3-Day Annapolis Adventure Itinerary

Day 1
Afternoon
3:00 PM: Arrive at the Annapolis Waterfront Hotel, where sweeping views of the Chesapeake Bay and the lively harbor set the stage for your getaway. Unwind in your room or suite, and take in the refreshing waterfront atmosphere.

4:00 PM: Head over to Dock Street Bar & Grill, a cozy, casual spot located right by the water. Relax with a drink on the patio and enjoy the view as you ease into the weekend.

Evening
7:30 PM: Dine at Choptank, a vibrant seafood restaurant just a short walk from the hotel. Enjoy fresh, local seafood including Maryland crab cakes, oysters, and shrimp, all paired with refreshing cocktails in a chic, nautical setting.

Day 2
Morning
8:00 AM: Start your day with a delicious breakfast at Iron Rooster, located just a short walk from the hotel. Known for their famous chicken and waffles, you can also enjoy other breakfast favorites like fresh pastries, omelets, and locally roasted coffee in a cozy, vibrant atmosphere.

9:30 AM: Take a guided walking tour of historic Annapolis. Discover the city’s rich past, visiting landmarks like the Maryland State House and the U.S. Naval Academy. Don’t forget to stroll along Main Street, lined with charming colonial-era shops.

Afternoon
12:00 PM: Grab lunch at The Annapolis Market House, a historic building filled with local food vendors. Enjoy Maryland specialties like crab soup, lobster rolls, or a fresh seafood salad, and perhaps pick up a souvenir from one of the artisan booths.

2:00 PM: No trip to Annapolis would be complete without getting out on the waters of the Chesapeake Bay. Embark on a Schooner Woodwind Sailing Cruise and set sail aboard one of the hotel’s 74-foot classic wooden yachts. Cruise past the historic Annapolis waterfront, under the Bay Bridge, and around the Severn River and Spa Creek.

4:00 PM: Take a peaceful stroll along the waterfront promenade or explore the boutique shops in downtown Annapolis. Enjoy a drink or ice cream while soaking in the waterfront views.

Evening
6:00 PM: Head to The Chart House for a seafood-filled dinner. This waterfront restaurant serves up delicious dishes such as lobster tail, steamed crab, and fresh oysters. Pair your meal with a crisp wine and enjoy the beautiful views.

8:00 PM: After dinner, venture over to Parley Room, for an after dinner cocktail.

10:00 PM: For a relaxed nightcap, check out The Pirate’s Cove, a local dive bar serving creative cocktails and offering a fun, quirky atmosphere.

Day 3
Morning
8:00 AM: Start your Sunday with breakfast at Miss Shirley's Café, just a short drive from the hotel. This cozy café is famous for their signature crab omelet, pancakes, and creative brunch options. It's a perfect spot to enjoy a delicious meal before your final day of adventure.

10:00 AM: Get out on the water with a paddleboarding or kayaking session. The hotel offers rentals and expert guides to show you the best spots to explore around the Annapolis harbor.

Afternoon
12:00 PM: Before leaving town, head to The Boatyard Bar & Grill, an Annapolis favorite with great views of the marina. Enjoy Maryland crab cakes, fish tacos, or shrimp & grits, and pair your meal with a refreshing cocktail.