Annapolis in summer is a humid flirt—it makes you glisten before 10 a.m., but charms you back with historic streets, breezy boat rides, and crab feasts that make the extra hair frizz worth it.

If you're planning a girls’ weekend with a mix of history, waterfront views, and seafood that lives up to the hype, Annapolis delivers. This Chesapeake Bay gem offers just enough adventure to keep things exciting and enough small-town character to make you want to extend your stay.

Why Annapolis is the Perfect Girls’ Getaway

Just 45 minutes from Washington, D.C., Annapolis is the kind of destination that balances coastal charm with serious historical credibility. It’s known as America’s Sailing Capital and was briefly the nation’s capital in the 1780s. Today, the cobblestone streets are home to independent boutiques, waterfront cafés, colonial landmarks, and a welcoming atmosphere that makes it easy to explore with your favorite people.

It’s compact, walkable, and packed with activities—from harbor cruises and garden strolls to kayak rentals and blue crab feasts. Whether your crew leans into the history, the seafood, or just catching up somewhere scenic, this city checks every box for a laid-back but memorable escape.

Day 1: Naval Traditions, Main Street Energy & Waterfront Views

Stop 1: U.S. Naval Academy – A Historic Start

Start your weekend with a visit to the U.S. Naval Academy, one of Annapolis’ most iconic landmarks. Founded in 1845, it’s home to striking architecture, fascinating history, and a beautifully maintained campus that’s open for guided tours.

Book through the Armel-Leftwich Visitor Center for access to the best highlights: the Naval Academy Chapel, the crypt of John Paul Jones, and Bancroft Hall, which holds the record as one of the largest dorms in the world. It’s an active military campus, so you’re not just looking at history—you’re walking through it.

Try to catch the Noon Meal Formation, a daily tradition where hundreds of Midshipmen line up in formation before heading into the dining hall. It lasts less than ten minutes but makes an impression. Tours at 11:00, 11:30, or 11:45 a.m. will get you there in time for a great view.

Location tip: You’ll need a valid ID to enter, and bags are screened, so pack light and wear comfortable shoes—you’ll be walking a good bit.

Stop 2: Lunch & Browsing Along Main Street

After the academy, head to Main Street for lunch. This stretch is lined with 18th-century buildings turned into shops, galleries, and restaurants. It’s the perfect spot to refuel and wander.

We grabbed a quick lunch and afterward window-shopped our way through a mix of local boutiques and home decor stores. If your group enjoys exploring independently, this area is ideal—you can split up, browse, and easily reconvene.

Shop to note: The Pink Crab is a favorite for resort wear and fun accessories.

Stop 3: Annapolis Harbor Cruise with Watermark Journey

When the afternoon heat kicked in, we jumped on a Harbor Cruise with Watermark Journey. It’s a one-hour ride with views of the Chesapeake Bay, the Naval Academy from the water, and some truly impressive waterfront homes.

The breeze was a welcome break, and the narrated tour added context to what we’d seen on foot. We got a second ride thanks to an especially sunny day (pro tip: talk to the crew nicely), and one of us even got a turn at the helm—supervised, of course. It helps to go at a random time on a weekday afternoon when they’re not crowded with tourists.

Best photo spots: Sit on the upper deck toward the front for clean skyline shots and sailboat views.

Stop 4: Dinner at Cantler’s Riverside Inn

Wrap up the day with a classic crab feast at Cantler’s Riverside Inn. It’s casual, loud, and absolutely the right choice for a group dinner. Since the 1970s, this spot has been serving up fresh Maryland blue crabs steamed and covered in Old Bay.

They don’t take reservations, so plan ahead. We got there at 7:30 p.m. and waited about 45 minutes, but exploring the dockside made it bearable. Plus you can see the live catch they’re planning to serve. Once seated, we laid down the paper, grabbed our mallets, and went to town. It was messy, fun, and exactly what the first night of a girls' weekend should be.

Not into crab picking? They’ve got great steamed shrimp, soft-shell sandwiches, and salads, too.

Day 2: Colonial Streets, Kayaks & Seafood Staples

Stop 1: Morning Walk Through Historic Annapolis

Kick off your second day with a quiet morning walk through Historic Annapolis, where history and charm meet on every brick-lined corner. This area is compact and walkable, making it easy to explore at your own pace (coffee in hand, obviously).

Must-Stops:

William Paca House & Garden
This 18th-century Georgian mansion belonged to William Paca, a signer of the Declaration of Independence and Maryland’s third governor. The inside offers a glimpse into colonial life, but it’s the garden that steals the show. We wandered under arched trellises and past neatly trimmed hedges—it felt like a peaceful secret in the middle of the city. Perfect spot for a group photo or a quick journal moment if you're into that kind of thing.

Maryland State House
This isn’t just a pretty building—it’s the oldest state capitol still in continuous legislative use. More importantly, it’s where George Washington resigned his military commission in 1783, a defining moment in U.S. history. The rotunda is stunning, and the self-guided tour makes it easy to explore without a guide breathing down your neck.

Logistics tip: Both of these landmarks are just a few blocks apart, so wear comfortable shoes and plan to spend an hour or two wandering. There are plenty of cafés nearby for a pit stop before the next adventure.

Stop 2: Lunch at Mason’s Famous Lobster Rolls

By midday, you’ll want something quick, cool, and satisfying—and Mason’s Famous Lobster Rolls delivers. This casual spot is great for groups: no-fuss ordering, fast service, and indoor seating with blessed air conditioning.

We went classic with buttery lobster on a toasted split-top roll, but the menu has options with a spicy twist, plus sides like slaw and chips. If you’re not feeling seafood (who are you?), they’ve got grilled cheese and chicken salad too.

Bonus: Grab your order to go and picnic by the water at nearby Susan Campbell Park—it’s just a 5-minute walk away.

Stop 3: Kayaking on Back Creek

Ready for something active? Book a kayak for a few hours and head out onto Back Creek for a group kayaking session. The water here is calm, the scenery is lush, and it’s easy enough for beginners. No guide is needed—just a quick safety rundown and you’re good to go.

We paddled past sailboats, under small bridges, and into shaded coves where it was cool and quiet. It was one of those moments where conversation slowed, phones stayed in dry bags, and everyone just took in the surroundings.

Pro tip: Go earlier in the afternoon to avoid the strongest sun, and bring a waterproof pouch for your phone if you want to take pictures mid-paddle.

Stop 4: Dinner with a View

For your final evening in Annapolis, wind down with a group dinner overlooking the water. Here are two solid options depending on your group's vibe:

Boatyard Bar & Grill

Laid-back, nautical, and known for ultra-fresh seafood. The energy here is lively without being loud, and it’s difficult to get a table SO GO EARLY. Highly recommend the oysters and oyster shooters, but you if need a little sustenance try the crab cake sandwich or the grilled rockfish—it’s a local favorite for a reason.

Carrol’s Creek Café

A little more polished but still relaxed. This spot sits right on the waterfront and serves elevated Chesapeake Bay cuisine with standout views of the harbor. We shared a few small plates and enjoyed a slow dinner while watching boats come and go. Great option if you’re celebrating a birthday or milestone with the group.

Photo moment: The outdoor seating at either restaurant offers golden-hour lighting that’s ideal for a group shot before dessert.

Extra Tips to Make the Most of Your Girls’ Weekend

Best Group Activities

Book a private sailing lesson or charter for a fun on-the-water experience
Do a free historic walking tour
Grab an ice cream from Annapolis Ice Cream Company and walk along Ego Alley to end the night (we grabbed multiple during our visit)

What to Pack

Lightweight dresses, walking sandals, and a casual jacket for breezy evenings
Sun protection (hat, SPF, sunglasses)
A small day bag or crossbody—most spots are walkable
Layers for restaurant A/C or waterfront breezes

Annapolis might be small, but it’s packed with moments you and your friends will talk about long after the group chat goes quiet. From its rich history and walkable charm to waterfront adventures and some of the best seafood on the East Coast, it’s the kind of place that leaves everyone feeling recharged, connected, and already planning the next trip.

Whether you're celebrating something big or just carving out time to catch up, Annapolis delivers an easygoing yet unforgettable girls’ weekend—sweaty, scenic, and absolutely worth it.

How To Spend A Perfect Girls’ Weekend in Annapolis, Maryland