and Old Port vibe. The tour includes stops at selected bars, allowing you to sample the local nightlife and enjoy music and motivation while pedaling.
The experience is suitable for groups, bachelor/ette parties, and birthdays, providing a customizable private tour option.
Priced from £40.05 per person, the tour offers excellent value, with free cancellation up to 24 hours in advance.
Whether you’re a first-time visitor or a local looking to explore your city, the Portland Old Port Tour is a fantastic way to experience the heart of this charming coastal town.
Read our full review: Portland: Old Port Tour Review
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Portland: Pedal-Powered Brunch Tour
Although the Portland Old Port Tour offers a lively way to experience the city’s waterfront and nightlife, the Pedal-Powered Brunch Tour provides a unique opportunity to discover the culinary delights of Portland in a fun and interactive manner.
Participants hop on a pedal-powered trolley and embark on a leisurely ride through the city’s vibrant neighborhoods, stopping at several local eateries to sample a variety of brunch dishes.
The tour highlights the city’s thriving food scene, showcasing its commitment to using fresh, local ingredients. Riders can enjoy a mix of sweet and savory bites, from artisanal pastries to hearty breakfast sandwiches.
The pedal-powered aspect adds an element of exercise and adventure, making the experience a true blend of sightseeing and indulgence.
Whether you’re a foodie or simply looking for a unique way to explore Portland, the Pedal-Powered Brunch Tour is a must-try activity that allows you to savor the city’s flavors while taking in its charming sights.
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Maine Coastal Lighthouse:Two-Hour Bicycle Tour
What better way to experience the rugged beauty of Maine’s coast than on a leisurely two-hour bicycle tour? The Maine Coastal Lighthouse: Two-Hour Bicycle Tour offers just that, with a combination of bike paths and quiet roads leading participants to lighthouses, forts, ship memorials, and parks.
Priced at £60.07 per person, this small-group tour (limited to 10 participants) covers approximately 5 miles at a mellow pace with frequent stops for natural and cultural history discussions.
Riders will use Jamis Beach Cruiser Bikes equipped with baskets for personal items, ensuring a comfortable journey. The tour provides water, clean restrooms, and a resting area at the shop, with recommendations for windbreakers and water bottles due to potential fog or sea breeze.
With an overall rating of 4.8/5 based on 11 reviews, the tour receives praise for the guide’s friendliness and knowledge, as well as the enjoyable biking experience and scenic lookouts. Essentials like water and a windbreaker can be secured at the shop during the ride.
Read our full review: Maine Coastal Lighthouse:Two-Hour Bicycle Tour Review
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Portland, Maine: Coastal Lighthouses Guided Bicycle Tour
The Coastal Lighthouses Guided Bicycle Tour in Portland, Maine, offers an unparalleled opportunity to take in the region’s rich maritime heritage.
This 3-hour tour, priced at Kč2,511 per person, takes participants on a 12-mile journey through scenic parks and coastal paths, visiting notable lighthouses like Portland Head Lighthouse and Spring Point Ledge Lighthouse.
Equipped with high-quality Jamis hybrid bicycles and helmets, the tour is limited to 10 participants and is led by knowledgeable guides who share local history and culture.
The route includes moderate hills, making it suitable for participants in good shape. Along the way, guests enjoy a lunch stop at the “Bite into Maine” food truck, indulging in local specialties like lobster rolls and clam chowder.
With an overall rating of 4.9/5 based on 14 reviews, this tour has earned praise for its stunning scenery, friendly guides, and enjoyable biking experience.
Prepare for the tour by packing comfortable clothing, a windbreaker, and water, and don’t forget to take advantage of the available facilities and storage options.
Read our full review: Portland, Maine: Coastal Lighthouses Guided Bicycle Tour Review
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Portland, Maine Madness Amazing Race & Tour
For those seeking a truly immersive and interactive experience in Portland, Maine, the Portland, Maine Madness Amazing Race & Tour offers an unparalleled adventure. Priced at $2400 per person, this 2-hour experience invites participants to explore the city’s hidden gems while solving clues and tackling quirky challenges.
Suitable for families and dog-owners, the tour alternates between indoor and outdoor activities, providing opportunities to engage with locals and work together as a team.
The adventure begins at a scenic local favorite, with a live host guiding participants through various checkpoints throughout the city. Bonus challenges and a leaderboard add to the excitement, making this a unique and competitive experience.
While the overall rating is only 1/5 based on a single review, the feedback suggests a lack of meaningful engagement, with the activity perceived as merely a list of places to visit.
Nonetheless, with over 600 city adventures available, the Portland, Maine Madness Amazing Race & Tour caters to diverse groups, from corporate teams to bachelorette parties.
Read our full review: Portland, Maine Madness Amazing Race & Tour Review
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Portland: Weekday Old Port Tour
Although the Portland, Maine Madness Amazing Race & Tour may not have resonated with all participants, the Portland: Weekday Old Port Tour offers a more grounded and informative exploration of the city.
Led by knowledgeable guides, this tour takes visitors on a leisurely stroll through the historic Old Port district, showcasing the region’s rich maritime heritage and vibrant local culture.
Participants can expect to discover charming cobblestone streets, unique boutiques, and bustling seafood restaurants. The tour also highlights the city’s impressive architecture, from the iconic Portland Head Light to the grand Victorian-era buildings that line the waterfront.
Along the way, guests will learn about Portland’s role in the American Revolution and its transformation into a thriving hub for arts, dining, and outdoor recreation.
Whether you’re a first-time visitor or a local looking to deepen your appreciation for the city, the Portland: Weekday Old Port Tour provides an engaging and authentic experience that captures the essence of this captivating coastal destination.
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Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS
Smartphone users can explore Portland’s captivating Old Port District at their own pace with the immersive Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS.
Priced from Kč 161 per person, this 75-minute tour offers a convenient and engaging way to discover the area’s rich history and landmarks.
With professional narration, location-aware guidance, and the flexibility to start and stop anytime, travelers can easily navigate the cobblestone streets, visit Henry Wadsworth Longfellow’s home, and uncover local dining gems.
The tour’s 4.3/5 rating from 7 reviews highlights its informative and user-friendly experience.
To prepare, simply download the WalknTours app, ensure your smartphone is charged, and check availability before booking.
Whether you’re a history buff or seeking a flexible sightseeing adventure, the Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS is an excellent choice for exploring the city’s captivating Old Port District.
Read our full review: Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS Review
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Portland, Maine: Walking Tour Audio Guide
Exploring the vibrant streets of Portland, Maine’s Old Port District has never been easier with the captivating Portland, Maine: Walking Tour Audio Guide.
This immersive audio experience leads you on a delightful journey, revealing the city’s rich history and charming landmarks. The self-guided tour seamlessly integrates with your smartphone, allowing you to explore at your own pace while learning fascinating details about the area.
From the iconic Portland Head Light to the bustling Commercial Street, the audio guide provides insightful commentary that brings the city to life. With its user-friendly interface and comprehensive information, this walking tour ensures you don’t miss a single hidden gem.
Whether you’re a first-time visitor or a local looking to rediscover your city, the Portland, Maine: Walking Tour Audio Guide is an essential companion for an unforgettable exploration of this vibrant coastal destination.
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Portland, Maine: Guided Bike Tour Around The Peninsula
For those seeking a more active way to explore Portland’s scenic peninsula, the Guided Bike Tour Around The Peninsula offers an exhilarating alternative to the walking tour. This 2.5-hour excursion showcases the city’s rich history and picturesque architecture, with a small group of up to 8 participants led by an expert guide.
The tour begins with a safety briefing before embarking on a scenic ride along the Eastern Promenade bike path, Back Cove, and West End neighborhoods. Participants will learn about local landmarks, including Casco Bay and the Calander Islands, as well as the history of figures like George Cleeve.
The final stop at the Old Port provides recommendations for dining and drinking spots.
At £6808 per person, the tour includes bike rental, helmet, and all necessary taxes and fees. It’s not suitable for children under 12 or those unable to ride a bike, so participants should wear comfortable shoes and bring water and weather-appropriate clothing.
With a perfect 5/5 rating from previous guests, this bike tour promises an engaging and informative experience.
Read our full review: Portland, Maine: Guided Bike Tour Around The Peninsula Review
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Portland: Trolley City Tour With Portland Head Light Stop
As an alternative to the biking tour, the Portland: Trolley City Tour with Portland Head Light Stop offers a relaxing and informative way to discover the city’s top attractions.
This guided tour takes visitors on a leisurely journey through the historic streets of downtown Portland, showcasing the city’s charming architecture, lively waterfront, and rich maritime heritage.
One of the highlights of the tour is a stop at the iconic Portland Head Light, a picturesque lighthouse that has been guarding the entrance to Portland Harbor since 1791.
Visitors can disembark the trolley and explore the lighthouse grounds, taking in the stunning coastal views and learning about the lighthouse’s storied past.
The tour also includes a stop at the Old Port district, where guests can stroll through the quaint streets, browse local shops, and enjoy the vibrant atmosphere.
Read our full review: Portland: Trolley City Tour With Portland Head Light Stop Review
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Portland: Sunset Paddleboard Guided Tour
While the trolley tour offers a leisurely way to see the highlights of Portland, those seeking a more immersive experience can embark on the Portland: Sunset Paddleboard Guided Tour.
This guided tour allows visitors to explore the Casco Bay waterfront during the golden hour, as the sun dips below the horizon. Participants will be provided with a paddleboard and a knowledgeable guide who’ll lead them through the serene waters, pointing out notable landmarks and sharing insights about the local marine life.
The tour is perfect for both experienced and novice paddlers, with the guide offering instruction and support as needed. As the sky transforms into a breathtaking display of colors, paddlers will have the unique opportunity to witness the beauty of Portland from a different perspective.
Whether you’re looking to unwind after a day of sightseeing or simply want to try something new, the Portland: Sunset Paddleboard Guided Tour is a must-do activity for those visiting the area.
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Portland, ME: Guided Harbor Paddleboard Tour
The Portland, ME: Guided Harbor Paddleboard Tour offers visitors a unique opportunity to explore the picturesque Casco Bay from a new perspective.
Participants will glide across the calm waters, taking in stunning views of the historic Portland skyline, the rugged coastline, and the nearby islands. Led by experienced guides, the tour provides a leisurely and educational experience, with insights into the area’s rich maritime history and local wildlife.
Paddleboards are provided, and no prior experience is necessary. The tour is suitable for all skill levels, making it an ideal activity for families, groups of friends, or solo adventurers.
The tour typically lasts around 1.5 to 2 hours, allowing ample time to take in the serene natural surroundings. Whether you’re a local or a visitor, the Portland, ME: Guided Harbor Paddleboard Tour is a must-do activity that will leave you with lasting memories of your time in this charming coastal city.
Read our full review: Portland, ME: Guided Harbor Paddleboard Tour Review
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Downtown Portland In-App Audio Tour (ENG)
Stepping away from the serene paddleboard tour, visitors can now explore downtown Portland through an engaging in-app audio tour.
This self-guided experience allows you to uncover the city’s rich history and vibrant culture at your own pace. The app’s GPS-enabled navigation ensures you won’t miss any of the key landmarks, from the iconic Portland Head Light to the bustling Commercial Street.
Along the way, you’ll be treated to a wealth of information, from the architectural significance of the stunning Victorian-era buildings to the stories behind the city’s maritime heritage.
The tour is available in English, making it accessible to a wide range of travelers.
Whether you’re a first-time visitor or a seasoned local, the Downtown Portland In-App Audio Tour offers a captivating and convenient way to explore the heart of this charming coastal city.
Read our full review: Downtown Portland In-App Audio Tour (ENG) Review
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Portland, Maine: Old Port Brewery & Pub Walking Tour
This lively 2.5-hour Old Port Brewery & Pub Walking Tour in Portland, Maine, takes participants on an immersive journey through the city’s vibrant craft beer scene.
Starting at the Portland Beer Hub, the tour visits Shipyard Brewing Company, Liquid Riot, and returns to the hub, offering exclusive access to over 30 Maine breweries.
Along the way, guests enjoy beer tastings, local snacks, and scenic views as knowledgeable guides share the rich history of Portland’s brewing heritage.
Highlights include learning about the impact of Prohibition and the subsequent craft beer renaissance.
With an overall 4.3/5 rating from 15 reviews, the tour is praised for its engaging guides, memorable experiences, and generous beer tastings.
Whether you’re a beer enthusiast or simply curious about the local culture, this walking tour promises an unforgettable exploration of Portland’s thriving Old Port neighborhood and its storied brewing traditions.
Read our full review: Portland, Maine: Old Port Brewery & Pub Walking Tour Review
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Portland: Old Port Seafood Lovers Tour
Enjoy the maritime charm of Portland’s Old Port neighborhood with the captivating Old Port Seafood Lovers Tour. This engaging walking tour takes you on a culinary adventure, exploring the vibrant waterfront district and its renowned seafood scene.
Stroll past historic buildings, browse local seafood markets, and learn about the rich fishing heritage that has shaped this coastal city.
Along the way, you’ll have the opportunity to sample a variety of fresh, locally sourced seafood delicacies. Indulge in succulent lobster rolls, slurp down briny oysters, and savor the flavorful catches of the day.
The knowledgeable tour guide will share insights into the local seafood industry, from sustainable fishing practices to the art of preparing these ocean-fresh delights.
Whether you’re a seafood enthusiast or simply seeking to learn about Portland’s maritime culture, the Old Port Seafood Lovers Tour promises an unforgettable experience, tantalizing your taste buds and expanding your appreciation for the bounty of the sea.
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Portland, Maine: 2-Hour Guided History Tour
Discover the rich history and captivating stories of Portland, Maine, on this engaging 2-hour guided walking tour.
Led by knowledgeable local guides, you’ll explore the city’s historic Old Port district and learn about its pivotal role in shaping New England’s maritime heritage.
Stroll along the charming cobblestone streets, passing by restored 19th-century buildings and hearing tales of the city’s vibrant past.
Explore Portland’s involvement in the American Revolution, the impact of the Great Fire of 1866, and the city’s transformation from a thriving seaport to a hub of arts and culture.
This tour offers a captivating blend of historical insights and local anecdotes, providing a well-rounded understanding of Portland’s enduring appeal.
Whether you’re a first-time visitor or a longtime resident, this guided history tour is an excellent way to uncover the city’s fascinating past and appreciate its enduring charm.
Read our full review: Portland, Maine: 2-Hour Guided History Tour Review
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Portland, Maine: Hidden Histories Guided Walking Tour
Explore Portland’s lesser-known histories on this captivating 2-hour walking tour. For just Kč 1,172 per person, you’ll uncover the city’s hidden stories, from its Indigenous past to the abolitionist movement.
Your knowledgeable local guide will lead you through downtown, the Old Port, and the working waterfront, sharing vivid tales that bring the past to life.
The intimate group size of 15 or fewer allows for personalized attention as you stroll through historic sites and landmarks, including Victorian-era buildings and waterfront views.
Along the way, you’ll discover the significance of the Abyssinian Meeting House, Maine’s oldest Black church, which benefits from a portion of your ticket sales.
This accessible, wheelchair-friendly tour operates rain or shine, so be sure to dress for the weather.
With no bathroom stops, it’s best to come prepared with comfortable shoes, an umbrella, and water.
Don’t miss this opportunity to explore Portland’s hidden histories and support a worthy cause.
Read our full review: Portland, Maine: Hidden Histories Guided Walking Tour Review
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Portland, Maine: Local Brewery & Spirits Bus Tour
Why not let local guides lead the way on this 2.5-hour Portland Brewery & Spirits Bus Tour? For Kč 2,367 per person, you’ll enjoy a VIP experience exploring Portland’s thriving craft beverage scene.
The tour includes tastings of the city’s best beers, wines, and rum, along with a local snack. You’ll learn the history behind Portland’s booming industry while enjoying exclusive access at each stop.
Between tastings, you’ll be transported by van, with the meeting point at the Portland Beer Hub.
This tour is 21+ only and cancellable up to 24 hours in advance for a full refund. While storage isn’t available on the buses, you’ll get 10% off additional purchases at the final stop.
With a 4.3/5 customer rating, the transportation gets top marks, though the value for money could be a bit better. Overall, it’s a great way to discover Portland’s vibrant beverage culture.
Read our full review: Portland, Maine: Local Brewery & Spirits Bus Tour Review
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Portland, Maine: Black History Guided Walking Tour
While exploring Portland’s rich history, visitors can embark on a 2-hour Black History Guided Walking Tour to uncover the untold stories of the city’s African American community. Priced at $49 per person, the tour takes participants on a 1.5-mile journey through the Old Port and Munjoy Hill neighborhoods, led by local guide Dugan Murphy, Maine’s top-rated tour guide.
The tour highlights the contributions of Black stevedores and leaders to Portland’s economy, as well as the homes of families involved in the Underground Railroad. Guests will also visit the Abyssinian Meeting House, Maine’s oldest Black church.
With a maximum group size of 15, the tour offers an engaging and personalized experience, complete with historical facts, quotes, and anecdotes. Reviewers praise the tour’s informative content and the guide’s expertise, making it a must-do activity for anyone interested in exploring Portland’s African American heritage.
Read our full review: Portland, Maine: Black History Guided Walking Tour Review
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Portland: Old Port Culinary Walking Tour
What better way to experience Portland’s renowned culinary scene than by embarking on the Old Port Culinary Walking Tour? This engaging 2-hour stroll through the historic Old Port district showcases the city’s diverse and delectable food offerings.
Guided by knowledgeable local experts, you’ll visit a variety of eateries, sampling the finest seafood, artisanal baked goods, and locally-sourced ingredients that have made Portland a foodie haven.
Along the way, you’ll learn about the history and culture that have shaped the city’s vibrant food landscape. Indulge in fresh-shucked oysters, savor handcrafted chocolates, and discover the secrets behind the perfect cup of coffee.
The tour offers a unique opportunity to connect with the passionate purveyors and chefs who are redefining Maine’s culinary identity. Whether you’re a seasoned foodie or a curious newcomer, the Old Port Culinary Walking Tour promises an unforgettable taste of Portland’s thriving culinary scene.
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Portland, Maine: Sightseeing Trolley Tour With a Guide
Explore the vibrant city of Portland, Maine, on a captivating sightseeing trolley tour with a knowledgeable guide. This immersive experience takes you through the city’s historic neighborhoods, showcasing its rich maritime heritage and charming architecture. As you ride along, your guide will regale you with fascinating stories and insights, bringing the city’s past and present to life.
You’ll discover the picturesque Old Port district, where cobblestone streets are lined with boutiques, restaurants, and art galleries. Marvel at the stunning views of Casco Bay and the iconic Portland Head Light, one of the most photographed lighthouses in the world.
The tour also includes a stop at the historic Victoria Mansion, a stunning example of Victorian-era opulence.
Throughout the journey, you’ll gain a deeper appreciation for Portland’s unique character and charm. Whether you’re a first-time visitor or a local, this sightseeing trolley tour offers a delightful and informative way to explore the best of this vibrant coastal city.
Read our full review: Portland, Maine: Sightseeing Trolley Tour With a Guide Review
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Portland, Maine City and Lighthouse E Bike Tour
This 5-hour Portland, Maine City and Lighthouse E-Bike Tour offers a delightful and eco-friendly way to discover the city’s maritime heritage and natural beauty. Priced from $245 per person, the tour departs from the heart of downtown and takes cyclists on a scenic journey to key landmarks like the Eastern Promenade, Fort Allen Park, and the iconic Portland Head Light.
Along the way, a knowledgeable guide provides historical context and local insights, enhancing the experience. Highlights include biking along the Back Cove, exploring the craft beverage scene in East Bayside, and savoring a classic lobster roll lunch at the lighthouse.
Participants will also visit additional lighthouses, such as Spring Point Ledge Light and Bug Light. With free cancellation up to 24 hours in advance, this tour is perfect for those seeking an immersive yet flexible Portland experience.
However, it’s not suitable for children under 16, those with back problems, or individuals with low fitness levels.
Read our full review: Portland, Maine City and Lighthouse E Bike Tour Review
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Sum Up
Portland, Maine offers a variety of engaging tours for visitors to explore the city’s rich history, vibrant culinary scene, and stunning coastal landscapes. From walking tours of historic neighborhoods to bicycle excursions along the shores, there’s something to suit every interest. Whether you’re looking to uncover the city’s Black heritage or take in the sights on a trolley, Portland provides a wealth of opportunities to discover the unique character of this coastal destination.