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When was the last time you and your ificant other made time for one another? Research consistently shows that traveling with your partner relieves tension, improves interpersonal communication, and strengthens your bond.


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So, if you want to impress that special someone, then you should for sure check out some of the ideas that are listed below for you! Not only does the Annapolis Valley have fantastic restaurants, they also have fabulous activities to do on your date. So, you should really start to plan a superb date for that someone special in your life.

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Some posts on this site contain affiliate links, meaning if you book or buy something through one of these links, we may earn a small commission at no extra cost to you. One of our very favorite places on the East Coast, the beautiful city of Annapolis often gets overlooked in favor of its larger neighbors like Baltimore or Washington, DC. But there are so many fun things to do in Annapolis, Maryland.

It has everything to do from visiting historic sites to wine tasting to sailing the Chesapeake Bay, and a lot in between, too. Although a stroll down Main Street gives you a great taste of Annapolis, the capital city is so much more than that. To gain a greater appreciation for all this cute place has to offer, hop on a trolley tour. In just an hour, the guide will give you a quick walk through years of history while driving by some of the prettiest buildings around.

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His estate, originally built between andnow stands as one of the greatest historical places to see when you visit Annapolis. The mansion, summer house, and sprawling two acres of formal gardens are certainly worth a tour and a stroll, especially on a nice day. Visit the William Paca House to see period furnishings and get an understanding of how the elite lived during the years before and after the American Revolution.

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Walk around the pond, stop to smell the many flowers, and admire the kitchen garden. We loved climbing to the top of the summer house for a view of the beautiful property. Today, you can visit the Old Senate Chamber and see old George dressed in his finest and letting his intentions be known. A stop at the State House is a quick visit and a must for anyone interested Annapolis date ideas history.

Just a few miles from downtown Annapolis is one of the top places to visit in Annapolis— Great Frogs Winery. The grapes are expertly crafted into more than a dozen wines showcasing white, rose, and red varietals and blends. Book a weekend tasting of their wines or a full wine, cheese, and charcuterie sampling experience to see the best of what Great Frogs Winery has to offer. Our favorites were the earthy Chardonnay and the spicy Meritage along with some fantastic local brie. It is named after Benjamin Banneker, a notable scientist and writer, and Frederick Douglass who escaped slavery to become one of the most prominent leaders of the anti-slavery movement.

Visitors can learn about Black life, art, music, and history in the state. The small but educational museum is truly a hidden gem in Annapolis.

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Upstairs, the rooms at Annapolis Waterfront Hotel are inspired by the setting on the water and have beautiful views of downtown or Spa Creek. Downstairs is Pussers Caribbean Grille, an outpost of the popular restaurant and bar that made its name far south of here in the British Virgin Islands.

The combination of style and relaxation gives you the best the city has to offer. Just on the other side of the Spa Creek Bridge is the community of Eastport. The City Dock is a fun place for people-watching on a nice afternoon.

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Crowds tend to gather by the water to watch the boats come in and dream about buying their own one day. Second is the morning ritual. Everything and everyone stops for a few brief seconds to salute the flag. And, depending on the time of year, you may just find yourself standing next to a state legislator or the governor himself.

He has his own booth, after all. Main Street is a haven for shoppers. And lovers of good food. And art aficionados. And people who like to relax. There are dozens of street art murals to see in Annapolis. Additionally, a local non-profit called Future History Now works with youth in underserved communities to add meaningful murals every year.

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Annapolis Ice Cream Company is one of our very favorite stops in the city. Annapolis Ice Cream Company has 36 rotating flavors made of super-premium ingredients. One of the most attractive features in the city is the waterfront.

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Two of the most popular ways to get out on the water are on the Harbor Queen or the Schooner Woodwind. Either way, your time on the bay will be fun. Annapolis Electric Boat Rentals offers a unique chance to take one of their boats out on your own. Gather some friends, your favorite snacks, and some beverages, and head out.

The electric boats can hold up to 11 people—captain included—for a few hours or a whole day on the water. What better way to experience the water?

12 exciting date adventures in the annapolis area

It is the only memorial of its kind in the country. The Memorial consists of three parts—a sculpture that depicts Haley reading to children of different ethnicities, a series of 10 bronze plaques on the nearby seawall, and a foot-wide granite and bronze compass rose. Right in the heart of downtown, the memorial is free to visit and always open. Annapolis is known for its seafood. From Maryland blue crabs to Chesapeake Bay oysters and rockfish, there are so many local types of seafood to choose Annapolis date ideas.

On a minute tour, guides take you to some of the main sites on the campus of this National Historic Site. Tours also visit the famous crypt of John Paul Jones, and most days there is a stop in the beautiful Naval Academy Chapel. For over 20 years, the Rams Head On Stage has been a mainstay of downtown. You can have a meal in the pub before the show or head straight into the club for dinner and drinks during the performance. Where to Eat For a town with a compact center, Annapolis is absolutely full of amazing restaurants.

Here are some of our favorites. All opinions of the charming and fun are our own. This site uses Akismet to reduce spam.

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Learn how your comment data is processed. Great itinerary and overview of Annapolis! I love the history of the city.

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We will give your suggested restaurants and taverans a visit. Nice post. This a good list for weekend visitors to gauge the nicer nightlife and daytime amenities that Annapolis has to offer.

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I came across this site looking for local events and ideas, as I am a born and bred Annapolitan my family has been here since the late 60sbut on a lovely Tuesday late afternoon, thought I'd see what I could get myself into. However, I want to make one thing very clear cause I very regularly hear this from tourists Annapolis is in NO way, shape, or form a "college town".

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We house the Naval Academy which is an academy and not your typical underage college students getting drunk in their dorm. It's a generational mix of a city; many retirees, working-class families, young yuppies, etc. There is an active young crowd that inhabits the downtown nightlife. A college town is explicitly an area where the demographic is dominated by the university population Sorry to rant, but I wanted to clear that up. I also enjoyed these most amazing things during my last journey of this fabulous destination and we came back with unforgettable memories.

There are great picks.

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My Family and I come to Annapolis often--especially during the summer and as many years as we've been hanging out there, there is always something new to do and discover. Take a trolley tour. The crypt of John Paul Jones. Bryson Fico Monday 12th of July Laura Tuesday 6th of October Aaron Saturday 2nd of November Veronica Monday 1st of April Julie k Thursday 21st of March As Seen On.