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One summer weekend, my husband and I realized we hadn’t planned anything for our anniversary so decided to book a weekend trip to Annapolis, Maryland! Living in Philadelphia at the time, Maryland is 2 hours away from Philly and a reasonable drive or train ride from many major cities – making this historical town an easy weekend trip. Here is my guide on things to do in Annapolis (based on our 3-day Annapolis itinerary).
Located in the Chesapeake Bay Region, Annapolis is the capital of Maryland and part of the greater Baltimore/Washington metroplex. But don’t expect a big, urban city!
Annapolis is easy to get to without a car (which I love) and it’s super walkable, especially the historic downtown area.
Bustling with community events, water activities, and tons of history, its relaxed vibe makes it a romantic destination for couples and family-friendly getaway. It was surprisingly diverse as well, which I don’t find in a lot of US coastal towns.
What to Know About Annapolis
Get to know the city of Annapolis, Maryland a little better!
Where is Annapolis Located?
Annapolis, Maryland is in Anne Arundel County on Maryland’s western coast of Chesapeake Bay. The Mid-Atlantic east coast city is about 2 hours from Philly, 45 minutes from Washington DC, and 30 minutes south of Baltimore. For my New Yorkers, it is a 4 hour drive (but if you don’t have a car, I provide alternatives later in the article).
Annapolis History to Know
The indigenous tribes, Piscataway and Pamunkey are some of the original inhabitants of the Annapolis, Maryland area. “Native Americans often crossed through the Annapolis area during hunting expeditions to the other side of Chesapeake Bay.” (Source)
Later settled in the 1600s, the bayside city of Annapolis was briefly the US Capitol at the end of the Revolutionary War and was once a slave trade port. St. John’s College was founded here in 1696 and the city was also home to many signers of the Declaration of Independence.
Today, the capital of Maryland is known for its well-preserved colonial buildings, and for the US Naval Academy.
Quintessential Things to Do in Annapolis
If you want a quick list of things to make sure you see and do while in Annapolis, use this bulleted list to help guide your weekend getaway:
- Try the seafood! Maryland is known for local oysters and Chesapeake blue crab. I don’t eat shellfish, but my husband is obsessed, so we made sure to go for those. I mention a few restaurants to consider in the itinerary further down.
- Order the Smith Island Cake (the official dessert of Maryland), a beautiful 9-layer yellow cake covered with chocolate icing layers. I’m not a big dessert person but I love classic cakes like this, and it was delicious!
- Check out the Naval Academy. You can take tours or visit the museum. Just do your research before you go. They’re very strict about forms of identification for entry, based on where you live.
- Check out a few of the many museums in the downtown area. Within walking distance, you’ll find history museums, historical homes, art museums, and more. And don’t forget about the Maritime Museum in Eastport.
- Ride a boat on the Chesapeake Bay. There are all kinds of fishing charters and sailboats for rent. You could rent kayaks and paddle out to Sandy Point Beach or book a cruise on the harbor.
3-Day Annapolis Itinerary
Here is my travel guide for 3 days in Annapolis.
Day 1 in Annapolis, Maryland:
On day one of your trip I recommend you take the morning to travel to Annapolis (directions/travel info further down this article), enjoy lunch and a stroll through downtown, and then check into your hotel and freshen up. Later you can take the evening to enjoy some of the most iconic attractions in Annapolis. Here’s a schedule breakdown below:
Morning
- Start with brunch on the water at the cozy Carrol’s Creek Café. You can watch the boats on the harbor while enjoying fresh seafood and other classics. This is a very popular spot!
Afternoon
- Enjoy a nice walk around Annapolis’s historic district with its beautiful brick buildings and cute shops.
- Head over to the William Paca House and Garden. This stunning home and 2-acre garden were once home to Paca, one of the signers of the Declaration of Independence. You can tour the property for a small admissions fee.
- Next, you’ll visit the Banneker-Douglass Museum on the other side of Church Circle. Learn about the important history of the African American community in Annapolis and the role of the city as a slave trade port. I thought this was a great museum with easy to digest exhibits. Admission is free and optional guided tours are $5 per person.
Evening
- For dinner, go out to the Anne Arundel Farmers Market for Food Truck Fridays! Take in the fun at Annapolis’ local food truck scene with live music (see Alex’s lobster roll in the photo below). There were also a ton of old style cars and small business vendors.
- End your first day in Annapolis by heading back downtown to watch the sunset at City Dock. Everyone comes out for this and just relaxes on benches or gets ice cream.
Day 2 in Annapolis, Maryland:
Day two is your one full day in Annapolis. We used this day to go boating, enjoy the local wine scene, and book a seafood dinner before strolling the heart of downtown Annapolis at night. Here’s a breakdown of the day with recommendations:
Morning
- Take a morning cruise and enjoy the breeze on the bay. I took a 40-minute Annapolis Harbor & USNA Cruise for $22 a person with Watermark. Their prices and times fluctuate so check the site first.
Afternoon
- You’ll be hungry after your morning on the bay, so visit the Great Frogs Winery on the southern shore. Go for a wine tasting and play bocce ball and other yard games in the vineyards! It’ll be lunchtime, so I recommend ordering the meats and cheese charcuterie to go with the wine.
- Next, you’ll take a relaxed stroll along the quiet Aberdeen Creek and South River at the park near the winery.
Evening
- Come back downtown and take a water taxi to dinner from City Dock. You can board water taxis easily and you pay with an app. I found the app “Where in Annapolis” to be so useful – including providing resources for water taxis. You can also pay by cash, or get a book of taxi vouchers on the dock beforehand. Taxis cost $4-9 per person depending on the distance.
- Take advantage of the day’s fresh catch with a seafood dinner. We went to Chart House Restaurant via Water Taxi and it was such a cool experience! It is an elegant seafood and steakhouse in a remodeled shipping boat and we entered through the back way since we came by boat.
- After dinner, enjoy one last sunset at City Dock. Grab ice cream at a local shop and enjoy the view! Beware: ice cream lines can get quite long so time it accordingly.
Day 3 in Annapolis, Maryland:
Make the most of your last day by enjoying a relaxing brunch and heading to one of the many museums in Annapolis.
Morning
- Check out of your hotel and have brunch before your last day of exploring. If you’re in the mood for romantic dining, head to Cafe Normandie. Or enjoy a classic, sweet brunch at the Iron Rooster. If you’re craving more seafood, check out a nautical-themed restaurant like Boat Yard Bar & Grill. We chose the latter.
- It’s museum time! The Museum of Historic Annapolis is a popular choice for visitors to the city, but honestly there are so many to choose from. Check out this list and choose the one you’re most excited about.
Afternoon
- Before you go home, take a few hours and visit the US Naval Academy if that interests you. From the visitor’s center, you can book a walking or driving tour or head to the museum. If you’re short on time there are great exhibits inside the visitor’s center as well.
Where to Stay in Annapolis
Hotels and other accommodations in Annapolis
If you’re looking for places to stay during your weekend in Annapolis, there are a handful of hotels located downtown and dozens of Airbnbs scattered all over. Lodging will be mid-range to expensive nightly rates during high season, so I recommend Priceline Express Deals if you’re on a budget.
I suggest looking at your plans for what you’ll be doing while you’re in town and deciding what’s a priority for you. If you don’t have a car, consider staying close to downtown. This way you’ll be close to everything you’ll be doing during your visit.
Hotels in Annapolis, Maryland
I stayed at the Historic Inns of Annapolis, a hotel made up of 3 gorgeous colonial-era buildings with contemporary classic interiors. It was awesome because it was walking distance away from the Naval Academy, the Annapolis Harbor, several museums, and more.
I would also recommend the Hilton Garden Inn Downtown or the Graduate Annapolis, both further down West Street. The Graduate is a fun boutique hotel themed around the Naval Academy. If I were to stay again I would choose the Graduate.
Airbnb/VRBO Options in Annapolis
Generally, I found Airbnbs to range between $200-$400 a night in the downtown and Eastport area, though you can find them further out as well. There are lofts, condos, apartments, guest houses, and full homes inside the city limits.
Downtown Annapolis home rentals:
Annapolis Neighborhoods to Stay In
Annapolis is pretty big and kind of merges further out with Baltimore and Washington DC. So, there are a lot of neighborhoods to choose from.
For me, the best part of town is the historic downtown area by the water. You’ll love the colonial-era architecture the house residence, shops, museums, galleries, and more. Keep an eye out for quirky things like this tiny mailbox!
Eastport is another very popular area with views of downtown from across the water. There are all kinds of waterfront restaurants and parks. It’s a great place to get on the water by renting a kayak or a boat!
When to Visit Annapolis
The best time to visit Annapolis
What’s the Best Time of Year to Visit Annapolis, MD?
I love visiting the Chesapeake Bay region in the spring and summer, but if you do, expect lots of people! The summer is a popular time to come with both the Annapolis Crab Feast and the Maryland Renaissance Festival in August. Be prepared for hot and humid conditions in July and August.
If you’re looking for things to do in Annapolis across the seasons, you can attend the St. Patrick’s Day Festival in the spring and or check out the Christmas festivities in December. October draws the seafaring crowds with boat shows.
Is it Better to Visit Annapolis on the Weekend or During the Week?
There’s plenty to do during the week, but it depends on what you want to do! If you want to check out Food Truck Fridays or enjoy full brunch menus, I suggest going on the weekend. But if crowds are your concern, it’s better to go during the week when things are a bit quieter. There just may not be as many special events hosted.
How to Get to Annapolis
Here are the different ways to get to Annapolis, MD
What Airport Do You Fly into for Annapolis?
There’s no major airport in Annapolis. You could fly into Reagan International Airport in Virginia, but I suggest you fly into the Baltimore/Washington International Airport. From the BWI Airport, Annapolis is just a 30-minute taxi ride away.
Does Amtrak Go to Annapolis, MD?
Not directly, but if you plan on taking Amtrak, you can take the train to Baltimore at the BWI Amtrak/MARC station just outside the airport. From there it’s a 30-minute taxi ride/rideshare or you can take public transportation.
That means, if you are coming from Philly, DC, NYC, and even Boston this might be a great alternative to driving. For example, Amtrak Acela trains from NYC will get you to Baltimore in less than 3 hours!
How to Get to Annapolis by Car
If you plan on driving, it’s pretty easy to get to Annapolis. From Baltimore or Washington DC, it’s less than an hour’s drive. From Philadelphia it’ll take about 2 hours. There are tolls so I recommend having spare change or your EZ Pass.
Have you been to Annapolis?
Annapolis is stuffed with history and outdoor fun. A weekend is the perfect amount of time to enjoy this city with a small town feel. If you have an extra day here, I suggest exploring a little further and taking some time to check out the Annapolis arts district.
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