Private sailing and powerboat experiences on the Chesapeake Bay. From sunset sails to fishing trips — with a captain who knows these waters.
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The classic Chesapeake experience. Watch the sun set over the Bay with a cold drink in hand. Perfect for couples, small groups, or a memorable date night.
Half or full day on the water. Explore the Bay, anchor in a quiet cove for lunch, or visit a waterfront town. Customize the trip to what you want.
Ready to captain your own adventure? I can help you find the right boat and prepare you for a successful charter — whether here or in the Caribbean.
Want to build your skills? I offer hands-on instruction aboard real cruising boats. From basics to advanced sail trim — learn by doing, not by classroom.
Explore the Chesapeake in comfort and style. Visit waterfront restaurants, cruise past historic landmarks, or just enjoy the scenery at cruising speed.
The Chesapeake is home to rockfish, bluefish, and more. Whether you're a seasoned angler or first-timer, I'll put you on the fish and show you a great time.
Same stunning Chesapeake sunset, but with the speed and comfort of a powerboat. Perfect for special occasions or when you want to cover more water.
Birthdays, proposals, corporate outings, or just a special day with friends. Let's create a custom experience tailored to your group.
The Chesapeake Bay is one of the best sailing grounds on the East Coast. Protected waters, beautiful shorelines, and enough variety to keep things interesting — whether you want a relaxing sunset or a proper offshore experience.
I've been sailing these waters for over 15 years. As a USCG 100-ton captain, I can take you out for a memorable experience, or help you gain the confidence to charter on your own.
I'm Shane Kilberg — USCG 100-ton Master Captain with experience from the Chesapeake to the Caribbean to the America's Cup.
When you charter with me, you get someone who genuinely loves sailing and wants you to have a great time. Whether it's your first time on a sailboat or you're looking to sharpen your skills, I'll make sure you leave with a smile.
Tell me what you're looking for — I'll get back to you within 24 hours.
Or call: 443-615-4413