THE CHILDCARE PEOPLE
POWERED BY WYNDY.COM
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THE CHILDCARE PEOPLE
POWERED BY WYNDY.COM
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THE CHILDCARE PEOPLE
POWERED BY WYNDY.COM
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Grace Foster
By Grace Foster
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Date Night Ideas in Chestnut Hill, MA

Cozy Dinner at Davio’s

Start your date night off with a delicious meal at Davio’s, a classy Italian steakhouse in Chestnut Hill. The elegant ambiance, attentive service, and mouthwatering dishes make it the perfect spot for a romantic dinner. Indulge in their signature pasta dishes, aged steaks, and decadent desserts while sipping on a glass of wine from their extensive selection.

Alternative options: Seasons 52, The Capital Grille, Barcelona Wine Bar

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Wine Tasting at Urban Grape

For wine-loving couples, a wine tasting at Urban Grape is the ideal date night activity. Explore a variety of wines from around the world as knowledgeable staff guide you through the tasting experience. You can even purchase a bottle of your favorite wine to enjoy at home as a memorable keepsake of your date night.

Alternative options: Brookline Fine Wine & Gourmet, The Urban Grape South End, Central Bottle Wine & Provisions

Stroll Through Hammond Pond Reservation

Enjoy a leisurely walk hand-in-hand through Hammond Pond Reservation, a peaceful oasis in Chestnut Hill. Take in the beautiful scenery, listen to the sounds of nature, and spend quality time together away from the hustle and bustle of everyday life. Don’t forget to pack a picnic to enjoy by the water!

Alternative options: Larz Anderson Park, Chestnut Hill Reservoir, Cutler Park

Comedy Show at Improv Asylum

Laugh your way through a date night at Improv Asylum, a comedy club known for its hilarious improv performances. Sit back, relax, and enjoy a night of gut-busting laughter as talented comedians take the stage to entertain you. It’s the perfect way to unwind and let loose with your partner.

Alternative options: Laugh Boston, The Comedy Studio, Nick’s Comedy Stop

Painting Class at The Paint Bar

Get creative with your date night by attending a painting class at The Paint Bar in Chestnut Hill. No experience is necessary as talented instructors guide you through creating your own masterpiece while enjoying a glass of wine. It’s a fun and interactive way to bond with your partner and unleash your inner artist.

Alternative options: Muse Paintbar, Pinot’s Palette, Sip & Script

Date Night Ideas in Chestnut Hill, MA

Couples Massage at Bella Sante Day Spa

Indulge in a pampering experience with a couples massage at Bella Sante Day Spa. Relax and unwind as skilled therapists melt away your stress and tension, leaving you both feeling rejuvenated and refreshed. It’s the ultimate way to relax and connect with your partner on a deeper level.

Alternative options: Exhale Spa, Bliss Spa, G2O Spa & Salon

Movie Night at Coolidge Corner Theatre

Catch a movie at the historic Coolidge Corner Theatre for a classic date night experience. Snuggle up in the vintage theater seats and enjoy a film together on the big screen. With a mix of indie films, classic favorites, and special events, there’s always something exciting to see at this iconic venue.

Alternative options: Kendall Square Cinema, AMC Boston Common, Showcase SuperLux

Dessert Date at J.P. Licks

Satisfy your sweet tooth with a dessert date at J.P. Licks, a popular ice cream shop in Chestnut Hill. Indulge in a scoop of creamy homemade ice cream, a decadent sundae, or a freshly baked cookie. With a cozy atmosphere and a wide variety of flavors to choose from, it’s the perfect spot for a romantic treat.

Alternative options: Toscanini’s, FoMu, Emack & Bolio’s

Live Music at The Burren

Experience live music at The Burren, a lively Irish pub and music venue in nearby Somerville. Enjoy a night of toe-tapping tunes, traditional Irish music, and lively performances by talented local artists. Grab a pint of Guinness and dance the night away with your partner for a fun and unforgettable date night.

Alternative options: Club Passim, Lizard Lounge, City Winery

Cooking Class at Create A Cook

Embark on a culinary adventure with a cooking class at Create A Cook in Newton. Learn new recipes, techniques, and skills as you work together to create a delicious meal from scratch. From pasta-making to sushi rolling, there are plenty of classes to choose from for a hands-on and interactive date night experience.

Alternative options: Boston Center for Adult Education, Sur La Table, The Cambridge School of Culinary Arts

Frequently Asked Questions

To book a sitter through Wyndy, simply download the app or visit their website, create an account, and enter your date night details. You can browse through available sitters, read reviews, and book your preferred sitter in just a few clicks.

Yes, you can request a specific sitter for your date night through Wyndy. Simply check the sitter's availability, send them a booking request, and wait for them to confirm. If the sitter is unavailable, you can easily browse and book another sitter that fits your needs.

The cost of hiring a sitter through Wyndy for a date night varies depending on the sitter's rate, the number of children, and the duration of the booking. You can view each sitter's hourly rate on their profile and calculate the total cost before booking.

Wyndy sitters undergo a thorough vetting process that includes background checks, reference checks, and in-person interviews. They are experienced caregivers with a passion for working with children and providing quality care. You can rest assured that your children are in good hands with a Wyndy sitter.

Yes, you can schedule a recurring date night with the same sitter through Wyndy for added convenience and peace of mind. Simply discuss your schedule and preferences with the sitter, set up a regular booking, and enjoy worry-free date nights knowing your children are well cared for.

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