Brunch at Carrol's Creek
Start your day by heading to the Annapolis City Marina, where Carrol's Creek is tucked away amid sailboats, yachts, and floating docks. Grab a table with a view and dig into the brunch buffet ($23.95), which includes your choice of a Bloody Mary, mimosa, or champagne.
Carrol's Creek, 410 Severn Avenue; 410-263-8102.
Refuel at Ceremony
Top-notch coffee roaster Ceremony supplies some of D.C.'s best java spots with quality beans, so take advantage of your proximity and head here for a mid-afternoon pick-me-up. You'll feel like you've been transported to Seattle or Portland with one sip.
Ceremony Coffee Roasters, 90 Russell Street; 410-626-0011.
Browse the racks at Navette
The sole consignment shop in the historic district, Navette is a charming mashup of vintage, modern, and designer finds. The operation is helmed by a design industry vet who sources plenty of wares from smaller NYC designers, so make this a must-visit on your itinerary.
Navette, 88 Maryland Avenue; 410-280-1590.
Get a sweet fix...
Treats from Caroline's Cakes are somewhat legendary among those with an insatiable sweet tooth — after all, Oprah deemed the 7-Layer Caramel Cake one of her favorite things. After a long day of sightseeing, stop by the bakery for a slice of the former, or branch out and try the Coconut Lemon Delight — four layers of yellow cake and lemon curd, topped with fluffy coconut frosting.
Caroline's Cakes, 1580 Whitehall Road; 410-349-2212.
...or a savory one
Want a snack that's a little less indulgent? Make your way to Bakers & Co., a newly opened hotspot for fresh-baked breads and pastries, tasty soups, and savory tarts. The earlier you can stop in, the better, since the small batches tend to sell out quickly.
Bakers & Co., 618 Chesapeake Avenue; 410-280-1119.
Savor the perfect glass of wine
In the eclectic Eastport neighborhood, this so-cozy dinner spot makes for a charming end to a day in Annapolis. With organic heirloom produce and meats provided by Groundworks Farm, the menu focuses on American classics with tasty Mediterranean flourishes.
Vin 909, 909 Bay Ridge Avenue; 410-990-1846.
Photos: Courtesy of Navette, Caroline's Cakes, Carrol's Creek
Shop the Amish Market
The Pennsylvania Dutch Farmer's Market at Annapolis Harbour Center is a haven for foodies and fans of handmade goods. Open Thursday through Saturday, the market offers everything from fudge and soft pretzels to spices, teas, and handcrafted furniture.
Amish Market, 2512 Solomons Island Road; 410-573-0770.
Get on the water
That's right — even if you didn't arrive in Annapolis by boat, you can still make the most of being on the Bay. If you have a weekend to spare, take a beginner's course with the Annapolis Sailing School and learn the basics, starting with sailing lingo and building up to operating one of the fleet's Rainbow vessels.
Annapolis Sailing School, 7001 Bembe Beach Road; 800-638-9192.
Crabs, crabs, crabs!
A trip to Annapolis isn't complete without smashing your way through a heaping pile of steamed Maryland blue crabs at Cantler's. Find a spot at one of the paper-covered picnic tables and be prepared to work for your supper. Pro tip: Order plenty of sides, so you're not picking on an empty stomach.
Cantler's Riverside Inn, 458 Forest Beach Road; 410-757-1311.
Catch some live music
Known for the stellar rooftop, Metropolitan Kitchen & Lounge is also home to a 2,000-square-foot live entertainment space, where you can experience indie musical acts, improv comedy, live DJs, performance art, and more.
Metropolitan Kitchen & Lounge, 169 West Street; 410-280-5160.
Make it two scoops
Order up some of the best ice cream in town at Annapolis Ice Cream Company, where flavors include Peanut Butter Oreo, Apple Pie, and Chocolate Brownie Batter. Even better? This stuff is made fresh in-house every day. Don't say we didn't warn you.
Annapolis Ice Cream Company, 196 Main Street; 443-482-3895.
Have a nightcap
Polish off a stellar day in Annapolis with a frozen concoction at The Severn Inn, where you'll be greeted with impressive panoramic views of Annapolis and the Severn River. Try to score a table outside for the full I'm-on-vacation experience.
The Severn Inn, 1993 Baltimore Annapolis Boulevard; 410-349-4000.
Photos: Courtesy of Annapolis Sailing School, Severn Inn, Cantlers