Sam & Leigh
Things To Do
Naval Academy
The Naval Academy, has been preparing officers of the U.S. Navy and Marine Corps since 1845 and is a must-see while in Annapolis. Take a guided tour or a self-guided stroll through the beautiful grounds. Be sure to bring a photo ID for the security access point. Enter through pedestrian Gate 1 located at Randall Street and Prince George Street.
Schooner Woodwind
There is no better way to see Annapolis than from the waters of the Chesapeake Bay. Recognizable from its cameo in Wedding Crashers, the Woodwind Schooner offers a number of cruise options and times.
Annapolis Water Taxi
Want to get on the water but don't want a full tour? For around $3, hop on the water taxi and take a short spin around the Annapolis Harbor; the taxi departs hourly on the hour from City Dock (look for the red Watermark sign). You can also use it as it was intended, for transportation. If you're staying downtown, hop on and ask to be taken to Eastport Yacht Club for the Friday night Welcome Party, Caroll's Creek for dinner, or anywhere else (check their stops on their website). The captain will typically give you a mini-tour and answer any of your burning Annapolis questions.
Carrol's Creek Cafe
Open since 1983, Carrol's Creek is an Annapolis favorite serving up seafood classics (try the crab cakes!) from a waterfront patio. This is walking distance to Eastport Yacht Club, so a great spot to grab dinner before the Welcome Party on Friday evening.
Boatyard Bar & Grill
You can't go wrong with Boatyard - award winning crab cakes, amazing raw bar, waterfront access, awesome happy hour where locals, sailors and fishermen join Annapolis visitors. This is walking distance to Eastport Yacht Club, so a great spot to grab dinner before the Welcome Party on Friday evening.
Reynolds Tavern
Opened originally by William Reynolds in 1747, Reynold's is the perfect spot to take in the history of Annapolis. Two great options: 1) upstairs/indoors is a full restaurant that offers an amazing afternoon tea and dinner 2) around the back/downstairs/outdoors is the 1747 Pub, a must-visit (one of Sam and Leigh's all-time favorite Annapolis spots). Make sure to check out the beer garden - the space originally housed stables kept by William Reynolds for his traveling guests (fun fact: the old Smoke House behind the outdoor bar dates back to 1737!).
Annapolis Ice Cream Company
No Annapolis visit is complete without a trip to Annapolis Ice Cream Company. Leigh recommends (demands!) you try the Peanut Butter Oreo.
Chick & Ruth's Delly
An Annapolis institution for over 50 years, Chick and Ruth's serves classic diner fare with major personality. For the early birds, the entire restaurant recites the Pledge of Allegiance daily (8:30am weekdays, 9:30am Saturday) - not sure why, but it feels right. The kind of place where you name it, and it's on the menu. Surprisingly amazing crab cakes.
Preserve
Perfect spot to grab brunch, lunch, dinner, or drinks. Prime people watching and amazing cocktails.
Old Fox Books & Coffeehouse
A bibliophile's dream - Old Fox offers a curated collection of books, stationary, and gifts. Grab a cup of locally-roasted Ceremony coffee and bring your literary treasures out back to their magical garden patio.
Market House
Dating back to 1784, the Annapolis Market House has had many lives. Today, the open-air market offers a variety of options for both grab-and-go and sit-down. The space also houses Rise Up Coffee - great spot to grab a coffee and sit on the water (across the street). Fun fact: Leigh's first high school job was at a donut shop inside the Market House... she still won't eat donuts to this day.
Rams Head Tavern
Home to Fordham beer, Ramshead is another Annapolis favorite. A casual spot with live music, amazing beer selection, and classic pub food. They have an epic patio out back. Highly recommend the crab dip.
Bakers & Co.
A Delavan family favorite. What started as a small stand at the local Farmers Market is now a thriving cafe with fantastic coffee, scones, breads, muffins, etc. Walking distance from downtown (*see bridge schedule below), a trip here makes for a lovely Saturday morning stroll.
Forward Brewing
Our new favorite spot! Adorable new brewery located in Eastport - great selection of beers and surprisingly amazing food. Great spot to spend a few hours in the sun!
Level a small plates lounge
Great dinner/drink spot for those staying on West Street (The Graduate, The Westin, The Hilton). The cocktails (or mocktails!) are the best in the city! We recommend asking to sit upstairs - great ambiance!
Metropolitan Kitchen & Lounge
Staying on West Street? Pop over to Metropolitan's rooftop bar! Great drinks and brunch.
Colonial Annapolis Walking Tour
For the history buffs: led by a tour guide in full colonial attire, these walking tours (1.5 hours) are a great way to learn a bit more about the history of Annapolis.
Spa Creek Bridge
As an FYI, if you'd like to walk to Eastport from Downtown Annapolis (a lovely walk!), you'll have to cross the Spa Creek Bridge. Walkable, safe, and providing gorgeous views, there is one important note: the bridge is an active drawbridge that opens 2x/hour to allow boats to pass (see times below). It isn't a huge inconvenience (only open for a few minutes), but something to keep in mind if you're hoping to get somewhere on time. Schedule: opens on the hour and half hour.