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Top Portland Historical & Heritage Tours

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Portland Tours

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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 …More

4.8 (1,442)

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...

1 hour 45 minutes Free Cancellation
4.8 (1,442)
from
$61
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 …More

Likely to Sell Out
Likely to Sell Out
5.0 (1,713)

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...

1 hour 45 minutes Free Cancellation
5.0 (1,713)
from
$74
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 …More

4.9 (821)

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...

1 hour 45 minutes Free Cancellation
4.9 (821)
from
$61
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 will …More

5.0 (674)

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 will...

2 hours Free Cancellation
5.0 (674)
from
$54
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 …More

4.9 (1,071)

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...

2 hours Free Cancellation
4.9 (1,071)
from
$79
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 …More

4.8 (329)

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...

1 hour Free Cancellation
4.8 (329)
from
$43
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 …More

4.9 (271)

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...

1 hour 45 minutes Free Cancellation
4.9 (271)
from
$71
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 …More

5.0 (174)

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...

2 hours Free Cancellation
5.0 (174)
from
$54
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 full …More

4.1 (74)

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 full...

1 to 2 hours Free Cancellation
4.1 (74)
from
$17
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. The tour …More

4.2 (76)

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. The tour...

60 to 90 minutes Free Cancellation
4.2 (76)
from
$8
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 Commercial …More

4.9 (520)

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 Commercial...

2 hours Free Cancellation
4.9 (520)
from
$49
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 …More

Likely to Sell Out
Likely to Sell Out
4.8 (241)

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...

2 hours Free Cancellation
4.8 (241)
from
$69
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 …More

5.0 (34)

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...

6 to 8 hours Hotel pickup offered Free Cancellation
5.0 (34)
from
$513
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 …More

4.8 (26)

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...

6 hours Hotel pickup offered
4.8 (26)
from
$735
Freeport, Boothbay Harbor, and Botantical Gardens Day Tour

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. From Portland travel along Maine’s …More

4.7 (13)

Freeport, Boothbay Harbor, and Botantical Gardens Day Tour

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. From Portland travel along Maine’s...

7 to 8 hours Hotel pickup offered Free Cancellation
4.7 (13)
from
$325
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 spectacular mountain scenery, historic …More

5.0 (8)

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 spectacular mountain scenery, historic...

6 to 8 hours Hotel pickup offered Free Cancellation
5.0 (8)
from
$395
Portland Maine Self-Guided Walking Audio Tour

Unearth the stories beneath historic downtown Portland, Maine on this self-guided walking tour! In the Old Port, colonial tales linger around the Customs House and …More

4.3 (14)

Portland Maine Self-Guided Walking Audio Tour

Unearth the stories beneath historic downtown Portland, Maine on this self-guided walking tour! In the Old Port, colonial tales linger around the Customs House and...

1 to 2 hours Free Cancellation
4.3 (14)
from
$13
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 …More

5.0 (4)

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...

6 to 8 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$325
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 blends grand …More

5.0 (3)

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 blends grand...

8 to 10 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$350
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 …More

5.0 (4)

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...

6 hours Hotel pickup offered
5.0 (4)
from
$1,508

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