Hosted Chesapeake Experience

Private Chesapeake Bay Dining Cruise

Chesapeake Hospitality Meets Incredible Local Food

Experience the Chesapeake the way it was meant to be enjoyed—with exceptional food, incredible scenery, and genuine Eastern Shore hospitality.

The Hosted Chesapeake Experience combines a private cruise aboard the Lois Ann with thoughtfully prepared local cuisine, a dedicated onboard host, and personalized service from beginning to end.

Choose from artisan grazing boards featuring local favorites, a traditional Maryland Blue Crab feast, or a chef-prepared Chesapeake supper while cruising the waterways of Maryland's Eastern Shore.

Whether you choose a daytime outing, a golden-hour cruise, or an unforgettable sunset dinner, every experience is customized for your group.

Experience Highlights

Duration

  • 4 Hours

What's Included

  • Private cruise aboard the Lois Ann

  • Dedicated onboard host

  • Complimentary bottled water, sodas, wine, beer, and seltzers

  • Personalized cruise itinerary

  • Branded keepsake

Dining Options

  • Eastern Shore Light Bites

  • Authentic Eastern Shore Crab Feast

  • Chesapeake Supper

Available for daytime, sunset, and evening cruises.

Perfect For

  • Romantic date nights

  • Anniversaries

  • Vacation celebrations

  • Small group gatherings

  • Intimate corporate entertaining

  • Food lovers exploring Maryland's Eastern Shore

Book Your Chesapeake Experience

Why Choose a Private Chesapeake Bay Dining Experience?

Dinner with a view is one thing. Dinner on the Chesapeake Bay is something entirely different.

The Hosted Chesapeake Experience brings together a private cruise, local Eastern Shore food, personalized hospitality, and beautiful Chesapeake scenery aboard the Lois Ann. With your own onboard host and a dining experience selected for your group, every detail is designed to make your time on the water feel special.

Choose a daytime cruise, sunset dinner, or evening on the Bay and enjoy an experience built around your group rather than a traditional restaurant reservation.

For couples, vacationers, small groups, and businesses searching for a Chesapeake Bay dinner cruise, private dining cruise, Eastern Shore date night, sunset cruise, or unique Maryland dining experience, this is the Chesapeake at its best.

Visiting St. Michaels, Cambridge, Easton or the Eastern Shore?

The Hosted Chesapeake Experience is a memorable addition to vacations in Cambridge, St. Michaels, Easton, Oxford, Tilghman Island, Hoopers Island, Taylors Island, and Kent Narrows.

Instead of another night at a restaurant, take dinner to the water with local flavors, Chesapeake views, and a completely private setting aboard the Lois Ann.

Looking for a Unique Experience From Annapolis or Baltimore?

Guests traveling from Annapolis, Baltimore, Severna Park, and Edgewater can make a private Chesapeake Bay dining cruise the centerpiece of an Eastern Shore date night or weekend away.

Come across the Bay for waterfront towns and local food, then experience both from the best seat in Maryland—the water.

Planning a Date Night or Getaway From D.C. or Northern Virginia?

For guests traveling from Washington, D.C., Bethesda, Potomac, Alexandria, or Arlington, the Hosted Chesapeake Experience offers something refreshingly different from another city dinner reservation.

Plan an Eastern Shore escape around a private sunset cruise, Chesapeake Bay dining experience, anniversary celebration, or intimate group outing aboard the Lois Ann.