Great Amenities and Beautiful Scenery AWAIT YOU

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

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.


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

Chesapeake Sailing Charters

  • 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 - Garmin chartplotter, autohelm, deck shower, microwave, iPod dock stereo
  • Close proximity to Annapolis and historic seaside villages


Call today for information or to book your charter: 410-870-9848

Carefree Cruising on the Chesapeake Bay