19 Fun Date Ideas Around Boston for Couples

Amanda Banta said:  Seeing a show at the Brighton Music Hall is a great way to catch an amazing performance at an intimate and unique venue. A variety of indie and alternative bands come through the hall each year, some of which you may recognize from their radio hits. Also, watch the schedule for stand-up comedians that fill the hall with funny jokes. With tickets costing a fraction of shows at the Garden or Xfinity Center you may want to splurge on a few rounds of pre or post-show drinks to make the most of your night.

Amanda Banta said:  Lace up your roller skates and get ready for the nostalgia to hit as you lap the Chez Vous Roller Skating Rink on one of their adult skate nights. You and your date can hold hands with each other, instead of holding onto a wobbly kid just learning to skate, as the DJ spins your favorite tunes.

Take a break and refresh with a cold drink and a slice of hot pizza. Honestly, what else goes better with skating than that?

Amanda Banta said:  Brookline Booksmith is a destination for any book lover and can be a great spot for a cheap date night. Browse the first floor's stacks of new releases in every genre then head downstairs to the Cellar, which houses a huge selection of used books.

The store regularly hosts author readings and events, many of which are held right in the store and free to attend. Listen to a passage from a new book, hear about the author's process or their take on current events, and maybe pick up their new or current volume. Many authors will sign books as part of their events.

Amanda Banta said:  Indulge in a romantic night gazing at the stars at the Coit Observatory, part of Boston University. Learn a bit about astronomy as you view the stars and constellations through telescopes and binoculars. Dress appropriately for the weather as you will be outside.

Amanda Banta said:  Head down to the basement of the Cantab Lounge for a night of original poetry by local writers as part of Boston Poetry Slam. The night begins as with an open-mic session and morphs into the poetry slam, a fast-paced competitive event with poems judged by selected members of the audience. You can bring your own food into the venue, though any drinks must be purchased at the bar.

Amanda Banta said:  Dining at the Top of the Hub can be a pricey Boston date night idea, but getting that view from the top of the hub doesn't have to be. The Skywalk Observatory offers 360-degree views of Boston from the top of the Prudential Center. Watch the sunset across the gorgeous skyline that Boston offers then take a romantic stroll, holding hands of course, down Boylston and Newbury Streets.

Amanda Banta said:  Learn how Taza makes their stone ground chocolate stand out from their competitors in a Taza Chocolate Factory Tour. You will get to see where and how the chocolate is made and, the best part for any chocolate lover, get to sample the product of those processes too! The 45 minute tour is held at the company's Somerville factory.

Kristy Pepping said:  The South End's Urban Grape is the perfect unique date for couples who love wine. Join one of their free tastings and try out some new wines, then select a bottle to take home.

Carly Follett said:  From April through much of September, the Boston swan boats glide across the Lagoon in the Boston Public Garden, just as they have every year since 1877. Snuggle up with your hunnie as you take a nice cruise around the lagoon. Afterwards, you can find a nice, shady spot in the garden for a romantic picnic in the park!

Amanda Banta said:  Bundle up, lace your skates and hit the ice of the Boston Common Frog Pond. Since you are kid-free, you can hold your significant other's hand as you loop around the pond under the twinkling lights and stars. Take a break to warm up with a hot coffee from the cafe and a little snuggling on a bench. The pond typically freezes over in late November and is open daily for skating throughout the winter.

Amanda Banta said:  Friday and Saturday nights at the Charles Hayden Planetarium feature the adults-only Music Under the Dome show series. Jam in your seat to the music of a favorite artist while an exciting visual display shows above and around you in the planetarium's theater. 

Amanda Banta said:  Couples can combine culture and a night under the stars by taking in a performance with Shakespeare on the Common, put on by the Commonwealth Shakespeare Company (CSC). The CSC has brought a different play to town each summer since 1996. Make a night of the event by packing up a cold dinner and spreading out a blanket to have a picnic on the Common before the show starts. Various food trucks and vendors will be on site during each performance as well.

Amanda Banta said:  Explore miles of waterfront Boston with a stroll on the Boston Harborwalk. The path stretches more than 40 miles from Dorchester to Charlestown and East Boston. Museums, restaurants, hotels, historic locations, shops, fishing spots and more can be found along the path, giving you many options to break up your walk and explore the various offerings of the neighborhoods. 

Amanda Banta said:  My husband and I waste a lot of time deciding what to eat on date nights, but one time he came up with a great suggestion - a food truck night!

We skipped the restaurant battle and instead picked a spot in town hosting food trucks, which have been popping up all over Boston lately. We each can choose what we want based on the available trucks. I suggest packing a blanket, grab your food and then heading to your favorite green spot for a date night picnic in the city.

Turn dinner at home into an extraordinary scenic night out by reserving "Balcony Table 77" at Tresca. The exclusive table for two set on the second story balcony overlooks Hanover Street, which is one of the most popular streets in the North End, and pedestrians consistently are looking up to see who are the night's lucky balcony diners. Tresca is co-owned by Bruins legend Ray Bourque and features a menu of traditional Italian cuisine. Reservations for the table can be made only by calling the restaurant.