With more surviving 18th century buildings than any other city in the United States, visiting Annapolis is like stepping back in time to the days when the city was a colonial seaport. Known as America’s Sailing Capital, the city is located on the shores of the Chesapeake Bay and is a paradise for water lovers, famous for its crab cakes, lighthouses, and 500 miles of gorgeous shoreline. Tour the campus of the US Naval Academy, or the Maryland State House, the oldest state capitol still in use.
Restaurants in Annapolis
5.0 based on 239 reviews
Annapolis Eventours offers unique and authentic day tours around Annapolis using all-electric, 5-passenger vehicles. They cover back streets, hidden gems and fascinating sights. Step into the lives of locals, find out what makes the city tick, and get acquainted with the local food, culture and history of Annapolis. A local, expert guide will lead you through a fantastic urban experience. Join us for our Explore the Heart of Annapolis history tour, or our Original Annapolis Seafood Crawl.
5.0 based on 123 reviews
Enjoy your private sail charter with captain (up to 6 people) for a half day, full day, or sunset cruise in the Chesapeake Bay. Sail under the Bay Bridge, tour the light houses, or sip wine with a special someone as the sun sets over Annapolis.
5.0 based on 48 reviews
FREE! ANNAPOLIS WALKING TOUR (Tips Only) JOIN US FOR AN UNFORGETTABLE JOURNEY THROUGH THE COLONIAL STREETS OF ANNAPOLIS, MARYLAND FOUNDED IN 1649 FASCINATING and OFTEN FUNNY & UNIQUE PERSONAL STORIES ABOUT THE REAL ANNAPOLIS FRIDAY, SATURDAY, and SUNDAY (No Rain Tours) Duration - 2.5 hours * Distance - 2 miles Meet @ Kunta Kinte Memorial @ City Dock
5.0 based on 39 reviews
FUNtastic and relaxing SAILING trips from historic Annapolis,MD less than an hour away from Washington or Baltimore. Join me, Captain Paul Foer on my restored classic sailboat 38' sailboat, "Non Sea Quitter", as we sail on the Severn River and Chesapeake Bay where I grew up boating with my family. We offer private trips for up to six guests. While visiting, you may enjoy waterfront dining, live music and lodging at nearby restaurants and other nearby tourist, historic and outdoor attractions. Come for a few hours, a day or even an overnight adventure. Sit back and relax or help us raise sails and take the wheel as we sail across the open Bay and see globe-trotting freighters, yachts racing, the Chesapeake Bay Bridges, osprey, ducks and maybe even rays or dolphins swimming. Funtastic sailing for all ages.
4.5 based on 950 reviews
Watermark is your destination for fun on land and sea in Annapolis through sightseeing cruises and walking tours. Come enjoy a 40 minute cruise on the iconic Harbor Queen or take a walking tour with our Colonial guides. Choose from our variety of regularly offered cruises, walking tours and special events. Watermark offers many ways to have fun in Annapolis! We also offer group tours, field trips and private events on our yachts.
4.5 based on 365 reviews
One of our favorite spots in Annapolis. Whether you go during they day to watch the large yachts turn around or sit there by night with all the glowing lights surrounding the alley, it's nice area to just sit and relax. There is plenty of seating around the entire alley. You can enjoy lunch or an ice cream cone at night and listen to live music. It's the perfect backdrop for selfies!
4.5 based on 307 reviews
The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. Come Sail Away!
4.5 based on 1,255 reviews
The ideal first stop here is the main Visitors Center (with the Gotts Court parking garage next door) to gather a map and info. This is just a block from the beautiful capitol building which is a MUST to visit (self-guided tour and photography allowed) and surrounded by gorgeous vintage buildings. Radiating like spokes from the street circling around the capitol are streets lined with unique shops, galleries, a pottery studio, restaurants... This is a delightful area and so easy to explore on foot while your car is tucked away in the parking garage.
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