Chesapeake Sailing Charters

It all started with One Sail...

We were on our boat in 2003 when we realized sailing had become an integral part of our lives by providing us with a true sense of joy and freedom. Today we are devoted to giving our customers the same experience.

DOUG and VERGIE THOM,  founderS

Enjoy a picture perfect vacation with us!

You want a carefree experience with the least amount of interference from your charter company and without add ons and restrictions. Chesapeake Sailing Charters is designed with your needs in mind.  


We are located at Herrington Harbour North, one of the most beautiful and environmentally conscious marinas on the East Coast. Your relaxing sailing vacation will start as soon as you leave the Washington beltway. You will travel through some unspoiled Maryland countryside and arrive at the marina refreshed and ready to begin your trip, not a bundle of nerves from  traffic.


Your first night go for a sunset cruise and return to the dock. Alternatively stay at the dock for cocktails and dinner  or visit the restaurants in town. There are no extra sleep aboard fees for your first night or after your cruise.


If city life is your desire, let Annapolis become your destination, not your starting point. Sail up to Annapolis and pick up a mooring buoy in Annapolis harbor on a first come first served basis, or anchor in the harbor or nearby Whitehall Bay. Then enjoy all that Annapolis has to offer after an enjoyable sail.


If you would like to visit a historic village, St. Michaels, Oxford and Solomon's Island are easily within your reach. Stay at local marinas or find a secluded anchorage. Enjoy nearby restaurants or eat aboard, its your choice. We will be happy to help you plan an itinerary if you would like some suggestions and each boat has helpful information aboard specially prepared for you.


Vergie and Doug Thom

Founded in 2004, Chesapeake Sailing Charters was the result of  Vergie's and Doug's Love of  sailiNG and  knowledge of the best spots on the Bay to sail, dine, anchor and dock.  Let Them connect you with the Best the  Chesapeake Has To Offer.

About US