Portland, Maine
Guided tours

Guided tours
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Top activities in Portland, Maine

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Our most recommended Portland, Maine Guided tours

Portland: Best of Maine Lighthouse Scenic Cruise

Portland: Best of Maine Lighthouse Scenic Cruise

Sit back and relax as you cruise along the serene Casco Bay in Portland, Maine. Immerse yourself in the rich history of Portland and see the four iconic lighthouses, the sights of Portland Harbor, and the picturesque waterway Diamond Pass. During the cruise, explore the bustling inner harbor and main shipping channel to get close-up views of civil war era forts and the lighthouses that guide mariners into Portland Harbor. Along with the historical waterfront, you'll also get the chance to see the Portland Head Light, Bug Light, and the Spring Point Ledge Lighthouse.

Portland: Casco Bay Sunset and Lighthouse Cruise

Portland: Casco Bay Sunset and Lighthouse Cruise

Meet at the Old Port in Portland, Maine and hop on board a boat that boasts ample outdoor deck space and indoor cabin space, ensuring your comfort no matter the weather. Feel free to purchase drinks at the well-stocked bar and have access to restroom during the trip. Expereince the salty air as you set out on the water in the warm glow of the evening light. Head into Casco Bay a scenic and ecologically rich area known for its beautiful islands, historical significance, and diverse marine life. Listen as your guide offers facinating insights into famous sights that you pass along the way. Navigate through island passages like Diamond Pass and around the Calendar Islands. Admire the lush islands, craggy rocks, and several Civil War forts. See a natural seal habitat and keep an eye out for graceful sea birds. Capture pictures of some scenic lighthouses that the area is known for as the sunsets and return to Portland as the city begins to light up for the night.

Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

Discover Portland's hidden histories on a guided, small-group walking tour of the Old Port, downtown, and 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. The group will include no more than 15 people, so there's plenty of room to interact and ask questions. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, on this tour you’ll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. Enjoy two hours to slow down and immerse yourself in the best Portland has to offer. 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. Entertainer-historian Dugan Murphy leads unforgettable jaunts through his hometown, telling an inclusive, empowering, and surprising constellation of tales you won't hear on other tours. Maine Historical Society likes him so much, they made him their official tour partner. Find out why Tripadvisor named him Maine's #1 tour guide!

Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS

Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

Portland, Maine: Local Brewery & Spirits Bus Tour

Portland, Maine: Local Brewery & Spirits Bus Tour

Our all-inclusive tours and experiences provide guests a behind-the-scenes look at Maine’s best craft breweries, distilleries, and wineries. Tour guests enjoy having an expert local guide to lead them to both established and up-and-coming producers in the heart of Portland, Maine. Experience as a VIP with transportation between each stop and exclusive access at each beverage producer or pub. This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine, many of which are stops on our most popular tours. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases at the Portland Beer Hub.

Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine, is a bustling hub for breweries, distilleries, beer bars, and cocktail lounges—a far cry from its historical stance against consumption. Ironically, it was Maine’s early adoption of Prohibition that set the stage for a booming craft libation industry, inspiring producers, restaurateurs, and creatives alike. Along the way, you’ll visit producers like Liquid Riot, a brewery and distillery that pays homage to the infamous Portland Rum Riots of 1855, and Shipyard Brewing Company, a cornerstone of Maine’s craft beer culture for over a quarter-century. This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases! Please note that tour stops may change without notice due to events and the availability of staff at each venue.

Maine Coastal Lighthouse:Two-hour bicycle tour

Maine Coastal Lighthouse:Two-hour bicycle tour

Welcome to Portland, Maine and thank you for choosing to spend your day with Lighthouse Bikes! Here are some tips to make sure that you are ready to have as much fun as possible on two-hour Lighthouse Bicycle Tour Along the Coast. When you arrive at the shop, we will size you with a bike and a helmet. There is water available. a clean restroom and a comfortable sitting area that you can use as you await your experience. Our ride will be around 5 miles on a combination of bike paths and quiet roads that will take us along the coast to area lighthouses, forts, ship memorials and some beautiful parks. Our route has a few short hills, but nothing too strenuous and nothing so big that you can’t walk if you are feeling a little lazy! You are on vacation after all. We will be riding Jamis Beach Cruiser Bikes with little baskets that can accommodate a windbreaker and a water bottle-both of which I strongly recommend. There can sometimes be fog or a sea breeze and we want you to be comfortable. If you need to purchase a water bottle here, we have them available. We will bike at a mellow pace and stop frequently to talk about the natural and cultural history of the area, as well as, share some local insights like where the best breweries are! You are welcome to leave backpacks etc. here while we ride and we will keep them secure. Feel free to peruse our website lighthousebikesportland.com to learn more about our company and our other offerings.

Maine Coast: Bicycle Rentals

Maine Coast: Bicycle Rentals

Bicycle rentals available. New Jamis Boss cruisers and Citizen hybrid bicycles and well as adult tricycles. We are two blocks from a bicycle trail connecting area lighthouses and beaches. Located on the South Portland side of the Casco Bay Bridge to help you avoid riding through the congestion of downtown Portland. All bicycles come with helmets, locks, maps and baskets. Rent for an hour, the day or for an extended journey, and take the bikes wherever your flight of fancy takes you. The Marine Coast was made for biking.

Portland, Maine: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour

Wind through the brick sidewalks and cobblestone streets of Portland's Old Port and working waterfront on this guided walking tour. Immerse yourself in the rich story of the 19th-century Black community in the East End neighborhood. The group will include no more than 15 people, so there's plenty of room to interact and ask questions. Meet your local guide at the First Parish Church, Portland's oldest church, and begin your journey back in time. Discover the monuments, places of business, and civic institutions where Black Yankees drove the economy and organized for political power. The air here still lingers with the notes of sea shanty songs, the crackle of rope from cargo hoisted aboard ships creaking in the waters of Casco Bay, and the myriad accents of Black sailors arriving from the Caribbean and Canadian provinces. Head to the East End neighborhood to see the homes of Black sailors and stevedores that served as stations on the Underground Railroad. Admire the churches where Black families worshipped, celebrated, and learned together from the 19th century up to the present day. Step on granite cobblestones crooked with age that once saw footfalls from national heroes like Frederick Douglass. Learn how Maine's earliest colonial settlements could not have survived without Black insight, skill, and labor. Uncover the story behind the enslaved Black maid who abolished slavery in Maine during the Revolutionary War. Discover the exceptional figures who shaped Portland and the State of Maine over more than 400 years of Black leadership. Printed images of the past, together with gifted storytelling, bring the past to life. Hear the stories that other history tours omit. A portion of every ticket sale will help fund the restoration of the Abyssinian Meeting House, Maine's oldest and America's third-oldest standing Black church. End your tour at Eastern Cemetery, one-half mile from where it began. Entertainer-historian Dugan Murphy leads unforgettable jaunts through his hometown, telling an inclusive, empowering, and surprising constellation of tales you won't hear on other tours. Maine Historical Society likes him so much, they made him their official tour partner. Find out why Tripadvisor named him Maine's #1 tour guide!

Portland, Maine: Guided Bike Tour Around The Peninsula

Portland, Maine: Guided Bike Tour Around The Peninsula

Cycle along the coast of Portland, Maine while learning about the colorful history of the city. This 2.5-hour guided bike tour will showcase the best of the peninsula, including famous landmarks and iconic neighborhoods.  Your trip begins with an easy ride along the Eastern Promenade bike path. Your professional guide will stop along the path to share the history of Casco Bay and the Calander Islands as well as the life story of George Cleeve, Portland’s co-founder. Next stop is Back Cove and Portland’s Deering neighborhood. This neighborhood was created in the 19th century by wealthy residents angry about Portland’s rising property taxes. From Back Cove you will cycle into Portland’s West End neighborhood. Historically the swanky part of town, the West End features broad tree-lined streets and beautiful homes in different styles.  Your last stop will be the Old Port where your guide will share some of their favorite eating and drinking spots with you. At the end of the tour, you will return back to where you met your guide at the start of the tour.

Portland, Maine

Portland, Maine

Our most recommended Portland, Maine Guided tours

Portland: Best of Maine Lighthouse Scenic Cruise

Portland: Best of Maine Lighthouse Scenic Cruise

Sit back and relax as you cruise along the serene Casco Bay in Portland, Maine. Immerse yourself in the rich history of Portland and see the four iconic lighthouses, the sights of Portland Harbor, and the picturesque waterway Diamond Pass. During the cruise, explore the bustling inner harbor and main shipping channel to get close-up views of civil war era forts and the lighthouses that guide mariners into Portland Harbor. Along with the historical waterfront, you'll also get the chance to see the Portland Head Light, Bug Light, and the Spring Point Ledge Lighthouse.

Portland: Casco Bay Sunset and Lighthouse Cruise

Portland: Casco Bay Sunset and Lighthouse Cruise

Meet at the Old Port in Portland, Maine and hop on board a boat that boasts ample outdoor deck space and indoor cabin space, ensuring your comfort no matter the weather. Feel free to purchase drinks at the well-stocked bar and have access to restroom during the trip. Expereince the salty air as you set out on the water in the warm glow of the evening light. Head into Casco Bay a scenic and ecologically rich area known for its beautiful islands, historical significance, and diverse marine life. Listen as your guide offers facinating insights into famous sights that you pass along the way. Navigate through island passages like Diamond Pass and around the Calendar Islands. Admire the lush islands, craggy rocks, and several Civil War forts. See a natural seal habitat and keep an eye out for graceful sea birds. Capture pictures of some scenic lighthouses that the area is known for as the sunsets and return to Portland as the city begins to light up for the night.

Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

Discover Portland's hidden histories on a guided, small-group walking tour of the Old Port, downtown, and 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. The group will include no more than 15 people, so there's plenty of room to interact and ask questions. Brick sidewalks beneath your feet and beautiful Victorian-era buildings nestled around you, on this tour you’ll casually stroll Portland’s lush, historic Old Port toward the sparkling waters of Casco Bay. Enjoy two hours to slow down and immerse yourself in the best Portland has to offer. 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. Entertainer-historian Dugan Murphy leads unforgettable jaunts through his hometown, telling an inclusive, empowering, and surprising constellation of tales you won't hear on other tours. Maine Historical Society likes him so much, they made him their official tour partner. Find out why Tripadvisor named him Maine's #1 tour guide!

Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS

Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

Portland, Maine: Local Brewery & Spirits Bus Tour

Portland, Maine: Local Brewery & Spirits Bus Tour

Our all-inclusive tours and experiences provide guests a behind-the-scenes look at Maine’s best craft breweries, distilleries, and wineries. Tour guests enjoy having an expert local guide to lead them to both established and up-and-coming producers in the heart of Portland, Maine. Experience as a VIP with transportation between each stop and exclusive access at each beverage producer or pub. This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine, many of which are stops on our most popular tours. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases at the Portland Beer Hub.

Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine, is a bustling hub for breweries, distilleries, beer bars, and cocktail lounges—a far cry from its historical stance against consumption. Ironically, it was Maine’s early adoption of Prohibition that set the stage for a booming craft libation industry, inspiring producers, restaurateurs, and creatives alike. Along the way, you’ll visit producers like Liquid Riot, a brewery and distillery that pays homage to the infamous Portland Rum Riots of 1855, and Shipyard Brewing Company, a cornerstone of Maine’s craft beer culture for over a quarter-century. This bus tour’s final tasting will be held at Portland Beer Hub, the home of Maine Brews Cruise. Portland Beer Hub is a combo beer bar and retail space in the heart of the Old Port. The selection here includes beers from over 30 breweries across the state of Maine. As a bonus, all guests snag a 10% discount on additional draft and to-go purchases! Please note that tour stops may change without notice due to events and the availability of staff at each venue.

Maine Coastal Lighthouse:Two-hour bicycle tour

Maine Coastal Lighthouse:Two-hour bicycle tour

Welcome to Portland, Maine and thank you for choosing to spend your day with Lighthouse Bikes! Here are some tips to make sure that you are ready to have as much fun as possible on two-hour Lighthouse Bicycle Tour Along the Coast. When you arrive at the shop, we will size you with a bike and a helmet. There is water available. a clean restroom and a comfortable sitting area that you can use as you await your experience. Our ride will be around 5 miles on a combination of bike paths and quiet roads that will take us along the coast to area lighthouses, forts, ship memorials and some beautiful parks. Our route has a few short hills, but nothing too strenuous and nothing so big that you can’t walk if you are feeling a little lazy! You are on vacation after all. We will be riding Jamis Beach Cruiser Bikes with little baskets that can accommodate a windbreaker and a water bottle-both of which I strongly recommend. There can sometimes be fog or a sea breeze and we want you to be comfortable. If you need to purchase a water bottle here, we have them available. We will bike at a mellow pace and stop frequently to talk about the natural and cultural history of the area, as well as, share some local insights like where the best breweries are! You are welcome to leave backpacks etc. here while we ride and we will keep them secure. Feel free to peruse our website lighthousebikesportland.com to learn more about our company and our other offerings.

Maine Coast: Bicycle Rentals

Maine Coast: Bicycle Rentals

Bicycle rentals available. New Jamis Boss cruisers and Citizen hybrid bicycles and well as adult tricycles. We are two blocks from a bicycle trail connecting area lighthouses and beaches. Located on the South Portland side of the Casco Bay Bridge to help you avoid riding through the congestion of downtown Portland. All bicycles come with helmets, locks, maps and baskets. Rent for an hour, the day or for an extended journey, and take the bikes wherever your flight of fancy takes you. The Marine Coast was made for biking.

Portland, Maine: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour

Wind through the brick sidewalks and cobblestone streets of Portland's Old Port and working waterfront on this guided walking tour. Immerse yourself in the rich story of the 19th-century Black community in the East End neighborhood. The group will include no more than 15 people, so there's plenty of room to interact and ask questions. Meet your local guide at the First Parish Church, Portland's oldest church, and begin your journey back in time. Discover the monuments, places of business, and civic institutions where Black Yankees drove the economy and organized for political power. The air here still lingers with the notes of sea shanty songs, the crackle of rope from cargo hoisted aboard ships creaking in the waters of Casco Bay, and the myriad accents of Black sailors arriving from the Caribbean and Canadian provinces. Head to the East End neighborhood to see the homes of Black sailors and stevedores that served as stations on the Underground Railroad. Admire the churches where Black families worshipped, celebrated, and learned together from the 19th century up to the present day. Step on granite cobblestones crooked with age that once saw footfalls from national heroes like Frederick Douglass. Learn how Maine's earliest colonial settlements could not have survived without Black insight, skill, and labor. Uncover the story behind the enslaved Black maid who abolished slavery in Maine during the Revolutionary War. Discover the exceptional figures who shaped Portland and the State of Maine over more than 400 years of Black leadership. Printed images of the past, together with gifted storytelling, bring the past to life. Hear the stories that other history tours omit. A portion of every ticket sale will help fund the restoration of the Abyssinian Meeting House, Maine's oldest and America's third-oldest standing Black church. End your tour at Eastern Cemetery, one-half mile from where it began. Entertainer-historian Dugan Murphy leads unforgettable jaunts through his hometown, telling an inclusive, empowering, and surprising constellation of tales you won't hear on other tours. Maine Historical Society likes him so much, they made him their official tour partner. Find out why Tripadvisor named him Maine's #1 tour guide!

Portland, Maine: Guided Bike Tour Around The Peninsula

Portland, Maine: Guided Bike Tour Around The Peninsula

Cycle along the coast of Portland, Maine while learning about the colorful history of the city. This 2.5-hour guided bike tour will showcase the best of the peninsula, including famous landmarks and iconic neighborhoods.  Your trip begins with an easy ride along the Eastern Promenade bike path. Your professional guide will stop along the path to share the history of Casco Bay and the Calander Islands as well as the life story of George Cleeve, Portland’s co-founder. Next stop is Back Cove and Portland’s Deering neighborhood. This neighborhood was created in the 19th century by wealthy residents angry about Portland’s rising property taxes. From Back Cove you will cycle into Portland’s West End neighborhood. Historically the swanky part of town, the West End features broad tree-lined streets and beautiful homes in different styles.  Your last stop will be the Old Port where your guide will share some of their favorite eating and drinking spots with you. At the end of the tour, you will return back to where you met your guide at the start of the tour.

Frequently asked questions about Portland, Maine Guided tours

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