Guide To Sailing Charters

March 28, 2013 7:00 AM

(credit: Jay Lloyd)

Reporting Jay Lloyd

For an almost gas free getaway, look no farther than the wind to carry a crew off to fun and adventure.

Go sailing.

You don’t even have to own a boat. Charter one, just like a house at the Jersey shore. The difference is that a boat takes you from port to port or from cozy cove to bustling cities like Baltimore and Annapolis, and the house doesn’t budge. To lock in preferred weekends and midweek sailing ventures, now is the time that most cruisers arrange their charters. And the best sailing ground for area getaway seekers is the expansive Chesapeake Bay, with nearly 6,000 miles of shoreline to explore on a 200 mile waterway from Havre de Grace in the north to the Virginia Capes. Here’s a rundown of what to look for, where to charter and what you’ll need. – Jay Lloyd

(credit: Jay Lloyd)

(credit: Jay Lloyd)

The Charter Boat

Charter sailboats that serve as both transportation and living accommodations are as compact as 26 feet (to sleep two or three people) to 50 feet (to sleep six). The boats are fully equipped with navigation and safety equipment as well as a galley with an ice box, sink and stove. They’ll have one or two heads (marine toilets), a shower and cabinets for storage. All kitchen utensils and supplies will be on board, right down to paper towels. Most boats will have stereo units with iPod docks. You will bring linens and personal items including bug repellant and sun screen. For a three day weekend, expect to spend between $875 for the smaller boats to $3,200 for a 50-footer capable of crossing oceans. Split among six people, it’s a bargain.

(credit: Jay Lloyd)

(credit: Jay Lloyd)

Am I Qualified to Charter?

Charter companies do want to know that the sailor is a sailor when they hand over a half-a-million-dollar yacht. They will require you to fill out a sailing resume that will ask whether you’ve owned a boat and if so, what type, how long you’ve been sailing, the waters sailed, what courses you’ve taken and whether you’ve acted in the role of skipper. It will also ask for sailing references. You may still be asked to demonstrate your abilities when you show up for the charter. If you don’t have the skills, include a friend who does in your crew, or hire a professional captain to skipper your cruise. He or she will also be more than happy to provide lessons along the way.

(credit: Jay Lloyd)

(credit: Jay Lloyd)

Where to Charter

The launching point for a great charter cruise is almost as important as the destinations themselves. I prefer two spots for their proximity to pristine anchorages and dynamic ports. Rock Hall, located on Maryland’s Eastern Shore, puts you in weekend range of Baltimore, Annapolis, St. Michaels and scenic coves on the Magothy, Severn, Chester, South and Rhode Rivers. A charter from Annapolis provides a southern reach to Oxford and Solomons, along with cozy anchorages in the Miles, Choptank and Patuxent Rivers.

Before becoming a boat owner, I chartered for many years with Haven Charters in Rock Hall. They have a well-maintained fleet of reliable boats docked at Haven Harbour Marina, just minutes from the protected “Haven” of the broad Chesapeake Bay. Jaqui Appleton and Dave Fife, the husband and wife team that runs the operation, offer solid ocean cruising boats ideal for families and sleek cruisers that have the ability to hold their own on the race course – a combination of speed and comfort. Talk to them about your crew, their abilities and their comfort levels to determine the best fit for sailors and boat. Jaqui and Dave, both Coast Guard-licensed captains, can help you with provisioning and finding a skipper if you aren’t ready to do it yourself.

Check out boats and prices at:

Annapolis is the nautical hub of America, home of the U.S. Naval Academy and the last resting place of the nation’s earliest naval hero, John Paul Jones. The harbor is awash in world class yachts flying an array of national flags. Pubs and eateries ashore buzz with boating conversation. Annapolis Bay Charters puts you right in the middle of the action with its modern fleet of traditional sailboats and catamarans. These are part of the same class of boats to be found in the charter fleets that sail the Caribbean as well as from exotic ports in the Mediterranean. When a craving for adventure under sail goes beyond the Chesapeake Bay, this Annapolis-based operation can set your crew up with dependable yachts in the Caribbean isles and the Med. Look over their Annapolis fleet and prices at:

The Crew

Getting Ready

Cruising under sail can provide a lifetime of adventure. It’s worth putting in a little time and money to learn the fine points or brush up rusty skills. A pair of highly regarded sailing schools near Rock Hall and in Annapolis can get you from classroom to boat in a weekend. Check out:



A Few Tips

Storage on sailboats is limited, so don’t over-pack. No dress clothes are needed. Shorts, t-shirts, golf shirts and one pair of slacks for men and women will be sufficient in the warmer months. Carry a slicker and white-soled boat shoes — do not bring leather soled shoes or high heels. You’ll need a good hat, sun screen and bug repellent. A sleeping bag is easier to bring than linens, and making a boat bunk is a pain. Keep provisions to a minimum. If you dock in towns rather than anchor in a secluded cove, you’ll be sampling wonderful Chesapeake restaurants, not cooking. Just carry enough for lunch while cruising and dinners for planned anchorage nights. On longer cruises, you can always stock up on provisions at ports along the way.

Also, make your itinerary realistic. Don’t overextend yourself. Get to your farthest point on the first night of a three-day charter. That gives you more time to return at a leisurely pace and manage any weather delays.

Now, go and have fun!

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