Since our stop in Oriental, NC we had solicited the advice of other more experienced cruisers on the must see stops on the Chesapeake. While the advice seemed to overlap on a number of points, there was but one city on which there was complete and utter concensus: St. Michaels, Maryland.
In fact we heard this refrain so frequently, that the prospect of not adding St. Michaels to our itinerary of the upper Chesapeake seemed folly. So with high expectations and dwindling Summer temperatures we set a course for St. Michaels.
Our arrival was late in the afternoon and after assessing our dockage and anchoring opportunities, we decided to spend the night on anchor just outside the harbor. This popular spot outside the main anchorage lacks significant wind protections but provides ample anchor swing room, which for us is a big advantage.

Sunset at St. Michaels 
We dropped anchor among the sailboats in the typical scenario: a dozen sailboats, a couple of trawlers and one 52' motoryacht named "Anthem". After the sailboats got over their initial shock and we were comfortable with the anchor set, it was time to take our front row seats on the forward deck to watch the sunset over the small city.
Our arrival was noticed not just by concerned sailboaters but also by the roaming band of swans that make their rounds in the city harbor as well as in the anchorages. We rounded up what scraps we could, to pay homage to these ornamental scavengers and enjoyed the beauty of the sinking sun framed by the harbor, with the silouettes of sails and swans.
With only one hour in the harbor, this mecca of the bay was certainly living up to expectations.
After a peaceful night, we hauled anchor and headed for St. Micheals town marina to get the best access to the city. This centrally situated marina was bordered by two restaurants and was within a five-minute walk to the center of town on Talbot St.

St. Michaels City Dock 
Once we were in the city, it was clear why this place has captured the attention of so many cruisers. It blends the charm of the many attractive elements of the bay in one place. Its got them all: small harbor with anchorage? check; historic church that chimes throughout the city? check; maritime museum, dozens of quaint shops, renowned seafood restaurant with the best crab cakes on the bay, check, check, check.

Street scene in St. Michaels 
It combines these elements in a town with authentic colonial history that has managed to hold back the pressures of hyper development that have victimized so many other quaint villages.
You get the feeling that real people live in this place despite the heavy tourist trade that drives at least the Summer economics of the place. Its a great tourist stop but it doesn't feel like a tourist haven.

Brenda in a park near the marina in St. Michaels 
The next day we headed out of the marina to anchor again outside the harbor. Our friends, Jim and Sylvia Huse were coming to visit from Atlanta. We prepared for their arrival by launching the dinghy that would ferry them from shore. When they arrived, Jeff headed for shore and loaded Jim, two suitcases and Sylvia (now 5 months pregnant) carefully into the dinghy. Sylvia’s lovely and stylish boots presented additional challenges as they had been specifically designed to be unstable and slippery on small boats (just a hypothesis).
With guests and luggage loaded on the mother ship, we were back underway to the Wye River. The Wye River, which is just a few miles from St. Michaels is just one more beautiful, unspoiled tributary of the Bay with anchorage after anchorage that border post card settings and cottages nestled in the trees. How much quaint beauty and idyllic charm can one couple take? We picked an anchorage from the many choices and determined to find out.
It was a great evening, enhanced by the company of the Huses who were veterans of many voyages aboard our first boat “Nameless Regal”. This trailerable 25 foot mega yacht was ferried over land, pulled behind our Ford Explorer to exotic destinations throughout the SE. The Huses suffered through the lack of A/C and heat, and were always great cruising companions. Together we had many good times for considerably fewer $$ than required by “Anthem”.
The following day we returned to St. Michaels and stayed at Higgins Yacht Yard. This slightly more humble marina also situated in the harbor gives equally good access to the city. From this location, we toured the city enjoying the many shops, pubs and restaurants of the small city center.

Jeff an Jim take turns at the crab boat helm 
We also visited the Chesapeake Bay Maritime Museum that sits on the point between the North and South Harbors. This working museum and boatyard offers perhaps the best collection of boats and marine artifacts anywhere on the bay. Even a landlubber can appreciate the demonstrations of craftsmanship and bay history featured at this popular attraction.

Exhibits at the Maritime Museum 
We finished our day with a meal at the renowned Crab Claw restaurant that is just outside the museum. This restaurant shares the title of “best crab cakes on the bay” with about 1000 other restaurants in the area. The cakes were good, but the best we had were in Solomon’s island. But that’s another story.

Crab Claw Restaurant 
With their business in St. Michaels concluded, the Huses prepared to return to the great Atlantan metropolis. We were sad to see them go, but happy we had enjoyed good weather for the entire trip.
We continued on in St. Michaels for a day or two enjoying the charm of the place and the company of one of our itinerant cruising friends aboard “Sails”. We finally rallied to leave port and prepared for a return to the true crab cake pinnacle, Solomon’s Island on the Western shore of the Bay.