1. Chester River Packet Company

    1. Chester River Packet Company

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    Chester River Packet Company

    3.8 (9 reviews)
    Closed 10:00 am - 5:00 pm
    Updated 2 months ago

    Services - Chester River Packet Company

    Boat charters

    Bartending services

    Catering services

    Chester River Packet Company Photos

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    Bob T.

    A pleasant way to spend a Sunday afternoon. We were staying at an Air BnB in Chestertown for the weekend and decided to give this a try. All in all, we are happy we did. The boat was comfortable. There was air conditioning for the enclosed main cabin. It was stressed a bit as people kept opening the door on their way to the two outside decks. Given it was a very hot day, I was surprised it was as cool inside as it was. The two outside decks provided chances to enjoy the ride and a nice breeze. The brunch was better than expected. Whenever smoked salmon is involved I am usually impressed and this was no exception. There was plenty of food to go around (even after I took my turn at the buffet) and lots of variety too. The bar service was outstanding for me and a bit iffy for the missus. They had Fat Tire on draft so I was happy, They were out of bloody mary mix and despite a decent pour, their Vodka Sour seemed a bit light on the alcohol. We're not sure what could have caused that. As a pleasant surprise, at the end of the trip, they handed out some of the best chocolate chip cookies I've ever had. All in all, it was a relaxing trip, a chance to learn a bit about the local geography, and an opportunity to enjoy decent food and beverages in the bargain.

    Have a seat.
    Seth G.

    To end my downrigging weekend experience with one more boat ride. It was 2.5 hour dinner tour and not a 3 hour tour, so no Gilligan Island jokes could be made. The boat is very nice. You can sit inside, on the bow, or on the top deck. Even that it was a cool late October evening I spent most of my on deck. Blankets are available if you need or desired one. Had a slight concern about what was going to be served for dinner, since when the ride was booked online it did not say. Any concerns went overboard when dinner was served. Our meal, as all meals are, was catered by Occasions Catering and they did a fabulous job.

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    Chestertown Marina

    Chestertown Marina

    3.4
    (7 reviews)

    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.

    Chester River Packet Company - boatcharters - Updated July 2026

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