How To Spend A Weekend in Annapolis, Maryland

I grew up in Maryland and have never been to our capital, so my family and I decided to fix that and recently spent a weekend in Annapolis. Here's a video of what we got up to, and keep scrolling for the full itinerary.

Trolley tour ($22)

Paca House and garden tour ($12)

Tasting at Great Frogs Winery ($30)

Stroll and shop on Main street

See street art (Along West street)

Cruise on the Chesapeake Bay or take water taxis

Sandy Point Beach ($3-$5 per person)

Rise Up Coffee

Curate Coffee, Wine, Kitchen

Cooper’s Hawk

Chick and Ruth’s Deli

Boat Yard Bar and Grill

O’Brien’s Oyster Bar and Seafood

Carrol’s Creek

Pusser’s Caribbean Grille

Annapolis Ice Cream Company

Days: Saturday-Monday

Where we stayed: The Graduate Annapolis

126 West St, Annapolis, MD 21401

Note: Great location. Located on West Street and just minutes from Main street.

Checked into the hotel at 4 P.M.

Drove over to Great Frogs Winery, which is less than 10 minutes away by car.

We were there from about 6-8 P.M., which is closing time on weekends.

We then headed over to Boatyard Bar and Grill for dinner. (Note: They’re known for their crab cakes. I didn’t think they were anything special but the crab dip was really good and the caesar salad too.)

We took a stroll along West street, taking in the sights and murals.

We grabbed brunch at Lighthouse Bistro.

We then drove to Sandy Point State Park. (It’s $5 a person and you have access to playgrounds, you can cook out, and of course enjoy the man made beach. It’s a great place to take the whole family. We had a great time.)

We drove back to Main street to have dinner at O’Brien’s, another well known Annapolis eatery and called it a night.

We checked out, left the car in the garage and took a stroll on Main street.

We stopped for brunch at the Iron Rooster. (Everything looked phenomenal. We got the crab stuffed avocado salad and chicken and pancakes.)

After brunch, we walked over to the Paca house and garden. We did our own tour and spent some time in the backyard. It’s so beautiful here. I highly recommend checking it out.

I grabbed a little sweet treat from Annapolis Ice Cream Company for the ride back home.