Annapolis is one of the most charming small towns near Washington DC. It is just 30 miles from Washington DC but still feels like a completely different world. It has cobblestone streets, waterfront views, the United States Naval Academy and some of the best seafood. It is the best day trip destination for people who are living or visiting DC.
An Annapolis day trip is easy because it is just an hour drive from DC. The problems that most people face are logistics. Parking in historic Annapolis is difficult because the area was not built to handle large numbers of cars. The streets are narrow and fill up quickly, even when the crowd is small. Driving through these small and unfamiliar streets can also be difficult. You may not know if your car can go down the next street, so sometimes you have to turn back and find a wider road.
This guide walks you through exactly how to spend a perfect day in Annapolis, with the best stops, the best food and the smartest way to get there and back.
Why Annapolis is a Great Day Trip from DC
Annapolis is the capital of Maryland and has a rich history. This city was actually the capital of the United States for a short time from 1783 to 1784. The State House here is also the oldest state capitol in the country that is still used for government work today. Beyond the history Annapolis also has:
- Working waterfront with active boating and harbor life
- Harbor with sailboats and yachts
- Fresh seafood
- Compact downtown that is easy to walk and explore
- Many attractions, shops and restaurants are close to each other
Morning: Start at the United States Naval Academy
The Naval Academy is the best place to start your day. This campus, also known as the Yard, covers 338 acres along the Severn River. Visitors can take a guided tour to see the chapel, the crypt of John Paul Jones, Bancroft Hall and the museum. Bancroft Hall is one of the biggest dorm buildings in the world and the chapel’s dome can be seen from many parts of the city.
Tip: Bring a photo ID with you when you come here for a visit. The security at Naval Academy gates requires identification for all visitors and the visitor must be over 18.
Mid-Morning: Walk Through Historic Downtown
After the Naval Academy, spend an hour or two simply walking the historic downtown streets. Annapolis is one of the best preserved old colonial areas in the country and most of it is easy to walk. Main Street goes from the City Dock up to the State House. Along the way there are small shops, art galleries and cafes in old colonial style buildings. The Maryland State House is at the top of the hill. It is the oldest capitol and free tours are available for it.
Lunch: Fresh Seafood by the Water
The City Dock area has good seafood restaurants with outdoor seating. A local favorite here is blue crab. You can have it in different ways like in a crab cake sandwich, a bowl of creamy crab soup or a full crab feast where you sit at a table covered with newspaper and crack the shells open by yourself. You can also have fresh oysters, rockfish, and other local food with water views.
Tip: Crab feasts are messy and take time. If you have a tighter schedule, try a crab cake sandwich that gives you the same flavor in less time.
Early Afternoon: Explore the City Dock and Harbor
After lunch, spend some time exploring the City Dock. It is the main waterfront area of Annapolis where you can see sailboats and fishing boats. You will also find the Wiley H. Bates statue and the Kunta Kinte-Alex Haley Memorial here.
From the dock you can also book a short sightseeing cruise on the Chesapeake Bay. Many companies operate here to give a tour that takes you all over the city. It’s a nice way to see the city from the water. It is something you cannot experience on foot.
Tip: If you want to add the boat tour, add an extra hour in your schedule. The views of Annapolis from the water are genuinely worth it.
Afternoon: Shopping and Galleries on Maryland Avenue
Maryland Avenue is one of the best shopping streets in Annapolis. The shopping area is not large, but it is unique. You will find:
- Handmade crafts
- Nautical gifts
- Small boutiques
- Art stores
Evening: Cross the Bridge to Eastport
Eastport is just across Spa Creek from downtown Annapolis. It is a waterfront area where people work with boats, like boat builders and sailmakers, so it still has a real working harbor feel. A walk across the Spa Creek Bridge gives you good photo opportunities of the Annapolis skyline and harbor.
A Sample Annapolis Day Itinerary
| Time | Activity | Location |
| 9:30 AM | Naval Academy tour | The Yard |
| 11:00 AM | Walk historic downtown | Main Street, State Circle |
| 12:30 PM | Lunch | City Dock seafood restaurant |
| 1:30 PM | City Dock and harbor walk | City Dock |
| 2:30 PM | Harbor boat tour | City Dock |
| 3:30 PM | Shopping | Maryland Avenue |
| 5:00 PM | Walk to Eastport | Spa Creek Bridge |
| 5:30 PM | Drinks in Eastport | Eastport waterfront |
| 7:00 PM | Dinner | City Dock or downtown |
| 9:00 PM | Return to DC | Home |
Explore Annapolis with AA Limousine and Sedan
A tour to Annapolis is more enjoyable when you do not have to worry about driving or parking. A comfortable car makes the day more relaxing.
AA Limousine and Sedan offers private transportation for Annapolis day trips from DC and other Maryland areas. Our chauffeurs know all the routes in the area and are experienced in navigating the narrow streets of Annapolis. Once you book a day tour with us, our professional chauffeur with a luxury car or limo stays with you for as long as you need. They provide rides to every stop and get you back home safely.
We provide luxury sedans, SUVs, stretched limos, and group travel options. Whether it is a solo trip, family trip, couple outing or small group tour, we have a fleet for each size of group. Our fleet consists of the latest model cars, which are cleaned and maintained before every trip.
Book your Annapolis car service with AA Limousine and Sedan and enjoy a relaxed day by the water.
Frequently Asked Questions
How far is Annapolis from Washington DC?
Annapolis is about 30 miles from DC, approximately a 45 to 60 minute drive depending on traffic.
Is one day enough to see Annapolis?
Yes. All attractions are close in Annapolis which can be visited in one day if the trip is well-planned.
What is the best time of year to visit Annapolis?
Late spring to early fall is the best time to visit Annapolis because at this time the harbor is full of sailboats and outdoor dining is at its best.
Do I need a car to get around Annapolis once I arrive?
No. The historic downtown, the Naval Academy, the City Dock and Eastport are all within walking distance of each other. A car is really only needed for getting to and from Annapolis.