Chesapeake Bay
“There are so many different places to go on the Chesapeake, more than people could ever see in a lifetime, so you can make each trip here different,” explains Erin Minner, manager at Dream Yacht Charter’s base in Annapolis, Md. “The fact that our home base is right in Annapolis is great. People can see the town and all its charm, and then take off sailing for however long they want!”
Wind and weather can always throw a monkey wrench in the best-made sailing plans. When the breeze is blowing out of the north, consider the following itinerary:
Day 1: Annapolis to Herrington Harbor. Here, on the western shore of the Chesapeake Bay, are overnight slips and the opportunity for waterfront dining in a classy-casual setting. It’s best, especially in the summer season, to reserve a slip in advance.
Day 2: Enjoy a leisurely sail to Oxford on the eastern shore. There you will enjoy a boater-friendly feeling as well as an easily walkable downtown with restaurants and shops.
Day 3: Cruise to Cambridge, the oldest town in Maryland, established in 1684. Cambridge Creek is a good, protected spot with ample room to drop anchor. Attractions include the Brannock and the Richardson Maritime Museums.
Day 4: Cross the Bay to St. Leonard’s Creek. Vera’s Beach Club, Restaurant & Marina is a good place to dock or anchor out. It’s a beautiful area surrounded by rolling hills, lush woodlands and shoreline marshes. Vera’s is one of the top seafood restaurants in the area.
Day 5: Seven miles downriver from Vera’s is picturesque Solomon Island. Stroll the Riverwalk, tour the Drum Point Lighthouse at the Calvert Marine Museum or enjoy one of several waterfront eateries.
Day 6: Enjoy an easy sail across the bay to St. Michaels. This is a lovely town with a lively shop- and restaurant-filled Main Street. There are marinas downtown or anchor out and dinghy in.
Day 7: Spend your last day under way for the 25 nautical miles (nm) or five to seven hour sail back to Annapolis.