December 22, 2024

Something different is always welcome when it comes to celebrating Valentine’s Day in Massachusetts and New England. Yes, we love the fancy dinners, but we also want to do something special and memorable that will stand out. These may not be a magical trip to Paris (or in my case Disney World) but they are experiences that should raise the bar for the evening.

PS Remember, with Valentine’s Day falling on a Tuesday, you can celebrate it the weekend before, or the day of!


Diablo Glass School, Boston

Warm up with a glass blowing demonstration and watch as wine glasses, jewelry and items are made right before your eyes. All classes are listed on their web page and they sell out fast… especially the wine tastings. WEB: https://diabloglassschool.com/


1620 Winery Tasting at Cordage Park, Plymouth

The ambiance of this winery has made it a fast favorite for weddings and date nights for everyone south of Boston. They also have a smaller Wine Bar overlooking the water in Plymouth with live music and a smaller menu. And if you do want to make an over night trip of it, we suggest staying at the John Carver Inn nearby. WEB: www.1620winery.com/1620-winery/ HOTEL WEB: https://www.johncarverinn.com/


Ice Castles NH

Once these Ice Castles opened they started to dominate everyone’s Instagram feed. A little bit of a drive, but we suggest staying at the Woodstock Inn and Brewery nearby if you want to turn this into an overnight trip! WEB: https://icecastles.com/new-hampshire HOTEL WEB: www.woodstockinnbrewery.com/


Tower Hill Greenhouses, Boylston

In addition to the beautifully packed, and warm, greenhouses, they are launching their PRISMATIC exhibition valentine’s weekend. It promises orchids, prisms, and iridescent hues. It will also feature music, drop-in crafts, and activities for all ages to add to the winter season. WEB: towerhillbg.org/prismatic-orchid-exhibition/


Harvard Square Chocolate Crawl Chocolate Tour, Cambridge

Treats, both cold and hot, and unique because of the plethora of great spots in Harvard Square. Off the Beaten Path provides some of the most popular tours in the Greater Boston area, and their Chocolate Crawl is a crown jewel of their offerings! WEB: https://offthebeatenpathfoodtours.com/tour/harvard-square-cambridge-chocolate-tour/


Classic Harbor Line Valentine’s Day Boston Harbor Jazz/Sunset Cruise

Romantic Valentine’s Day Jazz & Champagne Tasting Cruise! Start or end your romantic evening with a light champagne tasting and stunning views of Boston and enjoy romantic jazz tunes by their house jazz band WEB: https://www.boston-sailing.com/browse-by-theme/valentines-day/


S#!TFaced Shakespeare Romantic Comedy Taming of the Shrew!, Somerville

Yes, I took liberties with suggesting this one! But you will laugh! Taming of the Shrew could be called the first Romantic Comedy of all time, and the way this troop presents it will bring out even more laughs. Definitely an adult take on a classic Shakespeare play. WEB: https://www.goldstar.com/events/somerville-ma/sht-faced-shakespeare-the-taming-of-the-shrew-tickets-1