Annapolis Weekend Getaway: Boating, Seafood, and Waterfront Charm on the Chesapeake Bay

Known as the Sailing Capital of the U.S., Annapolis invites you to stroll its brick-lined streets, dine on fresh seafood, and spend your days soaking up the views from the deck of a boat.

If you’re craving a weekend that feels like a true vacation—but without the long flights or big planning—set your sights on Annapolis. This charming Chesapeake Bay town offers just the right mix of relaxation and adventure, perfect for couples, families, or friends looking to unwind by the water.

Whether you’re planning a romantic retreat or a last-minute escape, here’s how to make the most of your Annapolis weekend getaway.

Stroll through history in downtown Annapolis

Start your trip by exploring the heart of Annapolis. The city’s historic district is packed with colonial charm, boutique shops, and waterfront cafes. Meander down Main Street, grab a coffee, and take in the sights along Ego Alley—where sleek yachts and sailboats line the harbor, showing off the city’s nautical roots.

Tour the U.S. Naval Academy, visit the Maryland State House, or just relax and enjoy the small-town vibe that makes Annapolis so special.

Get out on the water: Boating and sailing in Annapolis

Why Annapolis is a sailor’s paradise

Located in the heart of the Chesapeake Bay, Annapolis boasts some of the best sailing conditions and water access on the East Coast. With protected inlets, steady breezes, and a vibrant boating culture, it’s a dream for seasoned sailors and newcomers alike.

The city is home to the U.S. Naval Academy, countless marinas, and a thriving community of yacht clubs, sailing schools, and regattas. Plus, its harbor sits just steps from one of the most walkable and welcoming downtowns in the region.

Whether you're here to cruise, race, or relax, Annapolis delivers an unforgettable Chesapeake Bay experience. Want to stay close to the action? Some Annapolis vacation rentals even offer dock access or are just steps from local marinas.

Top sailing experiences in Annapolis

From serene sunset cruises to hands-on lessons, Annapolis offers sailing experiences for every kind of adventurer:

Schooner Woodwind Cruises – Board this classic 74-foot sailing yacht for a two-hour public cruise or private charter. Departing from City Dock, it's a must-do with views of the U.S. Naval Academy and Chesapeake Bay Bridge.
Private Sailing Charters – Book a crewed sailboat or catamaran for a half-day or full-day voyage. Many charters offer custom itineraries, BYOB cruises, or romantic outings.
Sailing Lessons – Learn from the pros at Annapolis Sailing School, which offers both beginner and advanced programs.
Scenic Spa Creek Cruise – Stay close to shore with a casual cruise through Spa Creek or Back Creek, where brightly painted homes and iconic docks complete the view.

Signature sailing events to look out for

While Annapolis offers spectacular cruising year-round, a few signature sailing events stand out for visitors:

Wednesday Night Races (Spring–Summer) – A beloved local tradition, these weekly races fill Spa Creek with colorful sails and lively energy — watch from the water or the harborfront.
Annual Regattas – Hosted by the Annapolis Yacht Club, these events bring competitive sailors and a festive maritime vibe to town.
Eastport Yacht Club Lights Parade (Winter) – During the holiday season, sailing takes a festive turn as boats are adorned with lights and cruise through the harbor in a floating parade.

Feast on fresh seafood and dockside dining

No Annapolis weekend getaway is complete without indulging in the area’s legendary seafood. As a coastal city perched on the Chesapeake Bay, Annapolis offers a bounty of fresh, locally sourced favorites—from Maryland blue crab to briny oysters and buttery rockfish.

Start with crab cakes, a Maryland specialty often served broiled and packed with lump crab meat. Or go classic with a steamed crab feast, where you’ll crack into seasoned blue crabs with Old Bay seasoning and plenty of drawn butter. Local oysters—plucked fresh from the bay—are served raw, grilled, or fried, and pair perfectly with a crisp local beer or white wine.

Top seafood restaurants in Annapolis:

Boatyard Bar & Grill – A lively Eastport staple known for its award-winning crab cakes, raw bar, and laid-back sailing vibe.
Carrol’s Creek Café – Upscale yet approachable, this waterfront spot is perfect for date night. Try the cream of crab soup or the rockfish imperial.
Chart House – Set directly on Spa Creek, this scenic restaurant combines elevated seafood dishes with panoramic views of the harbor.
Osteria 177 – For a twist on traditional seafood, head here for Italian fare with local ingredients, including seafood pasta and fresh scallops.
Cantler’s Riverside Inn – A bit off the beaten path, this local institution is known for picnic-table crab feasts and unbeatable waterfront ambiance.

Many restaurants offer dock-and-dine options—so if you're out on a boat, you can pull right up to shore and enjoy your meal with a side of sea breeze.