• Special weekend discount, sail 3 days for the price of two!
  • Sleep aboard night before or night after  at no extra charge
  • Free travel planning
  • Charter amenities - Northstar chartplotter, autohelm, deck shower, microwave, iPod dock stereo
  • Close promximity to Annapolis and historic seaside villages

FEATURED Services

SAIL your heart away

At Chesapeake Sailing Charters, we know about the amazing experiences that occur when you charter a boat and explore a whole new world. Let us guide you in that amazing journey.

​​Chesapeake Sailing Charters

Great Amenities and Beautiful Scenery AWAIT YOU

Chart your course from land to bay and back again to view all the Chesapeake sites while enjoying privacy on your boat, an easy to sail and excellently maintained classic sloop.  Enjoy a weekend or a week aboard "Romper".

START EXPLORING Today!


Ask us about our Weekend Special
3 days for the price of 2! 

Carefree Cruising on the Chesapeake Bay