5 Hilariously Awesome Date Ideas

January 15, 2020

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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    Boston Harbor Sail (Liberty Clipper)

    (20)
    Set sail for the Boston Harbor on Liberty Clipper, a magnificent schooner! On your Boston sail, you'll see the sights in Boston Harbor and everything the ship has to offer. The crew will invite you to help hoist the sails and even to take a turn at the helm. There will also be a bar stocked with soda, water, Sam Adams on draft, mixed drinks, wine, and snacks. Take the wheel, set the sails, or just sit back and enjoy the sights and beauty of the Boston Harbor and her islands! The choice is yours!
    Boston Harbor Sail (Liberty Clipper)

    67 Long Wharf, Boston

    • Set sail into the Boston Harbor on the magnificent schooner known as Liberty Clipper
    • Enjoy the beautiful views of the harbor and have fun interacting with the knowledgeable crew
    • Partake in delicious refreshments and a bar stocked with your favorite drinks
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    20 positive reviews
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    Sunset Sail

    (28)
    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, as the Sun dips below the horizon, you'll get to see and hear it all. Experience the sights of the Boston Fish Pier, The Moakley Federal Courthouse at Fan Pier, Castle Island, the Donald McKay monument, the Charleston Navy Yard, and much more, on a sail aboard the Adirondack III, a classic 80 foot pilot schooner. Experience Boston like never before, on a schooner, a drink in hand, and a knowledgeable captain and crew to ask about all the stories behind some of Boston's most unforgettable sights.
    Sunset Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience a beautiful Boston Harbor sunset on the water
    • Ask your knowledgeable staff and crew anything you'd like to know about the sights
    • Enjoy the ride, see the sights and have a drink onboard
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    28 positive reviews
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    Art of Mixology

    (4)
    This comprehensive Art of Mixology course won't teach you to memorize drink recipes; it will rather focus on learning and understanding the essential skills behind making any alcoholic drink of your dreams -- even frozen drinks, cocktails, daiquiris, and layered shots! You'll learn the bar setup, how to distinguish between different alcohols and mixers, and how to use all the necessary bar equipment. Once you've mastered these skills, you will be equipped to make any drink imaginable! Memorization will come with time and "practice" that will surely make you the life of every party.
    Art of Mixology

    45 Quincy St, Cambridge

    • Begin to understand the essential skills behind bartending during this mixology class
    • Learn how to make beverages ranging from classic frozen drinks to layered shots
    • Practice using bar equipment, pouring, and distinguishing between alcohols
    • Receive a Harvard's "Art of Mixology" certificate after completing the course as veritable proof of your training
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    4 positive reviews
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    Codzilla: Thrill Boat Ride

    (5)
    Codzilla has arrived. And Boston Harbor will never be the same. Now there are more thrills, more laughs and more speed than you ever imagined as you zip across the ocean at up to 40 miles per an hour. But don't worry. A ride on Codzilla is as entertaining as it is thrilling. The wind roars. The music blares. And the waves will splash as the crew recounts the legendary tale of how Codzilla came to Boston. This wet and wild ride is 40 minutes of full blast, sensational fun for the entire family.
    Codzilla: Thrill Boat Ride

    Long Wharf, Boston

    • Move through the water at up to 40 miles an hour on a thrilling and entertaining boat ride
    • Enjoy the thrills and laughs while out on Boston Harbor aboard a ship named Codzilla
    • Experience what it's like to ride on a 2800 horsepower vessel for 40 full minutes
    • Prepare for a wet ride that mixes relaxation and enjoyment
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    5 positive reviews
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    Brunch Cruise

    (1)
    Admire the unforgettable sights of Boston on board this breathtaking climate controlled yacht. This cruise offers the most unique brunch setting on Boston's famous harbor. Relax and be captivated by the city skyline while enjoying a delectable buffet brunch menu. Your cruise experience begins as you board the luxury yacht at Rowes Wharf. After a quick stop for a commemorative boarding photo, one of the hosts will greet you and escort you to your private table. Enjoy a complimentary glass of champagne or tour the ship's three climate controlled decks. A great way to start your day is by watching the boat castoff from one of the observation decks. Bring your appetite when you return to your private table, the Executive Chef and galley staff present you with an imaginative buffet of appetizers, entrees, salads and desserts that is sure to please any number of tastes. Enjoy live entertainment while boarding and dance to music from the DJ on board. Return, 2 hours later. Relaxed. Refreshed. As you depart, you'll find your boarding photo ready for purchase. Cruise Route: Departing from Rowes Wharf, it cruises along Historic Boston Harbor from Castle Island to George's Island, then east to the Boston Light on Little Brewster Island, and back north to Charlestown Naval Yard before returning to the Wharf. Cruise Route may vary depending on weather.
    Brunch Cruise

    200 Seaport Blvd, Boston

    • Hop aboard a luxury yacht at Rowes Wharf for a relaxing brunch out on the water
    • Sip champagne and explore three climate-controlled decks while on board
    • Dance to a live DJ and have fun with the sights and entertainment to go along with your meal
    • Return to land relaxed and refreshed
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    1 positive reviews
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    The Ultimate Personalized Pedicab Tour

    This customized tour of Beantown is sure to be cool ... beans. (Sorry -- couldn't resist!) Hop into the back of a pedicab and get ready to enjoy a street-level introduction to the city like no other! Go where you want and see what you want, as you're driven around by a knowledgeable, local guide. Based on your interests and the sites you choose at the beginning of your tour, your guide will construct an impromptu exploration that will leave your head spinning. Whether you're interested in art, architecture, history, or romance, anything is possible on this choose-your-own-adventure tour!
    The Ultimate Personalized Pedicab Tour

    105 W Newton St, Boston

    • Embark on a customized pedicab adventure through scenic Boston where you choose the path to take
    • Create your own sightseeing tour as you pick out the collection of sites you want to see
    • Learn fun facts about the city and your chosen sites from your friendly, local guide
    • Enjoy a leisurely, intimate introduction to the city that won't tire you out completely
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