Tipsy History Tour: 300+ Years of Annapolis Drinking History

Prices start at $39 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.

Plan for about 2 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.

It holds an Outty Ranking of 82 out of 100, which we label "Exceptional". That score blends traveler sentiment (5/5 across 47 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Annapolis, and how flexible the cancellation terms are.

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.

Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

Around 16 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.

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 2-hour experience runs outdoors or after sunset.

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.

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 Historic Annapolis Food Tour, Annapolis Historic Walking Tour: Harbor and Colonial Downtown, Historic Annapolis Walking Tour - Small Group Guided Tour. 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.

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.

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.

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.