Rent a vacation home at the shore and it’s called a “rental.” Rent a boat for a cruising getaway and it’s called a “charter.” The other big difference is the house doesn’t move, while the boat — which also serves as lodging — carries you to fascinating ports or pristine coves. The nearby Chesapeake Bay is one of the largest and most varied waterways in America. Here’s a pair of first rate charter companies that will get you started on a nautical adventure without the expense of actually buying the boat. – Jay Lloyd

(credit: Jay Lloyd)

(credit: Jay Lloyd)

COMPANIES TO TRY

HAVEN CHARTERS
20846 Rock Hall Ave.
Rock Hall, MD 21661
www.havencharters.com

I like Rock Hall, a seafaring town on Maryland’s Eastern Shore, because it offers instant access to the 200 mile expanse of the Chesapeake Bay. There’s no long, winding river to navigate before reaching open water. It also puts you within a four- to five-hour sail of Baltimore and Annapolis, or six hours to St. Michaels. Haven Charters is long-established and where my crew of KYW buddies chartered our boats for a decade before jumping into ownership. Haven Charters meticulously maintains a fleet of 22 liveaboard sailboats from 32 to 48 feet. They provide comfort for a cozy couple’s getaway or for a crew of six. Owners Jaqui Appleton and Dave Fife can help you pick the right size and configuration. You can be casting off for a three-day weekend in a 32 footer for a little over $,1000. The boats come fully equipped — more on that and your skill requirements later.

DREAM YACHT CHARTERS
7080 Bembe Beach Rd.
Annapolis, MD 21401
www.dreamyachtcharter.com/english/destinations/usa/chesapeake-bay

If your port of choice is on the western shore of the bay, Annapolis is the spot. This is among the most nautically symbolic of American ports — home to the United States Naval Academy and the last resting place of our first naval hero, John Paul Jones. It takes about 20 minutes to sail from the Annapolis Harbor to the open water of the Chesapeake, and you’re on your way to a world of scenic shorelines and rivers or an isolated cove. Dream Yacht Charters maintains a fleet of 15 sailboats ranging from 34 to 53 feet, including catamarans and a trimaran. It’s a global operation with charter sailing fleets from the Indian Ocean to the Caribbean. Your crew can be shoving off for a 3-day weekend for just under $1,600.

(credit: Jay Lloyd)

(credit: Jay Lloyd)

REQUIRED SKILLS

It’s called “bareboat chartering” and has nothing to do with a state of dress. It simply means you are the skipper and are responsible for the safe navigation of the vessel. You’ll have to fill out a sailing resume that details your sailing experience, including the courses you’ve completed, and asks for references from other charter companies or captains that have sailed with you. If you do not have a sailing background, charter companies will provide a captain at an extra charge. An advantage to hiring a skipper is that, in addition to his or her knowledge of the bay and the best places to tie up or drop an anchor, there will be skills passed on during the voyage.

(credit: Jay Lloyd)

(credit: Jay Lloyd)

WHAT IS PROVIDED

The boat will be fully equipped with all navigation and safety equipment, including charts and life jackets. It will have a galley and all the necessary cookware and utensils. Many boats also have barbecue grills that attach to the stern rail. Paper towels and toilet paper are provided. The fresh water and fuel tanks will be filled. The boats will have auxiliary engines. Winches and all sail operating equipment are provided along with a basic first aid kit and fire extinguishers.

(credit: Jay Lloyd)

(credit: Jay Lloyd)

WHAT YOU SHOULD BRING

You and your crew will have to bring linens or sleeping bags, towels, all toiletries, bug repellent and sun block. Bring binoculars, sun glasses and hats, too. I prefer either a broad brimmed hat or a baseball cap with a kepi style neck protector. You must have boat shoes or sport shoes, preferably with white soles. Bring your own food for lunches while under way and dinners and breakfasts while anchored out. When in port, you don’t want to pass up some of the great restaurants and crab houses that line the Chesapeake waterfront.

BBQ

WHERE TO GO

From Rock Hall, a favorite itinerary is a first day run to St. Michaels for an evening ashore with hot, steamed crabs at the Crab Claw and then drinks at Foxy’s. If you have time, stroll through the fascinating Chesapeake Bay Maritime Museum. Enjoy a nice long sail on your second day to Annapolis (if you charter out of Rock Hall). Stroll the streets and shops, stop for drinks on the deck at Pusser’s Rum Bar, and then eat dinner at Harry Browne’s on the Capitol Circle. If you want to spend a night at anchor, head for the Rhode River on the western shore. If you charter in Annapolis, sail to Rock Hall for crabs at the Waterman’s Crab House and dancing at the Harbor Shack. Then head for either St. Michaels for the in-town experience or anchor in Shaw Bay off the Eastern Bay. Finally, take the return run to Annapolis.

Enjoy!

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