Published: June, 2026
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Annapolis, Maryland

A perfect historical stop between lacrosse tournaments!
— Courtney Leary
  • More about your Oliver Guide:
  • Trip type: Adult, Family, Group getaway, Solo, Beach, City
  • Activity level: moderate
  • Ideal length of trip: 2-3 days

to & from

Fly into Baltimore and drive about 45 minutes. You really don’t need a car for anything but golf while you are there so if this is not part of a bigger trip Uber would work fine.

Where to Stay

We have rented two different VRBO’s neither of which I would recommend for anything but their location– one was on Prince George Street and one was on Fleet Street. Both locations were very walkable to most everything we needed. The good rentals book up early so get ahead of it. Next time I might look in Eastport which is on the other side of the drawbridge but still walkable to shops and restaurants.

Hotel-wise, I have not stayed in any but did briefly check out the two below and think I would opt for one of these on our next visit:

The Historic Inns of Annapolis also seemed to be quite popular.

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