The start of spring never truly begins in Boston until the first day out on the water. Sailing along the Boston Harbor with friends has become an annual tradition and is personally one of my favorite quintessential New England activities. It's always a thrill seeing the city skyline from this perspective, imagining how different the views have changed since John Smith discovered Massachusetts Bay in 1614. In his description of New England, Smith pronounced the Boston Harbor the "paradise of all these parts"— I couldn't agree more.
Where: The Boston Harbor offers the best views, but the Charles River is equally as scenic with views of the Back Bay area. The Boston Sailing Center in the North End is popular for lessons and chartering a boat (they have a free open house every spring) while Community Boating along the Charles is one of the oldest public sailing centers and perfect for children who want to learn.
When: Summer ideally, but sailing starts in the spring and ends in late fall
Why: "I wanted freedom, open air, and adventure. I found it on the sea." ~ Alaine Gerbault