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Articles - Annapolis, Maryland, United States of America

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Waterfront Dining
10 Best Waterfront Dining Spots In Annapolis, Maryland

Annapolis is a gorgeous city packed with brick houses dating back to the 18th century. As it's situated on the Chesapeake Bay, this waterfront destination attracts many tourists every year. While you are in Annapolis, you can take a trolley ride to explore the city, stroll around Annapolis City Dock, marvel at the Georgian-era William Paca House & Garden, admire the architecture of Maryland State House, and sample wine at Great Frogs Winery. There are also a number of amazing accommodations available, such as Vrbo waterfront vacation rentals and hotels with hot tub, if you wish to make the most of your visit. Those looking to dine with a water view will love Annapolis. Here is a list of the best waterfront dining spots in Annapolis, Maryland.
Seafood Restaurants
12 Seafood Restaurants In Annapolis, Maryland

Maryland's 350-year-old capital, Annapolis, is a vibrant city renowned for its charming colonial history and venerated sailing tradition. With more 18th century buildings than anywhere else in the country, Annapolis is a great destination to spend time with your family and experience the cultural activities and explore the culinary scene that showcases the region's seafood fare. For the thrill-seekers, you can rent a boat to explore the Chesapeake Bay further. From shacks serving the world-famous Maryland blue crabs to waterfront dining spots with stunning views of the harbor, restaurants in Annapolis offers a little something for every taste. Let your taste buds savor the perfect meal in the sailing capital of United States. Learn more about the best seafood restaurants in Annapolis, Maryland.
Vrbo Waterfront
Top 7 Waterfront Vrbo Rentals In Annapolis, Maryland - Updated 2025

The capital city of Maryland is also known as the sailing capital of the United States. The city has carefully preserved its heritage, the remains from the colonial era can be seen in various parts of the city. The beautiful brick row houses, cobblestone streets, and the traditional colonial architecture exude the typical feel of a past era. It has a long maritime history, along with the largest in-water sailboat show of the world. This city is the home of the U.S. Naval Academy, and you can take the historical USNA tours to know more about it. Downtown Annapolis is very interesting too, you can explore its typical colonial architecture, or walk till Ego Alley to see the boats. Take a sip of the classic rum cocktails in Pusser's Caribbean Grille while watching the boats of Ego Alley. The most intriguing part of this town is most definitely the waterfront. Check out the waterfront Vrbo rentals in Annapolis, Maryland, to explore the town in detail.
Yacht Charter
5 Best Yacht Charters In Annapolis, Maryland

Annapolis boasts itself as a museum without walls and "America's Sailing Capital." As Maryland’s capital, it brims with an upbeat, modern vibe that blends well with centuries-old architectural works. It is renowned for its rich, nautical heritage, with its connection to Chesapeake Bay so you can expect to find various accommodations near the water, from luxury hotels to Vrbo waterfront vacation rentals. Famously, it is home to US Naval Academy (USNA), which has been providing education and training to US Navy officers since 1845. USNA has a museum commemorating the achievements and traditions of the US Navy and Marines. A trip to this historic city is not complete without touring Maryland State House, which once served as the capital of the fledgling United States. To have a genuine, local experience here, try sailing and rent a boat or yacht. Check out some of the best yacht charters in Annapolis, Maryland.
Hotels With Pools
10 Best Hotels With Pool In Annapolis, Maryland

Annapolis is an important part of American history. In this state capital, the Treaty of Paris was ratified, signifying America's official independence from Great Britain. This alone should make Annapolis part of every American's bucket list of go-to destinations. But if history bores you and you want the excitement of experiencing what happens in the now, all the more reason to visit Annapolis. Known as the "Sailing Capital of the US", Annapolis is ideal for adventurers who seek the water. Take part in one of the sailing competitions, or simply tour Annapolis by boat, kayak, canoe, or paddleboat. The city also has hotels with pools if you can't get enough of a day of adventure in the water. Read this list of the best hotels with pool in Annapolis, Maryland, to get your trip started.
Rent A Boat
Rent A Boat In Annapolis, Maryland

Annapolis, Maryland’s capital city, has incredible attractions for all types of travelers. The trolley tours, the museums, the wineries, and great outdoor opportunities provide an endless list of things to do and see. But how exciting would it be for you to retreat to a boat for the night once you are done with your day’s wandering? Well, having your accommodation in a waterfront Vrbo rental or on a boat is another great experience you should consider, given that Annapolis has many lovely vacation rentals with incredible sea views. Does going for boat accommodation on your next Annapolis trip sound like a good idea? Consider the following options if you would like to rent a boat in Annapolis, Maryland.
Airbnbs With Pools
7 Best Airbnbs With Pool In Annapolis, Maryland

A gem on the Chesapeake Bay, Annapolis, the capital city of Maryland, has plenty of opportunities for sightseeing and outdoor adventures. It takes pride in having beautiful parks, stunning colonial architecture, numerous art galleries, theaters, and festivities. Maryland State House, the oldest U.S. State Capitol, is a must-visit landmark in the city. You can also learn more about the U.S. Navy and Marines in the U.S. Naval Academy Museums. For hiking and biking trails, you can visit Quiet Waters Park. It has an enormous playground where children can run wild and a dog beach. You can also enjoy water activities such as kayaking, canoeing, and more. If traveling with family, visit Sandy Point State Park, a spot for bird-watching, picnics, and boating. For a comfortable stay, check out this list of the best Airbnbs with pool in Annapolis, Maryland.

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