10 Second Date Ideas: Boston

For a second date in Boston, go to a place that has a fun atmosphere, but does not cause a lot of pressure to have to speak the entire time. Second date ideas can be daunting because you want to get to know your date a little more, yet intimidation and nervousness may set in if conversation comes to a stand still. Try these places:

  1. Duck Tours.  Take a ride on a "DUCK," an authentic World War II amphibious landing vehicle, renovated for sightseeing. The tour passes by many of Boston’s historical sights and famous buildings, and then crashes into the Charles River. With a tour guide talking most of the time, there is no pressure to keep up a constant conversation. If it’s a little chilly, the open aired vehicle will provide an excuse to get a little closer to your date.
  2. Walk in the North End.  This trendy and chic neighborhood of Boston is bustling with great Italian restaurants and bakeries. Have dinner at Strega, maybe you’ll spot some celebrities, and then take a walk down to the water. Visit on a summer weekend when festivals are held. The streets close, the smell of fair food fills the air, and laughter from playing games sweeps through the crowd.
  3. Romantic Swan Boat ride.  Stroll around Boston Common and take a ride on the Swan Boats. For over 130 years, the Swan Boats have floated in the Public Garden, which was the first botanical garden in the U.S. These Swan Boats are the only boats of their kind in the world. This makes for a very romantic second date in Boston. 
  4. Faneuil Hall and Quincy Market.  These two buildings offer a great place to shop, eat, and relax on a second date. Park your car and walk over to the party! Faneuil Hall was erected in 1742 as a public market and place for town meetings. Quincy Market was also used since the Revolutionary war times for political meetings and the like. There are many street vendors and performers lining the outside cobblestone walkways and great food and shops on the inside.
  5. Ice Skating at Boston Common Frog Pond.  Opening in mid-November, the Frog Pond is a great place for a second date. Enjoy the crisp, cool air while getting to know each other. If you or your date is a novice skater, it is a chance to hold each other tight so nobody falls. The Frog Pond features concessions, skate rentals, rest rooms, and a warming area.
  6. IMAX at the Boston Museum of Science.  Experience the world's largest movie theater screen.  Movies are shown on a five-story-tall IMAX® Dome screen, which wraps audiences in larger-than-life images of flora, fauna, and faraway places. A state-of-the-art digital sound system completes the effect. This is a great way to take a second date on an adventure.
  7. New England AquariumBring your date into the enchanting world of fish and aquatic animals. In the center of the main building is the 200,000-gallon Giant Ocean Tank. The tank is encircled by a four-story spiral ramp. To help keep the peace, scuba divers feed the sharks several times a day.
  8. Comedy Connection.  The Comedy Connection in Boston was voted “The Best Comedy Club in the Country” by USA Today and “Boston’s Best Comedy Club” by the Improper Bostonian since 2000. It is one of the longest running comedy clubs in the country.  Take your date out for a night full of laughs where many famous people once stood.
  9. Blue Man Group.  An Award-winning theatrical production that has been described as “ground-breaking”, “hilarious”, and “visually stunning”, is the perfect second date place in Boston. This show is about three blue guys that take the audience through a multi-sensory experience that combines theatre, music, art, science, vaudeville, and humor.
  10. TOMB presented by 5WITS.  For those interested in Ancient Egypt, or like to have some structured fun planned for a second date, pretend you are an archeologist trapped in a Pharoah’s tomb. This is an interactive experience in which guests find themselves trapped in a tomb and the only chance of making it out alive is to solve riddles and puzzles.
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