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.

  • Power.

    Flybridge or Daybridge, Downeast or Sportfish, speed or cruising, back channels or open waters—in a powerboat you determine what joys await on the water.

  • Sail.

    The wind in your hair, sun on your face. Sometimes living the cliche isn’t a bad thing.

  • Featured Listing- 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 $32,500

SAILYARD TEAM

When you buy a boat with Annapolis Sailyard, it’s all hands on deck.

Cary Lukens, Owner

  • 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.

  • Cary’s most memorable boat experience was sailing off the Pacific coast of Mexico with clients and seeing the Lost Soul.

  • “In another life I’m pretty sure I was a pirate with a soft streak.”

  • 443.995.5553

    cary@sailyard.com

  • 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.

  • “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.”

  • 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.”

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Arn Reistad, Jr.

Arne Reistad, III

  • 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.

  • 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!

  • 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.

  • 717-250-2915 (mobile)

    arne@sailyard.com

Rich Kahn

  • 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.

  • 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.

  • 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).

  • 410-980-5096 (mobile)

    rich@sailyard.com

  • 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.

  • Shortly after high school, John joined the US Army and served for a couple decades, in Iraq, Texas, and California.

  • John is currently living the dream aboard his boat on the Chesapeake Bay, while helping others realize their own boating dreams.

  • Cell Phone: (209) 297-1314

    email: john@sailyard.com

John Guidotti

Randy Reese

  •  Although my job in the Navy allowed me to live next to the water for over 20 years, I got started with sailing within the last decade while stationed in North Carolina. I was hooked after my first class on New River and have been pursuing it ever since. Since leaving the Navy recently I've focused on my sailing interests, becoming a certified sailing instructor and earning my USCG OUPV.

  • Randy brings work experience in neuroscience, and he is thoughtful to say the least. He also brings his own experience buying, selling, and owning several boats of his own.

  • I've started as a yacht sales professional because I enjoy being around boats, and especially like being able to help people find the boat that is going to give them satisfaction and enjoyment.

  • 206-856-9020 (mobile)

    randy@sailyard.com

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 manufactures. Because we are experts in all things nautical, you can rest assured you will get the boat that’s right for you.

326 First Street, Annapolis, MD 21403

Hours: by appointment, widely available

Phone: 410.268.4100

Come see us in our beautiful location in Yacht Haven in Eastport/Annapolis. Walk-ins are always welcome!