Top Maryland Historical & Heritage Tours

Q: Which Maryland Historical & Heritage Tours have Instant Confirmation?

Maryland Historical & Heritage Tours with Instant Confirmation include: Baltimore Walking Foodie Tour in Fells Point Private and personalized tour of Washington dc 4- Hour Private customizable Washington DC Tour Baltimore History Sail on the Summer Wind Tipsy History Tour: 300+ Years of Annapolis Drinking History View all Tours with Instant Confirmation →

Q: I need a ride! Which Maryland Historical & Heritage Tours have Hotel Pickup?

No problem. These Maryland Historical & Heritage Tours include Hotel Pickup: Private and personalized tour of Washington dc 4- Hour Private customizable Washington DC Tour 3- Hour Private Customizable Washington, DC Tour Baltimore's Private Cultural Tour Harpers Ferry and Jefferson County 3 Hour Private History Tour View all Tours with Hotel Pickup →

Q: Got any more Maryland trip ideas?

We sure do. Check out our curated lists of hand-picked Maryland Tours. Top 10 Maryland 2026 Senior-friendly tours Maryland The best tours and activities for culture lovers in Maryland Top Day Trips from Maryland Things to do in Maryland this summer View all Maryland Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Maryland?

Based on our sales data over the past year, the most popular styles of tours and activities in Maryland are: Maryland Luxury & Special Occasions Maryland Luxury Tours Maryland Cultural & Theme Tours Maryland Historical & Heritage Tours Maryland Tours & Sightseeing View all tour styles in Maryland →

Baltimore Walking Foodie Tour in Fells Point

We do 3 things: Food, facts and fun! Welcome to Fells Point, the true heart of Baltimore. Picture this: cobblestone streets lined with charming eateries, …More

Baltimore, USA

4.9 (202)

Baltimore Walking Foodie Tour in Fells Point

We do 3 things: Food, facts and fun! Welcome to Fells Point, the true heart of Baltimore. Picture this: cobblestone streets lined with charming eateries,...

4 hours Free Cancellation

4.9 (202)

from
$104

Private and personalized tour of Washington dc

Ah, Washington DC. The capital of the United States always has something exciting to offer. Whether it’s the bright city lights, amazing shopping, or the …More

Baltimore, USA

4.9 (177)

Private and personalized tour of Washington dc

Ah, Washington DC. The capital of the United States always has something exciting to offer. Whether it’s the bright city lights, amazing shopping, or the...

3 to 4 hours Hotel pickup offered Free Cancellation

4.9 (177)

from
$343

4- Hour Private customizable Washington DC Tour

I have lived in the DC Metro Area for more than 30 years. Those years were spent as a limo driver, chauffeur, and private tour …More

Baltimore, USA

5.0 (89)

4- Hour Private customizable Washington DC Tour

I have lived in the DC Metro Area for more than 30 years. Those years were spent as a limo driver, chauffeur, and private tour...

4 hours 5 minutes Hotel pickup offered Free Cancellation

5.0 (89)

from
$550

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA

4.9 (72)

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes Free Cancellation

4.9 (72)

from
$65

Tipsy History Tour: 300+ Years of Annapolis Drinking History

Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended …More

Annapolis, USA

5.0 (53)

Tipsy History Tour: 300+ Years of Annapolis Drinking History

Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended...

2 hours Free Cancellation

5.0 (53)

from
$39

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, …More

Annapolis, USA

5.0 (51)

Annapolis Historic Walking Tour: Harbor and Colonial Downtown

Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions,...

1 hour 45 minutes Free Cancellation

5.0 (51)

from
$235

Mount Vernon and The Millionaires, 2 hour Walking Tour

Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in …More

Baltimore, USA

5.0 (27)

Mount Vernon and The Millionaires, 2 hour Walking Tour

Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in...

2 hours Free Cancellation

5.0 (27)

from
$30

3- Hour Private Customizable Washington, DC Tour

The tour is a unique experience that allows you to see the beauty of Washington DC all memorials. sine this is Private tours you always …More

Baltimore, USA

5.0 (23)

3- Hour Private Customizable Washington, DC Tour

The tour is a unique experience that allows you to see the beauty of Washington DC all memorials. sine this is Private tours you always...

3 hours Hotel pickup offered Free Cancellation

5.0 (23)

from
$450

Historic Annapolis Walking Tour - Small Group Guided Tour

Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles …More

Annapolis, USA

4.9 (23)

Historic Annapolis Walking Tour - Small Group Guided Tour

Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles...

90 to 120 minutes Free Cancellation

4.9 (23)

from
$35

Original Fells Point Haunted Pub Tour by Baltimore Ghost Tours

Step through the doors of some of Fell’s Point’s most haunted pubs for a fascinating haunted pub crawl tour of this historic maritime neighborhood. Taverns …More

Baltimore, USA

5.0 (20)

Original Fells Point Haunted Pub Tour by Baltimore Ghost Tours

Step through the doors of some of Fell’s Point’s most haunted pubs for a fascinating haunted pub crawl tour of this historic maritime neighborhood. Taverns...

2 hours Free Cancellation

5.0 (20)

from
$29

Annapolis Harbor and U.S. Naval Academy Cruise

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage …More

Annapolis, USA

4.9 (16)

Annapolis Harbor and U.S. Naval Academy Cruise

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage...

40 minutes Free Cancellation

4.9 (16)

from
$34

Our Baltimore Cultural tour allow you to get a personal perspective of why Baltimore is called "Charm City". …More

Baltimore, USA

5.0 (12)

Baltimore's Private Cultural Tour

Our Baltimore Cultural tour allow you to get a personal perspective of why Baltimore is called "Charm City"....

2 hours Hotel pickup offered Free Cancellation

5.0 (12)

from
$220

Best of Annapolis Tour: Colonial, State House, Naval Academy

Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a …More

Annapolis, USA

4.9 (10)

Best of Annapolis Tour: Colonial, State House, Naval Academy

Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a...

2 hours 15 minutes Free Cancellation

4.9 (10)

from
$34

Annapolis Thomas Point Lighthouse Cruise

The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not …More

Annapolis, USA

4.8 (8)

Annapolis Thomas Point Lighthouse Cruise

The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not...

1 hour 30 minutes Free Cancellation

4.8 (8)

from
$46

Sit back and relax on this up-close-and-personal cruise of Annapolis's waterways and scenic city shorelines on one of Watermark's 26-foot, open-aired vessels. Your captain will …More

Annapolis, USA

4.9 (7)

Scenic Spa Creek Cruise of Annapolis

Sit back and relax on this up-close-and-personal cruise of Annapolis's waterways and scenic city shorelines on one of Watermark's 26-foot, open-aired vessels. Your captain will...

45 minutes Free Cancellation

4.9 (7)

from
$34

Colonial Annapolis and Maryland State House Walking Tour

Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover …More

Annapolis, USA

5.0 (5)

Colonial Annapolis and Maryland State House Walking Tour

Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$26

Salty Old Fells Point 1.5 Hour Walking Tour

Baltimore's sassy seaside town played a critical role in defeating the British Navy (twice!) and has become our go-to neighborhood for live music, vintage shopping, …More

Baltimore, USA

5.0 (4)

Salty Old Fells Point 1.5 Hour Walking Tour

Baltimore's sassy seaside town played a critical role in defeating the British Navy (twice!) and has become our go-to neighborhood for live music, vintage shopping,...

1 hour 30 minutes Free Cancellation

5.0 (4)

from
$23

Harpers Ferry & Bolivar Heights: 2.5-Hour Guided Tour

Explore Harpers Ferry with a professional, highly knowledgeable guide who brings America’s history to life. Walk iconic Civil War sites, abolitionist landmarks, and scenic river …More

Frederick, USA

5.0 (3)

Harpers Ferry & Bolivar Heights: 2.5-Hour Guided Tour

Explore Harpers Ferry with a professional, highly knowledgeable guide who brings America’s history to life. Walk iconic Civil War sites, abolitionist landmarks, and scenic river...

3 hours Free Cancellation

5.0 (3)

from
$250

Baltimore Downtown Poe Ruth and More GPS Self Guided Walking Tour

This tour is all about the real Baltimore, the one shaped by sports, industry, invention, authors and community. Along the way, you’ll see statues that …More

Baltimore, USA

5.0 (3)

Baltimore Downtown Poe Ruth and More GPS Self Guided Walking Tour

This tour is all about the real Baltimore, the one shaped by sports, industry, invention, authors and community. Along the way, you’ll see statues that...

60 to 90 minutes Free Cancellation

5.0 (3)

from
$10

Day on the Bay Cruise from Annapolis to St Michaels

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, …More

Annapolis, USA

5.0 (3)

Day on the Bay Cruise from Annapolis to St Michaels

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining,...

8 hours Free Cancellation

5.0 (3)

from
$157

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Maryland Historical & Heritage Tours?

What are the best kid-friendly options for Maryland Historical & Heritage Tours Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Maryland Historical & Heritage Tours are:

View all kid-friendly Tours →

Which Maryland Historical & Heritage Tours have Instant Confirmation?

Which Maryland Historical & Heritage Tours have Free Cancellation?

Maryland Historical & Heritage Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Maryland Historical & Heritage Tours have Hotel Pickup?

Got any more Maryland trip ideas?

What are the most popular styles of Tours and Activities in Maryland?