Walking down the charming streets is one of the fun things to do in Annapolis Maryland

15 Ways to Have Fun in Charming Annapolis, Maryland

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One of our very favorite places on the East Coast, the beautiful city of Annapolis often gets overlooked in favor of its larger neighbors like Baltimore or Washington, DC. But there are so many fun things to do in Annapolis, Maryland. It’s a waterfront retreat, a vibrant town, and a picture-perfect capital city. It has everything to do from visiting historic sites to wine tasting to sailing the Chesapeake Bay, and a lot in between, too. Here’s a look at some of our favorite ways to spend time in the city.

Fun Things to Do in Annapolis

Trolley tour

Red Discover Annapolis trolley car

Although a stroll down Main Street gives you a great taste of Annapolis, the capital city is so much more than that. To gain a greater appreciation for all this cute place has to offer, hop on a trolley tour.

In just an hour, the guide will give you a quick walk through 350 years of history while driving by some of the prettiest buildings around. You’ll see lots of top Annapolis attractions, including Victorian houses, colonial mansions, views of the Severn River, and, of course, the Naval Academy. A trolley tour is one of the best things to do in Annapolis because you see a lot quickly, and it’s easy on your feet, which we always value.

For a small-group tour experience, check out this tour of downtown.

Overhead view of buildings, waterfront, and boats

William Paca House

William Paca was one of Maryland’s four signers of the Declaration of Independence and served as the state’s governor in the 1780s. His estate, originally built between 1763 and 1765, now stands as one of the greatest historical places to see when you visit Annapolis.

The Paca House dates from the “golden age” of the city and has been painstakingly restored using historic artwork and excavations around the property. The mansion, summer house, and sprawling two acres of formal gardens are certainly worth a tour and a stroll, especially on a nice day.

Tower and decorations in garden in Annapolis MD

Visit the William Paca House to see period furnishings and get an understanding of how the elite lived during the years before and after the Revolution. Walk around the pond, stop to smell the many flowers, and admire the kitchen garden. We loved climbing to the top of the summer house for a view of the beautiful property.

Maryland State House

Red brick building with a white coupola

In the heart of Annapolis is the oldest state house in the country that’s still in legislative use. It’s historic not only because it was America’s capital for nearly a year in 1783-1784 but because several nationally important events happened there.

The Maryland State House is the place where George Washington resigned as commander in chief of the Continental Army (intending to retire from public life, which didn’t work out so well) and where the Treaty of Paris was ratified. Today, you can visit the Old Senate Chamber and see old George dressed in his finest and letting his intentions be known. Washington’s original address is also on display. A stop at the State House is a quick visit and a must for anyone interested in history.

Great Frogs Winery

Foods for wine and cheese pairing at Great Frogs Winery

Just a few miles from downtown Annapolis is one of the top places to visit in Annapolis—Great Frogs Winery. Established in 1999 on an old tobacco farm, Great Frogs Winery takes advantage of Annapolis’ naturally sandy soil to grow French Bordeaux varietals. The grapes are expertly crafted into more than a dozen wines showcasing white, rose, and red varietals and blends.

Bottles of wine at Great Frogs winery in Annapolis MD

Book a weekend tasting of their wines or a full wine, cheese, and charcuterie sampling experience to see the best of what Great Frogs Winery has to offer. Our favorites were the earthy Chardonnay and the spicy Meritage along with some fantastic local brie. When you’re done, have a picnic outside the tobacco barn and wander among the vines.

Waterfront hotel

Although it’s hard to believe in a place as attractive as Annapolis, the city only has one waterfront hotel—the appropriately-named Annapolis Waterfront Hotel. Part of Marriott’s Autograph Collection, the hotel brings touches of elegance to an already serene location right along the harbor.

Building overlooking the water

Upstairs, the rooms at Annapolis Waterfront Hotel are inspired sophisticatedly by the setting on the water and have beautiful views of downtown or Spa Creek. Downstairs is Pussers Caribbean Grille, an outpost of the popular restaurant and bar that made its name far south of here in the British Virgin Islands.

The combination of style and relaxation gives you the best the city has to offer. It’s hard to beat curling up in a comfy chair with a fruity cocktail in-hand while watching the dance of the sailboats and yachts coming in and out of the harbor.


The Eastport flag: We like it this way, Maritime Republic of Eastport

Just on the other side of the Spa Creek Bridge is the community of Eastport. Technically—the proud residents will have you know—it’s the “Maritime Republic of Eastport.” Founded in 1998 when the drawbridge connecting Eastport and downtown Annapolis was temporarily closed, the “Republic” has its own flag, its own yacht club, and its own sense of community.

Every year, that camaraderie comes out when groups on each side of the water participate in the infamous “Slaughter Across the Water” tug-of-war. In the summer, head to Eastport’s Boatyard Bar & Grill to celebrate with the winners of the Wednesday Night boat races on the Chesapeake, or check out the great waterfront dining any time of the year. As a bonus, there’s no better view of downtown or the Naval Academy than on this side of the water.

City Dock

Boat in the Chesapeake Bay

The City Dock is a fun place for people-watching on a nice afternoon. Known as Ego Alley, it’s the spot for captains to show off their boats and their boating skills as they navigate the narrow area (and the other vessels that are also showing off). Crowds tend to gather by the water to watch the boats come in and dream about buying their own one day.

Chick and Ruth’s Delly

People saying the Pledge of Allegiance in a restaurant

There is more than one reason why Chick and Ruth’s Delly is the place to be for breakfast. First, of course, is the amazing food, including our favorite “world famous” seasoned crab and cheese omelet. Second is the morning ritual.

Every weekday at 8:30am and weekend at 9:30am, the staff of Chick and Ruth’s assembles for the daily Pledge of Allegiance. Everything and everyone stops for a few brief seconds to salute the flag. It’s so unusual, you almost have to see it to believe it. And, depending on the time of year, you may just find yourself standing next to a state legislator or the governor himself. He has his own booth, after all.

Main Street

Boutique with clothing and gifts for sale

Main Street is a haven for shoppers. And lovers of good food. And art aficionados. And people who like to relax.

This charming area offers a variety of unique boutiques, shops, and galleries you can browse to your heart’s content. When you’re ready for a break, stop at one of the many restaurants, bars, and cafes lining the street. There’s so much to choose from in these delightful blocks, you’re sure to find something that fits the bill.

Annapolis Ice Cream Company

Annapolis Ice Cream Company is one of our very favorite stops in the city. Made fresh at the shop almost every day, the ice cream here is some of the best you’ll find anywhere.

Cup of mint chocolate chip ice cream

Annapolis Ice Cream Company has 36 rotating flavors made of super-premium ingredients. You know it’s good stuff when it takes forever to melt, even in the heat of the summer. Our favorites are the mint Oreo and pretty much anything with peanut butter, but it’s impossible to go wrong no matter what you try.

Cruise the Chesapeake Bay

One of the most attractive features in the city is the waterfront. And there’s no better way to appreciate the beautiful Severn River and Chesapeake Bay than to go for a cruise.

Two of the most popular ways to get out on the water are on the Harbor Queen or the Schooner Woodwind. A 40-minute cruise on the Harbor Queen gives you a glimpse into the city’s history as you cruise around the harbor, past the Naval Academy, and within view of the Chesapeake Bay Bridge.

Sailboat in the bay

On the Schooner Woodwind—a 74-foot wooden schooner—you can participate in their regular 2-hour sails, cruise in search of local lighthouses, or cheer on your boat’s captain in the Wednesday night sailboat races during the summer. If you’re willing, there may even be a chance to pitch in as part of the Woodwind’s crew. Either way, your time on the bay will be fun.

Rent a boat

If cruising the Bay with someone else at the helm doesn’t do it for you (or, alternatively, it’s made you completely addicted to the water), be your own captain. Annapolis Electric Boat Rentals offers a unique chance to take one of their boats out on your own. Gather some friends, your favorite snacks, and some beverages, and head out. Cruise Spa Creek, see the waterside mansions of Back Creek, or even take your turn showing off in Ego Alley.

Woman kayaking in Spa Creek

The electric boats can hold up to 11 people—captain included—for a few hours or a whole day on the water. Believe it or not, no previous boating experience is required, and you’ll get a crash course on the spot. What better way to experience the water?

Eat all the seafood

Crabcake sandwich and French fries on a plate

Annapolis is known for its seafood. From Maryland blue crabs to Chesapeake Bay oysters and rockfish, there are so many local types of seafood to choose from. We’ve eaten our way across the city several times and have loved every minute. If you’ve ever wanted to try a crab or crack open an oyster, this is the place to do it.

Try this seafood tour to sample local specialties.

Naval Academy

One of the most popular things to see in Annapolis is the US Naval Academy. On a 90-minute tour, guides take you to some of the main sites on the campus of this National Historic Site.

Monument and canyons in a courtyard

On a Naval Academy tour, you can visit the gym to learn about the Academy’s athletic program and see its Athletic Hall of Fame that includes famous graduates like Roger Staubach and David Robinson. You’ll see Bancroft Hall, the mammoth dorm that houses all 4400 midshipmen, and the statue of Indian warrior Tecumseh. Tours also visit the famous crypt of John Paul Jones, and most days there is a stop in the beautiful Naval Academy Chapel.

Black marble crypt
The crypt of John Paul Jones

Along the way, you’ll learn about the history of the US Naval Academy and the lives of the students who work so hard to be there. We’ve taken the tour three times over the years and always seem to learn something new.

Rams Head Tavern

Painted red brick exterior of Rams Head Tavern

For over 20 years, the Rams Head On Stage has been a mainstay of downtown. Drawing famous comedians, nationally-recognized bands, and other acts with super star power, this venue is a perfect place to see your favorite performer or to discover someone you didn’t know you would love. You can have a meal in the pub before the show or head straight into the club for dinner and drinks during the performance.

Where to Eat

For a town with a compact center, Annapolis is absolutely full of amazing restaurants. Here are some of our favorites.

Bacon, pastries, and brunch dishes on table

Iron Rooster — With views of Ego Alley, Iron Rooster is the spot for breakfast or brunch. Their homemade pop tarts and eggs benedict are outstanding.

Carrol’s Creek — Carrol’s Creek has a huge variety of seafood options and is most well-known for its cream of crab soup and gorgeous waterfront views.

Miss Shirley’s — Serving breakfast, lunch, and brunch, Miss Shirley’s offers a hefty dose of Southern hospitality with some amazing eggs and French toast. Don’t miss the grits.

Where to Stay

Annapolis Waterfront Hotel — The city’s only hotel on the water, the Annapolis Waterfront Hotel offers sophisticated design in a comfortable environment. With a harbor view, you can watch boats come and go right from your room.

Westin Annapolis — Recently renovated, the Westin offers all the amenities you would expect from Marriott and even has an indoor pool.

Crowne Plaza Annapolis — Steps from the Westfield Annapolis Mall, the Crowne Plaza is a great value. It has comfortable rooms, an on-site bar and restaurant, and an indoor pool.

Our visits were sponsored by Visit Annapolis and the Annapolis Waterfront Hotel. All opinions of the charming and fun are our own.