Private Chesapeake Bay Sailing Charters

We work with you to create the perfect Private Chesapeake Bay Sailing Charters  for you, your family, your friends or your corporate team.

We offer two-hour, half-day and full day Private Chesapeake Bay Sailing Charters by reservation only. For an additional fee, we can arrange charters departing from different locations on the Bay. Some popular locations are Annapolis, Oxford, St Michaels or Cambridge.

Food & Beverages

Beer, wine and cocktail service is available on board all charters. Catered food is also available from fantastic local eateries by special arrangement. Of course it can be served to you by our crew while underway.


The rates for Private Chesapeake Bay Sailing Charters start at $575 + tax & tip for a mid-week morning or afternoon excursion from our home dockage on Tilghman Island.


Imagine a warm Bay breeze, a beautiful sunset, a glass of delicious champagne, a ring. and your special someone aboard a classic sailboat all to your selves. We are 12  for 12  so far. Be the 13th!

Wedding Charters

We love weddings! We have officiated intimate on-board weddings and they have all been stunningly beautiful. What better way to tie the knot then shaded by sails and surrounded by varnished teak and polished bronze while  sailing on the beautiful Chesapeake Bay.

We have also ferried the bride and bridesmaids from their waterfront inn to the wedding venue for the ceremony.  Would you like to really make a splash with your arrival to the wedding reception? Think about a short sail after the ceremony to enjoy a toast with your dearest friends, your wedding party.

We offer catered wine and hor devour sails that are perfect for birthdays, anniversaries or even bachelor / bachelorette parties!

Corporate Charters

We do team building exercises for business and  corporate groups. Do you really want to fine tune a teams ability to communicate and work together? Consider a race charter where you and your team are the crew.  Win or loose, you will develop skills that will benefit the group for years to come.

Call 410.886.1127 or email me to see how we can make your wedding, corporate retreat or vacation an experience that you will remember for a lifetime!


Private Chesapeake Bay Sailing Charters