Annapolis Summertime: Make the Most of Your Time Here

Summer in Annapolis is pure magic. From the sun-kissed shores of the Annapolis waterfront to the historic cobblestone streets and vibrant terrace cafés, the season buzzes with summer energy. Whether you're visiting the Yard or exploring downtown, there’s a perfect blend of Annapolis events, Annapolis attractions, and summer field trips awaiting you. And don’t forget—every bite, souvenir, and official USNA tour gives back to the midshipmen who call the U.S. Naval Academy home.

Dive Into Summertime on the Water

The Chesapeake Bay sets the stage for so much of what makes Annapolis special. This summer, the free and family-friendly Tunesday Floating Concert Series sails for its second season, every Tuesday from May 20th to August 26th (6:00 p.m. - 8:30 p.m.), transforming an anchored 40-foot-plus catamaran into a floating stage with local live music that drifts across Back Creek right up through sunset. Thursdays through Saturdays are for Wilma Lee Sunset Cruises for those 21 and older, letting you soak in waterfront vibes with a sunset soundtrack. Pair these with Wednesday Night Races (WNR) watch parties on the Bay throughout the summer (also for the 21+ crowd) and you’ve got yourself a perfect summer field trip.

Prefer to sit back and cruise? The Annapolis Harbor & USNA Cruise (40 minutes) and the longer 90-minute Scenic Severn River Cruise both let you admire Naval Academy architecture and sail past stately yachts and sailboats. The view of the Yard from the water is breathtaking—definitely an Instagram moment—and perfect for summer family fun.

Events to Explore: Arts and Community

Beyond the waves, the city thrives with must-do events that happily capture summer in Annapolis.

Annapolis Summer Garden Theatre: Steps away from the City Dock, an award-winning group performs outdoor musicals under the stars from Memorial Day to Labor Day.
Guided Garden Stroll at William Paca Garden: For a more serene pace, this beautiful English garden oasis offers weekly colonial-era charm on Friday mornings.

Each of these is a delightful summer field trip—immersive, enriching, and full of local flavor.

Enjoy “The Yard:” USNA Tours and Attractions

No summer in Annapolis is complete without visiting the Yard (the affectionate nickname for the Naval Academy campus). These public USNA Historical Walking Tours—offered from 9:30 a.m. - 3:00 p.m. daily (11:00 a.m. - 3:00 p.m. on Sundays) at 90 minutes apiece—are led by friendly, knowledgeable guides who bring behind-the-scenes midshipmen stories, Naval Academy history, and Navy traditions to vivid life.

Highlights include:

The Main Chapel and the Crypt of John Paul Jones: This beloved naval leader’s remains and legacy have rested in a stunning crypt below the chapel since 1913.
Bancroft Hall: It’s the country’s largest dorm with a grand rotunda and 4.8 miles of corridors.
The Triton Light: A beautifully touching tribute to service and tradition, standing watch near the cusp of the Chesapeake Bay.
The USNA Museum in Preble Hall: Don’t miss this maritime treasure trove spanning centuries.

Buy your tickets at the Visitor Center (9:00 a.m. – 5:00 p.m.) and show up early—especially on busy weekends. Be sure to bring a REAL ID or U.S. passport to get through security.

Where to Eat, Drink, and Recharge

Walking through the Yard (and downtown) builds up quite an appetite—and Annapolis delivers in style.

The Alley Restaurant: Nestled on campus at the historic Naval Academy Club (NAC), this midshipmen-approved spot dishes out Chesapeake-infused flavors and excellent standard fare. Think crab pretzels, summer chicken pasta, and a host of yummy handhelds, all delicious energy for a day of sightseeing. Please note that to non-members, this location is only available for lunch.
1845 Coffee: Just a quick walk from Main Street, this cozy café is perfect for summer mornings. Grab a cold brew, meet local students, and plot your day's adventures over a rich cappuccino.
Drydock Restaurant: Drydock Restaurant is back and better than ever. Located on the lower level of Dahlgren Hall, Drydock is a quick-service restaurant that is your one-stop choice for fresh options that appeal to all eaters.

Each directly supports the Brigade—so your coffee isn’t just delicious, it’s meaningful.

Related: Get a Taste of the Yard

Shop and Support: The USNA Gift Shop

Looking for a special keepsake? The USNA Gift Shop at the Armel-Leftwich Visitor Center is bursting with Academy pride: officially licensed hats, shirts, challenge coins, and more. Each purchase supports midshipmen programs here—so you get a tangible memory and help to boost Academy life. Not every store does this, so it’s a real win-win.

Summertime Shopping and Downtown Vibes

Beyond the campus, downtown Annapolis teems with charm. Main Street and the City Dock area are lined with boutiques, galleries, wine bars, and outdoor cafés. You’ll find summer market stalls, ice cream shops, and live street music—nostalgic yet lively. Look out for pop-up events featuring local artisans and Chesapeake-inspired craft goods.

Your Best Annapolis Summer

An idyllic summer in Annapolis begins with mornings on the harbor, continues with Yard tours steeped in naval history, and ends with meals shared among friends—whether at the Alley Restaurant or downtown favorites. It’s the richness of summer field trips, the sense of belonging from Annapolis attractions, and the satisfaction of knowing your purchases help to support the midshipmen.

So grab a map (digital or paper), plan your days, and let the Annapolis waterfront guide you. From the lively banter as you stroll along the cobblestones of Main Street to the hush of sunset cruises, this city knows how to celebrate summer. After all, a great Annapolis summer isn’t just an itinerary—it’s a connection to place, purpose, and pride.

Enjoy the sunshine, the sea breeze, and the genuine warmth of this historic maritime city. Here’s to your best Annapolis summer yet!

Neither the Department of the Navy, the United States Naval Academy, nor any other component of the Department of Defense has approved, endorsed or authorized any Non-Federal Entity, Company, Organization, or their Products.

On The Yard