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Portland, Maine
Architecture

Architecture
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Portland: Best of Maine Lighthouse Scenic Cruise

1. 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: Trolley City Tour with Portland Head Light Stop

2. 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: Sightseeing Cruise to Portland Head Light

3. 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: Sightseeing Trolley Tour with a Guide

4. Portland, Maine: Sightseeing Trolley Tour with a Guide

Hop on this classic 1-hour trolley tour and explore the rich history and beautiful sights of Portland! On this fully narrated tour, you’ll learn about hundreds of years of history and pass some of Portland's most iconic landmarks. Weaving between Old Port, East Bayside, Downtown, and the Arts District, you’ll learn about places like The Portland Observatory, The Longfellow House, and Victoria Mansion. Once the tour is complete, you'll have a wealth of knowledge and recommendations for the city of Portland. Please arrive to the tour meeting point 15 minutes before the tour begins.

Portland, Maine: Tour in Vintage Fire Engine

5. Portland, Maine: Tour in Vintage Fire Engine

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

Portland: Schooner Tall Ship Cruise on Casco Bay

6. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

7. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Enjoy a 1.5-hour cruise around the islands of Portland's Casco Bay. Pass historic lighthouses, early-19th century forts, and quaint fishing piers as you explore the area at sunset. Guests over 21 can enjoy 1 craft beer or hard seltzers per person. As you cruise, keep an eye out for seabirds and the occasional seal that call Maine's coast home. When the timing's right, the boat will turn its bow towards Portland so you can enjoy the sunset and the city's skyline from the water. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible!

Portland: Self-Guided Sightseeing Driving Audio Tour

8. Portland: Self-Guided Sightseeing Driving Audio Tour

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map. Purchase one tour per car, not per person. Everyone listens together! Note: This 10+mile-long tour covers the essentials of Portland in 1-2 hours. Travel through the neighborhoods of Portland on a self-guided driving tour. Learn about the city’s history and culture from an audio-guided app on your smartphone and get panoramic views from the Eastern Promenade.  Drive down Commercial Street and hear about the industrial beginnings of the city. Along the way, you’ll see the wonderfully preserved Victoria Mansion, dating back to 1858. That’s followed by the even older Danforth Inn, which goes all the way back to 1823. As you drive up the Western Promenade, you’ll hear about some famous folks who were laid to rest in Portland, including the poet Henry Wadsworth Longfellow (a statue of whom you’ll see next, in Longfellow Square). Go to the Art District (perfect for picking up a souvenir), followed by a church that was once destroyed by the British.  Continue toward the shore, passing the site of an observatory that once guided ships into Portland’s occasionally treacherous harbor. Spot a couple of picturesque lighthouses perfect for any photo collection. Explore the Eastern Promenade, a 68-acre seaside park sporting plenty of unforgettable ocean views. You’ll see the strange and controversial “baked beans” building, before passing through Old Port again for a second chance to stop at one of the neighborhood’s many restaurants and boutiques. Pass by a statue of Portland’s own John Ford. Cross the Casco Bay Bridge into South Portland, home to a quieter community than its buzzing northern neighbor. Finally, you’ll arrive at Fort Williams Park, full of beauty and history. The tour concludes here.

Portland: Old Port Culinary Walking Tour

9. 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.

Portland, Maine: Hidden Histories Guided Walking Tour

10. Portland, Maine: Hidden Histories Guided Walking Tour

Discover Portland's hidden histories on a guided walking tour of the Old Port, downtown, and the working waterfront. Marvel at images of the past and at the colorful storytelling your guide shares with you to make the past come alive. Hear stories only a local knows about the city's sights, streets, and buildings. 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. Find out why Tripadvisor named him Maine's #1 tour guide!

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Frequently asked questions about Portland, Maine Architecture

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Other Sightseeing Options in Portland, Maine

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What people are saying about Portland, Maine

Dugan is very knowledgeable and very personable. We really appreciated the photos he provided to give us context. Also, we enjoyed his bringing in personal anecdotes when appropriate and asking if we had questions at each stop.

Gary was a very informative and entertaining guide. We saw a lot of cool stuff in Portland and heard some great stories.

1 day in the city on cruise day. Excellent tour that showed the city off very well.

Dugan did an amazing job. Very knowledgeable on historical Portland.

Bill was very informative and knows a lot about the Portland area.