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t r a t s w o n A New Sailor Guide by

“Sailing balances my active career.”

“Offshore Sailing School gave me the conf idence and competence to feel comfortable in any situation on the water. Sailing has become my favorite recreational escape and a great adventure that balances my hardworking lifestyle.” Melinda Long – Richmond,VA VP, SunTrust Investment Services Courses taken: Fast Track to Cruising (Learn to Sail and Bareboat Cruising Preparation), Coastal Navigation and Coastal Passage Making

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Why Wait Another Year?

f you’ve ever uttered the words, “I’ve always wanted to learn to sail,” this is the perfect little book for you. For more than a decade, would-be sailors have called our Annapolis headquarters at SpinSheet asking us how to get started. Producing a sailing magazine for and about Chesapeake Bay sailors, we’re always happy to help. We’ll dish out as much information as we have about who to call, where to go to find skilled teachers, what to wear, what to beware of, which events longtime sailors love, and even where to relax and just watch a sailboat race. We’ve decided it’s time to write down that collective wisdom to share it with a wider audience. Start Sailing Now is the fruit of that decision.

Contrary to popular belief and (some well-earned) stereotypes found in movies and magazines, you don’t have to be rich to start sailing. Learning doesn’t require thousands of dollars—although if you’d like to spend that much, as in any sport, your options would be wide open. It wouldn’t hurt to have fancy gear, a boat, or a yacht club membership, but you don’t need any of it. We’d like to show you how to start sailing today on the Chesapeake Bay with nothing but a bare bones investment and a willingness to learn.

Here is the top truth about sailing: it’s more fun with friends. We’ve never met a sailor who doesn’t want any more sailing friends. We don’t know any sailors who haven’t taught new crew how to make their way around a boat, how to As passionate about the sport as we are, we can’t figure out why more would- decipher the lingo, or how to coil a line. be sailors aren’t active sailors now. Is it the We don’t know any sailors who haven’t time or money commitment that prevents gladly shared their jackets or gloves in foul weather or given a quick knot-tying new sailors from jumping in today? Is lesson. it a fear that they are not “invited” into the exclusive club? Is it the confusing The SpinSheet staff knows a lot about language of sailing? We think it might be sailing and a lot of sailors who are eager to a combination of all of the above. Our share their expertise. We’d like to introduce mission is to debunk the myths, to share a you to them. No need to defer your sailing few “secrets,” and above all, to invite more dream another year. You can start now. would-be sailors to become active sailors Welcome to the exciting and totally this season. addictive world of sailing! Molly Winans Editor, SpinSheet s t a r t s a i l i n g n o w.c o m



start now

Why Wait Another Year?........................................................................................ 3 Gybe Ho Is Not an Insult: 22 Terms All Sailors Know................................... 5

From Bike to Boat: Shifting Your Gear.............................................................. 9 Connecting to Sailing… for Free.....................................................................14 Don’t Be Offended If… .......................................................................................15 The Sailing School Scene....................................................................................17

The Boats We Love to Sail...................................................................................20

Ten Sailing-Crazy Spots.......................................................................................23

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Gybe Ho Is Not an Insult: 22 Terms All Sailors Know


f you’ve ever heard a sailor joke about do-hickeys or thingamabobs, you know that sailing has a unique language, confusing even to the saltiest among us. Even longtime sailors disagree about the meanings of certain terms. We all have sailing dictionaries on our shelves, and we look up the Old English origins of words to resolve disputes among crew. Learning the complex language is an ongoing process, and believe it or not, it’s fun. You don’t have to be a linguist to speak the language. Start with the basics:


when you go into the cabin, it’s never “downstairs.” It’s always down below.


the pole hanging horizontally above the cockpit that could boom into your head if you’re not careful.


the front end of the boat or as sailors refer to it with a grin, “the pointy end.”


classic ones are shaped like anvils, but there are more modern versions with pinching teeth for securing lines on deck and on the dock.


the area with seats near the steering area or helm.

Come   about:

to turn the bow of the boat through the wind. The skipper will say, “Ready about!” The crew responds, “Ready,” and they keep their heads down to avoid the boom. The skipper says, “Helms-alee” or “Hardalee” and turns.


anywhere you can walk around on the exterior of the boat.


sometimes spelled jibing (never jiving). This is when the boat turns with the wind at your back. The skipper says, “Prepare to gybe!” The crew says, “Ready,” and stays low to avoid the fast-moving boom. The skipper says, “Gybe ho” and turns.

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the boat heels or leans at an angle while sailing. It does not keel over as one might after too much rum.


where the skipper steers with a wheel or a sticklike tiller.


the smaller triangular sail attached at the bow.


the heavy fixed fin on the bottom of the boat. (see heel)


a rope on a boat is always called a line or a sheet. (see sheet)

Photo by Carrie Gentile


the big sail attached to the mast.


the vertical pole on deck or “the stick.”


a personal floatation device or lifejacket. If someone asks you to wear one, don’t be offended. Lifejackets are not as goofy looking as they used to be.



the left side of the boat facing forward. Port and left are both four-letter words. lines attached to the sails to control them. Crew members help with sheets.


a parachute-like, triangular sail attached at the bow and used to propel a sailboat with the wind behind it. Sometimes called the kite or chute.


the right side of the boat facing forward.


the back end of the boat, opposite the pointy end.


spherical metal hardware—beer- or paint-can sized—on either side of the cockpit where sheets are wrapped clockwise to crank sails in and out.

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From Bike to Boat: Shifting Your Gear


f you were to show up at a sailing outfitter in jeans, a T-shirt, and flip flops and gear up appropriately for a 60-degree spring sailing day on the Bay, you could easily spend $800 or more in a half an hour. If you knew you’d be sailing in that

gear regularly for the next decade, it would be a terrific investment. If you’re not sure about how often you’ll sail or if you’ll even like it, it would be pure craziness. Most sailors we’ve encountered over the years have other outdoor passions: skiing, cycling,



ike runners, many sailors like to have a visor to protect their eyes and face from sun and rain. A safe bet is an old-fashioned baseball cap. A hat strap with a collar clip is helpful, as more “man overboard” drills are done for runaway hats than for men. Nothing says “newbie” quite like a bad sunburn. Sunblock is a must, even when it’s cloudy. Skiers, snowboarders, waterskiers, paddlers, and surfers know that snow and water reflection make the sun twice as powerful. Effective, non-greasy, high-protection sunblock is available at ordinary drug stores. We recommend full head to toe coverage at all times.

kayaking, wake-boarding, running, white-water rafting, and hiking. All of those sports involve gear much like sailing gear. Before you go out and make any investment in new gear, check your closet and assess what you already have to cover you from head to toe.



s in any outdoor sport usually performed in temperatures between 50 and 100 degrees, high tech layers are the answer. A T-shirt, long-sleeved shirt, fleece vest, fleece pull-over, and nylon shorts/pants such as used for hiking and camping would almost complete your sailing gear kit. The outer layer or foul weather gear for sailing isn’t unlike hiking outerwear, except that the retro cheapie poncho, which might be useful and funny on a rainy hike, would be a nuisance in the wind. Make sure you find waterproof outer tops and bottoms that will not flap in the wind, and always assume it will rain. Rain usually brings wind, and

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wind is a good thing—a wet rear end is not. A cold and soggy behind could ruin an otherwise terrific sailing day. You may already have a functional Gortex shell, but do find yourself some waterproof bottoms as well.

You can buy reasonable, effective foul weather gear for $250 new. If you find a crew to sail with, it’s a guarantee they’ll each have some surplus gear to lend or donate. When it comes to lifejackets, your crew will have one on board for you, but you might want to invest in a more stylish one; lightweight and attractive lifejackets really do exist! The vest styles can be great for keeping you warm as well as safe.



lipping on a wet deck, stubbing your toe on metal hardware, or scuffing up the deck of someone else’s boat are the considerations when you choose sailing footwear. Flip-flops and dark-soled running or hiking shoes make lousy sailing shoes. Chuck Taylor high tops, white-soled tennis shoes, Keens, Tevas, and “old school” Topsiders make good non-scuffing sailing ailing gloves are reasonably priced and an shoes. High tech wicking socks are excellent investment for any new sailor. the best.



Necklaces, dangling earrings, and precious gems can make for difficult or dangerous sailing wear. Leave them in your jewelry box at home. Buy Croakies to keep your expensive sunglasses from going “in the drink.” s t a r t s a i l i n g n o w . c o m 11

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Connecting to Sailing... for Free


hen you don’t live on the water, it’s hard to imagine that there are sailboats on the Chesapeake Bay every day of the week during sailing season, which runs from April through Halloween for most sailors. A great way to start sailing is to get into the mood by watching and making your way to places (some virtual!) where you might meet a few sailors to chat with. From north of Baltimore to Norfolk, there are weeknight races, many of them visible from land for spectators. After work in Annapolis, it’s a tradition for spectators to line the seawall of the U.S. Naval Academy and the Eastport Bridge (right before sunset)

Photo courtesy of the Downtown Sailing Center



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where as many as 130 boats of various sizes cross the finish line of Annapolis Yacht Club’s Wednesday Night Races, which take place every Wednesday from May through September. If seeing more than100 sailboats sail by at sunset doesn’t make you want to get out on the water, you might want to choose another hobby. In every sailing town, there is at least one sailing pub. If pubs suit your fancy, ask a local where “the” sailing pub is; you’ll find it. After sunset on racing night, you will find some sailors who want to talk about sailing. You might also find a few who regularly look for crew. The SpinSheet Club Directory at has 170 listings, and those are active clubs that have contacted us—there are more. There are clubs for cruising sailors, racing sailors, small boat sailors, beginners, single sailors, and others. Contacting a few clubs will lead to a few invitations to new member parties and crab feasts. Before you know it, you will be invited to sail and join the club. also hosts online Crew Listings, where new sailors can register. Interested crew sign on by plugging in their experience (if any) and descriptions of the type of sailing they are interested in doing—casual daysailing, weekend cruising, or big and small boat racing. Hundreds of skippers and crew of all levels have found crew and boats to sail on through this effective, popular, free service. Registered new sailors are all welcome to attend SpinSheet’s “real time” crew listing parties in Annapolis and Hampton in April each year to meet sailors of all levels, listen to live music, and drink free rum, beer, and soft drinks. A free Start Sailing Now panel discussion and Q&A for beginners starts an hour before the Annapolis party, and then it’s time to mingle. Once you have an invitation to go sailing with a skipper, make sure to offer to bring lunch or snacks. Wear nonscuffing shoes (see p. 11). Be a courteous guest. Listen more than you talk. Enjoy yourself. And remember, the skipper who invited you needs crew. One good sailing day leads to many more invitations!

Don’t Be Offended If...

A skipper asks you to bring lunch. Fuel is expensive, as is boat maintenance. Just like bringing an offering to a dinner party host, it is standard for crew to pitch in for snacks or beverages. Cans and plastic bottles are always better than glass on boats.

A skipper asks you to wear a lifejacket. This doesn’t mean he or she questions your swimming abilities. Trust your skipper’s hunches. Lifejackets aren’t as silly looking as they used to be, and the vest styles can keep you warm on rough days.

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Don’t Be Offended If...

A skipper asks you to be quiet. Leaving and returning to a dock and certain on-the-water maneuvers require concentration and can be stressful. A quiet crew, who are ready to listen and jump into action, keep the tension level down on a boat. Crew members with open ears, open eyes, and open minds who keep their mouths shut get many more sailing offers than chatty ones.

• A skipper asks you to go down

below for awhile. Especially during a gybe (see page 5) or during rough weather, it is smart to have newcomers go down below rather than be on deck unsure of what to do. It is for your safety and that of the other crew members. Even if the skipper doesn’t have time to explain why, just listen, and trust his or her hunches.



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A skipper asks you to wear different shoes. Dark-soled shoes have always been a no-no on boats. Certain shoes such as Keens have dark, but non-scuffing soles (see page 11).

Be Offended If...

A skipper yells repeatedly at his or her crew. Despite the stereotype, this is not cool or acceptable behavior. It is often the sign of a skipper who lacks confidence, skill, and manners. Reconsider his or her next sailing offer for your own safety and sanity.

• Α skipper is offensive.

Unfortunately, such people show up on land and in boats. We’ve told you a few times here to trust your skipper’s hunches. Make sure to trust your own, too. If you have found your skipper through SpinSheet’s online Crew Listings, and you find him or her to be offensive or dangerous as a skipper, please report it to our offices at We will be happy to rescind his or her invitation to the dance.

The Sailing School Scene


hat can be more difficult than finding a sailing school is choosing which one suits you among the multiple options on the Chesapeake Bay. SpinSheet features an Adult Sailing School section every April to help new sailors navigate the many choices. It’s a great starting point for contacts, and we’re happy to send you a copy. As a new sailor, the first question you should ask yourself is what kind of sailing you want to do. Do you want to go daysailing or cruising overnight on a bigger boat? Do you want to race or relax with family? Would you like to learn with your spouse or on your own? Once you have a vision for what you hope to learn and what

learning environment sounds appealing, start calling and gathering information. Here is a sampling of the personalities you’ll find at sailing schools on the Chesapeake Bay…

Winds Blowin’ in Baltimore


teve Maddox and his wife learned to sail with nothing but an instructional video, a couple of books, and a 14-foot sailboat they got for free. “Although not the best method to s t a r t s a i l i n g n o w . c o m 17

Practice in Annapolis learn,” he admits, “the sailing fever rooted aised an “army brat,” Dan Wittig itself deeply in us. We worked to get as much started to sail at the age of five. He sailing experience as possible.” By fixing up started sailboat racing in high school out old boats and sailing them, the couple has of Annapolis shared their passion with family, friends, and Yacht Club and beyond. continued to Five years ago, this active sailor joined race through the Baltimore County Sailing Center as college, the summer camp director, a position that becoming grew yearly until he became the full-time captain of the executive director. Maddox recently became University the operations director for Baltimore’s of Maryland Downtown Sailing Center (DSC). He says, sailing team. “Although keeping the fleet at DSC is Around the same time, he started to teach my primary focus, sailor education is my sailing at J/World Annapolis, where he is passion. I believe quality education is the key now co-director. Although its tagline is to making sailing fun, and making sailing fun “the performance sailing school,” J/World is an integral part of quality education.” teaches beginners and cruisers as well as Photo courtesy of Steve Maddox “performance” racing skills.


You should be sailing!

Learn to sail big boats or small at our gorgeous location at the Tides Inn on the Rappahannock River. Friendly, safe, professional instruction on weekdays or weekends. US Sailing certification.


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Come catch the wind in our sailing programs: Learn-to-Sail, Advanced, Racing Team, and Private Lessons for Kids and Adults In affiliation with the Rock Hall Yacht Club Chuck Parry, Director 410-778-4560

Dan suggests to beginner sailors to “Make a plan for what your goals are in sailing—for instruction, practice, or a combination of both.” Photo courtesy of J/World Annapolis

Sailin’ in Solomons


isa and Andy Batchelor, co-owners and instructors for Sail Solomons, began sailing many years before they ever met each other. Each learned to sail in small boats or dinghies and progressed to larger boats and a variety of “do-it-yourself” and formal courses of

instruction. “We’ve made many of our lifechanging decisions while sailing—it clears your head and helps you focus on what’s really important in life,” remarks Andy. When the Batchelors founded Sail Solomons, they focused on accommodating all learning styles, age groups, and genders. The couple says, “We want to share our passion for sailing with people from all walks of life; sailing really can be for everyone.” The Batchelors recommend to new sailors to find schools that recognize their learning styles, help them achieve their individual goals, and connect them with other sailors. “We often tell our students to relax and stop over-analyzing. Instead, slow down and feel the wind and the boat. It helps you connect your actions with the boat’s reactions, and puts you in control.” Photo courtesy of Sail Solomons

Southern Bay Breezes


fter Arabella Denvir and her husband Philip had started the Malta Sailing School in the Mediterranean and had run it for five years, they moved to Irvington, VA to start the 10-year-old Premier Sailing School out of The Tides Resort. Both natives of Ireland, the Denvirs have a wide range of sailing and teaching experience from instructing beginners to racers. Premier is one of the few, if not the only school on the Bay to teach adult classes on both small and big boats, as well as being one of the few located in a resort.

Arabella recommends to new sailors who have taken lessons, “Keep practicing sailing so that you don’t forget. We offer skippered charters for sailors so that they can get back out there and brush up on their skills.” Photo courtesy of Premier Sailing School Three helpful links with lists of sailing schools: American Sailing Association: U.S. Sailing: Discover Sailing:

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The Boats We Love To Sail by Dave Gendell with reporting from Marine Surveyor Jack Hornor



daysailor is a fun boat to sail alone or with just a few people. Easy to trailer or strap on the roof of your car, daysailng is a great place to learn the sport, build your skills, become competitive (if you choose to), and meet other sailors. A Few Popular Daysailors on the Bay: Byte: One sail, one sailor. Good for kids and small sailors. Laser: One sail and one (bigger) sailor. Popular worldwide, sailed in the Olympics. Vanguard 15: Double-handed performance dinghy. Flying Scot: 19-footer can be used as a family boat, a racer, and a fun daysailor.




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Day Racer

ay racers, designed for competition, can be typically towed behind SUVs or trucks. Such boats may have small cabins, but they lack substantial overnight amenities. Although day racing can be a physical “ride,” it’s often drier sailing than on smaller daysailors. A Few Day Racer Designs: Laser SB3:A new 20-footer from Europe. Fast and stable. J/22: Typically sailed by three or four people. A popular Bay-racing keelboat. Colgate 26: Used for instruction at the U.S. Naval Academy and dozens of other venues. J/80: An open and sleek design, which is a popular racing and instructional boat.

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Accomplished sailors start here.

Racer/Cruiser Racer/cruisers are versatile boats, which can be used for racing, cruising, or daysailing. These boats have overnight accommodations and typically appeal to a wide spectrum of Bay sailors. Plenty of good used boats on the market. Some Racer-Cruisers Chesapeake Sailors Love: Catalina 27: A very popular first-timebuyer boat, moderately sized and priced. Pearson 30: A versatile family cruiser and racer with a roomy interior. Tartan 34: Very popular for its sound construction, moderate price, and pretty look. Beneteau 36.7: Modern racer/cruiser, sleek and stylish, with plenty of room below.

Racer/cruiser designs like the Tartan 34 are popular on the Bay for families, daysailors, and racers alike.

More than 80 used boat reviews and hundreds of used boats for sale are posted at Other popular sources of information about used boats are and

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A J/80 is a popular day racer and instructional boat on the Chesapeake Bay.

Sailed worldwide and all over the Bay, Lasers are good daysailors for learning and competing.

“One of the World’s Top Sailing Bars” Week Days Breakfast, Coffee 7:30 am WeekenD Brunch–Best in town 8 am MOnDay Crisfield Crab Cake Special 2 broiled crab cakes, fries, slaw: $14.95 TuesDay Famous Meat Loaf Special 1/2 price Bottles of Wine on wine list WeDnesDay AYC Wed Night Race Films Fourth St & Severn Ave Eastport–Annapolis 410.216.6206


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Ten Sailing-Crazy Spots 1




Havre de Grace, MD: City at the top of the Bay has a unique and fun vibe with sometimes challenging sailing conditions in the stretch where the Susquehanna River empties into the Chesapeake. Middle River: The creeks and coves are thick with sailboat-packed marinas. Close to the big city and I-95 and featuring a friendly spirit and a real dedication to the sport of sailing.


Alexandria: The Washington Sailing Marina, on the Potomac River in the shadow of Reagan National Airport, offers competitive and recreational sailing options within sight of DC’s monuments. Solomons: Home to a large contingent of sailors associated with the massive military presence along the Patuxent River and an increasing number of folks who have fled the heat of DC for the friendly sailing community in Southern Maryland.

Baltimore: The waterfront renaissance now comes with sailing options in and 9 Deltaville: The Richmond crowd near the Inner Harbor. A fun destination for beelines here for weekend sailing, and it cruisers as well. is increasingly a year-round home base for many sailors. Wonderful access to 4 Rock Hall: Popular with the many beautiful stretches of the Bay and its Pennsylvania and Delaware crowds and a tributaries. fun destination for all sailors. Annapolis: America’s Sailing Capital is 10 Hampton, VA: Sailing center of Tidewater Virginia. Southern hospitality centrally located and has something for everyone. Has it all, including big crowds in meets Chesapeake Country. the summer. October’s U.S. Sailboat Show is a must-see. Other great sailing centers on the Bay: 6 St. Michaels: A very popular overnight Chestertown, MD; Galesville, MD; Oxford, destination with an active and growing MD; Cambridge, MD; Irvington, VA; sailing scene. Home to the Chesapeake Bay Cape Charles, VA. Maritime Museum.


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Click here to start

601 Sixth Street Annapolis, MD 21403 410.236.8848


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Start Sailing Now  
Start Sailing Now  

A recource for new/begginer sailors