Romantic Dinner at Novara

For a romantic night out, head to Novara, a cozy Italian restaurant in Milton. Enjoy delicious pasta dishes, seafood specials, and a wide selection of wines in a warm and intimate setting. After dinner, take a leisurely stroll through Milton Village and admire the historic architecture and charming shops.

Alternative options: The Plate in Milton, Abby Park in Milton, Steel & Rye in Milton

On-Demand Childcare in Your Neighborhood

Book a Sitter

Outdoor Movie Night at Borderland State Park

Pack a picnic and cozy blankets for a romantic outdoor movie night at Borderland State Park. Watch a classic film under the stars while snuggled up with your partner. Don’t forget to bring some popcorn and your favorite snacks for a perfect evening under the open sky.

Alternative options: Pope John Paul II Park in Dorchester, Wollaston Beach in Quincy, Castle Island in South Boston

Wine Tasting at Granite Links Golf Club

Indulge in a wine tasting experience at Granite Links Golf Club, where you can sample a variety of wines while enjoying breathtaking views of the Boston skyline. Learn about different wine varietals and pairings from knowledgeable sommeliers for a fun and educational date night.

Alternative options: Boston Winery in Dorchester, Boston Harbor Distillery in Dorchester, City Winery in Boston

Couples Massage at Inman Oasis

Relax and unwind with a couples massage at Inman Oasis, a tranquil spa in Cambridge. Treat yourselves to a soothing massage that will melt away stress and tension, leaving you feeling rejuvenated and pampered. After your massage, take a dip in the hot tub for the ultimate relaxation experience.

Alternative options: G2O Spa + Salon in Boston, Bella Santé Day Spa in Lexington, Spa InterContinental in Boston

Live Music at Steel & Rye

Enjoy an evening of live music at Steel & Rye, a stylish restaurant and bar in Milton. Sip on craft cocktails and listen to talented local musicians as you unwind with your partner. Dance the night away or simply sit back and enjoy the music in this trendy and vibrant setting.

Alternative options: The Beehive in Boston, Scullers Jazz Club in Boston, City Winery in Boston

Sunset Kayaking at Houghton’s Pond

Experience a romantic sunset kayaking adventure at Houghton’s Pond in Milton. Rent a tandem kayak and paddle around the serene pond as you watch the sun set over the water. Enjoy the peaceful and picturesque surroundings as you bond with your partner in this unique and memorable date night activity.

Alternative options: Charles River Canoe & Kayak in Newton, Paddle Boston in Cambridge, Community Boating in Boston

Cooking Class at Sur La Table

Get creative in the kitchen with a hands-on cooking class at Sur La Table in Chestnut Hill. Learn new culinary skills and techniques as you prepare a gourmet meal together under the guidance of expert chefs. Enjoy the fruits of your labor as you sit down to savor your delicious creations.

Alternative options: Boston Center for Adult Education in Boston, The Cambridge School of Culinary Arts in Cambridge, The Paint Bar in Newton

Comedy Show at Nick’s Comedy Stop

Laugh the night away at a comedy show at Nick’s Comedy Stop in Boston. Enjoy a lineup of talented comedians who will have you in stitches with their hilarious jokes and anecdotes. Share a few laughs with your partner as you enjoy a night of comedy and entertainment.

Alternative options: Improv Asylum in Boston, Laugh Boston in Boston, The Comedy Studio in Cambridge

Painting Class at Muse Paintbar

Unleash your inner artist with a painting class at Muse Paintbar in Patriot Place. Sip on wine or cocktails as you follow along with a professional artist who will guide you step by step in creating your own masterpiece. Take home your painting as a special memento of your creative date night.

Alternative options: The Paint Bar in Newton, The Painted Burro in Somerville, Social Art in Boston

Hike at Blue Hills Reservation

Embark on a scenic hike at Blue Hills Reservation, where you can explore miles of trails and enjoy stunning views of the Boston skyline. Pack a picnic lunch and take in the natural beauty of this picturesque park as you reconnect with your partner in the great outdoors.

Alternative options: Middlesex Fells Reservation in Medford, Breakheart Reservation in Saugus, Arnold Arboretum in Boston

If you’re looking for a fun and romantic night out in Milton, MA, consider trying one of these date night ideas to unwind and reconnect with your partner. Remember, it’s important to take time for yourselves as a couple to nurture your relationship and create lasting memories together. So go ahead, hire a sitter through Wyndy, and enjoy a well-deserved date night in Milton, MA.