SAILYARD LEGACY
We're not just a yacht brokerage—we’re a legacy.
Buying or selling a boat is a commitment to new beginnings.It is a decision to invest in adventure and freedom as you set sail for highest potential.
Each boat and every person has a unique story and purpose. We will meet you where you are and deliver you to your desired destination.
When you embark upon a journey with Annapolis Sailyard at the helm, you can surrender to the process knowing that we value you, the customer, and are fully committed to service, relationship, and sustainability.
Annapolis Sailyard is the oldest yacht brokerage in the Maritime Republic of Eastport in Annapolis, Maryland.
For nearly five decades we have been providing high-quality service and expertise in yacht purchase and sales for both sailboats and power boats. We have long term working relationships with multiple highly distinctive yacht manufacturers.
At the Sailyard, we are experienced sailors who have walked the weathered deck and made passages of our own.
SAILYARD INVENTORY
Whether you want to power up or set sail, we can align you with the perfect boat for your lifestyle. Scroll and click through some of our compelling options below!
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Beautiful MJM 35Z
HUCKLEBERRY is a low hours, well equipped 2018 MJM 35Z. Maintained at Gibson Island Boat Works, ready for next owner! Make an appointment NOW!
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1984 Ta Shing Panda 38 "Blue Blaze"
Cruise-ready and well cared for, with an unmistakable pedigree, “Blue Blaze” is the exceptional choice to make ocean passages capably and then turn heads in any harbor. Exquisite work from Ta Shing, she holds up well and will make someone and lucky new owner. $89,500
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Camano Gnome 31!
With over 200 hulls in service, the Camano 31 packs a surprising amount of space and liveability into a pocket trawler platform. Well built and designed in Delta, BC, Canada, these seaworthy and strong boats are perfect for a coiuple cruising the ICW, Great Loop, or along the coast.
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Alerion 33 Express (sistership photo)
“It’s all about sailing” an Alerion 33. Elegantly appointed, this easy performing sailboat will have you enjoying your time on the Bay and beyond. Lovingly cared for on Gibson Island, MD, she is offered for prospective new owners. Click below for details.
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Najad Aphrodite 42
This is a PRISTINE, Swedish built, comfortable and stable blue water cruiser. She sails very well and looks even better. We have not seen a boat kept up better nor longer lasting than this beauty. She is fully equipped to cruise and ready for a lucky new owner.
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Mast and Mallet 43 "Sawdust"
This is a renowned vessel with a bona fide local pedigree and history of caring ownership. She is an elegant, fun vessel that has been cared for from day one. Built for a boating journalist who completed the Great Loop with her, she is a famous cover girl, pretty, and one of a kind!
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NEW Helmsman Trawlers!
Pictured is the 38 Sedan, in the middle of the range of these solid pilothouse and sedan trawler models, ranging from 31 to 46 feet. Quality craftsmanship, smart design and elegant comfort are among the hallmarks of the Helmsman tradition.
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2023 Helmsman 43 Pilothouse in Annapolis!
Here’s a chance to get IMMEDIATE delivery on a like new boat. The owners have had their adventure and reluctantly offer this fully outfitted, ready to cruise luxury trawler. She has all the bells and whistles, impeccable craftsmanship, and well designed layout and systems. Click on the FULL SPECS and then contact us or Waterline Boats to set up a showing.
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Taswell 44 AS
RARE OPPORTUNITY for this Taswell 44 AS- beautiful, capable cruiser, and very well kept! Ready for you now!
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Baba 30
Start your cruise in the EAST! This venerable Ta Shing built small cruiser has been updated with recent decks and engine (both replaced 2011). A beautiful world cruiser, ready for your adventure at only $39,900
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2001 Tad Roberts 38 classic design
Griselda is a classic, well built, comfortable and elegant cruiser. Lift kept and well loved, she is available to be seen any time in Pasadena, MD.
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Bristol 35.5- La Primera
Great updated example from this venerable New England builder. This stick built boat has a NEW 2017 Yanmar diesel with only 60 hours!
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School's Out! 1997 Catalina 30- pretty
This is one of the nicest Catalina 30’s out there, with all the refinements of 25 years of model production. Reliable diesel, canvas, step through transom, electronics, air conditioning, nice upholstery, lighter modern interior wood finish- your chance to cruise comfortably at the top of the fleet.
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Chapparral 29- great starter!
A well built, reliable boat to get you and your loved ones out on the water, “Just Peachy” features recently rebuilt engines, drives, and upgraded props. Start having fun NOW!
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Crownline 270cr
CLEAN, WELL EQUIPPED, NEVER BOTTOM PAINTED, LIFT KEPT. This is a very nicely preserved cruiser with a 2018 REPOWER!
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1986 Sabre 30- clean!
Sabre 30 is an "excellent pocket cruiser," known for its quality, handcrafted interior joinery, and spacious feel that makes it seem larger than it is. It's a comfortable and capable boat for a young family or a single-hander, with a well-appointed galley and a comfortable sleeping arrangement. Roller furling, stack pack, dodger and bimini.
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Morgan 38
The Morgan 38 is a venerable cruiser. This one has been lovingly cared for and updated. She is ready for you to step aboard and enjoy! New Beta Marine 50HP diesel, with only 126 hours, newer sails and rigging (including standing rigging), new portlights, and so much more!
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Dickerson 37
If you are looking for a well found, cruising boat in this size don’t miss out on this vessel. Extremely well maintained and updated, from rigging, to electronics, stack pack, dinghy and outboard, Morning Light is ready to cruise and bears an unmistakeable pedigree!
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Ericson 36
Bulletproof Atomic 4 engine, classic Ericson design and sail characteristics. A pretty, classic, sailboat!
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Panda 38, "Blue Blaze"
Begin your cruise in sunny Bonaire! Easy to get there to see the boat and make it happen. Well maintained, cruise ready, excellent quality and renowned pedigree. “Blue Blaze” is hull number 17 of the 29 Panda 38s built by the famed Ta Shing yard. She's been exceptionally maintained and is ready to go. Pandas are known to be exceptional blue water boats, built to the highest standard.
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Beneteau 41
This is a great sailing AND cruising boat with lots of room and comfort for the money. Seriously for sale in Annapolis!
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1987 Tashiba 36, $125k
ONE-OF-A-KIND opportunity to own a classic Ta Shing Tashiba 36 that is restored like new, at a fraction of replacement value. BEAUTIFUL, capable cruiser!
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1998 Legacy 40
Meticulously kept Legacy 40, classic downeast design with modern performance. Completely rebuilt Cummins engine, beautiful looks and lines, clean and elegant interior, fully equipped. Come and see!
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Allied Princess Ketch
CLASSIC cruising sailboat. Gabriel is a joy to sail and cruise aboard. Waiting for you at Kent Island Yacht Club. Exceptional value $37,500
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Carver 37 Aft Cabin
Liveability, space and comfort, as well as privacy, are the hallmarks of the bright interior on this cruiser. Comfortable flybridge, twin engine maneuverability, and walk around side decks make her easy at the dock. And her aft deck is a versatile perch.
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Marinette 32
VERY well kept cruiser on a lift, with clean engines, comfortable interior, newer canvas, and more. Lots to offer!
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J-boats J35
This fine racing vessel is currently owned by a veterans organization named Valhalla sailing. This boat is being sold to help the organization go forward and continue with the goal of helping veterans. It is a great opportunity to help out the community and get a great racing boat.
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2006 Chaparral 330 Signature!
Vessel has been constantly updated and all systems are in great shape. Highlights include rebuilt engines upgraded to 8.1 mercruisers, new touchscreen electronics by Raymarine, rebuilt through hulls and much more. Call Arne!
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Tayana 42!
Classic offshore Tayana design and build, beautiful woodwork, teak decks, updated chainplates and standing rigging (2017). A true bluewater cruiser.
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Southern Cross
A REAL bluewater cruiser, solidly constructed by CE Ryder Corp. of Bristol, Rhode Island, and well-finished, with versatile sail plan, modest draft, and 2001 Yanmar 3GM30F reliability.
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Albin 28
Very popular and versatile cruiser from a quality builder. Preferred Yanmar engine, great boat for short cruises, day cruising, picnics, swimming and fishing!
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Catalina 36 with lots to offer!
Roomy, comfortable, budget crusier offering easy maintenance, dingy and outboard, reliable diesel engine, dodger and bimini, solar, chatplotter, radar, and autopilot, recent standing rigging, windlass and Dutchman furling system make this a capable and versatile cruiser.
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Crownline Express Cruiser
Beautiful 2012 Crownline C260 CR, 5.7 Engine with Bravo 3 Outdrive 199 hours. Proactively maintained and well kept.
SAILYARD TEAM
When you buy a boat with Annapolis Sailyard, it’s all hands on deck.
Cary Lukens, Owner
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Cary is a native Annapolitan and accomplished sailor with a boatload of nautical experiences. His deep commitment to service buoys his intention to align the unique stories of his clients with their personal goals.
Cary’s best life includes spending lots of time with his daughters. So, when not on or around boats you’ll find him chilling with his daughters or practicing yoga -- and quite possibly eating carrots and listening to the Grateful Dead.
In his life before Annapolis Sailyard, Cary was an adolescent and family counselor at a state-run psychiatric hospital.
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Cary’s most memorable boat experience was sailing off the Pacific coast of Mexico with clients and seeing the Lost Soul.
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“In another life I’m pretty sure I was a pirate with a soft streak.”
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443.995.5553
cary@sailyard.com
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Arn, aka the Old Guy, has been at Sailyard since 1998, and when you sit down with him, you encounter a lifelong boater and natural storyteller who enjoys sharing his vast knowledge while making a new friend.
Before Sailyard, Arn was an Engineer in the Navy, a Hershey Executive, co-creator and patent holder of bicycle braking systems, and an Eagle Scout and Adult Scout Leader who helped pioneer a new innovative Boy Scout Leadership program.
When not on or around boats you can find Arn fly fishing for trout, trying new foods, or listening to the Big Bands of the 30’s and 40’s. And he never boards his boat without his knife, reading material, and sunglasses.
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“My most notable sailing experience was being in the middle of the Atlantic on a bright starry night and feeling I could scoop up a thousand stars in my hand.”
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Arn’s favorite quote is from the movie, Harvey, when Jimmy Stewart says, “Years ago my mother used to say to me, she'd say, ‘In this world, Elwood, you must be,’ she always called me Elwood, ‘you must be, oh so smart, or oh so pleasant.’”
“Well, for years I was smart. I recommend pleasant.”
Arn Reistad, Jr.
Arne Reistad III, Vice President
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A lifelong boater and liveaboard, Arne is eager to share his expertise and energy with you. When he is not out on boats, Arne travels and shares videos with his followers.
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While crossing the street at the Miami Boat Show, Arne encountered a cute little dog “directing traffic.” After he helped her to the sidewalk, Arne met the owner who confessed that he could not look after her, and offered Arne the dog. A few days and a one-way rental car later, “Chi Chi” was getting used to the weather in Annapolis, where she would become the Sailyard mascot!
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Whether my clients are buying or selling a sailboat or powerboat, my aim is to provide good service. I love helping my clients and sharing about the enjoyment of boating.
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717-250-2915 (mobile)
arne@sailyard.com
Rich Kahn
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Rich has been sailing and selling boats since the 1980’s. He is a former Baba 35 owner and has unmatched experience with Ta Shing boats. Rich is also a native “Baltimoron” and a former probation officer- so he’ll make sure you are on track. But the best part about Rich is his lovely wife Elaine.
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Rich and Elaine love boating on their current yacht, a Mast & Mallet Thomas Point 43. That boat, and their prior boat, a Baba 35, have both been up and down the coast and out to the islands; and so have Rich and Elaine.
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Rich and Elaine live two blocks from Annapolis Sailyard and are active in the Maritime Republic of Eastport. Knowing Rich is like knowing a whole community! Rich also loves sports and is an avid follower of University of Maryland Basketball, The Orioles, and The Ravens (but Yankee and Steeler fans still welcome here).
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410-980-5096 (mobile)
rich@sailyard.com
Elizabeth Fortunato
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I spent my youth on and in the water. My grandparents were avid sailors and split their time between the Abaco Islands, Bahamas, and Annapolis, Maryland. I got to experience some of their cruising life on the Chesapeake Bay and in the Bahamas aboard their 42-foot center cockpit motorsailer.
After 33 years in the Information Technology (IT) field, I retired in 2023. For the past four years, my husband and I have owned a 42-foot Marine Trader. I do most of the captaining, and he is ‘Scotty’ in the engine room. We spend most of our time cruising the beautiful Chesapeake Bay and its tributaries.
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I decided to take on yacht sales as my second career because I love the water and cruising lifestyle. I am passionate about learning and have fallen in love with the boating community and lifestyle. There is always a new adventure around the corner and some new challenge to face. The more I learn about cruising, the more I discover. I also love sharing my passion with others and can talk boats (and dogs) all day. So why not combine the two?
What is my next big adventure? Follow me on social media to find out, and hopefully, I can help you sail or motor away on yours.
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We are pleased and excited to have Elizabeth bring her experience, talents and expertise to bear in serving our clients!
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Capt. John grew up fishing and crabbing in Mayo and Edgewater, Maryland, and graduated from South River High School in 1996. After his military service, John found his way back to home waters in 2018 (the bay will always be his home). As a Professional Yacht Broker and licensed Captain, John is always searching for the perfect boat for his customers.
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Shortly after high school, John joined the US Army and served for a couple decades, in Iraq, Texas, and California.
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John is currently living the dream aboard his boat on the Chesapeake Bay, while helping others realize their own boating dreams.
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Cell Phone: (209) 297-1314
email: john@sailyard.com
John Guidotti
SAILYARD STORIES
For more than 40 years we’ve had a positive relationship with the Chesapeake Bay boating community.
Here are some of their stories.
SAILYARD GUIDE
Consider us boat matchmakers.
We have decades of experience with the best cruising boat manufacturers. Because we are experts in wide range, you can rest assured you will get the boat that’s right for you.
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Nordic Tugs
Nordic Tugs are hand crafted to for the cruising lifestyle. Wherever Nordic Tug owners go, they travel in comfort and confidence, knowing their vessel is one of the most seaworthy cruisers on the market today.
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Taswell
Taswell Yachts are high performance cruising yachts crafted in Taiwan by Ta Shing Yacht Building Company. Designer Bill Dixon combined the elegance of wood with the technology of fiberglass then created these vessels with comfortable interiors and suitable for the rough seas.
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Valiant
Designed by Robert Perry and built in America since 1972, these yachts have logged over 3,000,000 offshore miles including circumnavigations and short-handed ocean crossings, more than any other brand of sailboat ever built!
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Camano
These compact and versatile trawlers are designed by Bob Warman and known for their spacious comfort, easy handling, low maintenance and classic look. Take a look at our connection with Helmsman and see if you recognize the Camano in the Helmsman 31!
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Baba
Baba Yachts were designed by Bob Perry and built by Ta Shing from 1977 through 1985. They are sturdy vessels suitable for making long offshore and ocean passages needing only a couple of people to crew the boat.
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Tayana
Tayana Yachts are high quality offshore sailing vessels that are easily handled by a couple, powerful enough to cross oceans, comfortable enough to live aboard, and beautiful enough to bring tears to your eyes.
326 First Street, Annapolis, MD 21403
Hours: by appointment, widely available
Phone: 410.268.4100