by Kris Ankarlo

ANNAPOLIS, Md. (WNEW) — It’s a pretty nice place to be: Coasting with the wind, skipping along the surface of the Chesapeake while sipping drinks on a 74-foot sailboat as the sun sets behind the domed and steepled Annapolis skyline.

Now, if you don’t have a sailboat, or a rich friend who does … no worries, the Schooner Woodwind gives you a chance to ride the bay on the wind.

“I think it’s something that everyone should experience. The sails we’ve had today, the winds have just been phenomenal,” says Capt. Mickey Lawlor. “You definitely get a feel for Annapolis being out on the water.”

From April to October, the boat offers four public sails daily, leaving from the harbor in Annapolis. The most popular of those four sails is the sunset sail, for pretty obvious reasons. But to sweeten the pot even more, those sunset sails are themed Monday through Thursday.

On Mondays, a local historian talks in period dress telling a selection of the endless stories that Annapolis and the Chesapeake has to offer. It’s a good chance to glean some fun facts for your next trivia night.

“I love listening to the speakers. I learn a lot, so it’s very interesting,” Lawlor says. “For some reason, I ended up on a lot of Mondays last year, so I learned a lot about the area.”

On Tuesday’s it’s about the beer, the Woodwind offers up a tasting of local brews. The beers are all brewed somewhere in the Chesapeake watershed, and beer on a boat is about as good as it gets.

Every Wednesday night the waters around Annapolis become a race course, and you can be on the Woodwind as it chases down, or zips past, other sailboats. But if you’re looking for a more relaxing experience then come on a Thursday night when local musicians are on board adding a soundtrack to an already idyllic scene.

So which nights are most popular?

“It’s tough between the beer tasting and the racing,” Lawlor says.

Regardless of what night you go, it’s important to remember that on a vessel powered by the wind, the experience always changes. And, if you’re so inclined, you’ll have a chance to harness those winds.

“We have guest involvement on all of our sails. You can help raise the sails and help trim the sails,” says Lawlor. “On the race nights we get people involved in helping weigh the boat down and verbally abuse the other boats. It’s a lot of fun. They’re very fierce competitors so it’s always tight racing.”

And if you’re more type-A, you’ll even get a chance to steer the boat, just like Christopher Walken in “Wedding Crashers.” (It should be on everyone’s bucket list to stand where Christopher Walken once stood, no less while shouting out sailing instructions.)

A two-hour sail during the day will cost $39. The sunset and weekend sails cost $42. Depending on the winds, the sail will loop out into the Chesapeake for a nice view of the Bay Bridge and back through the Severn River. The schedule is posted and tickets are available on the Schooner Woodwind website.

Wine and beer is available for purchase on the boat, but make sure you bring cash. They also hand out light snacks about halfway through the sail.

There’s no need to worry about attire, dress casually. Although, this is probably the best chance you’ll have to tie a sweater around your neck while wearing pastels and boat shoes. Actually, shoes are the one part of your wardrobe to be conscious of.

“If you have a rubber soled shoe definitely wear a rubber-soled shoe,” says Lawlor.

Besides, high-heels on a boat only work in turn-of-the-millenium rap videos and SNL sketches. Do bring along a sweatshirt, even if it’s a warm day you’ll be dealing with the wind.

Boarding is on a wharf adjacent to the Annapolis Marriott Waterfront hotel (80 Compromise Street, Annapolis, MD 21401). The hotel does offer valet parking.

There is also a municipal lot next to the hotel, but note that those spots are metered and limited at two hours. It’s a good option for the sunset sail; but, during the day your best bet would be to park in one of the town’s garages or pay for valet.

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