A monument to the first person to sail around the world solo, nowhere close to where he was born, set sail, or landed.

A castle on a hill once named "the most beautiful high school in Massachusetts."

Historic seaside park featuring explorable, abandoned military structures.

The sea urchin sculpture is an unusual commemoration of a New England town's seafaring history.

Built to bless whalers before their voyages, this Massachusetts church now features a ship-shaped pulpit.

For 20 years, this whale skeleton has been slowly dripping oil on the floor of the museum where it hangs.

This statue is a commemoration of the only place where Freud spoke in the United States.

Ice cream stand, snack bar, and time capsule of milk conveyance.

What was once a true peninsula has now been filled in, causing the water to recede and leaving many streetside "waterfronts" and landlocked "islands."

An easy-to-miss garden in Boston's North End honors the mother of JFK and others who lost children in WWII.

Dedicated to nine marines from Massachusetts who perished during the Beirut bombings.

One of the indelible moments of the American Revolution took place at this location.

This area was once known for being a lawless haven for rough-and-tumble sailors, earning the maritime-themed nickname "the black sea."

The site of Paul Revere's historic two lantern warning.

Stolen goods adorn the organ at Old North Church.

The location of one of the first private Catholic schools in the country, providing a valuable sanctuary during the tumultuous period when Protestant and Catholic students were at odds.

This ambitious father and son team reigned supreme over the North End, and witches, for many years.

A centuries-old church stands as a testament to Boston's "father of architecture."

A school used as a model for public education across the country.

The site of one of the strangest disasters in history—a wave of deadly molasses traveling at 35 mph.

This memorial honors those who served on Gallops Island Radio Training Station during the second World War.

This parking garage was the site of what was - at the time - the largest cash robbery in history.

Historic Hull Street was actually the first street with a proper name in the Boston area.

Each August, one of the largest religious (and food) celebrations in the country is held in Boston.