Festivals & Expos

A running list of romantic things to do around Boston

Including Valentine's Day dinners, romantic wine tastings, a chocolate and ice sculpture festival, hotel packages, and more.

Boston Harbor Hotel during the Boston Wine & Food Festival.

While Valentine’s Day falls on a Tuesday this year, there’s still plenty to do around town on February 14 — or you can celebrate the holiday on another day in February.

Whether you’re celebrating with a significant other or some friends this year, set the mood with the below list of romantic things to do around Boston.

Raise your glass at the Boston Wine & Food Festival

The three-month long Boston Wine & Food Festival at Boston Harbor Hotel, which kicked off on Jan. 12 and runs through March 30, brings dinners and wine tastings to town just in time for Valentine’s Day. See the full lineup of events here, like the “Night in Paris” dinner on Feb. 11 or the “Valentine’s Champagne Brunch” on Feb. 12.

Join Eataly’s Valentine’s Day Soiree

Drink wine and nibble on cheese and sweets with your loved one at Eataly’s Valentine’s Day Soiree on Thursday, Feb. 9 from 6 to 9 p.m. Eataly is inviting guests to explore its marketplace while enjoying over a dozen wine, artisanal cheeses, sweets, and more. Finish off the evening by picking up your favorite ingredients for a home-cooked meal, or stay and grab dinner at Eataly.

Savor the chocolate at ‘Salem’s So Sweet’

Salem’s annual chocolate and ice sculpture festival returns for its 21st year this Feb. 10-12, celebrating sweets and local shops just in time for Valentine’s Day. The weekend begins with a ​​kickoff party on Friday evening, and other highlights include ice sculptures throughout downtown Salem on Feb. 10 and 11 and the “Chocolate Hearts Challenge” on Feb. 11 and 12, an app-based scavenger hunt where participants scan QR codes in Salem businesses for a shot at a prize.

Book a dinner cruise on Boston Harbor

Make your Valentine’s Day one to remember with a dinner or champagne tasting cruise around Boston Harbor. Start or end your evening with a champagne tasting cruise on Northern Lights, complete with live jazz music and chocolate-covered strawberries. Or kick the evening up a notch with a dinner cruise, including a plated dinner, champagne, music, and dancing. 

Take a cooking class

Spend time with your loved one, learn something new, and eat something delicious all at the same time. You can check multiple Valentine’s Day boxes with a cooking class in Boston. Pair wine, chocolate, and cheese at Formaggio Kitchen in Cambridge, make handmade pasta and tiramisu at Self Up, bake bread at Forge in Somerville, or stay home and bring the sushi class to you with Cozy Meal.

See ‘Casablanca’ at the Brattle

Head to the Brattle in Harvard Square for its annual Valentine’s Day showing of “Casablanca,” on Feb. 14. The 1942 romance film is about a nightclub owner in Casablanca and his old flame, starring Ingrid Bergman and Humphrey Bogart. There is only one screening this year and tickets are expected to go fast, according to the theater.

Enjoy a glassblowing class

Get crafty on Valentine’s Day with a class at Diablo Glass School. At the end of their 2 1/2 hour class on Feb. 14, guests will leave with their very own handmade stemless wine glasses, learning techniques like working with a blow pipe and adding color.

See a live show

Fancy a midweek night out? Some shows taking the stage on Feb. 14 include Hamilton at the Opera House, Ariel Posen at City Winery, Shawnn Montiero at Scullers Jazz Club, or Red Velvet Burlesque Show in Boston. Or secure tickets for another February day.

Attend a wine tasting

Bonde in Harvard Square hosts a “Love & Luxe: Sparkling Wines, Caviar, & Chocolate” a Valentine’s Day wine tasting on Feb. 14. The event, which starts at 7 p.m. and costs $120 per person, includes four wines plus snacks like chocolate and caviar. Rebel Rebel in Somerville also hosts a handful of wine tastings throughout the month of February.

Ice Skate at the Frog Pond

Celebrate the season by taking a spin around the ice with your partner at the Frog Pond on Boston Common. The outdoor rink is open throughout the winter. On Valentine’s Day, it will be open from 10 a.m. to 9 p.m. Check out the rink’s weekly hours. Admission is $8 and skate rentals are $15.

Pelham House Resort in Dennis Port is offering a Valentine’s Day package.

New England hotels offering romantic Valentine’s Day packages

Get rose petal turndown service at XV Beacon in Boston when you book the “Be Mine” package, which also includes a bottle of Moet Rosé, chocolate-covered strawberries, breakfast in bed (up to $50, room service only), late check-out at 2 p.m., and an upgrade upon arrival (depending on availability). Rates start at $700 plus tax, and the package is available Feb. 10-15.

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Feast on champagne and chocolate at the Boston Harbor Hotel when you book the Romance Getaway, which includes views of the city skyline or Boston Harbor, an $80 food credit for in-room dining or breakfast for two at Rowes Wharf Sea Grille, and overnight parking for one vehicle. The package starts at $795.

When you book the “Breakfast in Bed” package at Encore Boston Harbor during the month of February, you’ll get breakfast for two (valued at up to $35 per person, which can also be used at the Garden Cafe). The cost for the package is $314.

Guests receive homemade macaroons as part of the romance package at Revere Hotel Boston Common, which also includes a bottle of prosecco. The hotel is offering a special Valentine’s Day menu at its tavern-style restaurant Rebel’s Guild from Feb. 11-14. The hotel deal is available Feb. 1-28 and costs $223.

Sip wine and nibble chocolate-covered strawberries during the Valentine’s Getaway package at Pelham House Resort in Dennis Port. The package includes a dozen chocolate-covered strawberries, a local cheese plate, and a bottle of Josh Cellars chardonnay, cabernet sauvignon, or prosecco. The package, available Feb. 2-26, starts at $269 a night and there’s a two-night stay minimum.

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A concierge will assist with special romantic requests as part of the “Love & Luxury” romance package at Omni Mount Washington Resort in Bretton Woods, N.H. The package also includes a bottle of sparkling wine, artisanal chocolates, and late check-out at 1 p.m. The package starts at $314 per night, plus tax and nightly resort services charge.

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