This article collects the best date ideas and romantic things to do in Annapolis for couples based on major travel sites, blogs, reviews, and social media sites.
There are numerous romantic activities available in Annapolis. The city’s biggest attractions are listed below, along with ideas for romantic dates. These activities, which range from fine dining to sightseeing throughout the city, are free to attend.
Imagine surprising your loved one with a last-minute trip to Annapolis?
Have a date like you did when you first met. Bring back those memories by doing what you enjoy.
Here are 30+ romantic things to do in Annapolis with your partner.
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Table of Contents
Outdoor / Adventurous Date Ideas in Annapolis To Have Fun
Experience a thrilling racing event at Eastport
- Cost: $30/person (ticketing)
- Address: EastportAnnapolis, MD 21403, USA
- Phone: N/A
A town called Eastport is reached by way of the Spa Creek Bridge.
It has a unique flag and atmosphere, making it seem like its own world. Eastport makes excellent use of its waterfront location by offering many fantastic attractions and events.
The “Slaughter Across the Water” is one of the most excellent parts. In the summer, boat races are also held on Wednesdays. There are many top-notch restaurants in Eastport as well.
One of the top things to do in Annapolis is to visit Eastport.
It’s a lovely place with a beautiful community. In Eastport, sitting by the lake while taking a race or savoring a delicious lunch is a lovely experience.
Enjoy beautiful views at City Dock and go boating
- Cost: $10/hr (boating)
- Address: Dock St, Annapolis, MD 21401, United States
- Phone: +1 410-263-7973
You should love Annapolis if you enjoy the water.
On the City Dock, there are many beautiful sights to behold. Additionally, it’s an excellent location for onlookers and boating enthusiasts to assemble and display their yachts.
City Dock, also referred to as “Ego Alley,” is home to numerous fantastic vessels and excellent sights.
There are numerous places to eat and shop. Additionally, there are noteworthy occasions like the Spring Sailboat Show. After visiting, you might begin setting aside money for your boat.
Visits to City Dock are unique occasions. Observing these boats on the beautiful sea is an excellent sight-seeing activity.
Go for some adventurous cycling at B&A Trail
B&A to Annapolis, Maryland: Bicycling Day Tour
- Cost: Free
- Address: B&A Trail, Annapolis, MD, United States
- Phone: N/A
“One of the best trails in the area. Well maintained paved trail. Mostly tree lined and provides a nice amount is shade for those hot days. Well used by bikers, bladders, joggers and walkers.” Henry B
Check out B&A Trail if you enjoy being outside and are looking for free activities to do in Annapolis. B&A Trail, abbreviated for “Baltimore and Annapolis,” offers a wide variety of entertainment.
Even though the walk is somewhat long, it is bearable considering its beauty. There are slightly more than 13 miles on this trail.
It features a roomy, paved trail where people can stroll, run, ride bikes, and even ride horseback riding or rollerblading.
Be aware of your surroundings, giving other road users plenty of room and allowing them to pass if they move more quickly than you.
Explore the aquatic beauty on an electric boat
- Cost: $200/hr (boating)
- Address: 300 Second St, Annapolis, MD 21403, United States
- Phone: +1 443-433-2129
Be your captain if sailing the Bay with someone else at the helm doesn’t appeal to you. An exceptional opportunity is provided by Annapolis Electric Boat Rentals to use one of their boats independently.
Explore Spa Creek, visit the Back Creek mansions on the river, or even try your hand at egotism in Ego Alley.
The captain can go with up to 11 passengers on the electric boats for a few hours or all day. No prior sailing experience is necessary, and you’ll receive a crash course right away.
What could be a better way to enjoy the water?
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Experience the different flavors of wine at Great Frogs Winery
- Cost: $10/person (ticketing)
- Address: 3218 Harness Creek Rd, Annapolis, MD 21403, United States
- Phone: +1 410-626-6193
“Great Frogs Winery is a hidden gem in Annapolis. The wine is very well done for the mid-Atlantic region. But what separates Great Frogs is the beautiful venue and restored barn. Worth a day trip!” – William B
There is a winery called Great Frogs on the Harness Creek Vineyards on the Chesapeake Bay. It began operating in 1999.
Schedule a tasting to sample the various wine varieties from this winery. Lacked time to schedule an appointment? Purchase a bottle of wine from the Patio and enjoy it outside.
One of the romantic things to do in Annapolis is to stroll through the vineyards of a winery while drinking wine.
Enjoy a performance at Annapolis Summer Garden Theater
- Cost: Starts from $27-$69 (ticketing)
- Address: 143 Compromise St, Annapolis, MD 21401, United States
- Phone: +1 410-268-9212
An outdoor show is produced every weekend night for several months of the year by the Annapolis Summer Garden Theater. Since 2006, every performance has been a musical, including numerous current Broadway and off-Broadway productions.
There are five-week productions that have three performances per weekend day.
Catch the Blue Angels’ Airshow
- Cost: Free
- Address: Blue Angels’ Airshow, Annapolis, MD, United States
- Phone: +1 410-260-2211
During the yearly USNA Commissioning Week in May, if you’re in Annapolis, you may watch a unique Blue Angels airshow flying over the U.S. Naval Academy.
The graduation flyover at the Navy-Marine Corps Memorial Stadium occurs on the final day, while the two-day air show is held on the first two days.
The renowned Blue Angels, a group of 16 elite Navy and Marine jet pilots who tour the nation every spring and summer, lead the most recent grads in a series of performances throughout the air shows.
Visitors can view the performance from Navy-Marine Corps Memorial Stadium or the Severn River banks on the grounds of the U.S. Naval Academy.
Cheer up during sailboat races at Chesapeake Bay
- Cost: $10/person (ticketing)
- Address: Chesapeake Bay, Annapolis, MD, United States
- Phone: N/A
Watching a boat race in the Chesapeake Bay that starts at the Annapolis Yacht Club is one opportunity to honor the sailing heritage of Annapolis fully. The first race typically begins at around 6 p.m. and lasts from the final Wednesday in April through the second Wednesday in September.
More than 130 sailboats compete in the weekly race through the glistening Chesapeake Bay, around several marks, and back to Spa Creek for the finish in front of the Annapolis Yacht Club.
This year-round, full-service private yacht club offers several programs for members and a few special events others can attend.
Visit the Annapolis Yacht Club to learn about power and sailboat cruising, sign up for a challenging junior sailing program, participate in educational winter activities, or attend social or fine dining events.
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Music, Art, Historic, Cultural Date Ideas in Annapolis
Take a tour of United States Naval Academy
Visit The United States Naval Academy
- Cost: $12/person (ticketing)
- Address: United States Naval Academy, Annapolis, MD 21401, United States
- Phone:
“There is a lot of history here, and we highly recommend the walking tour, which was about 90 minutes.” – Robert T
The United States Naval Academy, headquartered in Annapolis, has produced great brains and bodies. This academy has been a part of the nation’s great military legacy since its foundation in 1845.
Visit the USNA to understand better how crucial discipline and tradition are to the Navy. You may learn about the academy’s fascinating past by taking a tour.
The building should also enthrall you because it adds to the school’s aura of magnificence. Those who feel the call to serve their country and develop personally at this academy have done well.
Attend a concert at Annapolis Symphony Orchestra
- Cost: Starts from $40-$60 (ticketing)
- Address: 801 Chase St Pro Shop, Annapolis, MD 21401, United States
- Phone: +1 410-269-1132
The Annapolis Symphony Orchestra is one of the top attractions in Annapolis for music fans. The fact that this orchestra performs so infrequently makes seeing a concert from them all the more amazing.
You’ll be in one of Maryland’s most beautiful buildings while also witnessing a fantastic ensemble at work. A 45-minute conversation precedes each performance.
This describes the show’s content and can increase your appreciation for the beautiful music and the effort to present it.
Maryland Hall for the Creative Arts, which features a stunning auditorium and top-notch sound, should also make you happy.
Give a tribute to heroes at Maryland World War II Memorial
- Cost: Free
- Address: 1920 Governor Ritchie Hwy, Annapolis, MD 21409, United States
- Phone: +1 800-446-4926
“The history at this memorial was wonderful. I enjoyed reading the plaques and understanding how many people were injured and died at the various battles. The view from the top was awesome. Truly worth a visit.” – Joann D
You can pay your respects to those who fought and gave their lives for their country in Annapolis.
The Maryland World War II Memorial honors these warriors admirably. Make sure to include it in your tourist itinerary. The design of the Maryland World War II Memorial is exquisite.
It is outside and is surrounded by 48 pillars. These represent the 48 states that made up the Union during the conflict. Each person from Maryland who lost their lives in battle is also listed by name. Additionally, some plaques discuss significant wartime events.
The Maryland World War II Memorial is vital in every aspect. They underscore Maryland’s contribution to the fight in addition to the bravery of these soldiers.
Pay a visit to the Maryland State House
- Cost: Free
- Address: 100 State Cir, Annapolis, MD, 21401, United States
- Phone: +1 410-946-5423
“Beautiful building with great decorations and paintings. Amazed to be surrounded by so much history that took place there.” – Eduardo bri
You should visit the Maryland State House since Annapolis is the state’s capital. If you are interested in politics, here is where you should go in Annapolis.
You can observe how a state’s government collaborates to provide leadership at the Maryland State House. Few tourist destinations in the US are as significant as The Maryland State House.
It is also the oldest state capitol and the final surviving colonial structure. In actuality, this was formerly the site of the US Capitol.
Here is where George Washington tendered his resignation as commander of the Continental Army. Additionally, this is where the Revolutionary War’s endgame, the Treaty of Paris, was approved.
Sit, relax and laugh at the The Colonial Players
- Cost: $10/person (ticketing)
- Address: 108 East St, Annapolis, MD 21401, United States
- Phone: +1 410-268-7373
“We really enjoyed Saturday’s performance of “The Merry Wives of Windsor” What a great community theater with intimate seating.” – Lucy
You can find vibrant culture all across Downtown Annapolis. The Colonial Players are one of the top attractions for fans of theater.
This theater company is historic, with more than 70 years of service to Annapolis. Numerous community productions are available from The Colonial Players.
There are comedies, dramas, shows for kids, and productions that are a little more difficult to categorize. The fact that it’s all top-notch entertainment, nevertheless, is the unifying factor.
Their headquarters are located in a former mechanic shop, which gives them an additional quirky charm. Fantastic tourism attractions support the cultural vitality of Annapolis, Maryland. Any production you witness will undoubtedly be great.
Learn about black history at Banneker-Douglass Museum
- Cost: $5/person (ticketing)
- Address: 84 Franklin St, Annapolis, MD 21401, United States
- Phone: +1 410-216-6180
The Banneker-Douglass Museum is among the best sites to learn about Black history. There are numerous significant documents here relating to Black Americans.
Benjamin Banneker and Frederick Douglass, two of Maryland’s most prominent Black Americans, are honored by the name of this museum, which was established in 1984.
Their ongoing display underlines the contribution that Black people made to Maryland. This contains details about Banneker and Douglass.
Temporary exhibits offer additional opportunities for discourse targeted at educating about the significance of civil rights. This city’s Banneker-Douglass Museum is a crucial component.
Pay your respects at Thurgood Marshall Memorial
- Cost: Free
- Address: Annapolis, MD 21401, United States
- Phone: N/A
“What a wonderful memorial that highlights the accomplishments of such an historic figure a must see if you’re in the area” – Anna H
Be sure to visit the Thurgood Marshall Memorial at the Maryland State House. Thurgood Marshall was the first Black justice to sit on the US Supreme Court and a true American legend.
An excellent spot to honor his life and legacy is at this memorial. Maybe you didn’t know Marshall was from Maryland.
He began his legal career in Baltimore, where he was born. He also passed away in the state, in Bethesda. Marshall had a distinguished legal career and was a formidable opponent.
In Brown v. Board of Education of Topeka, he successfully argued against school segregation, which ranks among his biggest successes. Thurgood Marshall demonstrated the value of standing up for what is right.
Take a tour to see exhibits at Hammond-Harwood House
- Cost: $12/person (ticketing)
- Address: 19 Maryland Ave, Annapolis, MD 21401, United States
- Phone: +1 410-263-4683
At Hammond-Harwood House, you may see examples of 18th-century art and architecture. On tour, visit the exhibits, including a gentleman’s study. Colonial tour interpreters are available to explain the shows more thoroughly.
Seek out the amazing street art of Annapolis
- Cost: Free
- Address: Annapolis, MD 21401, United States
- Phone: N/A
In Annapolis, there are numerous street art murals to view. Many artworks depict images from the city’s past or well-known Annapolitans, primarily grouped around West Street and Main Street.
Additionally, a nearby nonprofit organization, Future History Now, collaborates annually with young people in impoverished communities to add significant murals.
Highlight the history of boat building and the local oyster at Annapolis Maritime Museum
- Cost: $7/person (ticketing)
- Address: Annapolis Maritime Museum & Park, 723 Second Street, PO Box 3088, Annapolis, MD 21403
- Phone: +1 410-295-0104
“This place has beautiful views of the Bay and the Bridge, Plus it is a slice of real-life on the bay & history of the economy of the area. Worth stopping in.” – Sam B
On the banks of Back Creek, in the final working oyster packing mill in Annapolis, sits the Annapolis Maritime Museum. A collection of relics and documents shows the history of boat building and the regional oyster industry.
It also instructs visitors about the environment of an oyster reef in its 850-gallon tank.
Additional exhibitions explore the region’s maritime heritage and the cultural and economic impacts it had.
The Miss Lonesome, which has cutaway portions to illustrate its construction, and the 1940 Wilma Lee, which can be seen with a guide, are two examples of authentic oyster boats that visitors can see.
Tour the historic William Paca House and Garden
- Cost: $12/person (ticketing)
- Address: 186 Prince George St, Annapolis, MD 21401, United States
- Phone: +1 410-990-4543
The William Paca House and Garden is a venerable home from the 18th century. It was constructed in the years 1763–1765. Visit the residence of a former governor of the state and a signer of the Declaration of Independence.
Architecture enthusiasts will enjoy viewing the Georgian-style architecture of the mansion. The mansion’s grounds and 2-acre garden are like a sanctuary in the center of busy Annapolis. Be sure to take some time to unwind by taking a stroll.
Relish a show at Annapolis Opera
- Cost: Starts from $10-$60 (ticketing)
- Address: 801 Chase St, Annapolis, MD 21401, United States
- Phone: +1 410-267-8135
You’re in for a big treat if you’ve never seen opera performed. The Maryland Hall for the Creative Arts is where the Annapolis Opera performs throughout the city. Their performances exemplify their talent, passion, and storytelling skills.
In 1972, the Annapolis Opera Company was established. Its reputation as one of the top opera companies in the nation has grown over time. It has thrived because of community support, and your purchases can keep it alive.
Give succumbs to the spectacle of an opera performance; it should leave you with a lasting impression. Attending a performance by the Annapolis Opera allows you to engage with culture at its most significant level.
Explore the historic Chase Lloyd House
- Cost: $2/person (ticketing)
- Address: 22 Maryland Ave, Annapolis, MD 21401, United States
- Phone: +1 410-263-2723
In addition to being a historic house, the Chase Lloyd House plays a crucial role in the community. It was held by numerous people, including its builder Samuel Chase, Edward Lloyd IV, and others.
But it was Hester Chase Ridout who established the Chase Lloyd House as a vital fixture of the Annapolis neighborhood. Ridout’s bequest required it to become an older woman’s home. That’s still the case today.
Older women have significantly benefited from the exceptional accommodations the exquisitely constructed Chase Lloyd House provided.
The Chase-Lloyd House demonstrates how concerned Annapolis residents are for disadvantaged groups. If you’re trying to assist an aging relative in finding a new place to live, it’s a terrific place to go.
Indoor / Relaxing / Foodies Date Ideas in Annapolis
Dine at the Rams Head Tavern
- Cost: Starts from $20-$40 (food)
- Address: 33 West St, Annapolis, MD 21401, United States
- Phone: +1 410-268-4545
“This was my favorite place in Annapolis. The beers were delicious and so was the food. If I’m in Annapolis again this will definitely be a stop!” – Saman T
In Annapolis, Rams Head Tavern is one of the funniest spots for a delicious meal and a good time. Spend an evening at Rams Head Tavern this weekend if you’re going to be in Annapolis.
You should feel energized by a terrific sense of fun and warmth as soon as you enter.
The food and ambiance at Rams Head Tavern are legendary. Savory options on the menu include the Bourbonzola Strip, Vegan Papa Salsiccia, and Dynamite Burger.
Rams Head On Stage, a live entertainment facility with excellent musical and comedic performances, is connected to the bar. A trip to Rams Head Tavern is appropriate for an evening out in Annapolis.
Try some delicious frozen treats at Annapolis Ice Cream Company
- Cost: Starts from $5-$10 (icecream)
- Address: 196 Main St, Annapolis, MD 21401, United States
- Phone: +1 443-714-8674
You may have an excellent and sweet time at Annapolis Ice Cream Company with some delicious frozen desserts.
It has received the title of “Best Ice Cream” in the city for 17 years.
You’ll probably join the acclaimed chorus after observing what they accomplish with their ingredients.
The Annapolis Ice Cream Company transforms the creamy indulgence of a beloved dessert into something even more remarkable. The company was founded by New Englanders who wanted to bring the ice cream they grew up with to Maryland.
Their cones taste like they came straight from heaven and have a magazine-worthy appearance. Every customer at Annapolis Ice Cream Company can enjoy some fun and treats. Grab a cone or stock up on some beers when you get home.
Get a delicious underwater meal at O’Leary’s Seafood Restaurant
- Cost: Starts from $25-$40 (food)
- Address: 310 Third St, Annapolis, MD 21403, United States
- Phone: +1 410-263-0884
“Our server John was fantastic, and our crispy rockfish meal was out of this world. Our server John was very knowledgeable on all on the meals on and off the menu.” – James D
One of Maryland’s top tourist attractions is seafood. Annapolis has many dining alternatives, but O’Leary’s Seafood Restaurant is among the best.
You may experience a fantastic undersea supper here and discover why Maryland seafood is so beloved.
Fantastic crab cakes may be found at O’Leary’s, especially when served with corn relish. The mac & cheese and the Crab Cake BLT are other crabby dishes.
Ahi tuna, salmon, shrimp, and grits are a few other fantastic seafood recipes. Try dishes like the Bourdain Burger and chimichurri flat iron steak if you’re not ready for seafood.
O’Leary’s Seafood Restaurant further enhances Maryland’s already-high prestige. Come here for delicious food prepared with the finest ingredients.
Experience the local taste at Chick and Ruth’s Delly
- Cost: Starts from $9-$20 (food)
- Address: 165 Main St, Annapolis, MD 21401, United States
- Phone: +1 410-269-6737
One of the most popular dining destinations in Annapolis is Chick and Ruth’s Delly.
They not only offer delicious lunches, dinners, and breakfasts, but they also have a fascinating daily ritual.
Come early so you can participate.
Above, a flag flies with pride. They also have a great menu, with locally prepared crab cakes, pizza, bread, and pies. Both the excellent meal and fidelity to cherished traditions are huge draws.
Fun and Entertaining Date Ideas in Annapolis
Have some fun and entertainment at Annapolis Town Center
- Cost: Starts from $120-$360 (food+entertainment)
- Address: 1906 Towne Centre Blvd, Annapolis, MD 21401, United States
- Phone: +1 410-573-9050
The Town Center is one of Annapolis’ most outstanding features. It’s a fantastic location for entertainment and other enjoyable pursuits. Here are some enjoyable activities to do in Annapolis.
Taking a look at the Annapolis Town Center directory ought to interest you. There are numerous fantastic restaurants, a spa, a painting bar, and a fishing store. Love pizza, burgers, and Chinese food? You’ll discover a great restaurant.
Visit Annapolis Town Center if you’re looking for venues to go out at night. Bring some spending cash and get ready to experience a variety of enjoyable locations and activities.
Embrace the fun of a shopping spree at Main Street Shopping
- Cost: Starts from $50-$500 (shopping)
- Address: 26 West Street, Annapolis, MD 21401, United States
- Phone: +1 410-280-0445
Shopping on Main Street is one of the most well-liked pastimes in downtown Annapolis. There are a tonne of shops there, so your options are endless.
Just a word of advice: don’t blow all your money in one spot. Pace yourself. Lilac Bijoux, Hats in the Belfry, and Irish Traditions are some of the top leading street stores.
You can discover both the novel appearance you’ve been looking for and unexpected ones. Dinner at a local restaurant is another way to congratulate yourself after your successful shopping.
Treating yourself is a critical component of vacations. Shopping on Main Street demonstrates your self-love and desire for the finest in life.
Nature-Inspired Date Ideas in Annapolis
Treat your senses at Quiet Waters Park
- Cost: $6/person (ticketing)
- Address: 600 Quiet Waters Park Rd, Annapolis, MD 21403, United States
- Phone: +1 410-222-1777
Come to Quiet Waters Park if you’re looking for entertainment and peace. There are many activities available here, including picnics and canoeing. When you need to pamper your senses, go on a visit.
Quiet Waters Park is a stunning expanse of more than 300 acres. The entire family will enjoy Quiet Waters Park.
In addition to renting boats, you may stroll along the pathways, let your children run around on the playground, and visit the gardens and on-display artwork.
Even your dog will enjoy playing in the dog park at Quiet Waters Park. One of the best locations for outdoor activities is Quiet Waters Park.
Go for camping at Sandy Point State Park
- Cost: $5/person (ticketing)
- Address: 1100 E College Pkwy, Annapolis, MD 21409, United States
- Phone: +1 410-974-2149
Sandy Point State Park is one of the most beautiful spots to visit in Annapolis. There are about 800 acres of pristine terrain that are perfect for camping. Additionally, the Chesapeake Bay’s waters encircle the area.
Sandy Point State Park has been a fantastic treasure since its establishment in 1952. Spending the day at Sandy Point State Park is worthwhile.
Here, you can go swimming, fishing, and picnicking. Camping overnight is fantastic at this spot. The tranquil waters of the Chesapeake provide a beautiful contrast as you wind down for the evening.
Sandy Point State Park is home to numerous stunning sights. Even though you’ll live in the wild, it won’t be uncomfortable.
Enjoy the great scenery at Helen Avalynne Tawes Garden
- Cost: Free
- Address: 580 Taylor Ave, Annapolis, MD 21401, United States
- Phone: +1 410-260-8189
The Helen Avalynne Tawes Garden in Annapolis offers a wealth of beautiful sights for plant lovers. A botanist or florist is not necessary to enjoy yourself here. With so much beautiful landscape to enjoy, it’s a spot for everyone who needs to take a moment or several.
The surroundings of the Helen Avalynne Tawes Garden enrich the flora there. A brook, many ponds, and a forest are all nearby. This allows for some fantastic shots and pulls out the color in the plants.
You may also sign up for a tour to discover more about the garden and its features. An excellent spot to unwind is Helen Avalynne Tawes Garden.
Unforgettable Date Experiences in Annapolis
Enjoy a memorable cruise at Chesapeake Bay Cruise
- Cost: $45/person (ticketing)
- Address: 26 West Street, Annapolis, MD 21401, United States
- Phone: +1 410-280-0445
You can experience the Chesapeake Bay in a variety of ways. Taking a cruise is one of the most memorable ways to do it. The Harbor Queen offers stunning and thrilling rides that highlight what a fantastic body of water this is.
Large tour boat The Harbor Queen is owned by local company Watermark. In the city, it has somewhat of a celebrity status. Visitors have been astounded by this 65-foot-long sailboat for more than 45 years.
Various lengthier trips are available in addition to the highly popular 40-minute guided cruise.
Take a Chesapeake Bay cruise for a leisurely day on the sea in Annapolis. You’ll be surrounded by the magnificent Chesapeake Bay and many other content travelers.
Best Things to Do in Annapolis, Maryland
Final Thoughts
Annapolis, the capital of Maryland, is a beautiful city. The city’s attractions are museums, old structures, historic sites, historic buildings, romantic getaways, hiking trails, city tours, boat tours, amusement parks, food events, and renowned eateries.
You may have fun in Annapolis whether you want to stay a while or are just passing through.
| I like to travel but also be smart with money. Below are the places where I start my planning with. – ✈️Flights, Hotel, Tours – I seek out Flash Sales to guide my planning 👉 Find good deals – 🛡️Travel Insurance – I like to go to the source like Travelex instead of paying a broker 👉Here – 🚗Car Rental – Rental will save you lots of headaches. Search, compare, and save first up to 30-50% on Discover Cars. 👉 Save Now |
