This one was a no-brainer: the Omni Parker is the oldest continuously operating hotel in the U.S., having opened in 1855, and having hosted a plethora of notables, from Charles Dickens (who did his first reading of "A Christmas Carol" here) to JFK (who proposed to Jackie in the hotel).

For about a century and a half, the Liberty was the Charles Street Jail, repository for violent criminals. In 2007, it became the ironically named inn, retaining some features of the building's former life, like iron bars.

This palace opened in 1912, and JFK's grandfather, then the mayor of Boston, threw a party for it with more than 1,000 guests. Since, the Fairmont Copley has hosted every president since Taft and myriad celebrities. Sumner Redstone famously survived a 1979 fire at the hotel by dangling out of a third-story window.

The extended-stay hotel is housed in a building dating from 1847. It was an actual customs house for incoming ships, and for about 10 decades there was the tallest building in Boston.

A 2008 renovation buffed out a lot of the history of the second-oldest operating hotel in the U.S., but just know that the Copley Square has hosted many notables since its 1891 opening, including Babe Ruth, Billie Holiday and several presidents going back to McKinley.

For much of the 20th century, the 1920s building was the HQ of the BPD (there's a bar today there called Cuffs).

The site of the Boston Harbor has a pedigree dating back to the 17th century, first as a battery for the British and then as a shipping wharf for our side. Now, finally, after surviving Boston's bad, old years, it's the site of a thoroughly gentrified piece of the waterfront.

It was in this inn opened in 1897 that the plan to fix the 1919 World Series between the Reds and the White Sox was hatched. The Buckminster was also the site of the first network radio broadcast in 1929.