The Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and into the Chesapeake Bay. (New Vision Photography, Don Wolf/Schooner Woodwind Sailing Cruises)

‘Two, six, heave,” commands captain Nathan Hesse.

Another passenger and I pull hard on the rope attached to the mainsail of Woodwind II, sending it slinking up the yacht’s 64-foot mast.

“Two, six, heave,” Hesse booms out again, and again we pull.

After several more hearty heaves and some adjustments, he’s satisfied and we’re allowed to stand down. I pause for a moment to take in my surroundings. We’re cruising out of Annapolis on the Severn River toward the Chesapeake Bay. Although it’s a hazy day in early September, the midday sun is relentless. Sunscreen and sunglasses are a necessity; a hat is highly helpful. Fortunately the gentle zephyrs dancing across the water and the breeze created by our sedate passage provide some relief, as does the shade cast by the sails.

Off in the far distance to the port (left) side of the boat, I can see the Chesapeake Bay Bridge slung low across the horizon. There are a few boats crisscrossing in front, and colorful bullet-shaped buoys (marking crab pots) dotting the dark green waters around us, but we are generally alone. Oddly, there are three captains onboard — Hesse, Tom Stalder and Andy Barton, who commands the wheel located in the far aft (back) of the boat by the tiller. Normally, there would be just one, along with a couple of lower-ranked crew members, but that’s how the schedule worked out today. They’re all wearing some variation on a typical sailor’s getup: white T-shirt, khaki shorts, hat and sunglasses.

We departed from the dock in front of the Annapolis Marriott Waterfront hotel, just a five-minute walk from the city’s tourist-friendly historic district. Before the trip got underway, we were given a short safety spiel on where to find the “orange uglies” (better known as life preservers) in case of emergency and what would happen in the event someone fell overboard. Barton said the latter had never happened to a passenger on any of his cruises, although a chagrined crew member once accidentally ended up in the drink.

The engine was fired up, we cast off and a long warning horn blew. Once we were out of Annapolis Harbor, I was heaving away on the mainsail so we could switch over to wind power. According to Barton, the general rule of thumb for sailboats is they’ll go about two thirds of the wind speed if piloted properly. Unfortunately, the wind is only blowing approximately three knots (3.5 mph), which means we will only be going a little over 2 mph with natural power.

The 74-foot Woodwind schooner. Schooner Woodwind’s mini-cruises, which have been running since 1993, are a way to see the Annapolis area from another angle and relax on the open water. There’s no set itinerary on most of them (Schooner Woodwind Sailing Cruises)

This two-hour trip should not be mistaken for a tour. Barton points out several items of interest and peppers the outing with fun factoids — and all three captains are happy to answer questions — but there’s no continuous flow of narration. The company runs several cruises every day from spring through late fall on the Woodwind II and its sister ship, Woodwind. The mini-cruises, which have been running since 1993, are a way to see the Annapolis area from another angle and relax on the open water. There’s no set itinerary on most of them — they simply meander through the Severn River, Chesapeake Bay and neighboring waterways. Other specialty cruises are focused on watching the sunset, listening to local bands play mini concerts onboard or doing a beer tasting.

When I mentioned the trip to a friend, he kidded that it would be just like “Gilligan’s Island,” where the passengers of the S.S. Minnow were shipwrecked on a tropical island after getting swept up in a storm during a three-hour tour. I ask Barton whether many passengers make references to the ’60s TV show. “We tell them that’s why we do only two-hour cruises,” he shoots back.

The Woodwind. (Schooner Woodwind Sailing Cruises)

The boat does have a connection to the screen, though. It was used in a key sequence in the 2005 comedy “Wedding Crashers,” starring Owen Wilson, Vince Vaughn, Rachel Adams and Christopher Walken, all of whom were on the Woodwind II. There’s a scrapbook with photos of the stars during the shoot and pages of the script onboard.

After serenely sailing for a while towards the invisible line stretching between Greenbury Point to the north and Tolly Point to the south — which marks the mouth of the Severn River and the beginning of the Chesapeake Bay — Barton announces, “We’re going to raise the fifth sail.”

It’s a joke. The 74-foot-long schooner (a name that simply refers to a sailboat with more than one mast; Woodwind II has two) has only four sails. He fires up the engine again to supplement our progress.

Passengers are invited to steer, so I volunteer. Placing my hands at 11 o’clock and 1 o’clock on the giant wheel, I can feel the shifting currents on the rudder, gently flicking it back and forth. Barton tells me to aim back towards the shoreline, trying to keep the bow pointed towards a docked yacht with blue sails. We’re heading towards Back Creek, filled with marinas and boat maintenance businesses.

“Locals call it Debtor’s Creek because so many owners owe money on their boats,” Barton says.

There are hundreds, if not thousands, of pleasure vessels tied up along the shoreline. I can’t even begin to fathom their collective cost and upkeep fees. As a dear friend of mine once observed, “No one needs a boat. Everyone needs a friend with a boat.” I’m thankful that the extent of my financial commitment to the Woodwind II is just the price of a ticket.

Under the direction of Barton, I do a lazy half doughnut and turn the boat around. We’re heading home.

Martell is a Washington writer and the author of several books, including “Freak Show Without a Tent: Swimming With Piranhas, Getting Stoned in Fiji and Other Family Vacations.” On Twitter: @nevinmartell.

More from Travel’s Cruise Issue:

A transatlantic crossing on the Queen Mary

The realities of taking a cruise on a ‘mega-ship’

If you go
Schooner Woodwind

At the Annapolis Marriott Waterfront Hotel

80 Compromise St.


Trips depart daily from the dock in front of the Annapolis Marriott Waterfront hotel until Oct. 31; they resume in mid-April. $41, seniors $39, age 11 and younger $27

— N.M.