While I am a native New Englander, there is one thing that the Chesapeake Bay does better than the waterways of New England and that is the availability of a plethora of boating destinations. Summer on the bay is one of my family and my favorite times of year and we try to extend the boating season as much as we can. As boaters and parents, it is our responsibility and duty to pass along the passion of boating to our children and the younger generation. Whether this be cruising the bay, fishing, crabbing, sailing, racing or just paddling on a SUP or kayak, we try to showcase to our boys all the fun that can be had on the bay. While boats are fun, we also want to pass on the skills that make boating safe and fun. My boys know that the second we hit the dock, life jackets are on and we need to remember the rules of the boat. Teaching the rules of the road, proper knot tying, boating etiquette and most of all boating safety, falls on us to pass along to keep boating safe and fun. Let’s take a look at some ways we can enjoy the bay. 
My family boats out of the Annapolis area and have kept the boat on both Spa Creek and the South River. The Chesapeake Bay offers countless creeks to cruise or anchor in and each one allows for something a little bit different. If you find yourself leaning towards the weekend raft up scene, you probably want to stock your boat with some water toys to elevate the experience. This is especially key to add a level of fun for the kids that might be aboard. Inflatable docks offer an island oasis for kids to swim to, jump off of, and enjoy some time off the boat. If you have a boat with outboards this is a great way to have a floating swim platform. Raft ups at the start of the summer are the best with everyone crossing their fingers that the jellyfish stay away as long as possible. Once the jellies come in, the swimming doesn’t have to end as there are many nets that can be purchased to create a jelly free swimming oasis. Another must have boating accessory is a 5 gallon bucket. When our kids were young, we would fill it up and add some toys and enjoy the entertainment that followed. What kid doesn’t like to play fetch, tie a fender to a dock line and watch the fun ensue! Rafting up with family and friends will bring memories that last a lifetime.
Summer in Maryland offers countless days to get out on the water with friends and family and the boat is a great mode of transportation to day trip to the Eastern Shore and skip the bridge traffic. A favorite in our house is heading to St. Michaels for the day to enjoy museum time, lunch, and of course ice cream and/or a trip to the candy shop before our departure. Docking at the Chesapeake Bay Maritime Museum is convenient and annual membership provides docking options. Who doesn’t like putting dockage fee towards a good cause? Exploring the museum campus and learning about the history of the Chesapeake Bay enhances any boating experience. Chesapeake Beach is a small town with dockage, water slides, and mini golf within walking distance. There are many more towns all over the bay to explore!
If you are looking for more than just a day trip, the bay also offers hotels, marinas and yacht clubs to visit. Many Chesapeake boaters are lucky enough to have boats that allow for sleeping aboard. If your boat does not have this option, do not worry, the possibilities for land accommodations along the bay are abundant. Since our family cruises the bay in a center console, we plan our overnight trips around places that offer accommodations. The Hyatt in Cambridge has multiple restaurants and several pools, one of which has a water slide that is fun for ‘kids’ of all ages. If you are cruising with a group, Rock Hall is a great place that has plenty of docking for sleep aboards, but also a bed and breakfast for those who need accommodations. The pool, grills, and other marina amenities like free bikes, provide something for everyone and an opportunity to have a group cookout. The Wylder in Tilghman Island is on our list for summer 2024. It offers an on the water crab shack open on the weekends and often have hotel events for guests to partake in. The heated pool also allows for some great destination boating when the Maryland spring comes early, or for the early fall days that feel like a second summer! Of course the bay offers more options farther afield if you are looking for 1-2 nights aways. The Tides Inn in the southern bay has a small town resort feel with a local winery in walking distance.
The best part about traveling to places on the boat, is that the kids get to fish on the way to our destination. One important fishing rule we have had to learn in our house is “don’t let go of your rod.” To avoid a sad fishing day, a rod leash can be purchased to ensure the fishing rod stays on the boat and doesn’t get dropped in the bay out of fishing excitement. As you are cruising the bay, be sure to keep an eye out for cool wildlife sightings. The blue heron spotting are a favorite, but aren’t quite as exciting as the lucky people who have spotted dolphins in the bay. Running past lighthouses shows a part of our history before we had GPS units on all of our boats. In short, get out on the water and enjoy the Chesapeake Bay, teach your children to respect the water and they will have a lifelong passion.
There are many different activities the bay offers us to connect with our kids and the younger generation. This is just a few ways our family has been able to connect ourselves to the bay and benefit from all the beauty and activities offered. I hope you each choose your own way to spend time on the bay and pass along the passion and skills you have learned so the bay can be enjoyed for generations to come. I know I hope to pass along my love for the water and for boating to my sons.
