Things to do in Annapolis

Sailing capital with the Naval Academy and historic State House.

Annapolis, MD, USA· Airport: BWI
Annapolis — Things to do | CheapoTrav travel guide

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Call 1 (815) 473-8090

Key facts

  • Best time of year to visit varies by activity — see the timing tips below
  • Most attractions in Annapolis are walkable from the city center or a short rideshare
  • Free things to do: parks, public squares, viewpoints, and several no-admission museums
  • Family-friendly: most Annapolis attractions accept strollers and offer kids' pricing
  • Book attraction tickets in advance during peak season — many sell out

Whether it's your first trip or your fifth, Annapolis has more going on than you can fit in a long weekend. Sailing capital with the Naval Academy and historic State House. This guide is a tight shortlist of what's actually worth your time, organized by what you're in the mood for.

We've grouped picks by free activities, family-friendly outings, food experiences, and day trips. After you pick your itinerary, scroll down for our travel-desk number — we can quote the flights, hotels, and rental car as a package and often save 15–25% over booking each piece separately.

In this guide

  • Top sights
  • Free things to do in Annapolis
  • Best with kids
  • Day trips from Annapolis
  • Food experiences

Frequently asked questions

What is Annapolis most known for?
Sailing capital with the Naval Academy and historic State House.
What are the top free things to do in Annapolis?
Public parks, neighborhood walks, viewpoints, and select museums in Annapolis are no-cost. Our city guide breaks down the best free picks by neighborhood.
Call 1 (815) 473-8090 for phone-only fares
Is Annapolis family-friendly?
Yes — most major attractions in Annapolis cater to families with kids' pricing, stroller access, and child-safe transit. Ask our travel desk for an age-appropriate itinerary.
How many days do you need in Annapolis?
2–3 days covers the highlights; 4–5 days lets you add day trips and slower neighborhood exploration.
Call 1 (815) 473-8090 for phone-only fares
What are the best day trips from Annapolis?
Popular day trips include baltimore, washington dc, philadelphia.
Do I need to book attractions in advance?
For the top attractions in Annapolis, yes — especially in peak season. Walk-up tickets often sell out, and prebooking saves 10–20% on many experiences.
Call 1 (815) 473-8090 for phone-only fares

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