Headed on an East Coast road trip? Add Annapolis to your list! In this post, I’m sharing EVERYTHING you need to know about this captivating coastal town, including the best things to do in Annapolis, restaurants to check out, where to stay, and much more. Plus, I’ve got you covered with my favorite happy hour spots and the best Annapolis seafood restaurants you have to try!
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The ultimate travel guide for Annapolis Maryland
The next longer stop of our road trip was Annapolis, and let’s just say we can’t wait to go back! Annapolis, Maryland, nestled on the banks of the scenic Chesapeake Bay, is a charming city full of character that’s lined with cobblestone streets, beautiful colonial architecture, and stunning views around every corner.
Even though Annapolis is home to the United States Naval Academy and is known as America’s sailing capital, it often takes the back seat to its neighbors Baltimore and Washington D.C. That’s unfortunate because there are so many fun (and educational) things to do in Annapolis MD that I will go into more detail on below so KEEP READING!
If you enjoy indulging in lots of delicious seafood, touring 18th Century Georgian Mansions, eating & drinking your way around town, and sailing the Chesapeake Bay during sunset, then Annapolis is the perfect destination for your next vacation!
In this post, we’re going to be covering EVERYTHING you need to know about this maritime gem, including the best hotels Annapolis MD, favorite restaurants Annapolis, fun things to do in Annapolis, and so much more!
Planning in a hurry? Check out these quick links!
Travel resources:
- WayAway (Find the best rates on airplane tickets)
- Discover Cars (compare rental car prices and save $$$)
- Booking.com (my go-to when booking hotels ALWAYS)
Best hotels Annapolis MD:
- Annapolis Waterfront Hotel (stunning waterfront views)
- The Westin Annapolis (luxury hotel in Downtown Annapolis)
- Graduate Annapolis (boutique hotel with a rooftop bar)
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Things to know before you go
How to get to Annapolis
The easiest way to get to Annapolis is by flying by plane into the Baltimore/Washington International Thurgood Marshall Airport, about 24 miles north of Annapolis. All major domestic airlines do fly at this airport.
From there, you can either rent a car and follow I-97 to US Route 50, take a Super Shuttle, or grab a BWI airport taxi which is about $45. You can also take the Amtrak directly from the BWI terminal to your hotel or another destination in the Annapolis area.
As mentioned, this was one of the stops on our road trip, so we drove, but it was pretty easy to find our way to Annapolis. Once we got there, we barely had to move the car since everything was super walkable. Parking is challenging, so I recommend finding a hotel or Airbnb close to the city center like we did. See my recommendations below!
Need a rental car? Compare the best prices on Discover Cars!
Best time to visit Annapolis
Even though Annapolis is a great place to visit any time of the year, the best time to go is spring, when the sailing season is just beginning. Sailing is still pretty popular throughout summer. However, Annapolis weather isn’t as favorable, as average highs are in the upper 80s.
The most significant events in Annapolis are the Annapolis Boat Shows which bring in sailing enthusiasts from around the US and boast all of the latest boats, gear, and tech.
We visited in September, and the weather in Annapolis was absolutely beautiful! It was cool in the mornings, perfect for our AM walks, and warmed up throughout the day. The leaves were also starting to change, which made everything especially pretty!
Where to stay in Annapolis MD
Rentals in Annapolis
The Airbnb we stayed at in Annapolis might have been my favorite of our ENTIRE road trip! First, it could not have been in a more perfect location and was literally steps to downtown. Parking is pretty challenging in Annapolis, so it was nice to walk EVERYWHERE!
Secondly, our Annapolis apartment rental was well taken care of, nicely decorated, and extremely clean. I felt right at home (and so did Melvin)! As far as amenities, we had plenty of space to work during the day (since it was a two bedroom), we had a fully equipped kitchen so we could make most of our dinners at home, we had a lovely patio that was so perfect for HH, and it was dog friendly.
The only downfall of this Airbnb is that it was at the very top of a multi-story building and did not have an elevator, so we had to carry all of our stuff up several flights of stairs. Otherwise, we truly enjoyed our stay here, and I could not recommend this Airbnb more!
Want to see some other Annapolis rentals? Check them out here!
Annapolis hotels
Prefer to stay in a hotel? Compare the best hotels in Annapolis MD here, AND make sure to check out some of my recs below!
- Annapolis Waterfront Hotel offers a picturesque waterfront location with stunning views of the harbor. This upscale hotel offers elegant rooms, excellent dining options, and a convenient location for exploring the historic district. It’s also home to Pussers Annapolis, a Caribbean Grille filled with fresh seafood and seasonal specialties. It’s also the only true Annapolis waterfront restaurant.
- The Westin Annapolis is a contemporary and luxurious hotel with spacious rooms, modern amenities, and a tranquil atmosphere. It’s also within walking distance of downtown Annapolis and the State House.
- Graduate Annapolis is a boutique hotel featuring a stylish nautical theme and is located near the United States Naval Academy. It offers quirky, comfortable rooms and a rooftop bar with panoramic views that are unmatched.
- Hilton Garden Inn Annapolis Downtown is the perfect option if you’re looking for a more affordable hotel in Downtown Annapolis that’s still within walking distance of all the action. Located nearby are the Maryland State House, William Paca House, US Naval Academy, and many other attractions.
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Bars & restaurants in Annapolis
Out of all the things to do in Annapolis Maryland I think we probably spent most of our time eating and drinking (surprise, surprise, haha). As mentioned, we were so close to Downtown Annapolis, so everything was easily accessible, and there were also so many great places to try (including a plethora of happy hour spots). I mean, how could we pass that up?! Sharing some of my favorite Downtown Annapolis restaurants below!
Best Annapolis coffee shops
Rise Up Coffee Annapolis was by far our favorite coffee spot! Their coffee was not only delicious but also overlooked the Annapolis Harbor, so it was the perfect place to enjoy your espresso with a view! It also lives inside Annapolis Market House, a market and fantastic lunch spot with lots of delicious sandwiches, burgers, specialty boards, and more!
Best lunch in Annapolis
Masons’s Famous Lobster Rolls was the first lobster roll of our road trip, and it did not disappoint! They have a ton of different options, including both Connecticut style (warm with butter) and classic (cold with mayo), and it’s relatively affordable (for a lobster roll). I recommend grabbing it to go and heading down to the harbor to enjoy your lunch with a view.
If you’re looking for one of the best seafood restaurants in Annapolis, Cantler’s Riverside Inn is the one! This is the go-to Annapolis crab restaurant, and even though it was 20 mins away from where we were staying in Downtown Annapolis, it was well worth the drive. They could tell we had never cracked blue crab before, and they even gave us a tutorial on how to do it!
Best oyster restaurants in Annapolis
McGarvey’s Saloon & Oyster Bar might have been my favorite Annapolis restaurant we ate at! We just ordered apps and drinks, but their oysters were so yummy, and I highly recommend trying their crab pretzel. It was magical! They also have happy hour specials during the week from 2-6 pm, including select drinks and appetizers.
Check out this tour >> Embark on a Historic Annapolis food tour and enjoy a series of dishes from a variety of Downtown restaurants while learning a little bit about Annapolis along the way!
Best happy hour spots in Annapolis
You know your girl is always on the hunt for good happy hour spots to share with you guys, and let’s just say there is no shortage of them in Annapolis! If you’re in the mood for oysters, Obrien’s Oyster Bar is your go-to place, AND they’re only $0.99 Monday-Thursday during happy hour.
If you’re craving a glass of wine and some charcuterie, you need to check out Red Red Wine Bar, which has happy hour Mon-Fri from 3-6 pm. Included are select eats and glasses of wine for only $5!
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Best things to do in Annapolis
Even though Annapolis has a small-town feel, there’s still so much to explore! We were there for a week, and although we spent some time working, we never seemed to run out of fun things to do in Annapolis. Sharing some things to do in Downtown Annapolis below!
Take a boat tour on the Harbor Queen
Annapolis is a beautiful historic seaport that is great to explore by water! There are many different boat tours to choose from. However, we decided to board the classic Harbor Queen, which includes a narrated tour of the Annapolis Harbor and banks of the US Naval Academy. The boat also has a bar, so you can sip mimosas as you sail on the region’s beautiful waterways. The tour lasts less than an hour and is only $22/per person.
Visit the William Paca House
I’m not much of a history buff, but I really enjoyed touring the William Paca house. ICYDK William Paca is one of Maryland’s four signers of the Declaration of Independence and has one of the finest 18th-century homes in the country located in the heart of Annapolis.
For $12/person, you can take a guided tour of the house and gardens and learn about the people who lived and labored there. If you’re looking for a fun (and educational) rainy-day activity, this is definitely for you!
Explore Annapolis City Dock
City Dock is the Annapolis Downtown Waterfront which is considered the historic heart or city center of Annapolis. Within City Dock is Main Street, which has dozens of unique locally-owned boutiques and specialty shops tucked between galleries, restaurants, and inns.
Some of my favorite stores were 3 Sisters and Lou Lou, both really cute clothing & accessory boutiques. If you need to take a break from shopping, Ego Alley is also a part of City Dock and is the perfect place to relax by the water and watch the boats parade through the harbor.
Check out Eastport Annapolis
If you take a water taxi from City Dock or walk across the Spa Creek Bridge, you will enter the laid-back maritime district of Annapolis, known as Eastport.
Eastport is a great place to escape if you want a break from the busyness of the city, and it has lots of delicious restaurants, shops, and breweries with waterfront views. If you decide to venture over to Eastport, make sure to stop at Pussers for a drink, Boatyard Bar & Grill for a snack, and Forward Brewing for a beer!
Take a tour of the Annapolis Naval Academy
Unfortunately, we didn’t get the chance to visit the Naval Academy, but I would recommend doing this if you visit Annapolis! There are plenty of ways to learn about this important American Institution by taking a guided tour of the campus, stopping by the Naval Academy Museum, or even attending a sporting event at the Marine Corps Memorial Stadium.
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