Portland Cultural Tours

Discover Portland's rich history, culture, and scenic lighthouses with our curated cultural tours. Experience cruises, walking tours, and more in Portland, Maine.

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A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commerc

★ 4.9 (517)
From $48.99 USD
Audio Guided Walking Tour from Old Port of Portland, Maine

Audio Guided Walking Tour from Old Port of Portland, Maine

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. Th

★ 4.2 (64)
From $7.75 USD
Guardians of the Harbor Trolley Tour

Guardians of the Harbor Trolley Tour

Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disemb

★ 5.0 (9)
From $59.00 USD
Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that gu

★ 4.8 (803)
From $61.00 USD
Kennebunkport, York and Portsmouth NH Private Tour

Kennebunkport, York and Portsmouth NH Private Tour

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean v

★ 5.0 (2)
From $325.00 USD
Old Port Culinary Walking Tour from Portland

Old Port Culinary Walking Tour from Portland

- Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - whe

★ 4.8 (478)
From $159.99 USD
Portland City and Lighthouse Tour

Portland City and Lighthouse Tour

The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland p

★ 4.8 (1265)
From $61.00 USD
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailor

★ 4.9 (1004)
From $79.00 USD
Portland Explorer: Working Waterfront Walking Tour with Seafood

Portland Explorer: Working Waterfront Walking Tour with Seafood

Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the c

★ 4.9 (23)
From $79.00 USD
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone street

★ 4.0 (8)
From $24.99 USD
Portland Maine Self-Guided Walking Audio Tour

Portland Maine Self-Guided Walking Audio Tour

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picture

★ 4.3 (13)
From $12.99 USD
Portland Underground Railroad Self Guided Audio Walking Tour

Portland Underground Railroad Self Guided Audio Walking Tour

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour

★ 3.4 (9)
From $9.99 USD
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide wil

★ 5.0 (624)
From $54.00 USD
Private Day Tour of Salem MA, from Portland ME

Private Day Tour of Salem MA, from Portland ME

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide w

From $325.00 USD
Private Portland to Camden & Midcoast Lighthouse Experience

Private Portland to Camden & Midcoast Lighthouse Experience

Join us for an exciting **Private Coastal Tour from Portland to Camden**, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the

★ 5.0 (1)
From $350.00 USD
Private Portland to Cape Ann, MA Castles & Coast

Private Portland to Cape Ann, MA Castles & Coast

Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blen

★ 5.0 (3)
From $350.00 USD
Self-Guided Audio Tour of Portland’s Historic Old Port District

Self-Guided Audio Tour of Portland’s Historic Old Port District

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of

★ 5.0 (1)
From $9.99 USD
Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

Southern Maine Private Tour: Kennebunkport & Nubble Lighthouse

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group

★ 5.0 (3)
From $350.00 USD
Sunset Lighthouse Cruise

Sunset Lighthouse Cruise

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening

★ 4.8 (250)
From $71.00 USD
The Maine Experience: Coast, Culture & History

The Maine Experience: Coast, Culture & History

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day

From $300.00 USD
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock

★ 4.0 (68)
From $16.99 USD

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