Is Annapolis worth visiting?
Annapolis, Maryland might not be the first place that comes to mind when planning a weekend getaway but trust me, it should be! I live about an hour and a half from this charming waterfront city, and there’s no place like it. Annapolis is rich in history, beautiful views, and some seriously incredible food.
In this guide, I’ll help you decide, “is Annapolis worth visiting”, and walk you through how to make the most of a day in Annapolis, with a jam-packed day full of activities from morning to evening.
Short on Time?
Annapolis is definitely worth a visit, and if you’ve only got one day, here’s how to make the most of it:
- Explore the U.S. Naval Academy on this guided tour.
- End the day with this fun and spooky Annapolis ghost tour.
If you’re visiting from out of town, this car rental is a convenient option.
Where to Stay in Annapolis
Here are some of my top picks for where to stay in Annapolis:
- Budget Option: Graduate by Hilton Annapolis – This hotel is located right in the heart of downtown, just a short walk from the U.S. Naval Academy. With its cozy, quirky vibe and affordable rates, it’s a great budget-friendly choice. Book your stay.
- Mid-Range Option: The Annapolis Waterfront Hotel – This hotel is right on the water, offering beautiful views of the harbor, and just a stone’s throw from City Dock and all the best restaurants. You’ll get that perfect balance of comfort, convenience, and a touch of luxury without going overboard. Book your stay.
- Luxury Option: The Historic Inns of Annapolis – This collection of three charming inns is housed in beautifully restored 18th and 19th-century buildings, giving you an elegant, historical experience with all the modern luxuries. Book your stay.
Is Annapolis Worth Visiting?
The short answer? Yes, absolutely! Annapolis is packed with history, gorgeous waterfront views, and a laid-back, small-town vibe that makes it a perfect destination for a one-day trip or weekend getaway.
One Day in Annapolis, Maryland: A Full Guide
Morning at Sandy Pony Donuts and Main Street
Start your day in Annapolis with a coffee and a pastry at Sandy Pony Donuts. These donuts are a local favorite, and they’re the perfect balance of crispy on the outside and soft on the inside. The Sand Dune is heaven!!
While you’re there, grab a cup of freshly brewed coffee and enjoy the laid-back morning views of the Bay.
From there, take a stroll down Main Street, which is lined with cute boutiques and antique shops. Stop by The Annapolis Pottery, a small pottery store where you can pick up handmade ceramic pieces that make for great souvenirs.
If you’re looking for some history, head over to the Maryland State House (the oldest state capitol still in continuous use). You can take a self-guided tour and soak in the historical significance of the building, which also served as the temporary U.S. Capitol.
Nearby, The William Paca House and Garden offers a beautiful glimpse into 18th-century life, with restored gardens and a Georgian mansion.
Afternoon at The US Naval Academy
For lunch, visit Dock Street Bar and Grill. Formerly a city jail, it’s now a local favorite serving up SO much crab in their crab dip! The restaurant sits right on the water and offers stunning views of the harbor.
After lunch, it’s time to explore more of Annapolis’s waterfront charm. Walk along the City Dock, where you’ll see boats, charming little shops, and street performers.
Of course, a visit to the United States Naval Academy is a must. There are plenty of guided tours available to help you fully explore the stunning campus and iconic spots to see, like the Chapel and the memorials that honor U.S. naval heroes.
This specific tour is great because you can customize it on request, and you get to see other top sights in Annapolis, like the Georgian mansions, Maryland State House, and historic spots like where the Treaty of Paris was signed!
You also get to walk along the city dock, harbor, and see views of the Chesapeake Bay. It’s a great tour to see most of the historic spots in the city, in just 2 hours.
➡️ Click here for the best Annapolis guided tour!
Spend an Evening with Crabs and Ghosts!
As the sun starts to set, head to Chart House Prime for a dinner with a view. It’s a bit on the pricer side, but the seafood is fresh and the restaurant overlooks the scenic Chesapeake Bay.
O’Learys is another great restaurant that’s popular with a lot of veterans! They have a great, great selection of local seafood and a fun, lively atmosphere. Their crab risotto is amazing, and I love how you can actually see the crab + seafood coming out of it!
After dinner, see a new side of the city with a spooky Annapolis ghost tour. My friend and I recently did this ghost tour in Annapolis, and we had a blast! You can explore haunted sites like the Middleton Tavern and the James Brice House, and learn all about the haunted encounters that took place in the city.
The tour is about an hour long, and it recently won a Viator award of excellence! Sometimes the subject matter can get dark, but your tour guide does a good job of helping you find the balance between staying creeped out and having fun. I highly recommend it!
➡️ Explore this scary, but fun Annapolis ghost tour!
Getting Around
One of the best things about Annapolis is how walkable it is. Most of the attractions in the historic district are within walking distance, so you can easily explore on foot.
If you need a break or want to travel a bit further, there are plenty of bike rentals around, or you can take a quick ride with one of the local taxis or rideshare services.
➡️ Visiting from out of town? I recommend this car rental!
Is it Safe?
Yes! Annapolis is a super safe city for visitors, especially around the historic downtown and waterfront areas. Of course, like anywhere, it’s smart to keep an eye on your belongings and stick to well-lit streets at night, but most people feel completely comfortable exploring on foot.
The city is small, walkable, and full of friendly locals, so you’ll feel right at home. With just a little common sense, you can enjoy everything Annapolis has to offer without a worry!
Best Time to Visit
Annapolis is beautiful year-round, but spring and fall are truly the sweet spot. The weather is mild, the waterfront looks its best, and the city feels lively without the big summer crowds.
Summer is great too, just be prepared for hotter days and more visitors. Winter is quieter, but the holiday lights and cozy restaurants make it a surprisingly charming time to explore.
FAQs
Recommendations for a day in Annapolis?
Start with a hearty breakfast at Sandy Pony Donuts, then dive into history with a visit to the Maryland State House. Lunch by the waterfront, followed by an afternoon exploring the U.S. Naval Academy Museum, and finish with a sunset dinner at The Chart House.
Is Annapolis worth seeing?
Absolutely! The blend of history, scenic waterfront views, and delicious food makes Annapolis a must-see city with plenty of things to do, and has been frequently ranked as one of the best spots to visit on the East Coast.
What to expect when visiting Annapolis for the first time?
You can expect a charming, walkable town full of history, beautiful harbor views, and delicious local seafood. There are lots of boats, historic walking tours, and cobblestoned streets and to explore!
Final Thoughts
Annapolis is one of those hidden gems that deserves more attention, and after spending a day there, you’ll see why – it is SO worth visiting! Whether you’re looking to relax by the water or try some of the best crab cakes in the US, Annapolis has something for everyone.
Happy travels!
About the Author
Sasha is the founder of Little Happy Travels, a blog with tips and inspiration for combining work + travel and living the digital nomad lifestyle. As a business coach and remote worker, she’s spent the last few years traveling the world while helping others do the same. Follow for guides, tips, and personal stories on working from anywhere!
