Chartering the Chesapeake

With one of the East Coast’s premier cruising destinations right in our front yard, isn’t it lovely to think of spending time relaxing and taking in some of the Chesapeake Bay this season? Even if you don’t have a boat, don’t want to take her out, or flat don’t know how to sail and would like to know what the fuss is all about, chartering on the Chesapeake offers the opportunity to hear the crackle of a mainsail and creak of a jib sheet without the responsibilities of boat ownership.

[caption id="attachment_94082" align="aligncenter" width="600"]The Schooner Woodwind. Photo by Dan Myers The Schooner Woodwind. Photo by Dan Myers[/caption]

Reasons to charter on the Chesapeake are numerous: Perhaps you want to take a family vacation. Or a group of friends wishes to gather for a reunion. Or you want to take your sweetheart for a sunset sail. Or you’ve always sailed monohulls and want to know what catamarans are really like. Or you…

Luckily, charters on the Chesapeake are numerous, too, and companies up and down the Bay offer a wide range of options ranging from bareboat to captained charters and from week-long vacations to outings lasting only a couple of hours. Planning can take as little as 24 hours with a day charter and as much as six months with a multi-day charter.

Like many of us, Lawrence McAndrews began sailing on small boats on the Potomac in 1993. By 1999, he and his wife, Priscilla, had the itch for cruising, but had neither the time nor the inclination to own a big boat. So they started looking for other solutions and found that chartering a sailboat on the Chesapeake a few times a season answered their needs perfectly. Since then, they have chartered three to five times a season—sometimes as a couple, sometimes with family, and sometimes with friends or business associates—and have a lot of perspective to offer prospective charterers.


When choosing a charter company, McAndrews suggests getting recommendations from boaters you trust. Associates at sailing clubs and sailing schools often have helpful advice, and reviews can provide a wealth of information about charter companies and the services they offer. McAndrews notes that when you choose a well-run charter company with a high level of service, you benefit from years of experience in boat handling and maintenance on call when you need it.

Carolyn Schmalenberger of Norton Yachts in Deltaville, VA, also suggests choosing a charter company with a boat that fits your needs. She says, “The type of boat can depend upon how many people you have going with you, your comfort level with sailing, and even the location where you will be sailing.”

For a multi-day charter, booking at least three months in advance offers more chartering options. Schmalenberger advises, “Planning six months ahead guarantees that you get the boat you want for the dates you want. There are many popular times for chartering: for instance, Memorial Day, June when kids are out of school, and October for the beautiful fall weather and sunsets.”

[caption id="attachment_94084" align="aligncenter" width="600"]Photo by Gilles Martin-Raget/ Dream Yacht Charter Photo by Gilles Martin-Raget/ Dream Yacht Charter[/caption]

When the day finally arrives for your charter to begin, what can you expect? Following some routine paperwork and packing your things onto the boat, a briefing on the boat and its systems with the charter base captain typically takes place. Erin Houpt of Annapolis Bay Charters in Annapolis, MD, says the briefing is a great opportunity for charterers and the charter base captain to get to know one another and understand each other’s abilities. With bareboat charters, the charter base captain needs to feel comfortable with the charterer’s ability to operate the boat and get it back to port. Charter sailors, in turn, can use the briefing as a way to understand the boat and learn how to easily reach the charter base should any difficulties arise during the charter.

Houpt also recommends that charterers utilize their charter company as a resource. Not only do staff at the charter company know the boats like the backs of their hands, they are also local to the area and can offer some outstanding suggestions for itineraries and activities.

If you don’t have a few months to plan or even three days to sail, chartering options still lure with promises of relaxation and beautiful sunsets. Many towns along the Chesapeake offer two-hour cruises aboard historic or wooden sailing vessels. Some benefits of day charters include booking tickets after you know the weather forecast and being able to spontaneously plan an outing.


Captain Jennifer Kaye of Schooner Woodwind in Annapolis, MD, says two-hour cruises are very popular with sailors and non-sailors alike. Up to 48 passengers can set sail on either of their two schooners, and guests have the opportunity to simply enjoy the ride or to become actively involved in sailing the vessel.

Mark Einstein, who runs Blue Crab Charters out of Rock Hall, MD, offers a similar experience in a more intimate setting. Up to six passengers may set sail on each of three vessels for one of five daily cruises. Einstein tries to pace the cruise to the wishes of the passengers—hands-on for those who want to learn and relaxing for those want to watch the view. Over the years, he has found that guests with prior sailing experience prefer the morning cruise, sunbathers like the afternoon cruise, and romantics opt to sail out into the sunset.

What all these charters have in common is that the people who book them often hail from the Chesapeake Bay area and find chartering an accessible, even economical way, to experience this beautiful body of water so close to us.

Priscilla McAndrews sums up the benefits of chartering: “The boat is ready when you get there; someone cares when you are out there, and when you return you are done.” Well said. Now let’s get sailing.