Time on the water just feels different.
It’s where conversations flow easier, celebrations feel more meaningful, and the pace slows while the views go on forever.
When you charter with us, you’re not just booking a boat — you’re choosing an experience designed for connection, comfort, and fun.
We can’t wait to welcome you aboard and show you the Chesapeake Bay the way we love it — relaxed, authentic, and unforgettable.
Our Story
We’re Bob and Jeannie Waldron, a husband-and-wife team who turned our love for cruising the Chesapeake Bay into something we love sharing with others.
We’ve spent years exploring the Bay — visiting charming waterfront towns like Annapolis and St. Michaels — finding quiet coves, docking for fresh seafood, and enjoying Maryland’s famous blue crabs with friends.
Some days are peaceful and restorative. Others turn into lively dock-and-dine evenings full of laughter and great conversation.
We started Chesapeake Charter Experiences to share that feeling — the calm, the fun, and the little moments that make a day on the water unforgettable.
About Captain Bob
FOUNDER | USCG CAPTAIN
Bob brings years of hands-on boating experience and a genuine love for the water to every charter. As a U.S. Coast Guard–licensed captain, safety is always his top priority — and his deep knowledge of the Bay lets guests sit back, relax, and enjoy the ride.
Known for his warm personality and easygoing presence, he creates an atmosphere that feels both elevated and welcoming. With Captain Bob at the helm, your charter isn’t just smooth — it’s effortless, refined, and genuinely enjoyable from start to finish.
About Jeannie
FOUNDER | CHARTER EXPERIENCE CURATOR
Jeannie brings thoughtful planning and warm hospitality to each experience. With a professional background in Finance and Human Resources, she keeps the business running seamlessly behind the scenes — but her real joy is helping guests create moments that feel special and personal.
From sunset cruises and dock-and-dine evenings to milestone celebrations, Jeannie shapes each experience with care and creativity , ensuring your time on the water feels effortless, welcoming, and uniquely yours.
Meet Natalie Robbe
OPERATIONS | MARKETING | SOCIAL MEDIA
Keeping it in the family, Natalie leads our marketing operations and shapes our online presence, blending organization, creativity, and thoughtful communication to bring each charter to life — ensuring every guest experience feels seamless, intentional, and well planned.