The whole of Annapolis Bay is dense with destinations and restaurants. A weeklong Annapolis sailing charter is the perfect starting point for both land- and sea-based adventures. Easy day sails from the bay and back can be capped off by dining at any number of excellent options and, of course, you’ll return to the best accommodation – on a boat.
The Port Annapolis Marina on Back Creek is a likely starting point if you book a yacht charter, and it is ideal. Picturesque, with excellent services and a pool, you’ll want for nothing in terms of access to the city and provisioning your boat. From Back Creek, you can sail west and directly up the Severn River to Round Bay and other points, where you can spend a day paddling a kayak to get closer to the water. Note that swimming in summer months in both the Chesapeake Bay and its rivers is problematic due to the stinging nettle – a type of jellyfish – population, but the area is still beautiful to explore by boat.
Head north from Annapolis into the bay and then back west to explore the scenic Magothy River. You can make this outing a two-day jaunt, as there are many lovely anchorages in the area. Ferry Point Marina offers well-protected deep water slips – highly valuable around the Chesapeake – along with a beautiful restaurant offering crab and other delicious dishes.
Back in this beautiful city, take a water taxi from the marina at Port Annapolis and head across the creek for dinner at Vin 909, which is getting rave reviews (and the crowds to go with them) for its farm-to-table cuisine and wines. It doesn’t take reservations, so either don’t arrive hungry or be happy to enjoy wine while you wait.
The city rewards those who explore on foot, whether just wandering or as part of a walking tour – from which there are many to choose. Architecture lovers will get their fill at sites like the Paca mansion and gardens. In addition to the usual suspects like St. Anne’s Church, don’t miss lesser-known destinations like the Banneker-Douglass Museum, which is small but offers a lot of information about historically important African American Marylanders, including the museum’s namesakes of Benjamin Banneker and Frederick Douglass.