How to celebrate Valentine’s Day in and around Boston

Discover the most romantic things to do in Boston, including shows, wine tastings, dinners, and more.

Patrons at a previous Boston Wine & Food Festival event. Courtesy of Boston Harbor Hotel

Whether you’re celebrating with your sweetheart this year, with friends, or by yourself, there are plenty of ways to make Feb. 14 in Boston a little sweeter. Since it falls on a Wednesday this year, below you’ll find opportunities for mid-week date nights along with things to do on the weekends before and after V-Day, like cooking classes to take, wine tastings to book, and shows to catch. Read on for some of the most romantic ways to celebrate Valentine’s Day in and around Boston this February.

Visit Salem So Sweet

Witch City’s annual chocolate and wine festival returns for its 22nd year Feb. 9-11. All weekend long, visitors can find special deals at Salem’s shops and restaurants, along with a scavenger hunt to win prizes. Over 20 ice sculptures will be installed and illuminated throughout town on Friday and Saturday night, and guests can usually find free refreshments at many of the town’s shops. It’s a great excuse to visit the city during the off-season and try out a new restaurant or even head to the Peabody Essex Museum.

Attend the Boston Wine & Food Festival

The annual festival’s 35th iteration returns to the Boston Harbor Hotel this winter. While the festival features wine dinners, tastings, and seminars from Jan. 12 through March 29, it hosts a few events particularly suited to Valentine’s Day — like the Valentine’s Champagne Brunch on Feb. 11, Romeo & Juliet Amarone dinner on Feb. 15, and Wagyu and Wine Vintage Bordeaux dinner on Feb. 17.

Take a cooking class

Spend a romantic evening learning something new with your loved one at a cooking class this February. Formaggio Kitchen in Cambridge has some fun, cheese-based classes throughout February including “Charcuterie 101” and “French Cuisine and Rare Wines.” Selfup has cooking classes for couples at its downtown Boston location such as “Asian Dumplings and Dim Sum” and “French Steakhouse Dinner,” and Cozymeal lets guests book from dozens of classes like “Authentic Nepalese Cuisine” or “Regional Italian Favorites.”

See a classic romantic movie

The Brattle Theatre near Harvard Square in Cambridge hosts its annual screening of “Casablanca” this Valentine’s Day — but make sure to get tickets early, as it often sells out. The theater is also celebrating V-Day with a screening of “The Princess Bride,” opening Feb. 13.

Enjoy a live show

For a fun night out this February, head to one of several live shows playing in Boston this winter. If you’re looking for a show on Valentine’s Day itself, “The Book of Mormon” takes the stage Feb. 13-18 and the House of Blues hosts a Valentine’s Day burlesque show on Feb. 14. Other shows on Feb. 14: “Stand Up If You’re Here Tonight” and “John Proctor Is the Villain” by the Huntington Theatre Company, “Love’s a Joke” at Laugh Boston, and Patrizio Buanne at City Winery.

Head to a wine tasting

Get romantic while learning a thing or two on or around Valentine’s Day with a wine tasting. Formaggio Kitchen in Cambridge hosts a class on pairing wine, chocolate, and cheese on Feb. 14, while Wild Child in Somerville and curds & co in Brookline both host wine tastings on Feb. 15.

Go ice skating

Enjoy the winter weather and go outdoor ice skating in Boston — the perfect addition to date night. Some of the city’s best outdoor rinks include the Frog Pond on the Common, Skate @ Canal District Kendall, and the Rink at 401 Park in Fenway.