Dinner with a View at Mystic Brewery

Enjoy a delicious meal and craft beer at Mystic Brewery, while taking in views of the Chelsea River. The industrial-chic ambiance sets the perfect backdrop for a romantic evening. Alternative options: The Chelsea Station Restaurant & Bar, The New Bridge Café.

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Sunset Stroll at Admiral’s Hill

Take a leisurely walk along the waterfront promenade at Admiral’s Hill, and watch the sunset over Boston Harbor. The stunning views and peaceful atmosphere make this a picturesque setting for a romantic evening. Alternative options: Mary O’Malley Waterfront Park, Chelsea Street Bridge.

Comedy Show at Chelsea Theater Works

Laugh the night away with a comedy show at the Chelsea Theater Works. Enjoy talented local comedians and hilarious skits in an intimate setting. Alternative options: The Wilbur Theatre, Improv Asylum.

Wine Tasting at Apollinaire Theatre Company

Indulge in a wine tasting at the Apollinaire Theatre Company, where you can sample a variety of wines and enjoy a casual evening together. The cozy and laid-back atmosphere is perfect for unwinding and connecting. Alternative options: Boston Winery, City Winery Boston.

Paint Night at Art Factory Studios

Get creative and unleash your artistic side with a paint night at Art Factory Studios. Enjoy a fun and interactive activity while creating a unique souvenir to remember your date night. Alternative options: Paint Nite, Muse Paintbar.

Cocktails and Jazz at Ciao Bella

Sip on craft cocktails and listen to live jazz music at Ciao Bella. The intimate setting and vibrant atmosphere create the perfect backdrop for a romantic and relaxing evening. Alternative options: The Beehive, Wally’s Café.

Cooking Class at Chelsea Market Basket

Experience a hands-on cooking class at Chelsea Market Basket, where you can learn new culinary skills and enjoy a delicious meal together. The interactive nature of the class makes for a fun and engaging date night. Alternative options: The Urban Grape, Boston Wine School.

Movie Night at ShowPlace ICON Theatre

Catch the latest blockbuster on the big screen at ShowPlace ICON Theatre, and enjoy a movie date with your significant other. The luxurious amenities and comfortable seating provide a top-notch movie-watching experience. Alternative options: AMC Assembly Row 12, Showcase Cinema de Lux Revere.

Live Music at PA’s Lounge

Dance the night away to live music at PA’s Lounge, a popular local music venue in Chelsea. Enjoy a variety of musical acts and soak up the vibrant atmosphere for a memorable date night. Alternative options: Paradise Rock Club, Middle East Restaurant and Nightclub.

Dessert and Coffee at Pan y Café

End your evening on a sweet note with dessert and coffee at Pan y Café. Indulge in delectable treats and enjoy a cozy atmosphere for a relaxing and intimate end to your date night. Alternative options: Rossetti’s Café, Caffè Paradiso.

Parents, don’t let babysitting woes hinder your date night plans. With Wyndy, you can easily find and book a reliable and experienced babysitter to watch over your little ones while you enjoy a well-deserved night out. Hire a Wyndy sitter today and make the most of your date night in Chelsea, MA.