Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
Active
2h
For a full refund, cancel at least 24 hours before the scheduled departure time.
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About this experience
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. Perfect for whiskey enthusiasts and history buffs alike, this tour offers a relaxed atmosphere to toast the past and enjoy the present. Dress comfortably as you stroll through downtown, rain or shine, and prepare for a fun evening immersed in tipsy history.
- 2-hour historical pub crawl through downtown Annapolis
- Discover how drinking shaped Annapolis' history
- Enjoy recommended drinks at each stop, not included in the price
- Limited walking involved; dress for comfort and the weather
Available options
Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
What's included
A guided drinking history tour at iconic Pubs in Annapolis
Detailed itinerary
1
Stop 1
Come raise a glass with us on a historical pub crawl that shares the untold stories of how drinking shaped Annapolis, Maryland, and the nation itself. At each stop, we’ll dive into a different era— paired with a recommended drink that was the rage at the time. We will dive into the colonial rum obsession, Maryland’s rich whiskey distilling roots, and the bold few who treated Prohibition like a suggestion, not a law. We will roughly be at each pub for 30 minutes and will pass by some of Annapolis' most iconic places like the State House, Ego Alley and Main Street. Join us to toast the past, enjoy the present, and experience history with a tipsy twist.
What's not included
Although we have recommended drinks at each stop they are not included with the price of the tour. This allows our guests to enjoy alcohol at their own pace and responsibly.
Available languages
Guide guide
EN
Reviews breakdown
Tripadvisor
5.0
2 reviews
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Important information
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
Meeting point
See the hostess at Galway Bay and let them know you are with us.
Important notes
Please arrive at Galway Bay, 63 Maryland Ave. Annapolis, MD by 4pm.
Upon arrival tell hostess you are with the Tipsy Bay Co. Tour.
About Annapolis
Annapolis, the charming capital of Maryland, is renowned for its rich history, stunning waterfront, and deep maritime heritage. This city offers a unique blend of colonial architecture, vibrant naval traditions, and picturesque sailing experiences, making it a must-visit destination for history buffs and outdoor enthusiasts alike.
Top Attractions
United States Naval Academy
The United States Naval Academy is a prestigious military academy that trains future officers for the U.S. Navy and Marine Corps. The campus features historic buildings, museums, and the iconic Naval Academy Chapel.
Historical/Military
2-3 hours
Free
Annapolis Historic District
The Annapolis Historic District is a designated National Historic Landmark with over 200 buildings dating back to the 18th and 19th centuries. The district features colonial architecture, cobblestone streets, and charming shops and restaurants.
Historical/Architectural
Half-day to full day
Varies by attraction
Annapolis Maritime Museum
The Annapolis Maritime Museum showcases the city's rich maritime heritage and the history of the Chesapeake Bay. The museum features exhibits on sailing, boatbuilding, and the ecology of the bay.
Museum/Maritime
1-2 hours
Moderate ($10-$15)
Annapolis City Dock
The Annapolis City Dock is the heart of the city's waterfront, offering stunning views of the Chesapeake Bay, sailing activities, and a variety of shops, restaurants, and cafes. It's a great place to relax and soak in the maritime atmosphere.
Waterfront/Entertainment
Varies, can be a quick stop or a full day
Free to explore, costs vary for activities and dining
Kunta Kinte-Alex Haley Memorial
This memorial commemorates the arrival of Kunta Kinte, an African man who was brought to America as a slave and whose story was immortalized in Alex Haley's novel 'Roots.' The memorial is a poignant reminder of the city's role in the history of slavery and the transatlantic slave trade.
Historical/Cultural
30 minutes to 1 hour
Free
Must-Try Local Dishes
Crab Cakes
Made with fresh blue crab, these crispy, savory cakes are a must-try in Annapolis. They are typically served with a tangy remoulade or lemon aioli.
Appetizer
Contains seafood and gluten (if breaded)
Crab Soup
A creamy, tomato-based soup made with chunks of blue crab, vegetables, and spices. It's a comforting and flavorful dish that's perfect for cooler months.
Soup
Contains seafood and dairy
Crab Imperial
A luxurious dish made with lump crabmeat, cream cheese, breadcrumbs, and spices, baked until golden and served with a lemon butter sauce.
Appetizer
Contains seafood, dairy, and gluten
Oysters Rockefeller
Fresh oysters topped with a rich, creamy mixture of spinach, butter, and breadcrumbs, then baked until bubbly. This classic dish is a favorite in Annapolis.
Appetizer
Contains seafood, dairy, and gluten
Popular Activities
Sailing
Kayaking
Paddleboarding
Biking
Hiking
Waterfront dining
Sunset sailing
Spa treatments
Best Time to Visit
April to June, September to October
Spring and fall offer pleasant weather, vibrant foliage, and fewer crowds. These seasons are ideal for outdoor activities, sailing, and exploring the city's historic sites.
15-30°C
60-85°F
Practical Information
Language
- Official: English
- Widely spoken: Spanish, French, Chinese
- English: Widely spoken
Currency
United States Dollar (USD)
Time Zone
Eastern Time Zone (GMT-5:00)
Electricity
120VV, 60HzHz
Safety Information
Overall Safety Rating: Generally safe
Annapolis is generally a safe and welcoming city for visitors. However, as with any destination, it's important to be aware of your surroundings and take common-sense precautions to ensure a safe and enjoyable trip.
Important Precautions:
- • Be aware of your surroundings and keep valuables secure
- • Avoid isolated areas at night and stick to well-lit and populated areas
- • Use reputable transportation services and avoid fake taxis
Getting there
By air
- Baltimore/Washington International Thurgood Marshall Airport • 48 km (30 miles)
- Washington Dulles International Airport • 72 km (45 miles)
By train
Annapolis MARC Station
By bus
Greyhound Bus Station in Baltimore
Getting around
Public transport
The bus system is affordable and covers most major attractions and neighborhoods. Buses are a convenient way to get around, especially during peak seasons.
Taxis
Available • Apps: Uber, Lyft
Rentals
Car, Bike, Scooter
Neighborhoods
Downtown Annapolis
Eastport
West Annapolis
Day trips
Baltimore
56 km (35 miles) • Half day to full day
Baltimore is a vibrant city with a rich history, diverse neighborhoods, and a thriving arts and entertainment scene. It's a great day trip destination from Annapolis, offering a variety of attractions and activities.
Washington, D.C.
56 km (35 miles) • Full day
Washington, D.C. is the capital of the United States and a world-class city with a wealth of historical, cultural, and political attractions. It's a great day trip destination from Annapolis, offering a variety of museums, monuments, and iconic landmarks.
St. Michaels
64 km (40 miles) • Half day to full day
St. Michaels is a charming waterfront town on the Eastern Shore of Maryland, known for its historic architecture, maritime heritage, and beautiful natural surroundings. It's a great day trip destination from Annapolis, offering a variety of attractions and activities.
Festivals
Annapolis Boat Shows • October
United States Naval Academy Commissioning Week • May
Annapolis Film Festival • March
Pro tips
- Visit the United States Naval Academy for a fascinating look at the city's military history and culture
- Take a sailing lesson or charter to experience the city's rich maritime heritage
- Explore the historic district and its charming shops, restaurants, and attractions
- Visit the Annapolis Maritime Museum to learn about the city's maritime history and the ecology of the Chesapeake Bay
- Attend a performance at the Maryland Hall for the Creative Arts for a taste of the city's vibrant arts and culture scene
From $25
per person
Price varies by option
Secure booking
Free cancellation available
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