Under Sail

Jay Lloyd / KYW Newsradio

Getaway Guide to Charter Sailing

May 23, 2018 - 4:06 pm

By Jay Lloyd

PHILADELPHIA (KYW Newsradio) -- Tall Ships, under sail on the Delaware and moored at Penn's Landing have started a raging storm of fantasies. We dream of casting off the lines of daily life and raising the sails of adventure at sea - or at least a river and bay. But, most among us have no boat. What to do? Rent a boat like you do a house at the shore. In boating lingo, it's called "Chartering." Here's how and where.


Unlike a house, a boat moves. To charter we have to convince the owner that we are indeed, qualified to sail. If you're not yet ready to be a skipper, there are sailing schools nearby on one of the best sailing grounds in the country - the Chesapeake Bay. Two favorites are the Annapolis School of Sailing and the Maryland School of Sailing. Start with a weekend course on basics and sail handling. Follow it with one or more cruising courses. Work your way up to certification for "Bareboat Chartering." That simply means when you charter, it's your boat and your responsibility. Certification indicates you have the knowledge to safely handle the boat, navigate, dock and follow safety procedures and rules of the road.

Sail School
Jay Lloyd / KYW Newsradio


Until we became boat owners, my KYW crew chartered twice a year for 20 years. Many of the boats were sailed from HAVEN CHARTERS in Rock Hall, Maryland. Dave Fife and Jaqueline Appleton operate a fleet of 28 sailboats ranging in size from 32 to 51 feet. (More on size in a moment). Both are Coast Guard licensed Captains and have a lifetime of experience on the Chesapeake, in Bermuda waters and the Caribbean. They'll match you and your crew to an ideal boat for your planned cruise. I like Rock Hall because you have direct access to the bay and an average 4.5 hour sail to Annapolis or Baltimore and a six to eight hour run to St. Michaels, depending on your route. Literally hundreds of snug anchorages can also be found within an eight hour sail.

To comfortably cruise further south on the bay during a long weekend or midweek charter, look to ANNAPOLIS BAY CHARTERS. This long established charter operation maintains a fleet of 12 boats ranging from 38 to 53 feet in a combination of mono-hulls and catamarans. You'll sail from the historic port of Annapolis in the shadow of the U.S. Naval Academy and range south on a long weekend as far as the Patuxent River and the lively cruising port at Solomons Island. Or tuck into a protected anchorage in the Potomac.

If you're not quite ready to handle it yourself, both Haven Charters and Annapolis Bay Charters can provide a licensed captain. He or she will watch over your sail setting, navigation and helmsmanship, and do some valuable instruction along the way.

Jay Lloyd / KYW Newsradio


When you charter a boat it will have sleeping accommodations to handle the number in your crew. There will be one or two "heads" (bathrooms), most likely, a shower, a galley with stove, all cooking supplies, utensils, dinnerware, ice box and cleaning supplies. All safety equipment, including first aid kit, life jacket, throwable life ring and flare gun. You'll find all docking lines, electric cables, charts, navigation tools and usually a GPS unit.

Dinner aboard
Jay Lloyd / KYW Newsradio


You will bring linens, pillows, personal gear including boat shoes, toiletries, sun screen, a good wide brimmed hat, food and beverages. Do not bring high heels and leather sole shoes (they mark the decks). Leave behind jackets and ties. It can get cool at night so bring sweaters and sweat shirts. Carry gear in soft sided bags like duffles.

Sail Chesapeake
Jay Lloyd / KYW Newsradio


Look at the boat layouts to accommodate sleeping arrangements - singles and doubles, adults and children. A good rule of thumb in boat length is 30 to 32 feet for two to three adults. Thirty-six to 40 feet for four adults, over 40 feet for six. Why? The more people you have, the more storage space you need. You'll also need more water tank capacity and more holding tank capacity for the toilets. Yes. it stays on board till you reach a pump-out station. You also need more room on deck and in the cockpit. That only comes with additional length. You get the idea.

Charter Boat
Jay Lloyd / KYW Newsradio

Now, live the fantasy.