For the past three years that we have been learning to sail and sailing from O Dock, we have continually heard about this “must-sail-to” town along the Miles River called St. Michaels.  So we made it our goal to make this quaint, watermen’s village the first port we docked in for the season.  Hello St. Michaels!  Here we come!

Sailing from our Hidden Cove on the Wye East River to the mouth of the Miles was truly awesome!  The wind was definitely in our favor!  We made short tacks every few minutes the whole way down the river and really let the wind carry us.


We have discovered that on long hauls giving each other breaks with 30 minutes on and 30 minutes off enables us to stay focused and take a breather from the helm for a little bit.  This time we took turns at the helm and at adjusting the sails, so we were both working together to sail the Gem&I on to St. Michaels.

We made excellent time and pulled into St. Michaels ahead of schedule.  Higgins Yacht Yard, recommended by Andy from What’s the Fuss, was in the center of the harbor and the middle of town.  Sandwiched between the infamous Crab Claw Restaurant and Two Swan Inn, we could not have done better on a transient slip location.  The marina itself was completely “old school,” which Damian loved as it reminded him of his dad.

Our boat cat, Schnitzel, surveying the dock at Higgins Yacht Yard, with the owner and his wife’s sailboat sitting in the slip behind.


After docking across from the path that led to the Chesapeake Maritime Museum, we strolled up the dock to the large building that looked like an airplane hanger for sailboats.  A sign in the window read, “Office upstairs.”  We opened the door of the hanger and ascended the wooden steps that overlooked the yacht yard working garage full of boatwright tools equipment, boat parts, and the musty smell of yester-year boats from another era.  The man and woman in the office were the most genuine, welcoming people.  They oriented us to the facilities and various points of interest in the town and supplied us with informative maps and brochures, advertising the tourist attractions.

After refreshing showers and donning clean clothes, we sought out a rewarding restaurant to have dinner and investigate the town of St. Michaels.   Meandering up Carpenter Street, we found the Talbot Street, the main street of the town.  Rows of eclectic shops quaint restaurants lined both sides of the street, and I could not help but notice the historical charm of all the little houses that sprawled out from the village center.  Strolling hand-in-hand, I felt like I was on my honeymoon in a romantic destination that other honeymooners may–at that very moment–might be enjoying together too!

Even though the little shops were tempting, hunger remained our priority since the last time we had eaten was a mid-morning snack aboard the boat.  Blackthorn Irish Pub caught our eye, and a gracious hostess led the way to a high top in the back.  We feasted on half-priced wings, and I splurged on a white wine–because it was “happy hour,” and the prices reflected such!  I ordered the Shepherd’s Pie, and Damian devoured a cheeseburger with a slice of thick Irish bacon in the middle.  For two famished sailors, the meal was superb.

We wandered the town and discovered the library and the grocery store along with several intriguing specialty shops that wetted our appetites for tomorrow’s agenda.

Sunset over St. Michael’s Harbor from Higgins Yacht Yard