Like a favorite pair of jeans you’d wear every single day if you thought no one was looking, we tend to cruise the same water most every time we head out of the marina. Sure, exploration is the reason many of us boat; searching for something new to enjoy and add to the little black-book of destinations is a primal urge to most boaters. A little flirting with the wild side to keep things interesting. The missus often accuses me of being too predictable. For instance, I’ve been to Red Robin probably 15-20 times in my life and I’ve only ever ordered one thing off their menu! Boring? Predictable? Perhaps. But, when you’ve discovered perfection, why would a rational person search elsewhere? The Chester River, just east of the Chesapeake Bay Bridge, is exactly like that. Predictable? Perhaps. But, one more example where you don’t fix what’s not broken. We have only a few weekends available every season, thanks to our family’s differing land-based activities and schedules. Add in our guests’ schedules, plus the ever present risk of foul weather, and watch the number of days for entertaining aboard each season drop to just a handful of fingers. On those weekends where it’s just us, we’ll risk venturing to new places for reconnaissance. But for those weekends that must deliver, it’s the Chester River. We recently made another pilgrimage to Chestertown, MD, roughly 20 nautical miles northeast of Kent Narrows, when family came to town. For us boaters, a little rough water is akin to the rocking of a baby’s bassinette, but a green guest is something we try to avoid at all cost. The Chester is plenty long, plenty wide, plenty deep for both power and sail, and well marked all the way from the Bay to Chestertown. But her best feature is nearly full weather protection from her gorgeous shores that wind through the division between Kent and Queen Anne’s counties. Okay, there was this one time we cruised the Chester (August 2012) that was probably the worst storm we’ve ever boated through anywhere; a wall of wind, water, and lightning that looked like a sandstorm rolling in, bringing six- to eight-foot waves along with it. This is not the norm for the Chester, with water so smooth she’s easily cruised from end-to-end by everything from a bass boat to a hydroplane. My dockmate says his Jet Ski makes the 21-nautical mile trip to Chestertown “in under 20 minutes,” for reference. Someday I might test that statement with him, it’s normally that smooth. While the Fish Whistle Restaurant (N39.2055, W76.0635) is typically our final destination, there are other waypoints along the route like Rolph’s Wharf Marina and beach bar (N39.174, W76.038), plus all the maritime history of colonial Chestertown. For new cruisers to Chestertown, make sure you slow down to no wake speed as you approach Rolph’s; it’s not marked “no wake” and I still feel horrible for all the VHF calls I received my first time cruising these waters. All that said, the Chester River isn’t about all the destinations; this is about the journey. You can go fast on this wide river, if that’s your drive. You can play trawler if you just want to conserve fuel while making a day’s journey out of it. You can see and do things in Chestertown, or you can simply take in all the undeveloped beauty along both shores. The Chester is a relaxing ride from start to finish and is usually free of the jellies for swimmers and skiers, especially the further north you head. And she’s easily entered from northern ports like Annapolis, Baltimore, and Rock Hall at N39.074, W76.279, or out of the south from places like St. Michaels through Kent Narrows at N38.981, W76.243. Sometimes predictable is exactly what a boater needs.