One of the first women's college clubs in the country, this institution was founded in 1890 as a space for women from different universities to gather and grow intellectually. Today, it spans three adjoining Beaux-Arts townhouses, and anyone can book a stay in their 12-room bed & breakfast. The rooms—each named after a local university—have well-stocked bookshelves and writing desks tucked beneath bay windows overlooking leafy Commonwealth Ave.

How many oyster bars can say that they’re a national historic landmark? Union Oyster House is the oldest continuously operating restaurant in the US and has plenty of other claims to fame—Louis Philippe I taught French lessons there before he became King of France, and JFK dined there so often a plaque was made for his go-to booth (#18 upstairs). Oysters are obviously the claim to fame there, but you can’t go wrong with any of their New England classics.

After Charlestown was sacked by the British in the 1770s, Warren Tavern was one of the first buildings raised in the neighborhood. It was a favorite watering hole of George Washington and Paul Revere, and though the menu has evolved since (lobster mac & cheese is famously hard to eat with wooden teeth), the original low beamed ceilings and uneven floorboards remain.

Too many of Boston’s Irish bars are little more than divey sports bars hiding behind weathered wooden facades, Celtic fonts, and Fireball-soaked floors. But the original J.J. Foley’s in the South End (not to be confused with the Downtown outpost) is the real deal. The walls are lined with portraits of Popes, Kennedys and mayors past, and the white-haired bartenders won’t crack a smile but they will pour a perfect Guinness or Irish “cah” bomb.

This ornate 1,700 seat theatre is one of the oldest that’s still operating in the country (a theme in Boston). Take a tour of the gilded interiors or catch a show before it gets picked up for Broadway. Just don’t miss a pre-show drink in the Orchestra Bar, set in the former ladies’ lounge.

A shop that you have to see (and smell) to believe. This tobacco-focused specialty store opened over 140 years ago across from Harvard Yard to service the genteel students of the day. The heady mix of pipe tobacco, vintage colognes, and leather goods has been soaking into the wooden cabinets for well over a century, alongside hand-painted oars (they posted the crew schedule in the window pre-internet) and classic board games we imagine international students played to pass time on steamships.

This Ivy Style mecca once dressed Miles Davis and Chet Baker, and 75 years on, still ranks among the best men’s stores in America. The perfect synthesis of Anglo-American style, they have a killer collection of pieces with academic personality—think rowing scarves, herringbone blazers, Arran sweaters, and made-to-measure tailoring in rare English fabrics. But don’t sleep on their house cut: a two-button blazer with an undarted front.

One of the country’s oldest private libraries, this 19th century landmark building is open to the public with the purchase of a day pass. Its 12 spiral-staircase connected floors house over half a million books and inspiring reading corners decorated with exquisite art and worn Ottoman rugs. The top floor is a sanctuary for serious studying and research.

Tucked down a quiet alley in Back Bay, this bookstore is a treasure trove of used and out-of-print books, vintage photos, maps and art. The shelves are so full they’ve started making piles of books on the floor—you could spend hours navigating the labyrinth-like stacks or flipping through bins of interesting prints.

Owned by the same family since the 1940s, this bookstore dates all the way back to 1825, making it one of the country’s oldest and most storied (pun intended). Peruse the three floors of used, rare, and antique books, and on days when the weather cooperates, head to the outdoor sale lot that carries shelves upon shelves of $1-$5 books that’d make a great souvenir from a college tour.

This preserved 1860s Victorian row house is a time-capsule of 19th and early 20th-century Boston. Once home to three generations of the Gibson family, it's an unaltered glimpse inside the Gilded Age lives of Back Bay’s elite—with lots of ornate wallpaper, period furnishings and original details throughout.