Must See Attractions in Annapolis

One of America’s great historic cities, Annapolis is famous for its Georgian and beaux arts buildings, romantic cobblestone streets, and charming harbor district with shops, fine dining, and family-friendly attractions. This city by the bay is not shy about its love of the sea, from yachts to evening sails to decadent seafood, and that’s just how we like it. With so many historic sites, fascinating museums, and scenic waterways we know it can be daunting to plan your itinerary, but you won’t want to miss any of these must see attractions in Annapolis!

Sail On!

As the sailing capital of America, no trip to Annapolis is complete without a voyage out onto the charming waters of Chesapeake Bay. Take a romantic sunset cruise aboard a classic wooden schooner, learn to sail at Annapolis Sailing School, or simply hop aboard one of the water taxis linking all the points of interest along Annapolis’ shoreline. For a special treat check out Schooner Woodwind and indulge in one of their decadent dinner cruises, or stay overnight for their popular “Boat and Breakfast”, one of our favorite ways to catch a sunrise over the Bay (while enjoying a delicious breakfast, no less).

Historic Downtown and Other Must See Attractions in Annapolis

Founded around the confluence of the Severn River and the Chesapeake Bay, the historic downtown district is impossibly idyllic. Cobblestone streets intertwine around colonial-era architecture and historic builds. We love spending at least a morning here, though you can easily enjoy an entire day. Take in the manicured grounds of the U.S. Naval Academy and marvel at its classic Beaux Arts facades, visit the country’s oldest capital building, the Maryland State House (built in 1772), or grab a meal with a view at one of the many delicious restaurants lining the waterfront.

Ego Alley

The City Docks are also known as Ego Alley thanks to the penchant for captains of all classes to showcase their boats on this narrow waterway. Here the streets are lined with cafes, boutiques, gift shops, art galleries, and more. Nearly everywhere you go has splendid views of the river, harbor, and the bay, making it a perfect place to grab a meal any time of year but especially during the weekend sailboat races in May and the annual boat show in October. Which reminds us…

Eat Crab Cakes!

This one speaks for itself. Available in nearly every restaurant, this Maryland specialty is not to be missed! If your stay is over a first or third Sunday (July-Sept.), don’t miss the Annapolis Crab, Crash & Cruise at Chesapeake Brewing Co. of Annapolis. Eat your fill of steamed crabs, fried chicken, crab cakes, grilled corn, Maryland’s state cake (yeah, we have one), and of course, beer!

At Home Annapolis is proud to offer more than just the best selection of vacation rentals in Annapolis; we strive to provide you with the absolute best vacation possible. While you may have trouble deciding what to do when you visit, you can sleep easy knowing you made the right choice in your accommodations. Browse our wide selection of properties or contact our expert local guides to help you plan your trip, today!