Things To Do
Curate Annapolis Cafe & Bakery
Annie's favorite coffee shop in Annapolis. Annie gets an iced matcha and blueberry scone!
Naval Bagels
Great spot for breakfast or lunch bagels! Annie and Chris's go-to order is the Southerner bagel.
Bakers & Co.
Only go here if you want the best pastry of your life! Get an iced spiced tea while you are at it too!
Old Fox Books & Coffeehouse
Chris's all-time favorite bookstore. The coziest bookstore with a cafe and backyard seating.
Annapolis Canoe and Kayak
Rent canoes, paddle boards, and kayaks to explore Spa Creek, right in the heart of downtown Annapolis.
Quiet Waters Park
Great area for hikes, dog park, or canoe/kayak rentals!
Downtown Annapolis Partnership
Want to walk historic Annapolis for some window-shopping and water views? This is your place! Make sure to take advantage of the Water Taxi in Ego Alley.
Bread and Butter Kitchen
An everyday stop for the pirate world. Located in Eastport, across from Downtown Annapolis, Bread and Butter has the best scones ever! Chris is a huge fan of the BBK sandwich!
Annapolis Tours by Watermark
If you want to get some time on the water, Watermark has tours you can book ahead of time or walk-up slots. See Annapolis from a different perspective!
Pirate Adventures on the Chesapeake
If you are bringing your kids for the weekend, make sure to book a pirate adventure while you are here! They run six trips a day and are ABSOLUTELY incredible. Chris and Annie are a little bias :)
Sailor Oyster Bar
The Dolan family's favorite cocktail bar. Shucked oysters, tinned-fish plates, and amazing cocktails!
Joss Café & Sushi Bar
Annie's favorite sushi of all time! She hasn't found a place like it.
Leo Annapolis
A perfect spot for a cozy dinner with seasonal menus and craft cocktails! Walking distance from our hotel block.
Vin 909 Winecafe'
An Eastport staple! Delicious small plates, wood-fired pizza, and a wine cafe! Get there right at 5pm, or you might have a long wait.