Private sailing experiences on the Chesapeake Bay. From sunset sails to bareboat adventures — with a captain who knows these waters.
443-615-4413The 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.
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.
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.
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