There’s a good chance you’re planning a trip to Annapolis with family members from multiple generations. That’s good news, as we welcome visitors of all ages—from infants to centenarians—and our attractions have broad appeal. Check out some of our most popular things to do for the whole family. 

1. Tour the U.S. Naval Academy

The Naval Academy, situated where the Severn River flows into the Chesapeake Bay, has been preparing officers of the U.S. Navy and Marine Corps since 1845. Today, a mix of long-standing traditions and state-of-the-art professional training converge here. Glimpse monuments commemorating navy heroism. Take a guided tour that brings you into the very dormitory where midshipmen spend four years. Visit the Naval Academy Museum, with two floors’ worth of world-class exhibits covering the history of the Naval Academy and the U.S. Navy. Catch the excitement of one of 50-plus Navy Men’s and Women’s sporting events. 

Naval Academy Tower

2. Get out on the Water

Annapolis is often referred to as the Sailing Capital of the World. Surrounded by the Chesapeake Bay, four rivers, and more than 400 miles of shoreline and infused with an enthusiastic sailing community, it’s no wonder. There are plenty of ways to enjoy the waterways of the region, regardless of your sailing experience. Learn to sail at a local sailing school. Enjoy a cruise on one of the area’s tour boats: Choose from a historical tour, sunset cruise, pirate ship, or even an overnight ‘boat and breakfast’. That’s not all. Charter a fishing boat in one of the county’s maritime villages; rent a kayak, canoe, or stand-up paddleboard (the latest water sports craze!); or steer an electric boat. Or, take the Water Taxi from one popular neighborhood in Annapolis to the next.

Annapolis Harbor in the Summer

3. Feast on the bounty of the Chesapeake Bay

A visit to Annapolis & the Chesapeake Bay region is not complete without a taste of fresh, local seafood straight from the Bay. Whether you’re a pro at picking steamed crabs smothered with spicy Old Bay or don’t know the claw from the lump meat, a waterfront patio around town is the place to share this local tradition with friends and family. You’ll find plenty of other fresh, seasonal seafood on area menus as well. 

Dinging on Crabs Waterfront

4. Discover the area’s rich and diverse history

Walking the streets or gliding through waterways in and around Annapolis, you trace the steps of colonial, maritime, and African American history dating back more than 300 years. Historic sites also reveal this history. Visit The Maryland State House, the oldest state house in continuous legislative use. Stop into the Banneker-Douglass Museum, the state’s official museum of African American heritage. Overlooking the Chesapeake Bay, the Annapolis Maritime Museum demonstrates the area’s rich maritime heritage and ecology of the Chesapeake Bay. And there’s so much more. To experience our history, take a guided or independent walking tour (stop in the Visitors Center for maps and information), or download one of Mobile Apps for self-guided history tours of Annapolis and Southern Anne Arundel County.

State House with Statue

5. Explore one of the area’s scenic parks and other natural landmarks

Over 87 miles of trails and hundreds of miles of shoreline span the county, waiting to be discovered on foot, bike, or boat. Special landmarks blend nature and culture. The Smithsonian Environmental Research Center (SERC), where scientists conduct world-class research on the Chesapeake Bay and other global coastlines, doubles as a public nature and cultural center. Another must-see is Historic London Town and Gardens. On the South River in Edgewater, it combines history, archaeology, and horticulture.

6. Shop ‘til you drop

If you like to shop, you’ll love Annapolis and Anne Arundel County. A multitude of fantastic retailers cater to every age, gender, and style. You’ll also find distinct types of shopping districts. For one-of-a-kind boutiques that offer products you won’t find anywhere else, head to Downtown Annapolis. You’ll find big-name retailers, specialty shops, and nationally known restaurants at Westfield Annapolis Mall. For the largest outlet and value retail shopping destination in Maryland, featuring more than 200 stores showcasing the best names in fashion, go to Arundel Mills Mall. The Towne Centre offers high-end shopping and fun food options with a neighborhood feel. 

Shopping at the Fall festival

7. Enjoy a fun local festival or event

You’ll get a real sense of Annapolis’ spirited personality when you attend one of scores of local festivals and events that occur throughout the year. First Sunday Arts Festival is THE place to be every first Sunday of the month, May through October. Some quirky local events you won’t find anywhere else include the Tug of War, literally the longest tug of war across any body of water (Eastport vs. Downtown Annapolis), and the spring rite of passage, Sock Burning, a tradition picked up from sailors of yore who shed and burned their socks come springtime. The Annapolis Film Festival, one of the biggest crab feasts in the world, a phenomenal St. Patrick’s Day Parade, and so much more round out our annual calendar of festivals and events. 

Live Music at the First Sunday Arts Festival

8. Experience the Annapolis Countryside

The Annapolis Countryside, just minutes from the center of Annapolis, is not to be overlooked. Scenic bypasses take you to authentic maritime villages, where some fishermen still ply the waters as their ancestors did. History and heritage sites also shed light on the ways of the watermen throughout past decades. It’s very quaint and quiet out here, but you can find luxury too: a modern, eco-friendly waterfront resort and marina is the perfect spot for an overnight stay. 

9. Experience the biggest entertainment complex in the region 

It’s like a mini-city centered entirely on entertainment for fun-seekers of all ages. The Arundel Mills District boasts Arundel Mills Mall, the biggest retail mall in the state, with several brand-name factory stores. In the same complex is Arundel Mills’ Maryland Live! Casino, a $500 million, 300,000-square-foot, world-class casino with Las Vegas-style slot machines, traditional poker tables, plus nationally acclaimed restaurants and a 500-seat live-entertainment venue, Rams Head Center Stage. For family fun, head to Medieval Times Dinner & Tournament, where guests enjoy a ‘royal feast’ and a rousing display of heroic knights jousting atop live horses. Or, relax at the Cinemark Egyptian 24 and XD Movies, with state-of-the-art sound system and stadium seating. 

Maryland Live! Casino at Night

10. Pay a visit to these favorite ‘must-see’ spots around town

Some, like Ego Alley—where City Dock meets the water’s edge in Downtown Annapolis and pleasure boaters gather in the warm weather—are in the center of town. Others, like the Thomas Point Shoal Lighthouse, are tucked out of the way. Still other sites you may have heard about, but until you explore them you can’t appreciate their beauty, like the garden at the William Paca House. This 18th-century pleasure garden, an oasis in the heart of Annapolis, is the only one of its kind in the state.