Cruising the Chesapeake Bay is never just about getting from one harbor to another—it’s about savoring the small joys along the way. Each marina and town has its own personality, offering everything from friendly staff and loaner cars to cozy cafés and world-class ice cream. Over the course of three cruises, I’ve built a list of favorite stops, each one tied to fond memories and unique local experiences. Whether it’s wandering thrift stores, walking forested trails, or enjoying a perfectly cooked meal, these places make the Bay feel like a second home.
Here’s my journey through some of my favorite Chesapeake Bay destinations, where the water meets hospitality, charm, and discovery.
Chesapeake Boat Basin – Kilmarnock, Virginia
There’s something immediately welcoming about pulling into the Chesapeake Boat Basin in Kilmarnock. The staff greets you with genuine warmth, making it one of the friendliest marinas on the Bay. What really sets it apart, though, are the thoughtful amenities. The loaner car is a game-changer, allowing boaters to explore town at their leisure and obtain provisions. After long days on the water, I appreciated their clean laundry facilities and showers, which make an extended cruise far more comfortable.
Kilmarnock itself has its own treasures, most notably its wonderful thrift stores. You never know what you might find while wandering through—vintage housewares, nautical trinkets, and even books and movies for those slower evenings aboard. It’s the combination of marina hospitality and small-town charm that makes this stop so memorable.
Spring Cove Marina – Solomons Island, Maryland
Farther north, Spring Cove Marina on Solomons Island, located at the mouth of the Patuxent River, is another favorite haven. Here, comfort is the priority. Although the park-like setting is beautiful, watch for tree sap during certain parts of the season, which can make boat cleaning memorable. Like Kilmarnock, they offer a loaner car, making grocery runs or sightseeing incredibly convenient. On hot summer days, nothing beats lounging by their pool, a rare luxury when cruising. For more active exploration, the marina has bikes available, perfect for pedaling around Solomons Island at an easy pace.
Nearby, the Weis Market is an ideal spot for restocking the galley. It’s one of those reliable grocery stores where you can always count on quality produce and essentials. After errands, it’s easy to spend the rest of the day enjoying the island’s laid-back atmosphere, knowing that the marina has everything you need for a restful stop.
Onancock Marina – Onancock, Virginia
Crossing back into Virginia, Onancock Marina is a destination that captures the heart. Docking here feels less like stopping at a marina and more like arriving at the center of a vibrant little community. Just a short walk from the docks, you’ll find a café and a bakery. We especially loved catching an entertaining musical rendition of “Gilligan’s Island” at the Roseland Theatre.
Onancock’s walkability is one of its greatest charms. The streets are lined with quaint shops, art galleries, and plenty of local history. A leisurely stroll through town makes this stop feel like a cultural retreat as much as a boating destination.
Cambridge Yacht Basin – Cambridge, Maryland
For food lovers, few places compare to Cambridge Yacht Basin. This town is home to the best fish and chips I’ve ever had, served at Port Side Seafood Restaurant. It’s the kind of dish that keeps you coming back—crispy, perfectly seasoned, and best enjoyed while overlooking the water.
Cambridge is also home to Simmons Center Market, a local grocery store renowned for its quality meats. Stocking up here is always a treat, as you can count on bringing premium cuts back aboard for grilling. Like Onancock, Cambridge is also a great walking town, with historic streets that invite exploration. It’s a place where good food and a relaxed pace of life offer a mix of history and culture.
Safe Harbor Marina – Oxford, Maryland
When cruising to Oxford, the stop at Safe Harbor Marina is always worth it. Oxford itself feels timeless—a classic Chesapeake Bay town steeped in history. But what truly makes it shine is the Scottish Highland Creamery, serving what many consider the best ice cream on the Bay. Rich, creamy, and made with care, it’s a stop no cruiser should miss.
The town also offers nice walking routes, from shaded streets lined with historic homes to the town beach, where you can relax with sand between your toes. Oxford’s slower pace makes it feel like an escape within an escape—a chance to pause and savor simple pleasures.
St. Michaels – Maryland’s Quintessential Bay Town
If there’s a crown jewel among Bay towns, it’s St. Michaels. Known for its charm and vibrant history, this stop never disappoints. A highlight for us was an anniversary dinner at Theo’s Steakhouse, where a delicious, perfectly cooked steak, warm atmosphere, and excellent service made for a magnificent evening.
But St. Michaels isn’t just about dining. The Treasure Cove Thrift Shop is a fun place to browse, often yielding unexpected finds. History buffs will love the Chesapeake Bay Maritime Museum, which tells the story of the Bay’s working watermen and showcases beautifully preserved vessels. Between shopping, dining, live music, and culture, St. Michaels truly has it all—making it one of the favorite and most rewarding destinations for cruisers.
We weathered two significant thunderstorms storms complete with tornado warnings about a week apart anchored close to town, finding the holding excellent in winds up to 60 knots. We first anchored in Fogg Cove just off the Maritime Museum, however, we found there were many wakes from boats departing the harbor, so moved and enjoyed anchoring closer to the docks near town.
Wye Island – Granary Creek
Sometimes, the best stops are the ones where there’s nothing but nature. Wye Island, particularly Granary Creek, close to St. Michaels, is one of those magical places. Here, you won’t find marinas or bustling streets. Instead, you’ll discover quiet trails and serene waters.
Anchoring in Granary Creek feels like stepping back in time. The absence of other boats means no wakes rocking you through the night, and the stillness of the creek provides unmatched peace. Exploring the island’s trails offers a chance to connect with nature, from towering trees to wildlife that thrives in this untouched environment. For boaters seeking solitude, Wye Island is a true sanctuary.
Pickering Creek – Audubon Trails
Another natural treasure is Pickering Creek, home to an Audubon Center, a 410-acre wildlife sanctuary located in Easton, MD. The anchorage here is peaceful, and going ashore offers the chance to immerse yourself in conservation land dedicated to preserving the Bay’s ecosystems.
The trails are varied and rich with birdlife, making this a dream stop for nature lovers and photographers. While the Chesapeake is filled with charming towns and bustling harbors, Pickering Creek stands out as a safe anchorage where the reward is simply being present in the natural world.
Chestertown – History and Quirky Charm
Last but not least is Chestertown, a destination steeped in history and creativity. We almost skipped this stop because we thought the Memorial Day activity would be busy and were glad we didn’t miss it. Chestertown’s real charm lies in its events and unique attractions.
The Tea Party Festival is a highlight, featuring hand-built boat races that celebrate the town’s revolutionary heritage in a lively, fun way. Just like the famous Boston Tea Party, Chestertown residents in May 1774 also tossed tea overboard to protest British Parliament’s taxation. The annual reenactment is the centerpiece of the Chestertown Tea Party Festival along with other colonial-themed activities.
For something truly unusual, there’s the not-for-profit Cat Colloquium, where you can visit with cage-free cats rescued from around the world. One of our favorites was Rose Arnold, who loves to be picked up and purr in your lap. Grocery delivery from Acme market made provisioning easy and the paved old railroad trail made for an interesting walk through town. This mix of history, whimsy, and community spirit makes Chestertown unlike anywhere else on the Bay and well worth the extra time to get there.
The Joy of Cruising the Chesapeake
Taken together, these destinations paint a portrait of the Chesapeake Bay that goes far beyond the water itself. Each harbor and town offers a different kind of reward.
For cruisers, these stops remind us that the Bay is more than just a body of water—it’s a collection of communities, traditions, and landscapes waiting to be explored. Every town and harbor brings new opportunities: a friendly face, a memorable meal, or a quiet trail under the trees.
The Chesapeake has a way of turning routine cruising into something deeply personal. My favorite places aren’t just waypoints on a chart; they’re the highlights of journeys, each with their own story to tell. The Chesapeake Bay offers a unique blend of comfort, history, and adventure, and we hope to keep coming back to these harbors and towns for many years to come.
About the author: Tim Smale and his wife Jennifer started sailing on a Newport 28 sloop on Lake Erie and a Cape Dory 36 ketch in the Great Lakes and on the west coast from San Francisco to Mexico, where they spent two years cruising. They moved up to a Sealine 47 and cruised the Great Lakes and Canadian North Channel, then downsized to a Rosborough 246 and trailered between Florida and Maine. They found that trailering is the best of all worlds and, with their Ranger Tugs R-31CB Scout, travel back and forth from Florida to Maine, stopping along the way to enjoy the Chesapeake Bay and cruising Florida in the winter and New England in the summer.
Editor’s Note: If you missed Tim’s first article in the September PropTalk, check it out at Trailering to the Cruising Grounds. There he shares helpful planning and logistics tips for trailering his Ranger Tugs R-31CB up and down the East Coast to various cruising grounds.