Experiences on the Chesapeake
Whether you're looking for a relaxing afternoon on the water, an unforgettable meal, a hands-on Eastern Shore adventure, or a full day exploring the Chesapeake, every Tides & Traditions experience is private, personalized, and centered around the historic Lois Ann. All cruises are designed for small groups, allowing you to slow down, enjoy the scenery, and experience the Chesapeake the way locals do.
Signature Cruise
A Relaxed Private Cruise
Perfect for sightseeing, celebrating a special occasion, or simply spending quality time on the Chesapeake.
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 couples, families, small groups, Airbnb and hotel guests, or anyone celebrating a birthday, anniversary, or special occasion.
Hosted Chesapeake Experience
A Curated Dining Experience on the Water
A fully hosted experience combining incredible local food, thoughtful hospitality, and unforgettable Chesapeake views.
Duration
- 4 Hours
What's Included
- Private cruise aboard the Lois Ann
- Dedicated onboard host
- Complimentary bottled water, sodas, seltzers, wine, and beer
- Personalized cruise itinerary
- Branded keepsake
Choose Your Dining Experience
Eastern Shore Light Bites
- Local artisan grazing boards
- Seasonal Eastern Shore favorites
Authentic Eastern Shore Crab Feast
- Steamed Maryland Blue Crabs
- Traditional local accompaniments
Chesapeake Supper
- A locally prepared meal featuring regional favorites
Available for daytime, sunset or evening cruises.
Perfect for date nights, anniversaries, small group celebrations, vacation guests, and intimate corporate entertaining.
Waterman's Way Experience
Become a Chesapeake Waterman for the Day
Experience the traditions of the Chesapeake firsthand with an authentic crabbing adventure led by your captain.
Duration
- 4+ Hours
What's Included
- Hands-on crabbing experience
- Guaranteed bushel of Maryland Blue Crabs
- Captain-led education about local watermen traditions
- Complimentary bottled water, sodas, and seltzers
- Boxed lunch
- Eastern Shore boat snacks
- Branded keepsake
Optional Add-On
Crab Plant Tour & Picnic Cruise
- Local crab processing facility tour
- Authentic Eastern Shore crab feast picnic
- Everything needed to pick and enjoy your fresh crabs
Captain's Charter
Your Day. Your Adventure.
Spend an entire day exploring the Chesapeake with a completely customized itinerary designed around your interests.
Duration
- 8 Hours
What's Included
- Fully customizable itinerary
- Lighthouse tours, waterfront towns, secluded anchorages, or build-your-own adventure
- Catered breakfast
- Catered lunch
- Eastern Shore light bites
- Fine wines, craft beer, sodas, and refreshments
- Branded keepsake
Perfect for family outings, special celebrations, photography excursions, corporate retreats, and unforgettable full-day Chesapeake adventures.
Sea Duck Hunt
Chesapeake Waterfowl Experience
Join us during waterfowl season for a guided sea duck hunt aboard the Lois Ann.
Available seasonally, November through January
Duration
- Half Day
What's Included
- Guided sea duck hunt
- Decoys and equipment provided
- Hot breakfast served onboard
Requirements
- Valid waterfowl license required
Planning Your Chesapeake Bay Experience!
Tides & Traditions offers private Chesapeake Bay cruises and authentic, hands-on experiences aboard a traditional Chesapeake Bay deadrise. Departing from Maryland’s Eastern Shore, each experience is designed to give guests a closer look at the waterways, traditions, food, and working-waterman culture that make the Chesapeake so special.
Whether you're planning a day on the water, a private group outing, a Chesapeake Bay crabbing experience, or a one-of-a-kind addition to your Eastern Shore getaway, we welcome guests from across Maryland and the surrounding Mid-Atlantic region.
Visiting Maryland’s Eastern Shore?
Tides & Traditions is a unique addition to a stay in Cambridge, St. Michaels, Easton, Oxford, Tilghman Island, Hoopers Island, Taylors Island, or Kent Narrows. Spend part of your Chesapeake Bay vacation aboard the Lois Ann, experiencing the Eastern Shore from the place that shaped so much of its history and culture: the water.
Coming From the Western Shore?
Guests visiting from Annapolis, Baltimore, Severna Park, and Edgewater can trade the city and Western Shore for an authentic day on Maryland’s Eastern Shore. Make Tides & Traditions part of a weekend getaway or plan your trip around a private Chesapeake Bay cruise, crabbing experience, and Eastern Shore hospitality.
Visiting From Washington, D.C. or Northern Virginia?
Looking for a Chesapeake Bay getaway from Washington, D.C., Bethesda, Potomac, Alexandria, or Arlington? The Eastern Shore offers an easy escape from the city and a completely different way to experience Maryland.
Come for the water, stay for the waterfront towns, local seafood, and laid-back Eastern Shore lifestyle — with Tides & Traditions at the center of your Chesapeake experience.
Be the First to Plan Chesapeake Bay Experience
Your time on the water starts here. Share a few details about your ideal charter, and our crew will help bring your experience to life.