12 Romantic Things To Do In Annapolis, Maryland

Welcome to Annapolis, Maryland - a charming coastal town with a rich history and an abundance of romantic activities for couples. From taking a sunset sail on the Chesapeake Bay to strolling hand in hand through the historic streets, Annapolis offers countless opportunities to create unforgettable moments with your significant other. Whether you're celebrating an anniversary, planning a weekend getaway, or just looking for some quality time with your loved one, here are 12 of the most romantic things to do in Annapolis that are sure to sweep you off your feet.

Take a sunset sail on the Chesapeake Bay

Are you looking for a romantic getaway in Annapolis, Maryland? Look no further than a sunset sail on the Chesapeake Bay.

As the sun begins to dip below the horizon, board a sailboat with your significant other and set off on a peaceful and serene excursion. The gentle sound of the waves lapping against the boat and the wind in your hair create the perfect ambiance for a romantic evening.

Take in the stunning scenery as you sail along the bay, passing by the historic landmarks of Annapolis and the Naval Academy. The soft glow of the setting sun casts a warm and romantic light over the city as you enjoy the beauty of your surroundings together.

As the evening progresses, sip on wine and indulge in delicious snacks while you watch the sky turn shades of pink, orange, and purple. The colors of the sunset reflecting off the water create a stunning and romantic atmosphere.

Whether you're looking to celebrate a special occasion or simply spend some quality time with your loved one, a sunset sail on the Chesapeake Bay is the perfect way to create lasting memories. Book your romantic Annapolis getaway today and experience the beauty and tranquility of the Chesapeake Bay at sunset.

Enjoy a romantic dinner at Osteria 177

Characteristic	Description
Name	Osteria 177
Type	$$$
Website	Go to website
Rating / Review count	4.7 / 567
Address	177 Main St, Annapolis, MD 21401
Phone	(410) 267-7700
Hours	Saturday - 5–10 PM Sunday - 5–9 PM Monday - 5–10 PM Tuesday - 5–10 PM Wednesday - 5–10 PM Thursday - 5–10 PM Friday - 5–10 PM
Profiles

Annapolis, Maryland is known for its picturesque waterfront views, historical significance, and charming streets. But it's also a perfect destination for a romantic getaway due to its rich culture, food, and calm beauty. If you're looking for a romantic dinner spot in Annapolis, we recommend Osteria 177.

Located on Main Street in the heart of Annapolis, Osteria 177 is a fine-dining Italian restaurant that has been consistently named one of the best restaurants in Annapolis. Its romantic ambiance, excellent service, and exceptional food make it a perfect place for a special occasion or date night.

Upon entering Osteria 177, the elegant and classic decor will transport you to Italy. The cozy atmosphere, perfectly dimmed lighting, and beautiful displays of wine bottles set the mood for a romantic evening. The restaurant also offers an outdoor seating area, which is a perfect spot during the warmer months.

The menu at Osteria 177 is filled with authentic Italian cuisine prepared by Chef/Owner Arturo Ottaviano, who was born and raised in Naples, Italy. Chef Ottaviano is known for his innovative and contemporary twist on traditional Italian dishes, making the dishes both hearty and light at the same time. The restaurant's menu includes homemade pasta, fresh seafood dishes, and mouth-watering meat options.

For a romantic dinner, we recommend starting with the Burrata, which is creamy mozzarella cheese served with fresh tomatoes and basil oil, or the creamy risotto with truffles. For the main course, the signature "Spaghetti alla chittara" with lobster, crab, and scallops is a must-try dish. If you love meat, try the Filetto di Manzo, which is the restaurant's top choice for meat lovers. Don't forget to pair your dish with an exquisite bottle of Italian wine from their extensive list, expertly curated by the restaurant's sommelier.

The restaurant's excellent service is another reason why Osteria 177 is a perfect romantic spot. The servers are knowledgeable about the menu and wine list, which makes the dining experience more comfortable. They also offer great suggestions and are attentive to all your dining needs.

In conclusion, Annapolis offers many romantic dining options, but Osteria 177 stands out with its authentic Italian cuisine, fine-dining atmosphere, and exceptional service. Its excellent combination of food and ambiance makes it a perfect spot for a romantic dinner, a special occasion, or a date night.

Stroll hand in hand through the historic streets of downtown Annapolis

There's something undeniably romantic about the historic streets of downtown Annapolis. Perhaps it's the charming brick buildings and cobblestone streets, or the picturesque waterfront views. Whatever the reason, it's no surprise that Annapolis is a popular destination for couples looking for a romantic getaway.

One of the best ways to experience the romance of Annapolis is to take a leisurely stroll through the downtown area. Start your journey at City Dock, where you can watch sailboats bobbing in the harbor while you hold hands with your sweetheart. Then, make your way up Main Street, taking in the sights and sounds of the bustling district.

As you walk, you'll notice an abundance of historic buildings and landmarks, each with its own intriguing story. Make sure to stop by the Maryland State House, the oldest state capitol still in continuous use, and take a tour of the grand building with your partner. You'll learn about the state's history and see some truly impressive architecture.

For a bit of added romance, plan your walk for the evening hours, when the streetlights cast a warm glow over the town. You'll have the perfect opportunity to duck into one of Annapolis' cozy pubs or restaurants for a candlelit dinner or drink. Try the Federal House Bar and Grille or the Oyster Bar at Vin 909 for a bite to eat in a cozy atmosphere.

Another romantic option is to take a sunset sail on the Chesapeake Bay. Companies like Schooner Woodwind and Annapolis Sailing Cruises offer scenic cruises that take couples past some of the Bay's most beautiful sights, like the Thomas Point Lighthouse and the Bay Bridge. Sipping wine and watching the sunset with your loved one is the perfect way to cap off a day of romantic strolling in Annapolis.

Whether you're celebrating an anniversary, planning a proposal, or simply want to spend a romantic weekend away, Annapolis is the perfect destination. With its historic charm, waterfront views, and cozy restaurants and pubs, this charming town is sure to steal your heart.

Take a scenic walk through Quiet Waters Park

Romantic Annapolis: Take a Scenic Walk Through Quiet Waters Park

For couples looking for a romantic getaway in Annapolis, there's one location that stands out among the rest: Quiet Waters Park. If you're looking for a beautiful, peaceful place to spend some time with your significant other, there's no better spot in Annapolis.

The park offers a range of activities that are perfect for couples, but one of the best ways to experience the beauty of Quiet Waters is by taking a scenic walk through the park. There are a variety of trails available that showcase the natural beauty of the area, from dense forests to tranquil streams.

One of the most popular walking trails in the park is the South River Promenade, a paved path that winds along the South River for approximately 1.1 miles. The path is surrounded by lush vegetation and beautiful views of the water, making it an ideal spot for a romantic walk.

As you follow the path, you'll encounter various lookout points with benches where you can stop and take in the stunning vistas. There's even a gazebo overlooking the river that provides a perfect spot for couples to sit and watch the sunset.

Another great walking trail in the park is the Red Maple Trail, a 1.8-mile loop that takes you through wooded areas and along the banks of the serene Hillsmere Creek. The trail is a bit more rugged than the South River Promenade, but it's still an easy hike that offers plenty of opportunities to experience the beauty of the area.

If you want a longer walk, the Serenity Trail is a 2.8-mile trail that takes you through diverse landscapes and beautiful views of the park's quiet forests and wetlands. The trail is also great for cycling and bird watching, making it a perfect spot for couples with various interests.

No matter which trail you choose, a walk through Quiet Waters Park is an ideal way to spend some quality time with your romantic partner in Annapolis. The park is also home to a variety of other activities, including kayaking, paddleboarding, and even ice skating in the winter, so you can easily spend an entire day exploring all that the park has to offer.

In conclusion, if you're looking for a romantic, nature-filled experience in Annapolis, take a walk through Quiet Waters Park. With its beautiful trails and stunning views, it's the perfect spot for couples to connect with each other and the beauty of the natural world.

Watch the city lights from a rooftop bar at the Graduate Annapolis hotel

Annapolis, the capital city of Maryland, is known for its historic charm and scenic waterfront. It's a perfect destination for couples looking for a romantic getaway. If you're looking for an unforgettable experience in the city, head to the Graduate Annapolis hotel to watch the stunning city lights from their rooftop bar.

Perched atop the Graduate Annapolis hotel, the rooftop bar offers an unparalleled view of the city. You can see the historic Maryland State House, the US Naval Academy campus, and the Chesapeake Bay in the distance. The view is particularly mesmerizing at night when the city lights up, creating a magical atmosphere that's perfect for a romantic date.

But the view isn't the only thing that makes the Graduate Annapolis rooftop bar special. The bar itself is a charming and stylish spot with comfortable seating, a great drink menu, and a friendly atmosphere. Whether you want to sip on a classic cocktail or try a local beer, they have something for everyone.

The rooftop bar is not only a great spot for a date night, but it's also perfect for special occasions. If you're planning a proposal, celebrating an anniversary, or just want to create a magical moment with your loved one, the rooftop bar is the ideal place to do it. Just imagine popping the question with the stunning city lights as your backdrop!

Apart from the rooftop bar, the Graduate Annapolis hotel is a great place to stay for a romantic getaway. The hotel is located in the heart of downtown Annapolis, which means you'll be close to all the attractions the city has to offer. You can take a stroll along the waterfront, explore the historic streets of the town, or dine at one of the many restaurants in the area.

In conclusion, a romantic trip to Annapolis is incomplete without a visit to the Graduate Annapolis rooftop bar. The stunning view, charming atmosphere, and great drinks make it a must-visit spot for couples. So, book a room at the hotel, and spend your evening watching the city lights with your loved one. It's an experience that you'll never forget!

Visit the William Paca House and Gardens

Characteristic	Description
Name	William Paca House & Garden
Type	Mansion in Annapolis, Maryland
Website	Go to website
Rating / Review count	4.5 / 419
Address	186 Prince George St, Annapolis, MD 21401
Phone	(410) 990-4543
Hours	Saturday - 10 AM–3 PM Sunday - 10 AM–3 PM Monday - 10 AM–5 PM Tuesday - 10 AM–4 PM Wednesday - 10 AM–5 PM Thursday - 10 AM–5 PM Friday - Closed
Profiles

Annapolis, the capital of Maryland, is a city that is steeped in history and charm. With its winding brick streets, cozy cafes and quaint inns, it is a great destination for a romantic getaway. And one of the most romantic spots in Annapolis is the William Paca House and Gardens.

The William Paca House is a beautifully preserved 18th-century mansion that offers a glimpse into the lives of Annapolis' elite during the early days of the United States. The house was built in 1765 and was the home of William Paca, a signer of the Declaration of Independence and the third governor of Maryland.

The house is open to visitors and tours are available that provide insight into the house's history and architecture. But what makes the William Paca House particularly special for couples is its stunning garden.

The William Paca Garden is a two-acre oasis of manicured lawns, flower beds, and fountains. It is one of the most beautiful and peaceful places in Annapolis. Walking through its winding paths, it is easy to forget the hustle and bustle of daily life and feel transported to another time.

The garden is divided into several smaller gardens, each with its own character and charm. The Lower Garden features a fish-shaped pond, a grape arbor and a labyrinth. The Fountain Garden is a formal garden with a central fountain and surrounded by hedges. The Kitchen Garden is filled with vegetables and herbs and is a great place to learn about the types of plants that were grown during Colonial times.

The William Paca Garden is a great place for a romantic stroll, a picnic or just to relax and enjoy the peaceful surroundings. Roses, peonies, and other blooms provide colors and fragrance throughout the year. And the garden is a popular spot for wedding ceremonies, making it an ideal place to pop the question or renew your vows.

Visiting the William Paca House and Gardens is a must-do for any couple visiting Annapolis. Whether you are interested in history, architecture or just looking for a peaceful and romantic place to spend some time together, the William Paca House and Gardens offers something for everyone.

Take a carriage ride through the city

Annapolis, the capital of Maryland, is a city steeped in history and beauty. It's the perfect destination for couples who want to spend a romantic weekend away. The quaint, charming streets of the city are lined with historic homes and bed and breakfasts that offer a comfortable and cozy getaway. However, nothing beats the romance of taking a carriage ride through the city.

A carriage ride is a classic and timeless way to see Annapolis and is the perfect way to spend a romantic evening. The clip-clop of the horse's hooves, the gentle swaying of the carriage, and the soft glow of the gas lamps create a magical atmosphere that is hard to replicate. Whether you're celebrating an anniversary or just want to spend some quality time with your significant other, a carriage ride is an experience you won't forget.

The ride itself lasts approximately 40 minutes and takes you through the city's historic district. You'll see the famous brick-lined streets, historic homes, and buildings that date back to the 18th century. You'll also pass by some of the city's most notable landmarks, such as the State House and the Naval Academy.

One of the best times to take a carriage ride is at night when the city is lit up with charming gas street lamps and festive holiday lights. You'll feel like you've been transported back in time as you glide through the city streets. It's the perfect way to cap off a romantic evening in Annapolis.

To make your carriage ride even more special, consider packing a picnic. You can stop at one of the city's many parks and enjoy a romantic dinner under the stars. Make sure to bring a blanket and some candles to add to the ambiance.

In conclusion, taking a carriage ride through the city of Annapolis is a romantic and unforgettable experience. The historic charm of the city, the gentle clip-clop of the horse's hooves, and the soft glow of the gas lamps create an unforgettable ambiance that will help you create lasting memories with your significant other. It's an experience you won't forget and a perfect way to spend a romantic weekend in Annapolis.

Watch a movie under the stars at the Annapolis Summer Garden Theatre

Annapolis, the capital city of Maryland, boasts a romantic atmosphere that can be enjoyed by couples. One of the most exciting things to do in Annapolis during summer is watching a movie under the stars at the Annapolis Summer Garden Theatre.

The Annapolis Summer Garden Theatre is located at 143 Compromise Street in downtown Annapolis. The theatre offers outdoor productions during the summer season, featuring classic and contemporary musicals, comedies, and dramas. However, one of the main highlights of the theatre is its outdoor movie screenings.

The theatre provides a unique experience where you can enjoy a movie in an outdoor setting. You can cuddle up with your loved one under the stars while watching a romantic film, making it a perfect opportunity for a date night. The outdoor theatre has a cozy atmosphere, with blankets, picnic baskets, and lawn chairs available for rent.

The theatre screens movies on selected days throughout the summer season. All movies begin at sunset, which varies throughout the season. Admission to the theatre is affordable, and you don't have to worry about bringing food and drinks. The theatre has a concession stand where you can buy popcorn, candy, sodas, and alcoholic beverages.

The theatre also provides a safe environment for moviegoers. The theatre has its security personnel who ensure that everyone adheres to the theatre's rules, such as no smoking, no pets, and no outside food and drinks.

In conclusion, watching a movie under the stars at the Annapolis Summer Garden Theatre is a unique and romantic experience that you don't want to miss. The theatre provides an outdoor setting that creates a cozy and intimate atmosphere for you and your loved one. So, the next time you are in Annapolis, make sure you add this experience to your bucket list.

Have a drink at Pusser's Caribbean Grille while watching the boats in the harbor

Characteristic	Description
Name	Pusser's Caribbean Grille - Annapolis Restaurants
Type	$$
Website	Go to website
Rating / Review count	4 / 1,589
Address	80 Compromise St, Annapolis, MD 21401
Phone	(410) 626-0004
Hours	Saturday - 8 AM–11 PM Sunday - 8 AM–10 PM Monday - 7:30 AM–10 PM Tuesday - 7:30 AM–10 PM Wednesday - 7:30 AM–10 PM Thursday - 7:30 AM–10 PM Friday - 7:30 AM–11 PM
Profiles

If you're looking for a romantic getaway in Annapolis, look no further than Pussers Caribbean Grille. Located on the waterfront in the historic district, Pussers is the perfect spot to have a drink while watching the boats in the harbor.

With its nautical decor and Caribbean-inspired menu, Pussers has an ambiance that will transport you to another world. Whether you choose to sit indoors or outside on the patio, you'll have a stunning view of the water and the boats coming and going.

Start your evening off right by ordering one of Pussers' signature drinks, like the Painkiller or the Rum Runner. Made with their house-made Pusser's rum and fresh ingredients, these drinks are the perfect way to set the tone for a romantic night out.

As you sip your drink, take in the sights and sounds of the harbor. You'll see sailboats, yachts, and even the occasional kayaker or paddleboarder. If you're lucky, you might catch a glimpse of the Chesapeake Bay Bridge in the distance.

When it's time to order dinner, you won't be disappointed by the menu at Pussers. From seafood classics like crab cakes and fish and chips to steak and pasta dishes, there's something for everyone. And don't forget to save room for dessert – the Key Lime Pie is a must-try.

As the sun sets, the atmosphere at Pussers only gets more romantic. Strings of lights illuminate the patio, adding a soft glow to the already picturesque setting. You and your date can relax and enjoy each other's company, surrounded by the beauty of Annapolis.

In short, if you want to experience the romance and beauty of Annapolis, a night at Pussers Caribbean Grille is a must. Savor a delicious meal and drinks while enjoying the view of the harbor, and make memories that you'll treasure for a lifetime.

Visit the Maryland State House and take in the history

If you and your significant other are looking for a romantic getaway, Annapolis, Maryland should be high on your list. Not only does this picturesque town offer stunning views of the Chesapeake Bay and a charming downtown area, but it also boasts a rich historical presence that'll transport you back in time.

One of the most noteworthy historical sites in Annapolis is the Maryland State House. This stunning building dates back to the 1770s and served as the nation's first peacetime capitol. It's also the oldest statehouse still in use today, which makes it a must-see for history buffs.

As you take a leisurely stroll through the buildings' grand halls and awe-inspiring architecture, you'll find yourself immersed in the states' history. Admire the intricate details of the rotunda; it's been home to numerous historical events, including George Washington's resignation from his post as commander-in-chief of the Continental Army in 1783.

For those interested in politics, a visit to the Maryland Senate and House of Delegates chambers is a must. You'll be transported to a time when America was just getting started, and the ideals of liberty, justice, and freedom were being forged.

Suppose you're interested in art and culture. In that case, the Maryland State House still has plenty to offer, with rotating exhibitions showcasing the state's talented artists and artisans.

While history may be the main draw to the Maryland State House, its scenery and environment lend themselves to romance as well. Take a walk along the manicured gardens or pack a picnic and enjoy a meal on the sprawling lawn.

Visiting the Maryland State House is a great way to experience both the rich history and romantic scenery of Annapolis. So, if you're looking for a unique and romantic adventure, set your sights on Maryland's capital, and take in the sights and sounds of this vital piece of American history.

Take a wine tour at Great Frogs Winery

Characteristic	Description
Name	Great Frogs Winery
Type	Vineyard
Website	Go to website
Rating / Review count	4.5 / 112
Address	3218 Harness Creek Rd, Annapolis, MD 21403
Phone	(410) 626-6193
Hours	Saturday - 11 AM–8 PM Sunday - 12–4 PM Monday - Closed Tuesday - Closed Wednesday - Closed Thursday - Closed Friday - 5–8 PM
Profiles

Are you looking for a romantic weekend escape that is filled with wine and beautiful scenery? Then head to Annapolis and join a wine tour at Great Frogs Winery.

Located in beautiful Annapolis, Great Frogs Winery offers a unique and memorable experience with its charming winery and scenic surroundings. The winery is known for producing some of the finest wines in Maryland and has become a popular destination for wine lovers.

The vineyard at Great Frogs Winery is nestled in the heart of Annapolis with a beautiful view of the countryside. The vineyard is home to several grape varieties such as Cabernet Franc, Merlot, Chardonnay, and Pinot Noir. The winery uses a traditional approach to winemaking and only uses handpicked grapes. Their wines are aged in oak barrels, which gives them a unique taste and aroma.

Great Frogs Winery offers a range of wine tours that will take you through the winery and vineyards. During the wine tour, you will get a chance to see the beautiful grounds, learn about the winemaking process, and sample some of the best wines in Maryland. The vineyard is a romantic setting that is perfect for couples looking for a romantic getaway.

The Great Frogs Winery tasting room is open to the public and offers a range of wines for visitors to try. The tasting room is cozy and intimate, with comfortable seating and a warm fireplace to keep you comfortable during the colder months.

If you are looking for a unique romantic getaway, then a wine tour at Great Frogs Winery is a perfect option. It offers a chance to explore the beautiful countryside of Annapolis, taste some of the best wines in Maryland, and enjoy a romantic setting that is perfect for couples. So why not book a wine tour today, escape the hustle and bustle of the city, and experience the beauty of Annapolis in a whole new way.

End the evening with a dessert and coffee at City Dock Coffee

Characteristic	Description
Name	City Dock Coffee
Type	$
Rating / Review count	4.4 / 185
Address	18 Market Space, Annapolis, MD 21401
Phone	(410) 269-0969
Profiles

Annapolis, Maryland may be famous for its rich history and naval presence, but it's also an incredibly romantic spot for couples looking to spend some quality time together. One of the best ways to end a romantic evening in Annapolis is with a delicious dessert and coffee at City Dock Coffee.

Located right on the waterfront in the heart of downtown Annapolis, City Dock Coffee offers a cozy and intimate setting for couples to relax and unwind after a day of sightseeing or exploring. Whether you're looking to indulge in a sweet treat or simply sip on a hot cup of coffee, City Dock Coffee has it all.

Their dessert menu boasts a variety of mouth-watering options, from classic pastries like croissants and scones to more decadent treats like chocolate-covered strawberries and artisanal gelato. Paired with a steaming cup of freshly brewed coffee or tea, it's the perfect way to round out a romantic evening in Annapolis.

But what really sets City Dock Coffee apart is its stunning waterfront location. Situated right on the edge of the harbor, couples can enjoy their dessert and coffee while watching the boats sail by and taking in the breathtaking views of the Chesapeake Bay.

So if you're looking to add a little romance and sweetness to your trip to Annapolis, be sure to stop by City Dock Coffee. With its delicious treats, cozy atmosphere, and incredible waterfront location, it's the perfect spot to end a perfect evening with your partner.

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