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Annapolis, Maryland, isn’t just a sailing town; it’s a living museum of American history, culture, and culinary tradition. On this immersive walking food tour, you’ll explore the historic heart of the city while enjoying a progressive tasting menu curated from some of its most beloved eateries. Winding through centuries-old streets and past iconic landmarks, you’ll sample an array of local specialties, from seafood classics and colonial tavern fare to chef-inspired modern dishes.
This guided experience blends storytelling, architecture, and food into a memorable afternoon. Along the way, you’ll hear tales of the city’s founding, its role during the Revolutionary War, and the rich legacy of the homes, taverns, and markets that helped shape the Chesapeake region. Whether you’re a first-time visitor or a local looking for a deeper connection to your city, this tour offers a taste of Annapolis like never before.
This experience includes six curated tasting stops at a mix of historic taverns, modern restaurants, and local institutions. Stops on the day typically include:
Reynolds Tavern
Enjoy bites from one of the city’s oldest pubs, where George Washington and Thomas Jefferson are rumored to have dined.
Annapolis Ice Cream Company
Savor a scoop of handmade ice cream from a local shop that puts seasonal ingredients front and center.
Middleton Tavern
Sip and sample regional classics like crab soup and oyster shooters in a legendary establishment dating back to the 1700s.
The Maryland Inn
Taste house-made popovers while learning about one of the city’s original hotels, steeped in colonial lore.
Galway Bay Irish Restaurant
Delight in authentic Irish cuisine with a Chesapeake twist in one of downtown’s most welcoming pubs.
Vin 909 Winecafé or Osteria 177
Experience innovative fare at one of Annapolis’ top-rated dining spots, featuring pasta, flatbreads, or chef’s selections.
Along the way, you’ll pass some of the city’s most iconic landmarks, including the Maryland State House, the Hammond-Harwood House, Paca House & Gardens, and even private residences like the Sands House, occupied by one family for over 200 years.
Our Guides
Led by a trained and passionate local expert, your guide will bring Annapolis to life with captivating stories, historic insights, and culinary knowledge. Expect humor, history, and helpful tips for exploring more of the city after the tour ends.
This experience does not have a physical location and can be attended online.
This experience will be held at a location of your choice within the service area.
