Annapolis is the capital of Maryland, known for its gorgeous waterfront, coastal charm, and rich history. Founded in 1649, it has a long history and a thriving cultural scene. Even though neighboring cities like Washington, DC, and Baltimore are much larger, a day trip to Annapolis is well worth it on a trip.
As someone who has lived in Maryland, DC, and Virginia (yes, I’ve lived in all three!), I’ve had the chance to visit over the years and have crafted this perfect day trip to Annapolis for you! Throughout this itinerary, I’ll give options depending on the type of traveler you are.
Table of Contents
Getting to Annapolis
The easiest way to get to Annapolis is by renting a car, whether coming from the north or south. Below are the highways and distances.
- From Washington, D.C.: Take US-50 East/US-301 North. Annapolis is about 30 miles east of Washington, DC, and the drive typically takes around 45 minutes to an hour, depending on traffic.
- From Baltimore: Take I-97 South, then follow signs to US-50 East. Annapolis is about 25 miles south of Baltimore, and the drive usually takes about 30 to 40 minutes.
Annapolis is not connected to the Amtrak system of trains along the East Coast and doesn’t have a public train that takes people from Annapolis to any major cities.
Greyhound and Mega Bus do have stops in Annapolis. You could also consider taking a day tour of Annapolis from Baltimore or DC.
You can also join a tour that will handle all transportation for you, linked to the one below!
Tips for Visiting Annapolis
- Getting around: Annapolis is a very walkable city, especially within the historic district. Wear comfortable shoes for exploring and park your car for the day.
- Parking: Street parking can be challenging, particularly in the historic district. Most parking is 2 or 3 hours and under the same parking zone so will expire before you want to leave. Utilize public parking garages instead and pay the day rate.
- Parking garages (from their website): Park free at City garages (Gott’s Court, Knighton, Park Place) on Sunday mornings (enter after 6 a.m. and exit before 2 p.m.). The State Garage (19 St. John’s Street) offers free parking from 6 p.m. to 6 a.m. Monday through Friday and all day on weekends. Whitmore Garage (37 Clay Street) offers free parking on Sundays.
- Public Transportation in Annapolis: The Annapolis Circulator is a free shuttle service that loops around downtown, making it easy to get to key spots without a car.
- Best Time to Visit: Late Spring and early fall are ideal times to visit Annapolis due to the mild weather and fewer crowds. Summer is popular for sailing and outdoor activities, but can be hot and humid.
- Accommodations: Book your accommodations in advance, especially during peak seasons. Consider staying in the historic district for easy access to major attractions or one of the cute historic homes on the water.
Morning in Eastport
Start your day off in Eastport, this area of Annapolis is the maritime district with the chance to take in beautiful views of the Chesapeake and Annapolis, enjoy a quiet morning and get a taste of the local life!
The views alone make visiting this part of Annapolis worth it, but you’ll love the quiet charm of the homes and many different harbors as you enjoy this neighborhood, too.
Coffee at Oscar’s Coffee
Oscar’s Coffee is located in one of the cute marinas in Eastport, in a 1972 Shasta. As we waited in line for our coffees and bagels, we could hear the baristas chatting with the regulars. We also met lots of friendly pups (Oscar is a dog, after all!). and truly felt at home in Annapolis right away!
The coffee is excellent, the vibe is relaxed, and there’s lots of outdoor seating to start off your day with a slow and wonderful start!
Choose an Adventure
After getting some coffee to start your day, it’s time for an adventure! There are so many great ways to get on the water in Annapolis; you don’t want to miss it while you’re here. I loved kayaking in Annapolis, but boating and sailing are also a big part of the culture here. So, choose what works best for you!
Option 1: Kayak, SUP, or Canoe Rental
Rent a kayak, stand-up paddle board, or canoe from Annapolis Canoe and Kayak, which offers rentals and sales of different equipment right in East Port. Rentals are by the hour, and you’ll enjoy amazing views of historic Annapolis and the coves surrounding the harbor.
Summer Hours: Mon-Fri 11am-7pm; Sat/Sun 10am-5pm
Option 2: Cruise on the Chesapeake
You can charter your own boat at many different places; one of the most affordable is from Annapolis Electric Boat Rentals, which starts at $185.
Summer Hours: Mon – Fri 11 am – 7 pm; Sat – Sun 8 am – 7 pm
You can also take a boat right in Eastport from the Annapolis Maritime Museum. Their boat tours are aboard a historic skipjack. Built in 1940, the boat is one of 23 floating skipjacks and only 5 that commercially dredge for oysters. The season runs in October. Note that most of their tours are not in the morning, so consider that in your day itinerary!
Tours: 1 pm
Lunch in Eastport
Located on Restaurant Row in the historic maritime district of Eastport, this is a must stop on a day trip! Annapolis is known for its seafood, and there’s really no better crab cake than at Boatyard Bar & Grill.
The crab cakes here have been voted best in Annapolis for 20 years in a row by Best of Annapolis, Best Crab Cake in Maryland by the Baltimore Sun, and featured on several TV shows! We also loved the raw bar options and how fast the service was there!
Expect a wait here, even for lunch on a weekend. If there is a wait, I recommend hitting up some of the local shops on the street or stopping for a drink at Forward Brewery that’s next door. Our wait was about 30 minutes on a Saturday in June.
They also offer crab cakes raw to go if you want to take some home!
Early Afternoon Explore History
Annapolis was founded in 1649 and has a long maritime history. Since it has a lot of history, it’s well worth spending some time learning about the historical significance of the city or some of its most well-known residents.
Pro-tip: Many of the historical sites in Annapolis close early (around 3 pm), so it’s best to make sure you have ample time after lunch to visit one, or swap the morning and afternoon of this itinerary!).
Below are a few of the top historical sites.
Option 1: William Paca House
The William Paca House and Garden is an 18th-century Georgian mansion right in Historic Downtown Annapolis. William Paca is one of the Founding Fathers who signed the Declaration of Independence and was the three-term governor of Maryland. The house was built between 1763 and 1765 and gives a look into life around the American Revolution.
You can visit the gardens on your own but must join a tour to visit the inside of the house. It costs $12 for adults, $7 for children.
Summer Hours (March 20 – August 31):
- Monday – Thursday: 10 am – 5 pm
- Friday: 9 am – 5 pm
- Saturday: 10 am – 3 pm
- Sunday: 10 am – 4 pm
Option 2: US Naval Academy
The US Naval Academy Museum is located in Preble Hall within the US Naval Academy. The Museum has two floors and shares US Naval history and more about the Naval Academy. Many people choose to take a tour of the Naval Academy to see the boats and campus and learn about Navy history.
Hours: 9 am – 5 pm
Option 3: Banneker-Douglas Museum
The Banneker-Douglass Museum, named for Benjamin Banneker and Frederick Douglass, is the state of Maryland’s official museum of African American heritage. It documents, interprets, and promotes African American history and culture (particularly in Maryland) through exhibitions, programs, and projects to improve everyone’s understanding and appreciation of America’s rich cultural diversity.
Hours: Tuesday – Saturday 10 am – 4 pm, Sunday – Monday: Closed
If you’re interested in more African American history in Annapolis, consider taking this tour!
Late Afternoon and Evening in Historic Downtown Annapolis
After taking in some history, it’s time to explore the historic downtown! Annapolis is extremely walkable which is why I mentioned earlier just parking your car for the day, but this part of Annapolis is especially easy to navigate!
The quaint waterfront offers tons of options for things to do! You can go shopping at cute boutiques, stop in art galleries, grab a drink on a rooftop, stop in at a pub to listen to live music, or just stroll the 300 year old streets looking at colonial architecture.
Many of the shops will close at 5 pm, even on weekends, so make sure to stop in anywhere you really want to see early! Then, hit the town to head to some restaurants or bars.
Some of my favorite places in Historic Downtown Annapolis
Local Shops and Art Galleries:
- Old Fox Books
- Maryland Ave for Antiques
- Trendy Tides Boutique
- Back Creek Books
- Kim Hovell Fine Art
- Brightside Boutique
Food:
- Annapolis Ice Cream Company
- O’Brien’s Oyster Bar & Seafood Tavern
- Chick & Ruth’s Delly
- The Choptank
Bars:
- Ponche Tiki Bar
- Fox’s Den
- DRY 85
- Parley Room
Ending the Day in Annapolis
Still interested in something else after dinner? Consider one of the things below to end your day. I wouldn’t recommend these if you’re planning on driving back because they do go til after dark, and it could make for an extremely long and exhausting day! Consider staying in Annapolis overnight!
- End your day with a sunset cruise on the water.
- Take a ghost tour to hear about the spooky past of Annapolis.
A day trip to Annapolis is well worth the time! You’ll love the historical charm and coastal vibes enjoyed in this town. Have you visited Annapolis? Leave your thoughts below!
It looks like we need to plan a visit to Annapolis the next time we are road tripping in that area. You know we would want to start our visit on the waterfront and enjoy a trip out on the water. Glad to know we can start with a good coffee! As former Navy, hubby would definitely want to explore all the naval history in the area.
Yes! Well worth adding to an itinerary when in the area, especially for those with ties to the Navy or US history!
Great post about Annapolis. I love the mix of cultural things, like a museum visit, and activities, like going on a kayaking trip. Good coffee is always a plus!
Good coffee is definitely a necessity for me to find on a trip ha! And agree – a mix of activities is the best way to spend a trip.
aw this post makes me miss Maryland! my grandparents lived there so I spent a ton of time there growing up 🙂 Annapolis is so cute and has so much history (and I miss the crab cakes lol), thanks for this great post!
What a fun place to visit as a kid growing up! Agree – so much fun history and great food there.
This looks like a great way to spend a day! Looks like they have some cute places to check out!
Lots of cute places in Annapolis! It’s such a fun coastal town.