The journey begins on the water as the vessel departs from Annapolis, known as America's Sailing Capital at the mouth of the Severn River. Passengers pass by the historic waterfront and city harbor without stopping on land, enjoying initial views of Maryland's vibrant maritime culture and the iconic backdrop of the city as the cruise kicks off.

Relax during the scenic crossing of the Chesapeake Bay, the largest estuary in the United States. Passengers remain on board the vessel throughout the transit, taking in expansive views of the open water and surrounding natural scenery. Guests can sip on an included non-alcoholic beverage while watching for native wildlife along the way, such as osprey, bald eagles, and cownose rays.

Spend approximately 3 hours and 20 minutes exploring the historic Eastern Shore village of St. Michaels. Travelers step ashore to discover well-preserved 19th-century architecture, boutique shops, and local seafood restaurants where lunch can be purchased independently. Included in the tour is admission to the Chesapeake Bay Maritime Museum, where guests can explore interactive exhibits dedicated to traditional shipbuilding and oystering heritage. Comfortable walking shoes are recommended for strolling through the museum grounds and historic town streets during this free time ashore.