Summertime on the Chesapeake Bay

We feel lucky to have spent a number of weekends getting out on the Chesapeake Bay to sail and anchor out. We visited Worton Creek, Solomon’s Island, Gibson Island, Oxford, St. Michaels and Yantz Creek + Lloyd Creek (which we wrote about previously).

This Summer we also crossed a personal milestone of sailing over 2,000 nm since we started sailing 3 years ago during COVID. It’s a small victory considering we changed boats, moved states, changed jobs, refit this boat, bought a car, sent our oldest back to college, watched our 2nd son graduate, spring sports, and drivers training for son #3. We somehow managed to keep all 4 kids (and a dog) fed and sheltered on land. We love sailing, but family is so much more important.

Although we started our sailing journey in the NY/NJ area, that didn’t entirely prepare us for sailing the Chesapeake Bay. When we left the mooring at Atlantic Highlands for a sail, we could be in the ocean within 60-90 minutes, and we often had good wind. But to get to any decent anchorage or stopping point meant either a 4 hour run into NY Harbor to drop anchor at the Statue of Liberty or a 8+ hour run up the East River into Long Island Sound. We made that trip several times, and it became normal for us to transit North that distance to experience new destinations. Most towns are well-established with a lot of restaurant options, shopping, and most importantly, ice cream.

We have learned that the Chesapeake offers a lot of anchorages within a 5 hour radius of Annapolis. There are a lot of places to go and explore that are either quiet anchorages with small beach areas or small / isolated villages and towns with a limited number of food options. There are as many maritime museums on the Chesapeake as there are diners in New Jersey.

Destination	What we liked	What we would do differently
Yantz Creek area	Excellent access to the nearby neighborhood park via dingy. Easy to set anchor.	Can’t avoid power boaters that speed through the anchorage and rock us or cut across our anchor line. Be ware!
Lloyd Creek	Peaceful and quiet anchorage. Dinghy access to Shaw Bay.	A little big buggy and poorly marked for deep draft boats. Follow the charts!
St. Michaels	It was great to dock at the Museum, excellent docking support. Great place to paddleboard in the early morning.	We are challenged to find a great restaurant in this town.
Worton Creek	Absolutely lovely sunset and beaches for small bonfires. Great place to paddleboard. Good holding. No nettles!	Making the mistake to go around green can “11” on the way towards Shaw Bay instead of taking the shortcut.
Gibson Island	We didn’t anchor here, but we drove in to take a look. Very pretty scenery with the horse farm nearby.	A lot of boats here in the anchorage; many of them “lake boats” and partiers.
Solomon’s Island	Anhorage near the Tiki Bar. Excellent location near the public dinghy dock. Fun activities in town. Great place to walk with an awesome maritime museum.	Wind in the wrong direction getting there…wouldn’t do that again. Wind in the anchorage from the North West blew on us causing a lot of swinging. We dragged quite badly in the morning.
Oxford	Anchorage in Flatty Cove was spectacular with no dragging and very quiet. Great sunset and dinghy access to some small beach areas.	Nothing other than take another day to dinghy into town and get some ice cream.

We had had a great time sailing on the Chesapeake Bay this Summer, and all of these learnings we will take into the Summer 2024. But now we are getting ready for sailing in the Fall and Winter on the Bay.