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    Sailing Associates

    4.8 (4 reviews)

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    Chestertown Marina

    Chestertown Marina

    3.4(7 reviews)
    14.5 mi

    Well worth the trip up the beautiful Chester River, especially for one of the Chester's many…read moreregattas and for Chestertown's many annual festivals. Enjoy comfortable new Marina infrastructure and new restaurant (98Cannon) on site! Walkable to natural foods grocery store, liquor store, many restaurants, bars, coffee shops, bread bakery, Saturday Farmer's Market at Fountain Park, visitor's center, Realtors (visit me: Beth O at Coldwell Banker on Cross St!), gift shops, galleries, and apparel. Dogs are welcome! Wilmer Park is adjacent to the marina with a walking trail and a rails to trails bike/walking trail you can follow to Washington College where many musical, educational, and cultural events are held that are open to the public. The entire marina property was raised to handle higher water and sinking ground, the waterways were dredged to keep the tall ships coming for Downrigging weekend in Fall and Tea Party in Spring. The Schooner Sultana is a permanent resident here! The new marina facilities include: beautiful Ipe floating piers, brand new conditioned bathrooms, shower facilities, laundry, and a lovely marina office with a comfy lounge area and water view deck. There's a handicap accessible boat ramp, gas & diesel, pump-out, travel-lift, and transient slips available for all sizes. Of course there's also a friendly staff. Samantha and Chris are great to work with! Our boat (DOGONIT) is resident here & we love seeing all the new visitors that are coming in under sail and power from Annapolis and beyond. The new Marina does not have a mechanic on staff, but should you find yourself in need, you can call good local mechanics who will help you on site.

    Bring your life vest with you when you get off your boat because the dock is sinking!…read more At high tide the water covered the dock in several places and was halfway up my calf when I was walking to shore. I also took a bad fall at low tide because the boards that submerge are so moss covered that it's like walking on ice. The boating amenities are ok, but coming back to the boat at high tide and finding our shore line hanging in the water because the dock was submerged was very disconcerting.

    Rudy Marine - Jeanneau NC 795 Series 2 - Coast Guard documentable boat!

    Rudy Marine

    2.7(29 reviews)
    66.4 mi

    I had thought that buying a new boat is never expected to be a completely hassle free, nor is it…read morealways easy to work with the sales team to get what you want. Rudy Marine proved me wrong. From the moment I first contacted them, they have been responsive, helpful, courteous, patient, and professional. They have provided the best customer experience I have ever had when dealing with anyone in the boat sales industry. in addition to the amazing customer service, their pricing is very competitive. The quality of service matters a lot to me, and between their top quality service and their prices - one cannot go wrong by choosing Rudy Marine!

    Stopped in yesterday to purchase a trolling motor for my boat, The young lady behind the glass wall…read morewas as pleasant as you could ask for, She said she would have a trolling motor salesman right out to help me, Then this salesman sitting at his desk ask me if I was planning to install the unit myself,, Yes I said, ,,,He then told me he { Would not sell me a trolling motor} that THEY were known for their professional installation , insinuating that I was not capable in installing the unit, I hold a Master License in HVAC, Retired from Lockheed Martin as a Defense Contractor, Now service, Build and sell Golf Carts, I think Im more than capable of installation of a trolling motor, I walked out with a pocket full of cash knowing I will never step foot in that establishment again,,,,You missed out on a 4k sales yesterday,,,,

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    Rudy Marine
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    NauticStar Deck Boats

    Sailing Associates - boating - Updated May 2026

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