Nestled on the Chesapeake Bay 25 miles south of Baltimore and 30 miles east of Washington D.C., Annapolis might just be the most charming capital city in the United States. They say it’s easy to fall in love with Annapolis, and speaking from experience, it is 100 percent true. My family recently relocated nearby and find ourselves driving into the city as often as possible – and have come up with the ultimate day trip itinerary for history buffs, foodies, bookworms, and caffeine addicts alike.

With its 18th-century brick homes, a gorgeous waterfront, the striking and prestigious United States Naval Academy, and countless charming shops and restaurants, there’s no better place to soak in the history and beauty of the Chesapeake Bay.
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Whether you have a full day to spare or just a few hours, Annapolis is sure to impress.
We always begin our day at the Light House Bistro.
Light House Bistro/Facebook
Part of the Light House Homeless Prevention Support Center, this cozy eatery is a social enterprise that gives people with employment barriers the opportunity to learn, develop their resumes, and earn a living wage. As soon as I walked in for the first time, I felt right at home. With exposed brick, warm wood tones, and plenty of charming decor, I love being able to eat, drink, and give back to the community here.
Light House Bistro/Facebook
Brunch is served from 8 a.m. to 3 p.m., and I highly recommend the meatloaf hash served with two over-medium eggs and the blueberry, blueberry pancakes. Pair it with a latte or glass of wine and you're sure to leave happy. The staff is friendly, and the open kitchen creates a true sense of community. Reservations are encouraged and you can learn more on their website.
From here, we enjoyed a leisurely stroll down West Street towards State Circle for a unique history lesson.
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Sitting in the center of this bustling city is the Maryland State House. Not only is the Maryland State House the oldest state capitol in continuous legislative use in America, but it also served as the capital of the United States for less than a year – from 1783 to 1784. We took in the beauty of the grounds, looked out over Annapolis’ charming streets, and then it was straight inside to take a step back in time.
Inside, we learned about the history of the building and its importance in the American Revolutionary War.
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Did you know this is where George Washington resigned his post as commander in chief of the Continental Army or where the Treaty of Paris was ratified? I sure didn't. This National Historic Landmark is open to the public every day from 8:30 a.m. to 5 p.m. and is a fascinating stop for any history or architecture buff - or anyone who loved learning new things (like me).
This next stop’s for bookworms.
The Old Fox Books & Coffeehouse/Facebook
As soon as I stepped inside Old Fox Books, I was greeted with a treasure trove of unique reads – a curated selection of both old and new titles for all ages as well as unique stationery and gifts. Whether you love expanding your child’s at-home library like I do or are looking to brush up on your local history, Old Fox Books has the perfect title.
And if you’re anything like my husband, you’ll need a second cup of coffee.
The Old Fox Books & Coffeehouse/Facebook
Luckily for you, tucked right inside this charming bookstore is Brown Mustache Coffee. Grab a honey latte (my personal favorite), browse the tightly-packed shelves, and get lost in a book.
Once we secured a book (or four, if we're being honest with ourselves), it’s back to the bustling Main Street we go.
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With picturesque storefronts and historic homes painted in a variety of cheery colors, Annapolis quickly captured my heart. Walking towards the City Harbor on Main Street, we passed by unique boutiques, historic hotels, restaurants and so much more. Shall we do some shopping at the Annapolis Exchange (for t-shirts and souvenirs), Capital Comics, Seasons Olive Oil & Vinegar Taproom, or The Spice & Tea Exchange of Annapolis?
Popular restaurants along Main Street include Fox’s Den, Preserve, Mason’s Famous Lobster Rolls, Vida Taco Bar, and Middleton Tavern – known as one of the oldest continuously operating taverns in the entire U.S.
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On this particular day, we ended up at Buddy’s Crabs and Ribs, a haven for seafood lovers. Now I know this might come as a shock, but I don't actually like seafood -- so, the rest of our group enjoyed plenty of crab and lobster while I shared chicken strips with my daughter (10/10 recommend, by the way).
There’s nothing better than a stroll along Annapolis’ waterfront.
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Listen to the street musicians play near the Kunta Kinte-Alex Haley Memorial, watch the boats pass by from Susan Campbell Park, and snap a few photographs. This might have something to do with spending most of my adult life in Hawaii before moving to Maryland, but there is absolutely nothing more serene about being near the water, don't you agree?
Now, as a Navy family, a trip to Annapolis isn’t complete without a visit to the United States Naval Academy, though I understand this stop might not be for everyone.
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Known for its beaux-arts architecture, monuments, and the 12,000-square-foot United States Naval Academy Museum, this is quite the picturesque university. Military ID holders can drive right onto the base, but the general public may walk through the Visitors Access Center at Gate 1 during general visiting hours.
Though we have yet to spend the night in Annapolis, I know just where we’ll stay when we do: The Maryland Inn.
Historic Inns of Annapolis/Website
With 18th-century architectural details galore and direct access to the Drummer's Lot Pub, the Maryland Inn appears as luxurious as it is historic. Part of the The Historic Inns of Annapolis along with the Governor Calvert House and Robert Johnson, this Annapolis icon tops my travel bucket list this year.
Home to a bustling downtown, more charm than anyone could possibly know what to do with, and plenty of history, this is easily one of my current favorite day trip destinations.
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So, what are you waiting for? One of the most charming capitals in the country is just begging for a visit. For more trip inspiration, head over to the Visit Annapolis website.

To discover more incredible boots-on-the-ground adventures across America from our team of local travel experts, check out all of the articles in OnlyInYourState’s Everyday Explorers series. What destinations would you like to see featured next on OnlyInYourState’s Everyday Explorers? Tell us where we should go on our nominations page.

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