Maine
Sightseeing walking tours

Booked 100+ times last week

Sightseeing walking tours
23 activities found
Sort by:

Traveling now? See what’s available for your dates

Our most recommended Maine Sightseeing walking tours

Portland: Trolley City Tour with Portland Head Light Stop

Portland: Trolley City Tour with Portland Head Light Stop

Enjoy a fully-narrated trolley tour of scenic and historic Portland and visit Maine’s oldest lighthouse, Portland Head Light, during a 30-minute stop in Cape Elizabeth. Hop onboard a trolley and journey from city streets to the rocky coast. Cruise past landmarks such as the childhood home of Henry Wadsworth Longfellow, the Victoria Mansion, the Arts District, and the bustling Old Port. With forward-facing seats and big windows, you won't miss a thing. See as your guide points out the famous sites and hidden gems of Portland and shares interesting stories behind them. Upon arrival at Cape Elizabeth, along the spectacular shores of Fort Williams Park, disembark for a 30-minute stop to explore the Portland Head Light on your own. Choose to walk around Maine's oldest lighthouse or visit the maritime museum inside.

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, Maine: Sunset Windjammer Cruise Along the Coast

Portland, Maine: Sunset Windjammer Cruise Along the Coast

Step onboard a historic schooner, some of which are over 100 years old, and set sail on Casco Bay in Portland, Maine. Help the boat crew hoist the sails or even get behind the wheel. Step into history aboard a locally-built wooden windjammer, with three of these vessels listed on the National Register of Historic Places. Experience the beauty of the rugged coastline, complete with a beautiful sunset, lighthouses, seals, and seabirds. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay.

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: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

Enjoy this fully narrated 60-minute scenic cruise through busy Casco Bay and its iconic islands to see lighthouses, forts, lobster boats, seals, and seabirds. Take in the views of Portland's historical lighthouses, including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse. As you cruise along the Casco bay, keep an eye out for Spring Point Ledge Light, Portland Breakwater Light (Bug Light), Ram Island Ledge Light, Portland Head Light, Fort Scammel, Fort Gorges, and Portland Harbor.

Portland, Maine: Tour in Vintage Fire Engine

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.

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

Go on a delightful harbor cruise, passing summer colonies, lighthouses, small islands, and out to see the seals on the ledges. Fun for the whole family. Pass by 2 lighthouses, islands, coastline, inner and outer harbor, and seals at the seal rocks. Experience a Boothbay classic that has been enjoyed for over 50 years and find out why it's so popular. Get an idea of how those delicious lobsters you enjoy at your favorite restaurant are caught, how the traps are hauled, and a little background of Maine’s famous lobster industry. Enjoy the seals basking on the rocks. Pass by two major lighthouses, Burnt Island Light, and Ram Island Lighthouse. This Boothbay Harbor lobster tour is educational and fun for the whole family. Don't forget to bring your camera. Step aboard a vessel that has the largest and most comfortable main salon in the region with padded seats and tables. Relax with food and a drink from the galley, which features a 360-degree view of the outside. Enjoy the sun and fresh Maine air on the upper deck. Hear the narration no matter where you choose to be, with speakers throughout the vessel.

Portland, Maine: Coastal Windjammer Sailing Cruise

Portland, Maine: Coastal Windjammer Sailing Cruise

Experience the beauty of Portland, Maine's rugged coastline on a historic windjammer sailing ship in Casco Bay. Sail by lighthouses, seals, and seabirds as you feel the wind in your hair. Learn how the wooden windjammer you are sailing on was built in Maine and is listed on the National Register of Historic Places. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. Let your skipper take charge and take in the marine wildlife and views surrounding you. See Portland from a unique vantage point. Have fun with the whole family or with friends on a day out at sea, before heading back to port.

Penobscot Bay: Historic Schooner Day Sailing Trip

Penobscot Bay: Historic Schooner Day Sailing Trip

Experience one of the top things to do in Camden sailing along Maine's magnificent rocky coastline. Climb aboard the elegant Appledore II, a historic schooner. Feel like an adventurer from the 19th-century while enjoying state-of-the-art accommodations onboard a modern windjammer. Stroll along the wide decks as you take in the sights without needing to duck beneath the rigging. With a capacity of only 49 passengers, there is abundant seating to make yourself comfortable for this intimate sailing trip. Enjoy the chance to sail your own wooden ship as the crew welcomes your participation. Offer to help raise the sails and take a turn at the wheel of this hard-working, seaworthy schooner. Ask your crew about the history of the boat which has sailed around the world, docking at many harbors along the way. Twice a year, she still sails the Eastern seaboard between her 2 home ports of Camden, Maine and Key West, Florida.  Start the tour by departing from Bayview Landing and heading out of Camden Harbor. Discover why Camden is often called the jewel of the Maine coast as you sail past the impressive lighthouse, Curtis Island Light, dating from 1836, and into Penobscot Bay. Considered to be one of the top cruising bays in the world, Penobscot Bay will amaze you with its uninhabited islands, wildlife, and views of Camden Hills and other coastal mountains dropping off into the sea. During the tour, look along the shore for Mount Battie, historic inns, and elegant summer mansions of the rich and famous with their million dollar yachts. Watch lobstermen hauling in their traps. On a typical day, you may see porpoises playing in the water, ospreys, eagles hunting for fish, and even the occasional whale. Watch for seals sunning themselves on rocks and cute guillernots (cousins of the puffin), with their bright red feet, wobbling as they walk along the rocky shoreline. Quench your thirst with cocktails, beer, wine and soft drinks, all available for purchase during your sailing cruise. As Camden Harbor comes back into view, relax and feel the wind sweep through your hair as your memorable sailing ship cruise draws to a close.

Portland: Old Port Culinary Walking Tour

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. You’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages.  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 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. 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 honey wine, and dark chocolate truffles made with Aroostook County potatoes.

Maine

Maine

Our most recommended Maine Sightseeing walking tours

Portland: Trolley City Tour with Portland Head Light Stop

Portland: Trolley City Tour with Portland Head Light Stop

Enjoy a fully-narrated trolley tour of scenic and historic Portland and visit Maine’s oldest lighthouse, Portland Head Light, during a 30-minute stop in Cape Elizabeth. Hop onboard a trolley and journey from city streets to the rocky coast. Cruise past landmarks such as the childhood home of Henry Wadsworth Longfellow, the Victoria Mansion, the Arts District, and the bustling Old Port. With forward-facing seats and big windows, you won't miss a thing. See as your guide points out the famous sites and hidden gems of Portland and shares interesting stories behind them. Upon arrival at Cape Elizabeth, along the spectacular shores of Fort Williams Park, disembark for a 30-minute stop to explore the Portland Head Light on your own. Choose to walk around Maine's oldest lighthouse or visit the maritime museum inside.

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, Maine: Sunset Windjammer Cruise Along the Coast

Portland, Maine: Sunset Windjammer Cruise Along the Coast

Step onboard a historic schooner, some of which are over 100 years old, and set sail on Casco Bay in Portland, Maine. Help the boat crew hoist the sails or even get behind the wheel. Step into history aboard a locally-built wooden windjammer, with three of these vessels listed on the National Register of Historic Places. Experience the beauty of the rugged coastline, complete with a beautiful sunset, lighthouses, seals, and seabirds. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay.

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: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

Enjoy this fully narrated 60-minute scenic cruise through busy Casco Bay and its iconic islands to see lighthouses, forts, lobster boats, seals, and seabirds. Take in the views of Portland's historical lighthouses, including a close up view of Portland Head Light, Maine’s oldest and most photographed lighthouse. As you cruise along the Casco bay, keep an eye out for Spring Point Ledge Light, Portland Breakwater Light (Bug Light), Ram Island Ledge Light, Portland Head Light, Fort Scammel, Fort Gorges, and Portland Harbor.

Portland, Maine: Tour in Vintage Fire Engine

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.

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

Boothbay Harbor Cruise: Lighthouses, Lobster Haul, and Seals

Go on a delightful harbor cruise, passing summer colonies, lighthouses, small islands, and out to see the seals on the ledges. Fun for the whole family. Pass by 2 lighthouses, islands, coastline, inner and outer harbor, and seals at the seal rocks. Experience a Boothbay classic that has been enjoyed for over 50 years and find out why it's so popular. Get an idea of how those delicious lobsters you enjoy at your favorite restaurant are caught, how the traps are hauled, and a little background of Maine’s famous lobster industry. Enjoy the seals basking on the rocks. Pass by two major lighthouses, Burnt Island Light, and Ram Island Lighthouse. This Boothbay Harbor lobster tour is educational and fun for the whole family. Don't forget to bring your camera. Step aboard a vessel that has the largest and most comfortable main salon in the region with padded seats and tables. Relax with food and a drink from the galley, which features a 360-degree view of the outside. Enjoy the sun and fresh Maine air on the upper deck. Hear the narration no matter where you choose to be, with speakers throughout the vessel.

Portland, Maine: Coastal Windjammer Sailing Cruise

Portland, Maine: Coastal Windjammer Sailing Cruise

Experience the beauty of Portland, Maine's rugged coastline on a historic windjammer sailing ship in Casco Bay. Sail by lighthouses, seals, and seabirds as you feel the wind in your hair. Learn how the wooden windjammer you are sailing on was built in Maine and is listed on the National Register of Historic Places. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. Let your skipper take charge and take in the marine wildlife and views surrounding you. See Portland from a unique vantage point. Have fun with the whole family or with friends on a day out at sea, before heading back to port.

Penobscot Bay: Historic Schooner Day Sailing Trip

Penobscot Bay: Historic Schooner Day Sailing Trip

Experience one of the top things to do in Camden sailing along Maine's magnificent rocky coastline. Climb aboard the elegant Appledore II, a historic schooner. Feel like an adventurer from the 19th-century while enjoying state-of-the-art accommodations onboard a modern windjammer. Stroll along the wide decks as you take in the sights without needing to duck beneath the rigging. With a capacity of only 49 passengers, there is abundant seating to make yourself comfortable for this intimate sailing trip. Enjoy the chance to sail your own wooden ship as the crew welcomes your participation. Offer to help raise the sails and take a turn at the wheel of this hard-working, seaworthy schooner. Ask your crew about the history of the boat which has sailed around the world, docking at many harbors along the way. Twice a year, she still sails the Eastern seaboard between her 2 home ports of Camden, Maine and Key West, Florida.  Start the tour by departing from Bayview Landing and heading out of Camden Harbor. Discover why Camden is often called the jewel of the Maine coast as you sail past the impressive lighthouse, Curtis Island Light, dating from 1836, and into Penobscot Bay. Considered to be one of the top cruising bays in the world, Penobscot Bay will amaze you with its uninhabited islands, wildlife, and views of Camden Hills and other coastal mountains dropping off into the sea. During the tour, look along the shore for Mount Battie, historic inns, and elegant summer mansions of the rich and famous with their million dollar yachts. Watch lobstermen hauling in their traps. On a typical day, you may see porpoises playing in the water, ospreys, eagles hunting for fish, and even the occasional whale. Watch for seals sunning themselves on rocks and cute guillernots (cousins of the puffin), with their bright red feet, wobbling as they walk along the rocky shoreline. Quench your thirst with cocktails, beer, wine and soft drinks, all available for purchase during your sailing cruise. As Camden Harbor comes back into view, relax and feel the wind sweep through your hair as your memorable sailing ship cruise draws to a close.

Portland: Old Port Culinary Walking Tour

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. You’ll sample a delectable mix of classic Maine, Maine-inspired, up-and-coming, cultural, fancy foods, and beverages.  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 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. 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 honey wine, and dark chocolate truffles made with Aroostook County potatoes.

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:

Top Attractions in Maine

Experiences in Maine

Things to do in United States

Other Sightseeing Options in Maine

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