Rebecca & Casey
Things To Do
Annapolis Lunch + Dinner Recs
Jalapeños (Spanish Tapas) – Rebecca’s favorite restaurant in Annapolis! The Point (Seafood) – Casey’s favorite restaurant in Annapolis! Boatyard Bar & Grill (American/Seafood) – Tied for best crabcake in Annapolis, try an Orange Crush! Paul's Cafe (Greek/Seafood) Carrol's Creek Cafe (American/Seafood) – Best view in Annapolis, tied for best crabcake in Annapolis Acqua al 2 (Italian) – The only other location is in Florence, Italy! The Big Cheese (To-Go Sandwiches) – Try the St. Mary’s Slugger! Giolitti’s (To-Go Sandwiches) Carpaccio Tuscan Kitchen and Wine Bar (Italian) Cantler's Riverside Inn (Crabs) – Best spot to pick Maryland crabs Seasalt Annapolis (Seafood) Lemongrass (Thai) Joss Cafe & Sushi Bar (Japanese/Sushi) Lewnes' Steakhouse (Steakhouse) – Go for a nice steak! Vin 909 Winecafe (American) Timber Pizza Co. (Pizza) Vida Taco (Tacos) Davis' Pub (American) - a local favorite with a water view, local beers, and jumbo pretzels topped with crab dip
Annapolis Breakfast, Brunch + Coffee Recs
Boatyard Bar & Grill (American/Seafood) – Often packed with locals and visitors seeking crabcakes or a weekend brunch Eggcelence (American) – Good breakfast/brunch spot Naval Bagels (Bagels) Rise Up Coffee (Coffee/Quick Breakfast) – Our favorite coffee spot in Annapolis! Rebecca loves the Cinnamon Toast Crunch Coffee Smoothie Bean Rush Cafe (Coffee) Ceremony Coffee Roasters (Coffee) Rutabaga Juicery & Eats (Smoothie Bowls) Call Your Mother Deli (Bagels) The Iron Rooster (American) – Try a homemade poptart!
Annapolis Drink Recs
Chessie's Wharf (Brewery) – Our favorite day-drink and happy hour spot in Annapolis, love the lactose-base sours, smash burgers are great! Harold Black Annapolis (Speakeasy) – Below Acqua al 2! Good post-dinner drink spot, great espresso martinis Galway Bay (Irish Pub) Fox's Den (Gastropub) – Good post-dinner drink spot. It's just a narrow door on the street, but downstairs you’ll find a big, buzzy space with a bar and tables shared by locals. Forward Brewing (Brewery) – Good day spot The Choptank (American/Cocktails) - among the town’s newer bars/restaurants, with great water views Parley Room (Cocktail Bar) Sailor Oyster Bar – Great for pre/post dinner cocktails with a warm neighborhood vibe
Annapolis Sweet Treat Recs
Annapolis Ice Cream Company (Ice Cream) – Our favorite ice cream in Annapolis Always Ice Cream (Ice Cream) The Red Bean (Ice Cream) Sandy Pony Donuts (Donuts) – Yummy cake donuts Carlson’s Donuts (Donuts) – Traditional housemade donuts Harvest Bread Company (Bakery) – Great baked goods Black Market Bakers (Bakery)
Walk Along Maryland Avenue, Main Street & Ego Alley
Lots of cute shops and restaurants!
Tour the Annapolis Harbor and Naval Academy By Boat
See the Naval Academy and Annapolis on a narrated public tour aboard the Harbor Queen! We did this on Casey's first visit to Annapolis and had a blast. This 40-minute narrated cruise on the double-decker Harbor Queen powerboat ($25 for adults, $10 for children, departs hourly) describes key sights and history — especially of the Naval Academy — as the boat cruises through Spa Creek, the Severn River, and a large mooring field where recreational sailboats and powerboats anchor for the night. You’ll get a good view of the four-mile-long Chesapeake Bay Bridge, connecting Maryland’s mainland and Eastern Shore.
Go sailing in the Chesapeake Bay
The 74-foot schooner Woodwind, which can accommodate up to 48 passengers, provides two-hour sailing excursions on the Chesapeake Bay. You’re in the self-proclaimed Sailing Capital of America, so join the fun! Leaving from the Annapolis Waterfront Hotel’s dock several times a day, the boat will cruise past the Naval Academy before venturing into the Chesapeake Bay. Depending on the wind, it might head north toward (and possibly under) the Chesapeake Bay Bridge. Or it might turn south, toward Thomas Point Lighthouse, still active after 150 years. Passengers can help hoist the sails and even steer. Here’s your chance to learn some sailing basics: Why are you heading this way if your ultimate goal is over there? What’s the difference between tacking and jibing? Tickets are $79.65 on Saturdays, $75.25 on Sundays.
Book a Private Boat Charter
Book a private boat ride with Darling Charters Annapolis. A great way to see Annapolis from the water!
Stand-Up Paddleboard or Kayak with Capital SUP
A great way to exercise and have fun. The Eastport location is most convenient!
Explore the Maryland State House
Go on a self-guided tour of the Maryland State House! The State House is open to the public every day from 8:30 a.m. - 5:00 p.m. The Maryland State House is the nation’s oldest state capitol in continuous legislative use and was briefly the U.S. capitol (1783-84). See where George Washington resigned his commission! Plaques will tell you the building’s top — assembled with wooden pegs, not nails — is the nation’s largest wooden dome. Maryland legislators still convene here January through April. In the floor, look for ancient snail fossils that were embedded in the stone eons ago and included by builders to highlight Maryland’s coastal geology.
Tour the Naval Academy
You can either walk on base or book an official tour of the Academy! The U.S. Naval Academy is home to future officers, the nation’s largest dorm, and the crypt of the naval hero John Paul Jones. Tour the visitor center, Preble Hall museum, and the main Chapel, which includes the crypt of the Navy icon John Paul Jones.
Hike the Annapolis Waterworks Trail
This is really the only hike you can do in Annapolis - it may surprise you! Park at the shopping center across the street (2601 Housley Road, Annapolis, MD) and walk over.
See a Show at Rams Head on Stage
Hosts nationally known musicians... check out the lineup! Even if you don’t see the stage acts, the adjacent Rams Head bar and restaurant is one of Annapolis’s biggest and most popular bar scenes.
Reserve a Walking Ghost Tour of Historic Annapolis
Make sure you select the Annapolis location. We did this with friends at another location and had a great time!
Walk Through the Pennsylvania Dutch Farmers' Market
We love the soft pretzels and pretzel dogs! Open Friday and Saturday, closed Sunday.
Go for Traditional English Tea at Reynold's Tavern
Scones, tea sandwiches, bottomless tea... have yourself a day!
Tour the William Paca House & Garden
The William Paca House & Garden, a beautifully restored colonial mansion and grounds, was home to a signer of the Declaration of Independence. Paca — who signed the Declaration of Independence and was Maryland’s third governor — helped design the impressive home built in the 1760s. Restoration began in 1965, and it’s now a National Historic Landmark. Guides describe a typical day for the wealthy owners, middle-class craftsmen, and enslaved servants who intermingled in the house. The two-acre garden has terraced landscapes with boxwoods, a latticework bridge over a fish-shaped pond, a wilderness section, and a two-story summer house. A guided tour of the house and access to the garden is $12 for adults, $7 for children. Garden access only is $5.
Tour the Banneker-Douglass-Tubman Museum
The Banneker-Douglass-Tubman Museum celebrates African American heritage, focuses on the underground railroad network that helped enslaved people escape to freedom, and also features modern artworks (closed Sundays). Harriet Tubman’s name was recently added to those of the scientist Benjamin Banneker and the abolitionist Frederick Douglass. Tiny but worthwhile, the museum in 2025 features works by the Washington-based multi-media artist Jabari Jefferson. His website says he searches local communities for discarded items and “believes in the transfer of energy in the materials from their previous owners.”
Check out the Visit Annapolis Website
There are always things going on!