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L.A. Burdick Handmade Chocolates

Boston MA    $1-10    www.burdickchocolate.com/

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Submitted By: Angela

AKA a little chocolate house nestled between the infamous Newbury and Boylston streets. If you weren’t looking for it, you would never experience the best drinking chocolate in all of the land.

Saturday Chocolate Bar

Boston MA    $10-50    www.langhamhotels.com/en/the-langham/...

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Submitted By: Angela

Attn. chocoholics: this one’s for you. Desserts galore. (And if you’ve got extra money to spend, a bed in the Langham Hotel itself would be the cure for your chocolate coma.)

Taco Monday @ Lolita

Boston MA    $10-50    www.lolitatequilabars.com/

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Submitted By: Angela

All-you-can-eat hard shell tacos for $9?!? #YesPlease. As you’re about to leave, you’ll catch yourself devouring cotton candy topped with Pop Rocks (on the house).

Cambridge Center Roof Garden

Boston MA    Free    www.cambridgeusa.org/listing/cambridg...

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Submitted By: Angela

A secret garden so secret, locals barely know about it.

#mfaNOW Overnights

Boston MA    Free    www.mfa.org/programs/series/mfanow-ov...

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Submitted By: Angela

Everything is more fun when it takes place afterhours, especially fine art museums. With live entertainment and DJs poppin’ up a formal spot, this event series is the hot thing to do this fall/winter in Boston.

Verb

Boston MA    $200-500    www.theverbhotel.com

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Submitted By: Mikey

A retro and insanely cool “Rock Hotel” right next to Fenway Park. Ridiculously cheap for the area and definitely photoworthy.

The Institute of Contemporary Art

Boston MA    Free    https://www.icaboston.org

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Submitted By: Mikey

Play the “is it trash, or is it art?” game with friends at this absolutely amazing museum.

The Liberty Hotel

Boston MA    $200-500    www.libertyhotel.com

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Submitted By: Kirk

Formerly known as the Charles Street Jail. You once had to commit crimes to stay in places like this.

Warren Anatomical Museum

Boston MA    Free    https://www.countway.harvard.edu/chom...

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Submitted By: Kirk

Guarantee any first date is a last date – take your date to the weirdest collection of bullet wounds, deformed skeletons, and crazy medical equipment Harvard Medical School has to offer.

Getaway (in a cabin)

Boston MA    $200-500    https://getaway.house/bookingboston/

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Submitted By: Kirk

Rent a tiny, ~100 square foot microcabin in the woods and escape for a weekend.  Locations are kept secret but guaranteed to be no more than two hours drive from Boston.