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Have you ever thought about living in a city that has a wealth of rivers where you can enjoy the water as much as you like? Having the possibility to explore these waters or rejoice is some of your favorite water activities. Being surrounded by cruises, yachts, and other people that enjoy sailing just as much as you do.


One such place is Annapolis, a small town of about 40,000 people that is located on the Chesapeake Bay in Maryland. However, “small” is not the right word to describe the amazing city of Annapolis, MD. It is after all the capital of Maryland and it was titled the Sailing Capital of the US.


Many consider Annapolis, MD to be a sailors paradise and because of the family-friendly environment along with top-notch amenities, it makes the city one of the best places to live in Maryland. You would be amazed at how much Annapolis has to offer, it’s like a treasure waiting to be discovered. If you happen to come by this amazing city then, here are five things to do in Annapolis MD during a weekend.

Heritage Region Wine Tour

You might think that being close to the water, the food industry would be saturated with seafood and nothing more. It is true that Annapolis, MD stands out for its local fresh seafood and also by having some of the best places to eat. But, did you know that the area is also known for its vineyards and local wine producers?


Yes, that’s right, Mayland’s countryside is home to some large wine producers and the quality of their products is undeniable. How can you get to visit and sample some of the best-tasting wine in the area? Simply by attending one of their wine tours. If you have the opportunity to spend a weekend in Annapolis, this is definitely a tour you have to attend to.


Just a few miles away from downtown Annapolis, lies the Great Frogs, Thanksgiving Farms as well as Friday’s Creek. Book a weekend of sampling a variety of wines along with different cheeses or snacks that mix and match perfectly with the wines. This 5-hour small-group tour offers you a complete experience where you get to taste the region’s famous popular white wines along with exploring one of the most historic areas in the country.

US Naval Academy

Another important reason why the city is called the Sailing Capital of the US is the fact that within its boundaries lies one of the most prestigious academies, the US Naval Academy. The next generation of midshipmen is born within the academy, and it is dedicated to forming the leaders of tomorrow. Attending a military education at the academy is hard and graduating is challenging. Many plebes fail to get through boot camp, but graduating is a very rewarding experience.


However, as a tourist, you might not be interested in military education, but getting to explore the history behind the academy and getting to know some of the bravest midshipmen, is definitely something you have to do.


By far one of the most popular things to do in Annapolis is taking a 90-minute guided tour through the main sites of the campus. It is a National Historic Site and you get to visit the gym and learn about the Academy’s athletic program and see its Athletic Hall of Fame with famous graduates. You will also have the opportunity to see the giant dorm that houses 4400 midshipmen, the statue of Indian warrior Tecumseh, the famous crypt of John Paul Jones as well as the Naval Academy Chapel.

Explore the Heart of Annapolis

A small and hearty town is the perfect way to describe the city of Annapolis, MD and if you don’t believe us a stroll through downtown Annapolis will surely change your mind. The rich history of the city and the fact that it was amongst the first planned cities in America make it a beautiful place that keeps most of its original features.


If you have the opportunity to spend a weekend in Annapolis, MD you can discover the rich history along with the hidden gems of Annapolis, through a small-group tour. Make yourself comfortable in one of the open-air eCruisers and enjoy the sights. Sit back, relax, and enjoy the unobstructed views while your diver guides you through the city’s heritage to life.


Pass through the historic district that is lined with colorful homes and thought out neighborhoods that very few visitors know about. Not to mention the fact that downtown Annapolis has some of the best restaurants in town and now that you know the city better you are free to navigate through Annapolis independently.

Have a shopping spree on Main Street

Annapolis, MD is famous for its red-brick Main Street and one of the reasons for that is the fact that this area is a haven for shoppers and food lovers. Art enthusiasts will also be glad to find a variety of boutiques and galleries where they could buy whatever their heart desires. Main Street is not exclusively destined for shoppers, it is also the perfect place for a stroll or for people who just want to relax.


The amazing area holds a variety of shops and boutiques where you can browse for anything that you might find interesting. If you get tired of shopping you can have a set at one of many restaurants, coffee shops, or bars while you have a beverage, coffee, and dessert or spoil yourself with some of the local favorite seafood dishes.


If you have the opportunity to spend a weekend in Annapolis, MD this definitely should be on your list of things to do. You will love the city and you might even consider moving here, which is not an unreasonable decision if you find real estate agents in Annapolis MD who can help you transition easily in your new home and live your best life.

Rent your own boat

If you don’t like cruising along the river with other people you have the alternative to be your own captain and drive your own boat. The Chesapeake Bay, as well as Severn River, are so beautiful that it entices you into exploring them. Now it is possible thanks to Annapolis Electric Boat Rentals, who give you a unique opportunity to take a boat out on your own.


Gather your group of friends, grab some food and beverages to help you along the way, and head out into the open. You can cruise Spa Creek and have a look at the impressive mansions that line up the waterfront of Back Creek and take turns in showing off in Ego Alley. You will surely have a blast, and this should definitely be high up on your list of things to do in Annapolis, MD.


Overall, we can say that Annapolis, MD is one of the best places to spend a weekend and there are so many things you can do that it is hard to cover everything in a single weekend. You will not leave disappointed, and you will surely want to come back for round two after you get to enjoy some of what this city has to offer.


If you had the chance to visit Annapolis, MD, and do some of the things mentioned above make sure you spread the word by sharing this article with your friends on your social media accounts.

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