Things to do in Annapolis

Planning questions about Annapolis

What are the best things to do in Annapolis?

Tipsy History Tour: 300+ Years of Annapolis Drinking History is the highest ranked experience in Annapolis, scoring 83 out of 100 on the Outty Ranking from 51 traveler reviews. Annapolis Historic Walking Tour: Harbor and Colonial Downtown, Historic Annapolis Food Tour, Historic Annapolis Walking Tour - Small Group Guided Tour, Best of Annapolis Tour: Colonial, State House, Naval Academy round out the top five. Outty ranks 35 bookable experiences in Annapolis, United States, and 0 of them score 90 or above.

How much do activities in Annapolis cost?

The median price across everything we rank in Annapolis is $35 per person, and the cheapest starting price is $8 on Annapolis Murder Mystery Self Guided City Detective Game. Guided, small-group and skip-the-line versions sit above the median, and peak weekends price higher than midweek mornings.

Can I book something in Annapolis for today?

Yes. 35 of the top 35 experiences we rank in Annapolis currently show same-day availability. Same-day slots are limited, so book early in the day where you can.

Is Annapolis good for families?

Yes. 10 of the experiences we rank in Annapolis are family friendly, covering short, low-cost activities as well as full-day outings. Check the minimum age on each experience page before booking.

How many days do you need in Annapolis?

Three full days covers the headline sights without sprinting: one anchor experience each morning, 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.

When is the best time to visit Annapolis?

Spring and fall bring the best weather and lighter crowds in Annapolis, while summer has the widest choice of tours and evening activities. 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.

Can I cancel a booking in Annapolis?

35 of the 35 experiences we rank in Annapolis offer free cancellation, usually up to 24 hours before the start time. The exact window is shown on each experience page before you book.

How does the Outty Ranking work?

Every experience in Annapolis gets a single 0 to 100 score built from traveler sentiment, the depth of review evidence, recent booking momentum, price fairness against comparable options in the same city, operator standing and cancellation flexibility. Scores are benchmarked within Annapolis so a strong local option is not buried by global volume, and anything at 90 or above joins the Outty 90+ Club.