Romantic Dinner at Terrain Garden Café

Indulge in a romantic dinner at Terrain Garden Café, located in the heart of Westport. The restaurant offers a cozy and intimate atmosphere, perfect for a date night. Enjoy seasonal dishes made with locally sourced ingredients, paired with a selection of fine wines.

Alternative options: Artisan Restaurant, The Whelk, Pearl at Longshore

On-Demand Childcare in Your Neighborhood

Book a Sitter

Wine Tasting at Black Bear Wines & Spirits

Sip on some fine wines at Black Bear Wines & Spirits, where you can enjoy a wine tasting experience with your partner. Explore a variety of wines from around the world and learn about different tasting notes and pairings.

Alternative options: Castle Wine & Spirits, Saugatuck Grain and Grape, Match Restaurant

Comedy Show at the Treehouse Comedy Club

Laugh the night away at the Treehouse Comedy Club, where you can catch a hilarious comedy show with your significant other. Enjoy some drinks and get ready for a night of non-stop laughter and entertainment.

Alternative options: Fairfield Comedy Club, Stress Factory Comedy Club, Bridgeport Comedy Club

Painting Class at The Painted Cookie

Unleash your inner artist at The Painted Cookie, where you can enjoy a fun and creative painting class with your partner. Sip on some wine, nibble on delicious treats, and create a masterpiece to take home as a memento of your date night.

Alternative options: Muse Paintbar, Pinot’s Palette, Painting with a Twist

Live Music at The Spotted Horse Tavern

Enjoy live music at The Spotted Horse Tavern, a cozy spot in Westport known for its great atmosphere and talented musicians. Sit back, relax, and let the music transport you to a world of romance and relaxation.

Alternative options: Amis Trattoria, Rizzuto’s, The Boathouse at Saugatuck

Moonlit Stroll at Compo Beach

Take a romantic moonlit stroll along the shores of Compo Beach, where you can enjoy the peaceful sounds of the ocean and the twinkling stars above. Hold hands, breathe in the fresh sea air, and enjoy each other’s company in a serene setting.

Alternative options: Sherwood Island State Park, Jennings Beach, Burying Hill Beach

Movie Night at the Garden Cinemas

Catch a movie at the charming Garden Cinemas, a local theater in Westport known for its cozy ambiance and diverse film selection. Snuggle up with your partner, enjoy some popcorn, and escape into the magic of the big screen.

Alternative options: Showcase Cinemas, Bow Tie Cinemas, Ridgefield Playhouse

Couples Massage at Adam Broderick Salon & Spa

Treat yourselves to a relaxing couples massage at Adam Broderick Salon & Spa, where you can unwind and de-stress together. Let the expert masseuses work their magic as you both sink into a state of pure bliss and relaxation.

Alternative options: Massage Envy, Aetheria Day Spa, Oasis Day Spa

Cooking Class at Bistro du Soleil

Get hands-on in the kitchen with a cooking class at Bistro du Soleil, where you and your partner can learn to whip up some delicious dishes together. Enjoy a fun and interactive culinary experience, followed by a romantic meal made with your own two hands.

Alternative options: Terrain Kitchen, The Pantry, Stew Leonard’s

Sunset Cruise with SoundWaters

Embark on a romantic sunset cruise with SoundWaters, where you can enjoy breathtaking views of the Long Island Sound as the sun dips below the horizon. Snuggle up on deck, enjoy a glass of champagne, and create memories that will last a lifetime.

Alternative options: Odyssey Cruises, Atlantic City Cruises, Hornblower Cruises

If you’re looking for a reliable and trustworthy sitter to watch your kids while you enjoy a much-needed date night in Westport, CT, look no further than Wyndy. With Wyndy, you can easily find experienced babysitters in your area who have been thoroughly vetted and background-checked. Don’t let childcare get in the way of your quality time as a couple – book a Wyndy sitter today and enjoy a night out on the town!