Portland Historical Tours

Discover Portland's history with our curated tours, including lighthouse cruises, city explorations, and vintage fire truck sightseeing. Book your adventure today!

No tours match these filters.

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

6 Hours Private Lighthouses and Kennebunkport Tour in Portland

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. Thi

★ 4.7 (22)
From $735.00 USD
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
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with li

★ 4.7 (271)
From $69.00 USD
Amazing Scavenger Hunt: The Maine Event

Amazing Scavenger Hunt: The Maine Event

Step into the world of Let’s Roam, the undisputed champion of app-led scavenger hunts! Imagine strolling through city streets, hunting down top landmarks and un

★ 3.0 (4)
From $14.99 USD
Around The Peninsula Bike Tour

Around The Peninsula Bike Tour

Discover the rich history and stunning architecture of the City of Portland . Only 3.5 miles long and 3/4 miles wide, the Portland peninsula is packed full of f

★ 4.6 (44)
From $89.00 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
Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

Boothbay, Freeport and Maine Botanical Gardens Private Day Tour

Experience the beauty of Maine’s central coast on a fully private, all-day tour designed just for you. Unlike crowded bus tours, our small-group experience offe

From $325.00 USD
Camden, Rockland, Pemaquid, and Belfast Private Tour

Camden, Rockland, Pemaquid, and Belfast Private Tour

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 towe

From $325.00 USD
Castles of Cape Anne, Massachusetts - Private Day Tour

Castles of Cape Anne, Massachusetts - Private Day Tour

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Glouces

From $350.00 USD
Folklore and Fishy Tales Portland Outdoor Escape Game

Folklore and Fishy Tales Portland Outdoor Escape Game

Uncover the mysteries of Portland’s history with an innovative outdoor escape game that weaves together facts, folklore, and fishy tales. Venture through the ci

From $49.95 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
New Hampshire White Mountains Day Tour

New Hampshire White Mountains Day Tour

Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covere

★ 5.0 (2)
From $325.00 USD
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

Learn about Maine's most famous crustacean and the men and women who make their living from trap to table. Stroll along Portland's vital working waterfront , vi

★ 4.8 (157)
From $159.99 USD
Phantoms Penance and Poltergeists Portland ME Ghost Tour

Phantoms Penance and Poltergeists Portland ME Ghost Tour

As night falls on Portland’s historic waterfront, discover why this is the #1 ghost tour in Portland, ME. Operating nightly, year-round, this one-mile walking t

From $26.00 USD
Port City Lights Cruise

Port City Lights Cruise

A fully narrated 60-minute scenic cruise through busy Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, and seabirds. As many

★ 4.8 (317)
From $43.00 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 Pedicab Taxi Reserve

Portland Pedicab Taxi Reserve

It is the only regularly operating pedicab in Portland. Portland Pedicab creates the feeling of joy for all by allowing passengers to spend the time viewing Por

From $50.00 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: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour

Trace the steps of the Black Portlanders who moved our city, state, and country closer to the ideals of freedom, democracy, opportunity, and equality. Maine’s e

★ 5.0 (162)
From $54.00 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
Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Portland, Maine is known for its culinary scene, including amazing donuts. With this tour, you'll get to sample from the city's best donut shops, while also lea

★ 4.8 (231)
From $69.49 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 Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19

★ 4.9 (83)
From $109.00 USD
Private Portland Head Light & Midcoast Explorer

Private Portland Head Light & Midcoast Explorer

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begin

★ 4.5 (14)
From $350.00 USD
Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

Private Portland Lighthouses and Kennebunkport Tour - 12 Pax

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger

★ 5.0 (4)
From $1,508.00 USD
Private Portland to Acadia & Bar Harbor Experience

Private Portland to Acadia & Bar Harbor Experience

Experience the beauty, history, and charm of coastal Maine on this full-day adventure from Portland. Plan for 10–12 hours, with about three hours of travel each

★ 4.9 (32)
From $400.00 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
Private White Mountains Tour with Mount Washington Cog Railway

Private White Mountains Tour with Mount Washington Cog Railway

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacul

★ 5.0 (6)
From $395.00 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
Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Small Group Afternoon Lighthouse Boat Cruise With Local Drinks

Have you seen these iconic beacons from the water? Now is your chance! Board the Elizabeth Grace to cruise around Portland Harbor on this one of a kind sightsee

★ 4.7 (61)
From $87.00 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
Sunset Sea Kayak Tour on Casco Bay

Sunset Sea Kayak Tour on Casco Bay

The hours just before sunset offer the best time for paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy a

★ 4.8 (129)
From $60.00 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
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced gu

★ 5.0 (1656)
From $74.00 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
Vintage Fire Truck Sightseeing Tour of Portland Maine

Vintage Fire Truck Sightseeing Tour of Portland Maine

This 50-minute sightseeing tour is a fun and unique way to discover Portland, Maine. Board a Vintage Fire Engine and travel back in time as your knowledgeable g

★ 4.8 (954)
From $45.00 USD

Reliable & Guaranteed Tickets

Browse trusted tours and experiences in Portland. Compare options, read ratings, and book with confidence.

Prices and availability are subject to change. Product details are provided by our partners and may be updated without notice.

You may also like

Honeymoon Packages Category

Honeymoon Packages

1 experiences

Involves Animals Category

Involves Animals

3 experiences

Jet Boat Rentals Category

Jet Boat Rentals

1 experiences

Kayaking Tours Category

Kayaking Tours

4 experiences