We continued our journey from Casco Bay’s Jewell Island to the bustling town of Freeport, where we spent an afternoon shopping, dining and stretching our sea legs. But this enjoyment proved to be short lived. I was anxious to return to more peaceful and unpopulated surroundings. Our next anchorage did not disappoint.

Just off the coast of Cape Elizabeth, Maine lies the 226-acre Richmond Island. Though it was once home to Native Americans and 17th century English fishermen, it is now privately owned but generously shared by a local family. We anchored in Seal Cove and rowed to the north side of the island where shells were abundant and sheep roamed freely, grazing in the setting sun. It was impossible not to fantasize escaping life’s frenetic pace and living out the rest of my days on an island like this.

Our next stop was Portsmouth, New Hampshire where the above picture was taken after a spectacular storm.

From there we sailed to Massachusetts, anchoring first in Rockport (above), then Marblehead, where I’d never counted so many masts! There the girls contemplated and took a very chilly (and very brief) dip, and we puttered around exploring the historic town.

The final leg of our journey was to Boston. Sailing into a bustling city provided quite the visual contrast!

We took advantage of the beautiful day, walking the city for miles. Hannah and I then tossed our duffels aboard a water taxi and headed to the airport. It felt like a fitting way to say goodbye to our summer ending week on the sea.