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Great places to cruise on the Chesapeake Bay with kids

Nothing beats sharing the fun of sailing with your kids, especially on the Chesapeake Bay. Depending on where you start from, there are some great kid-friendly spots on the Bay, which can be reached in a single day sail. Here are a few of our suggestions.

  1. Baltimore. Compared to some other city harbors, Baltimore is remarkably accessible to cruising boats. There are many marinas to choose from along the shore if a pool and shore facilities are required. The kids will love attractions such as the National Aquarium, the Children’s Museum, and historic ships such as the USS Constellation, the USS Torsk Submarine, and the Lightship Chesapeake. It is easy to walk to everything you would want to do in a day. Find more suggestions on things to do in Baltimore here.
  2. St. Michaels. St. Michaels is a popular cruising destination for families. The quaint town on the Eastern shore of Maryland has both marinas and anchorages, all close to town. For activities, we suggest the Chesapeake Bay Maritime Museum or the Phillips Wharf Environmental Center. The kids may be just as satisfied with an ice cream treat from one of the many shops in town. Find more ideas on what to do in St. Michaels here.
  3. Oxford. Oxford is also on Maryland’s Eastern shore on the Tred Avon River. It is an old town with a rich maritime history and a much more quiet scene than some other cruising destinations. There are a few shops and restaurants, and plenty of places to spend the night in a slip or anchor, but the fun of coming here with your kids will really be in making your own fun. We suggest taking a dinghy to one of the beaches in town or walking up to a nearby park.
  4. Annapolis. Historic Annapolis is a busy destination with plenty of options for places to stay overnight. Hanging out with the kids at City Dock counts as an activity here. There is always a vibrant scene to take in, and plenty of kid-friendly shops and restaurants right near the water. There is no shortage of scoop shops here. Choose a park to play in or just walk around the Naval Academy.

Get started with planning your next family sailing vacation by contacting one of our experienced staff members today.

USS Torsk

Submarine USS Torsk tied up in Baltimore’s Inner Harbor