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Explore the Best of Annapolis Historic District

Immerse yourself in the colonial charm of the Annapolis Historic District, where cobblestone streets and stunning maritime architecture tell stories of American history. Discover top-rated walking tours, lively pub crawls, and expert-led cultural excursions that bring the past to life. Whether you are exploring legendary landmarks or enjoying a local tasting experience, our curated activities offer the perfect way to experience Maryland's breathtaking heritage. Book your unforgettable Annapolis adventure today and uncover the hidden gems of this historic seaside treasure!

4.7/5 avg visitor ratingTours from $304 top historical experiencesFree cancellation available

At a glance

Tour Price

Tour Price

$30–$462 typical

Median price is $35, with a wide range up to $1,476

Rating

Rating

4.73★ average

Based on 38 pooled reviews with ~100% positive sentiment

Tour Length

Tour Length

2–4.1 hours typical

Median duration is 2 hours

Best For

Best For

History & Pub Crawls

100% of tours are historical, 75% are pub crawls

Booking Perks

Booking Perks

75% free cancellation

75% of options also offer instant confirmation

Experience

Experience

Knowledgeable guides

Reviewers highlight interesting and great tasting experiences

4 Products

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis

2 hrsEco-FriendlyFree cancellation
$30
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Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
Summary

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 drinks at each stop. From rebels to rum-runners, each location reveals fascinating stories paired with a drink that defines the era...

Inclusions
  • A guided drinking history tour at iconic Pubs in Annapolis
Itinerary
  • Colonial Annapolis Historic District
Good to know
  • Service animals allowed, Public transportation options are available nearby, Suitable for all physical fitness levels
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

2 hrs
$40
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Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Summary

Pull up a bar stool and lean into tales of murder, debauchery, and gruesome tragedies on this dramatic haunted pub crawl of the Annapolis historic district.

Colonial Annapolis and Naval Academy Half Day Private Bus Tour

Colonial Annapolis and Naval Academy Half Day Private Bus Tour

5 hrsPrivate tourFree cancellation
$1,729
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Colonial Annapolis and Naval Academy Half Day Private Bus Tour
Summary

Let us take you, and up to 12 of your friends, on an adventure through Navy culture and heritage. Historic Annapolis is Americas' sailing capital and home to the US Naval Academy, nestled along the Chesapeake region. We will help explore the sites, sounds and taste of "Nap Town". Annapolis has bee...

Inclusions
  • Step on tour guide
Exclusions
  • Tips/gratuity for driver/guide
Itinerary
  • U.S. Naval Academy
  • Chase-Lloyd House
  • Hammond-Harwood House
  • Colonial Annapolis Historic District
  • St. John's College
Good to know
  • Infants and small children can ride in a pram or stroller, Service animals allowed, Infants are required to sit on an adult’s lap, Suitable for all physical fitness levels, This tour is not wheelchair accessible
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Hidden History Pub Crawl of Historic Annapolis

Hidden History Pub Crawl of Historic Annapolis

2 hrsFree cancellation
$30
Book now
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Hidden History Pub Crawl of Historic Annapolis
Summary

The Hidden History Pub Crawl is a tour through Annapolis' scandalous past. Sip on a beverage while entertained by stories of historical conspiracies, murder, riots and forgotten tales as your guide brings to life the city’s juiciest stories. With different stories every night, this is the most intri...

Inclusions
  • Local guide
Exclusions
  • Alcoholic drinks (available to purchase)
Itinerary
  • Colonial Annapolis Historic District
Good to know
  • Travelers should have at least a moderate level of physical fitness, Minimum age is 21 years! No exceptions, Dress code is smart casual, Due to uneven surfaces, this tour is not recommended for those with walking disabilities or using a wheelchair. However, many guests in wheelchairs have been more than capable of traversing the route. Please call before booking to discuss!, Operates in all weather conditions, please dress appropriately. Disposable ponchos available for $1 each, please call first to make sure are fully stocked.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.