The largest estuary in the United States.
Sailing the Chesapeake is an experience. Changing depths, brackish water, Eastern Shore twang… nothing compares. Sailors come from all over the world to enjoy the challenges the beautiful body of water has to offer. Whether you are looking for a night out in Downtown Annapolis or an ice cream cone in Rock Hall, there’s a locale for everyone.
Hailing from the region, Captain Michael loves working with the ingredients. Blue crabs, fresh oysters, and rockfish - come hungry for seafood!
Explore our gallery below of our favorite highlights on the bay.
Join us for our all-inclusive 5 day excursion…
Cruise the Chesapeake on a sailing catamaran with our curated itinerary designed to cater to you and your guests’ every need. Click to learn more!
Two cabins are available each with a queen-size bed.
St. Michael’s
Rockhall
Oxford
Herrington Harbour South
Wye River Sanctuary
Cambridge
We proudly work with Waypoints Charters located in Annapolis, Maryland.
Fox's Den - Annapolis - pizzas, duck fat fries, and excellent beer selection are all found down a flight of stairs off the main drag. The fox marks the spot!
Preserve - Annapolis - upscale dining focused on the preservation of seasonal food. Excellent cocktails and food in an airy, comfortable setting.
Pusser's - Annapolis - Come for the rum, stay for the shenanigans. A great place to enjoy the passing vessels as they make their harrowing turn in the iconic Ego Alley.
Two If By Sea - Tilghman Island - Owned by two Culinary Institute of America chefs, this kitschy diner slings up amazing benedicts and mimosas.
Ride a Bike - Tilghman Island - Take one of the marina's bikes on a cruise out to the point of Tilghman Island. Offering beautiful views of the bay and a little salty air through your hair!
Marker Five - Tilghman Island - Delicious wings and brick oven pizza! This sailor bar is a great place to rub elbows with the locals while telling tales of the high seas.
Fresh Start Food & Garden - Rock Hall - Check out this farm stand for local goods from all over the Eastern Shore. Jams, pies, breads and so much more... this little grocery store is a great place to snag a gift for the land lover you left at home.
Harbor Shack - Rock Hall - A little tiki never hurt anybody. This marina shack is a great place to have a little fun in the sun with bar snacks and great beers.
Java Rock - Rock Hall - Locally owned and operated coffee spot that will make you say, "Star-who?". They also carry a fantastic selection of wine and gifts. Highly recommend the donut holes (if they have any left!).
Ava's Pizzeria - St. Michael's - Grab a pie at this local pizza joint that also has a great selection of wine. Enjoy an evening stroll after dinner through the beautiful downtown area.
Maritime Museum - St. Michael's - Not only is this a wonderful museum, but it's also where you can sleep! We have access to the marina for your sleep aboard so you can enjoy a morning of the rich history the bay has to offer. It also happens to be an easy walk into the downtown area.
Eastern Shore Brewing Company - St. Michael's - Enjoy a locally brewed pint of beer at this great little spot. Indoor and outdoor seating offers a little people watching while you sip your suds.