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Valentine's Day Roundup

Whether you're single, newly attached, or celebrating decades of Valentine's Days together, Charles Square is your one-stop-shop for dining and entertainment. And if you forgot to order those roses- do not fret. Our concierge team can help with that, too. Just ask for Charlotte, Frank or Patrick!

Here's a roundup of everything available in Charles Square on February 14:


Voted most romantic restaurant in Massachusetts by Reader's Digest - you'll want to book your table immediately.

This is the kind of occasion that white table cloths are meant for…an intimate meal, decadent Italian food and Ornellaia wines. Guest sommelier Lois Leonard of Classic Wines will be will be pouring Ornellaia's premier wines to accompany Chef Pagliarini’s four-course menu starting with sfizi, moving to a shareable Antipasti San Valentino, a choice of pasta or secondi and ending with Pastry Chef Renae Connelly’s jewel-like "Cioccolatini fatti in Casa” that can be ordered ahead and waiting on the table. Head bartender Charles Coykendall also will be offering a special lover’s cocktail to kick off the evening. The four-course dinner is $85 per person and $50 for wine pairing (special pricing for some wines).

Antipasti San Valentino (example selection)
• Bruschetta with ricotta, roasted walnuts, pomegranate and aged balsamic
• Italian white cilento figs with prosciutto di parma
• White anchovies with fennel pollen, charred peppers, golden raisins and pine nuts
• Warm marinated olives and salame felino and winter citrus
• Burratina with sea salt and sicilian extra virgin olive oil

Dinner: 5pm

Make your reservation now.

Henrietta's Table

Looking for something a tad more casual? You won't see a prix fixe menu from Chef Davis and his team. Instead rely on their consistent à la carte menu - and definitely save room for dessert. Chef Danny's Chocolate Peanut Butter Mousse Cake is cause for celebration on its own. American beers and wines are also on tap, as well as a special Valentine's cocktail (also known as Just-a-Typical-Wednesday-Night cocktail).

Supper: 5:30-10pm

Make your reservation today.


Leather booth seating, dimmed lights, specialty cocktails. Noir has all of the makings for a romantic evening or a fabulous gossip session with girlfriends. The Black Dahlia is a staple order - vodka, triple sec, blackberries, pomegranate juice - but you can also never go wrong with a bottle of Nino Franco Rustico Prosecco. It's also open until 2am every evening for all of you night owls.



Joelle Lurie is no stranger to The Regattabar or to Boston. Holding a Bachelor of Music from Boston University's College of Fine Arts, Joelle has has released 2 albums & 1 EP, earning accolades from the likes of NPR and performances at Lincoln Center, Rainbow Room, and more. The intimate vibes at Regattabar make for the ultimate date night as Joelle serenades you for the evening.

Show starts at 7:30pm and tickets are $25.

Purchase tickets here.


Looking to take the elevator home after dinner or the show? Or perhaps postponing Valentine's Day celebrations until the weekend? Then book the Suiteheart Romance package, which includes:

  • suite accommodations
  • complimentary overnight parking
  • breakfast for two at Henrietta's Table or through in-room dining
  • bottle of sparkling wine
  • chocolate-covered strawberries

Book your romantic getaway in Harvard Square today.

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