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25 Jul 2025 Local Adventures & Superhost Shawn’s Travels
Some days are made for wandering.
Not with an agenda—but with the kind of open-hearted curiosity that invites surprise. That’s the magic of Annapolis. Just a short, scenic drive from Chesapeake Paradise, this waterfront capital quietly delivers charm, depth, and delight around every corner. It’s where cobblestone meets coastline, and where history and hospitality live side by side.
Whether you’re retreating solo, building bonds with your team, or simply ready to swap your view for a few hours, Annapolis offers a nourishing contrast: bustling streets lined with stories, breezy harbor walks, irresistible seafood, and shops that feel more like treasure hunts.
Let me show you how I love to spend a day there—and how you can, too.
Historic, walkable, and buzzing with local flavor, Annapolis is the soul of the Chesapeake. Known as America’s Sailing Capital, it’s also the capital of Maryland and home to the U.S. Naval Academy. But don’t let its stature fool you—this city knows how to slow down and savor. The architecture is elegant, the shops are eclectic, and there’s a strong current of creativity and community that makes it feel both rich and relaxed.
Whether you’re a history buff, a foodie, a boutique browser, or someone simply craving a change of pace, Annapolis offers something nourishing for the senses.
Start with a stroll down Maryland Avenue and Main Street, where every brick seems to have a story. You’ll pass 18th-century buildings, hidden gardens, and the iconic St. Anne’s Church, which anchors Church Circle with quiet grandeur.
Don’t miss the Maryland State House, the oldest U.S. state capitol still in continuous legislative use. It’s where George Washington resigned his commission—a defining moment in American democracy. Entry is free, and it’s a powerful reminder of Annapolis’s place in the nation's story.
If you have time and a valid ID, walk over to the Naval Academy. The museum houses ship models and naval history that even non-military guests find fascinating. The campus itself is stunning—quiet, formal, and beautifully kept.
My go-to spots for meaningful gifts and personal treats are nestled just off the main drag. Annapolis Bookstore is cozy and charming, often hosting events or live music. And spots like Local by Design and The Red Bean offer everything from handmade pottery to Chesapeake-themed art and jewelry.
For fun fashion or accessories, check out The Pink Crab for preppy coastal wear, or Hats in the Belfry, which has been serving up classic and quirky hats since the ‘70s. Everything here feels unique and rooted in local flair.
If your trip falls on a weekend, look out for local farmers’ markets or seasonal art fairs, where you’ll meet regional makers selling soaps, snacks, and handmade goods you won’t find anywhere else.
Carrol’s Creek Café and Chart House both serve excellent seafood with sweeping waterfront views. Think jumbo lump crab cakes, rockfish imperial, and oysters on the half shell. Grab a table outside if the weather allows.
Looking for something more casual? Try Mason’s Famous Lobster Rolls, Chick & Ruth’s Delly (famous for their pies and over-the-top sandwiches), or Iron Rooster for a breakfast-all-day vibe. Most are walkable from the main strip.
End your food crawl with a scoop from Storm Bros. Ice Cream Factory on Dock Street or Kilwins on Main. It’s a classic Annapolis experience—and the perfect way to end a sweet stroll by the water.
Downtown Annapolis can be busy, especially in summer. Park in the Hillman Garage or use the Annapolis Circulator Shuttle for easy access to key areas.
Weekends buzz with energy, but weekdays offer a quieter charm—perfect for deeper reflection and more elbow room in popular spots.
While it’s easy to plan a full itinerary, some of the best moments come from sitting on a bench near the docks, people-watching, or exploring a back alley bookstore. Let your day breathe.
After a few days of stillness, water views, and reflection at Chesapeake Paradise, this gentle city buzz can feel like a breath of fresh air. It’s a way to expand your perspective without overwhelming your senses—to see what the broader region holds while staying grounded in your own experience.
Whether you go solo, take a few retreat friends, or bring your whole group, a trip to Annapolis rounds out your time with culture, flavor, and flow. You return to your waterfront porch with a little more appreciation for both the stillness and the stimulation that make life beautiful.
If you’re staying with us at Chesapeake Paradise, just ask—we love curating little off-property adventures like this. We'll share up-to-date hours, favorite local tips, and maybe even a crab cake recommendation or two. 😊
📍 Located just 35 minutes away, Annapolis is the perfect half-day or full-day getaway to enhance your stay on the bay.
Explore the quiet. Embrace the culture. Come home to the water.
Gorgeous August days are ahead—and we have some last-minute availability! [Check out our accommodations and book here.]