Things To Do
Sailing, Fishing & Boat Charters
Naptown Tiki Club
A fun booze cruise through the Severn River!
Shopping!
Explore downtown Annapolis and shop at some of the best local boutiques. Find fair-trade, artisan-made goods at Mango & Main, trendy jewelry and accessories at Lilac Bijoux, and stylish coastal clothing at The Cotton Company. Brightside offers colorful, fun fashion, while The Cottage is perfect for unique gifts and home décor. Check out Cupla for chic, modern styles and The Pink Crab for all things preppy and nautical. Don’t forget to stop by Hobo, home to beautifully crafted designer leather bags.
Restaurants & Sweet Treats!
While in Annapolis, be sure to check out Boatyard Bar & Grill for their famous crab cakes, Dry 85 for a top-notch bourbon bar experience, and Fox’s Den for incredible truffle fries. For speakeasy vibes, head to Harold Black, and if you’re looking for waterfront dining, The Choptank offers stunning harbor views. Enjoy fresh sushi at Joss, live Irish music at Galway Bay, and a cozy wine selection at Red Red Wine Bar. Don’t miss McGarvey’s for their famous crab dip or ACME for their legendary wings! Start your morning with a bagel from Naval Bagels, brunch at Iron Rooster, known for their homemade pop-tarts, or Metropolitan, a great spot for breakfast and craft cocktails. Need a caffeine fix? Grab coffee from Bitty & Beau’s or Rise Up for a local favorite. Need a sweet treat? Checkout Annapolis Ice Cream Company, Kilwins or Storm Brothers!
Fun Tours & Sightseeing
Discover Annapolis through its rich history and unique experiences. Take a guided Historic Annapolis Walking Tour to explore the city’s colonial past, or visit the U.S. Naval Academy for an insider’s look at this prestigious institution. Step back in time at the William Paca House & Garden, a beautifully restored 18th-century home with stunning grounds. For something spooky, join an Annapolis Ghost Tour, which even offers a haunted pub crawl—a perfect mix of history and spirits! Prefer to explore on wheels? Hop in a Discover Annapolis Trolley for a fun and informative ride through the city’s charming streets.