Former Boston Jail Delivers A Dynamic Luxury Hotel Experience

Despite the recent unfortunate COVID outbreak in Provincetown, Massachusetts, it undoubtedly will remain one of the most visited LGBTQ+ tourism destinations in the country. Though some tourists opt to fly into The Cape Cod area and others drive, the most popular way to get to PTown is by taking a picturesque ferry ride from the Boston Harbor out to the tip of the Cape.


It’s a trip I just made this weekend but first with an overnight stay in Boston before taking the ferry in the morning. And I’m so glad I did.

Boston is a terrific city full of beautiful smiling faces, lovely shops, tons of history, culinary delights, landmarks, and of course, the most incredible views of the Boston Harbor and the Charles Street River. I took in a few cocktails at the outside eateries like the Landing on the Wharf — a staple for kicking back with harborside libations.

Motorboats and Long Wharf with Customhouse Block, Skyscrapers of Custom House and Financial District of Boston, MA, United States.

My partner knows I’m an avid fan of boutique hotels so he chose one of Boston’s most unique hotels for our overnight getaway and it blew my mind. It’s called the Liberty Hotel, formerly known as The Charles Street Jail. The Jail opened in 1851 and closed on Memorial Day Weekend 1990. At the time of its closing, it was condemned for unacceptable conditions and for violating inmates’ constitutional rights. The remaining prisoners were transported to the new Suffolk Country Jail, and shortly after that, the plans for conversion – from prison to luxury hotel began.


Initially, I was a bit freaked out by the idea of staying in a hotel converted from a notorious prison, but once I learned that the developers flew in a group of Tibetan monks to bless away the potential evil spirits, I felt much better about it.

Liberty Hotel has emerged as one of Boston’s top hotels and hotspots just blocks away from hipster areas like Charles Street, Beacon Hill, Boston Park, and all the fabulous high-end shops of Newbury Street. The neighborhood encompasses all you need for culinary delights, culture cocktails, history, lush gardens, and all within short proximity of a quick Uber ride to the Long Wharf and the New England Aquarium.



The hotel’s main attractions are the popular restaurant Scampo by Lydia Shire, nightlife lounge experience Alibi, and the main hotel restaurant, “Clink!” (Think the sound of handcuffs.) It’s a gorgeous hotel, located just across from Charles Street station.

Doing my best anguished inmate impression at The Liberty Hotel – Formerly Charles Street Jail

The architecture incorporates much of the original prison structure, including reimagined cells and actual prison bars – some in their original position, others repositioned into the decor throughout. It’s all very Shawshank Redemption meets neon chic Boston Nightlife with it’s eclectic Liberty Bar. And more importantly, not only are the hotel interiors gorgeous, but the guest rooms are also fabulously comfortable with art deco details and luxury thread count bedding. One of my favorite details is the whimsical way you let housekeeping know you don’t want to be disturbed: A sign labeled “Solitary.” 


A definite must see and do for your first or next trip to Boston!  I can’t wait to come back. I’ll see you in the clinker! 


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