I was born and raised on the waterfronts of Annapolis until the age of 18 years old. As a little girl, I remember spending summers on my mom’s motor boat, speeding to her secret spots along the Severn River and playing with jellyfish and horseshoe crabs that washed up on the beach. And as a teenager, I spent many nights huddled around beach bonfires with my friends and watching stars shoot over the Chesapeake Bay. After a 15 year hiatus from the city, I was lucky enough to call Annapolis home again in my 30s – at least for a few years. My husband and I took sailing lessons and explored all of the city’s creeks on our jet ski. This summer, I’m so excited to be visiting Annapolis and I can’t wait to do all my favorite things again! Here’s my perfect itinerary for visiting Annapolis.
Explore the William Paca House Gardens
Anyone can take a self-guided tour of the gardens during opening hours. The meticulously kept 2 acre garden is completely walled off creating a treasure that is only visible as you exit the back doors of the House.
Get lost wandering around downtown Annapolis
Put away the map and just walk. Annapolis is too small to get lost. Just meander down all the little colonial residential brick streets and absorb the history under your feet.
Take the water taxi to Eastport
Hop on at the Annapolis city dock and hop off at the Chart House. It will set you back just $3.
Have dinner at the Chart House
The Chart House is the best place to watch the action happening on Spa Creek. You’ll see sailboats, motor boats, kayaks, and stand-up paddle boards. All that, and you’ll have a beautiful view of the Eastport Bridge. I usually eat a light dinner (their Caesar salad and Cream of Crab Soup are my faves) so I can leave room for dessert. Be sure to order your chocolate lava cake in advance!
Have brunch at 49 West on Sunday
If you can catch Jonathan Stone playing and singing bossa nova on a Sunday morning at this European style café, you will swear you died and went to heaven. I can’t imagine a better way to spend a Sunday morning.
Go for a sail on the Woodwind
The Woodwind is a gorgeous 74 foot wooden Schooner. Sailing on the Woodwind is truly a quintessential Annapolis experience.
Have dinner and a Painkiller at Adam’s Taphouse Grille in Eastport
Now that you’ve spent the day at sea, it’s time to hang out where the local boaters hang out! Head to Adam’s Taphouse Grille for a yummy and VERY reasonably priced dinner. Be sure to wash it down with a Painkiller (sailors love their Painkillers) or a craft beer.
Wander around the Naval Academy and St. John’s College campus
Annapolis is a college town so why not explore these two beautiful historic campuses? (Or “yard” as the Naval Academy campus is called.) Visitors can enter Gate 1 of the Naval Academy on foot with a driver’s license. Once inside, be prepared to walk. St. John’s College campus is much more manageable as far as size and walkability. Personally, I love the contrast between these two colleges and also between their students, the “Johnnies” and the midshipmen.
Have an ice cream from Storm Brothers
Be prepared to wait in a long line, but know that it’s a tradition in Annapolis. I’ve been going there since I was a little girl!
Have dinner at VIN 909
VIN 909 is a house in Eastport that has been converted into a restaurant, offering the perfect “neighborhoody” feel.
Ride bikes around Bay Ridge
You won’t find this activity on any other list because this exclusive neighborhood peninsula happens to be private property. Much to the dismay of the residents of Bay Ridge, I’m here as your insider to get you in unnoticed. Since there is a strict “no parking” rule on all the streets in the community, simply park at the Club House at 80 East Lake Drive. That’s it! That’s your ticket in! Unload your bikes and ride all along the waterfront of the entire peninsula. You’ll want to pull over more than once to take it all in, trust me. I recommend biking over walking simply because the distance around the peninsula is a few miles.
Wander around Murray Hill
Murray Hill is so quaint and filled with the most adorable homes you’ll ever see. You’ll want to move here. I know I do… some day.
Have dinner and drinks at Tsunami
Tsunami is located just a hop, skip, and jump from Murray Hill. Tsunami offers delicious sushi, great drinks, cool bartenders, and awesome music. It’s is about as “hipster” as this colonial town gets.
There you have it – all the insider tips for visiting Annapolis you could ever ask for. If you love Annapolis as much as I do, please list your favorite things to do in the comments section below!