Signature Cruise

Private Chesapeake Bay Cruise on Maryland's Eastern Shore

Slow Down and Experience the Chesapeake

Escape the crowds and discover the beauty of Maryland's Eastern Shore aboard the historic Lois Ann. Our Signature Cruise is a private Chesapeake Bay boat tour designed for couples, families, friends, and visitors looking to experience the Bay at a slower pace.

Whether you're celebrating a birthday, anniversary, engagement, or simply spending time together, your captain will customize the route around your group, showcasing scenic waterways, local wildlife, waterfront communities, and hidden corners of the Chesapeake that few visitors ever see.

Unlike traditional sightseeing cruises, every trip is completely private, allowing you to relax, reconnect, and experience authentic Eastern Shore hospitality.

Experience Highlights

Duration

  • 3 Hours

What's Included

  • Private cruise aboard the Lois Ann

  • Complimentary bottled water, sodas, and seltzers

  • Flexible itinerary customized to your group

  • Scenic cruising throughout the Chesapeake Bay

Perfect For

The Signature Cruise is ideal for:

  • Couples

  • Families

  • Small groups

  • Birthday celebrations

  • Anniversaries

  • Airbnb and waterfront vacation guests

  • First-time visitors to Maryland's Eastern Shore

Book Your Cruise

Why Choose a Private Chesapeake Bay Cruise?

The Signature Cruise gives you the freedom to experience the Chesapeake without a crowded tour boat, rigid route, or packed itinerary. Your cruise aboard the Lois Ann is completely private, giving your group the space to relax and enjoy Maryland's Eastern Shore at your own pace.

Spend three hours taking in quiet waterways, working waterfronts, local wildlife, historic scenery, and the unmistakable character of the Chesapeake Bay. Your captain can personalize the route based on your group, the conditions, and what you'd most like to experience.

For visitors searching for a private Chesapeake Bay cruise, Eastern Shore boat tour, private sightseeing cruise, or a unique thing to do while visiting Maryland's Eastern Shore, the Signature Cruise offers an authentic look at the Bay from the water.

Visiting Cambridge, St. Michaels, Easton & Maryland's Eastern Shore?

Staying in Cambridge, St. Michaels, Easton, Oxford, Tilghman Island, Hoopers Island, Taylors Island, or Kent Narrows? Add a private Chesapeake Bay cruise aboard the Lois Ann to your Eastern Shore itinerary.

The Signature Cruise is perfect for visitors who want to get beyond the waterfront and actually experience the waterways that have shaped these historic Maryland communities.

Coming From Annapolis, Baltimore or the Western Shore?

If you're visiting from Annapolis, Baltimore, Severna Park, or Edgewater, spend a day discovering a different side of the Chesapeake. A private Eastern Shore boat cruise makes an easy centerpiece for a day trip or weekend getaway filled with waterfront towns, local seafood, and time on the Bay.

Planning a Chesapeake Getaway From D.C. or Northern Virginia?

Trade the city for the water. Guests traveling from Washington, D.C., Bethesda, Potomac, Alexandria, and Arlington can turn the Signature Cruise into a memorable part of an Eastern Shore getaway.

If you've been searching for a private Chesapeake Bay boat tour from the D.C. area, this is your invitation to experience Maryland from an entirely different perspective.