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14 Ways to Have Fun in Charming Annapolis, Maryland

Charming street in downtown Annapolis, Maryland

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. It’s a waterfront retreat, a college town (if we’re referring to the United States Naval Academy as simply “a college”), and a picture-perfect capital city. Annapolis 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 Annapolis.

Check current hotel prices in Annapolis here

Taking a trolley tour is one of the fun things to do in Annapolis, Maryland

Hop on a trolley tour

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 an Annapolis 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 Victorian houses, colonial mansions, views of the Severn River, and, of course, overlook 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.

Visiting the William Paca House -- a signer of the Declaration of Independence -- is one of the most historic things to do in Annapolis, Maryland.

See how the colonial elite lived at the 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 sites in Annapolis. Dating from the city’s “golden age,” the mansion, summer house, and sprawling two acres of formal gardens are certainly worth a tour and a stroll.

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 great view the beautiful property.

Trying a wine and cheese pairing at Great Frogs Winery is one of the most fun things to do in Annapolis.

Book a tasting at Great Frogs Winery

Just a few miles from downtown Annapolis is one of the town’s standout attractions—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.

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.

The Annapolis Waterfront Hotel provides great views of Spa Creek leading out to the Chesapeake Bay

Stay at the 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.

Upstairs, the rooms at Annapolis Waterfront Hotel are inspired sophisticatedly by the setting on the water and have beautiful views of downtown Annapolis 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 give you the best Annapolis 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 in Annapolis, Maryland

Cross the bridge to Eastport

Just on the other side of the Spa Creek Bridge is the Annapolis 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.

The Pledge of Allegiance is a daily occurrence at Chick and Ruth's Delly in Annapolis

Experience breakfast at Chick and Ruth’s Delly

There is more than one reason why Chick and Ruth’s is the place to be for breakfast in Annapolis. 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.

There are so many fun shops, galleries, and boutiques to choose from in downtown Annapolis, Maryland

Wander Main Street

Annapolis’ red-brick 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 makes some of the best ice cream around

Indulge at 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. 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.

Sailing on the Schooner Woodwind is one of the best ways to explore the water around Annapolis, Maryland

Cruise the Chesapeake

One of the most attractive features in the city is the Annapolis 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 history of Annapolis as you cruise around the harbor, past the Naval Academy, and within view of the Chesapeake Bay Bridge. 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.

With Annapolis Electric Boats, you can drive your own boat and see views like this along the creeks

Get behind the wheel of your own 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 Annapolis’ Ego Alley.

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 in Annapolis?

Touring the US Naval Academy is one of the most popular things to do in Annapolis, Maryland

Walk the Yard at the Naval Academy

One of the most popular things to do in Annapolis is to visit the Naval Academy. On a 90-minute tour, guides take you to some of the main sites on the campus of this National Historic Site. You can visit the gym to learn about the Academy’s athletic program and see its Athletic Hall of Fame including 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.

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 a couple of times over the years and always seem to learn something new.

Annapolis, Maryland, is full of amazing places to eat


For a town with a compact center, Annapolis is absolutely full of amazing restaurants. Try them! Head to our favorite Iron Rooster for the best breakfast or brunch you’ve ever tried—from homemade pop tarts to their standout eggs benedict, it’s one of the yummiest places around. For a spot on the water, Chart House and Carrol’s Creek are great options for steaks and seafood. For more casual options with excellent food, stop by the Boatyard in Eastport or Galway Bay. We can’t list all the great restaurants in Annapolis, so take our word on this handful, or find your own new favorite.

The Rams Head On Stage is a great venue for performers of all types in the heart of downtown Annapolis

Stop in for a show at the Rams Head

For 20 years, the Rams Head On Stage has been a mainstay of downtown Annapolis. 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 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.

The State House in Annapolis, Maryland, is the location where George Washington resigned his commission of the Continental Army

Visit America’s oldest State House

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.

Check current hotel prices in Annapolis here

Our visits to Annapolis were sponsored by Visit Annapolis and the Annapolis Waterfront Hotel. All opinions of the charming and fun are our own. Note: Some links may be affiliate links, which means Travel Addicts may earn a few pennies if you buy something.

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What do you think about 14 Ways to Have Fun in Charming Annapolis, Maryland?

  1. Jeffrey Wettif June 29, 2017 at 1:47 pm #

    Don’t forget Kayak Annapolis!

  2. L. Winther-Hansen July 1, 2017 at 9:44 am #

    Good picks! Also, in the summer you should see a show at Annapolis Summer Garden Theatre. It’s an outdoor community theatre presenting Broadway musicals (featuring live music) in a unique outdoor space. Very cool!

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