5 Hilariously Awesome Date Ideas

August 10, 2016

Charlie Chaplin once said, “A day without laughter is a day wasted.”

We’d like to revise that to say that a date without laughter is indeed a date wasted. But what if you and your date aren’t in the mood for a good ol’ rom com? You, my friends, are in luck.

There are a ton of great live comedy shows near you! And they’ll be sure to leave you both having a great time. Below, we’ve handpicked some of the best.

(6 activities)
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    Sunset Harbor Cruise

    (26)
    Treat yourself and someone special to a relaxing, romantic sunset cruise. Take in Boston's skyline as the sun slowly sets and turns brilliantly orange or red. As you cruise further throughout the Boston Harbor, you'll pass by historical and cultural points of interest, such as Fort Independence, Tobin Bridge, the U.S.S. Constitution, the Old North Church, and North End. Enjoy views of Boston on the open back deck or in the shade at midship. The boat features wraparound seating and a crowd-free environment, so you're ensured a great, comfortable view. On top of all that, you'll be provided complimentary soft drinks, water and light music to set a relaxing mood -- but feel free to bring your own picnic on board and purchase drinks from the cash bar!
    Sunset Harbor Cruise

    60 Rowes Wharf, Boston

    • Enjoy a romantic sunset cruise on a classic 1920s style yacht
    • View Boston's city skyline, Fort Independence and other historical points of interest
    • Experience the romantic side of Boston with a scenic and relaxing tour
    • Bring a picnic and enjoy complimentary soft drinks on board
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    26 positive reviews
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    Escape from Death Row

    (3)
    You're on death row: You and your mates have found yourself in REAL jail cells. But I'm innocent, I swear! -- Hey, save it for that maker you're about to meet. Oh, b-t-dubs, you don't even get a last meal, because we're out of pork. Deal with it. Enjoy your last hour! Sheesh. So prison's tough, and you're starting to think it's not the life for you. Hey, it's never too late to start over. Well actually, you have exactly 60 minutes to start over, THEN it's too late. Hope you brought your "Get out of jail free"card! What would you actually do? Book this exciting escape room, set in a REAL jail cell (creepy!) to see if you're a survivor or a...die-er. :/ Will you make it? Can you save your cell mates? Be a hero. If nothing else, do it for the pork.
    Escape from Death Row

    7 Central St, Arlington

    • Use your wits to get out of this high-security puzzle room that takes place in an ACTUAL jail cell!
    • Find out if you have what it takes to break out of prison
    • Show off your problem solving skills, your attention to detail, and your quick wits
    • Invite a friend and work your way out as a team
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    3 positive reviews
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    Boston Haunts Tour

    Do you believe in ghosts? Whether you're a terrified believer or a staunch skeptic, this spooky tour will engage, fascinate, and surprise you. Venture out into Boston and see all the bone'chilling sights and hear the sweat'causing stories of ghouls, spectors, and other paranormal phenomenon. This lantern-led walking tour will uncover all the skeletons in Boston's closet on this frightening New England experience where anything and everything will happen. Don't expect anything boring, dull, or familiar, but do expect an astonishing and eerie experience.
    Boston Haunts Tour

    24 School St, Boston

    • Scour Boston on a walking tour for all its dark tales of spooky revenants and haunting phantoms
    • See areas where paranormal activity is the norm and the stories are frightening
    • Uncover all the skeletons in Boston's closet with a guide knowledgeable of unearthly dealings
    • Enjoy being scared, shocked, and amazed as you learn all about Boston's dark secrets
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    The Sip of Boston Brew Tour

    (20)
    Boston nightlife plus the Boston brews equals the best night you can have in Beantown. Begin your night on the town with a quick bar crawl to get ya in the mood. On this Brew Pub Crawl, you'll taste twenty different beers, enjoy an artisan dinner at Area Four, and you'll receive round-trip transportation throughout the evening. Taste the array of stouts, pilsners, and ales that call Boston home. You'll visit the city's top breweries in its after hours. Are you ready yet? Because it's time to taste some beer!
    The Sip of Boston Brew Tour

    143 Charles St, Boston

    • Taste twenty different beers, including various stouts, pilsners, and ales, on this Boston brew pub crawl
    • Enjoy an artisan dinner at Area Four
    • Travel with round'trip transportation throughout your entire evening
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    20 positive reviews
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    Saturday Night Comedy Show Hosted by Rick Jenkins

    (6)
    Looking for an exciting Saturday night comedy show to have you rolling on the floor with laughter? Come see this comedy showcase where you can see everything from a newcomer to a seasoned veteran gearing up for a set on the Tonight Show. You never know who is going to show up for a set, so expect to see really talented people ready to entertain you with new material and old favorites. No two shows are the same, and you never know what new places will be explored!
    Saturday Night Comedy Show Hosted by Rick Jenkins

    1238 Massachusetts Ave, Cambridge

    • Enjoy a Saturday night comedy show that mixes the best of newcomers and veterans
    • Experience the finesse of comedy perfected as a technique and science
    • Embrace a set list featuring some of the best and brightest in stand-up
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    6 positive reviews
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    Rum and Revelry Sail

    (10)
    Sail Boston Harbor at night and enjoy all facets of live entertainment on a tall ship! Actors dressed in period attire with play their fiddles or hornpipes as you sing and dance to sea shanties. You'll have a great time enjoying the entertainment and historic feel of the experience. The bar will be stocked with Madeira, Port, and the sailors favorite, the Dark 'n Stormy. This event will attract many singers and lovers of naval history and, of course, grog! Prepare for a rousing chorus of shanty singers and musicians of all sorts!
    Rum and Revelry Sail

    67 Long Wharf, Boston

    • Enjoy a sail out into the Boston Harbor with entertaining period actors and musicians
    • Sit back and relax with your favorite drink supplied by a well-stocked bar
    • Explore the naval history and prepare for a rousing chorus of shanty singers
    • Partake in the drinking festivities with Madeira, Port, Grog and delicious beverages
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    10 positive reviews

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