Boston's best kept secrets

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Read our Showtime® Inspired City Guide to Boston


There’s a sexy ruggedness that makes Boston a very appealing weekend getaway. Get in fast, take it all in, and then settle back into your own reality. For Ray Donovan, that reality exists behind the scenes, discreetly fixing Hollywood’s dirtiest secrets. Strong Boston roots and gritty experiences make the SHOWTIME® Original Series Ray Donovan one of the edgiest things you’ll see on TV.

You don’t have to miss out by tuning in Sundays at 10PM, nor when you stay at the Sheraton Boston Hotel. This historically rich city has a flashy exterior only matched by the secrets lurking in its own shadows. That’s usually where you’ll find Ray and his cronies, and it’s where we think you’ll have the most fun in Boston.

Let Sheraton take you off the beaten path and back to where Donovan learned everything he knows. We’ll show you places even these locals may not know about.

Shoe Shopping Behind a Snapple Machine

The coolest place to buy shoes in Boston (and maybe anywhere) is hidden behind a Snapple machine. Bodega operates under the cover of a grocery store and is a “refuge...for a clandestine group of artists.” The hottest sneakers, and even snacks, await those who can find it.

A Secret Parking Garage Garden

Park your car in Kendall Square then head straight up six stories for one of the lushest gardens in Boston. At 4 Cambridge Center, look for the sign off Broadway that reads “Roof Garden.” Pack a lunch, take a date, or arrange an off-the-books meeting surrounded by surprising peace.

Patron Saint of Back Alleys

One of the most impressive art installations in Boston is tucked inside an alley in the North End. All Saints Way is where Peter Baldassari has curated a collection of portraits of nearly every saint that’s been canonized. Often locked, you can steal a peek through the iron gates.

Behind the Green Monster

Touted as the number one tour experience in Boston, going behind the scenes at Fenway Park is not to be missed. If it’s a Red Sox home game, you should certainly stick around to watch the game with a hot Italian sausage and a cold Sam Adams beer.

Sheraton can even hook up MLB fans with a 20% discount when they book 2 nights.

Seek the Speakeasy

Hidden in plain sight in Union Square, Back Bar Union is a lucky discovery for those who can find their way there. Look for a red door down an alley, then navigate another hallway that leads to a heavy door, behind which is a menu of inspired craft cocktails.

Ask for the Secret Slice

The chef may concoct something with scrambled eggs, basil, and sopressata, but it’s nothing you’ll find on the menu at Area Four. Truly artisan pizza is being prepared here with dough made from a 12-year-old starter and handcrafted cheese all baked in a wood-fire oven.

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