
Annapolis Scandalous History Walking Tour
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Quick answer
Is Annapolis Scandalous History Walking Tour worth booking?
Annapolis Scandalous History Walking Tour is a 1.5-hour experience in Annapolis, United States, from $32 per person. It scores 48 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 48 / 100
- Rating
- Not yet rated
- Duration
- 1.5 hours
- From
- $32 per person
This lighthearted, adults-only, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. During your wal
What you get
About this experience
This lighthearted, adults-only, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. During your walking tour in Historic Annapolis, you’ll hear scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns. Colonial Founding Fathers, Annapolis gentry, renowned portrait artists, and regular folk, too, were all up to their tricks! There was revenge, murder, spying, drinking, political discord, and pleasures of the night.
What's included
Included
- Colonial-attired guide
Not included
- Gratuities
What you'll see and do
Annapolis
Stroll the cobblestone streets of historic Annapolis with your guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet
Pass by without stopping
William Paca House & Garden
Learn little-known facts about one of Annapolis richest colonial founders and one of its four signers of the Declaration of Independence.
Pass by without stopping
Maryland State House
In 1704 Maryland's colonial seat of government (later its state house) was burned. The suspected arsonist was hanged in 1708.
10 minutes here
United States Naval Academy
On an October night in, 1907, Lieutenant James Sutton, a student at the Naval Academy, got into a fight with some other young officers. He ran a short distance to his tent with two pistols. Sutton fired a couple of shots before being wrestled to the ground. The men later told investigators that Sutton felt remorse for his misconduct and pulled a pistol out from under his body and shot himself in the head. Sutton also had a dent in one side of his skull that never got explained, and he didn't bleed from the gunshot, which caused his mother to conclude that her son was dead or dying by the time the shot was fired. Rosa Sutton said her son's ghost visited her at the family home in Oregon, and told her he had been murdered.
Pass by without stopping
Where it starts and ends
Meeting point
Annapolis
Your colonial-attired guide will meet you at Market House Park in the heart of downtown Annapolis. Plan to arrive 15 minutes early to check in, as the tour will leave promptly at 7:30pm.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Your colonial-attired guide will meet you at Market House Park in the heart of downtown Annapolis. Plan to arrive 15 minutes early to check in, as the tour will leave promptly at 7:30pm.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Sat
- Group size
- Up to 15 travelers per booking
- Operated by
- Watermark Harbor Cruise
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Photos





Good to know
- Duration
- 1.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 48
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Annapolis Scandalous History Walking Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Annapolis.
How much does Annapolis Scandalous History Walking Tour cost?
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Prices start at $32 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Annapolis usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Annapolis Scandalous History Walking Tour take?
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Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Annapolis is not rushed.
Is Annapolis Scandalous History Walking Tour worth it?
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It holds an Outty Ranking of 48 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Annapolis, and how flexible the cancellation terms are.
Can I cancel or reschedule Annapolis Scandalous History Walking Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Annapolis Scandalous History Walking Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Annapolis Scandalous History Walking Tour?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Annapolis can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Annapolis and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.
Where does Annapolis Scandalous History Walking Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Annapolis within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Annapolis?
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Annapolis, MD packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Annapolis by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Annapolis experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Tipsy History Tour: 300+ Years of Annapolis Drinking History, Historic Annapolis Food Tour, Annapolis Historic Walking Tour: Harbor and Colonial Downtown. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Annapolis?
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Spring and fall bring the best weather and lighter crowds in Annapolis, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Annapolis?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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