Greenwich Date Night: 6 Romantic Restaurants Perfect for a First Date (or the 50th)
By Cassindy Chao | Elite Matchmaker & Founder of AWM Love
Let’s be honest: where you go matters.
Whether it’s a first date with butterflies or your 12th anniversary dinner, the setting can shape the entire experience. And luckily, Greenwich is full of swoon-worthy spots that make romance feel effortless—even if the conversation needs a little help from the wine list.
Here are six of our go-to romantic restaurants in Greenwich, CT—places we actually recommend to clients who want more than just a nice meal. Each one brings its own kind of magic to the table.
1. L’Escale – French Mediterranean Elegance by the Water
📍 500 Steamboat Road, Greenwich, CT
🌐 lescalerestaurant.com
L’Escale is what happens when the south of France vacations in New England. Tucked into the Delamar Hotel on the harbor, it offers rustic stone floors, candlelit interiors, and waterfront views that practically guarantee a second date.
Why we love it: It's elegant without being stuffy, and the setting makes you feel like you’ve stepped into a movie.
Client Tip: Try the Bouillabaisse or Herb-Crusted Lamb Chops. Sip the Harbor Breeze cocktail (gin + elderflower = flirty and fresh), and end with the Profiteroles—because every date should finish on a sweet note.
2. Tony’s at the J House – Stylish and Modern with Fire Pit Vibes
📍 1114 E Putnam Ave, Riverside, CT
🌐 jhousegreenwich.com/dining
Tony’s is where sleek design meets modern comfort. Nestled inside the chic J House Hotel, it’s a favorite for clients who want something stylish, sexy, and not too over-the-top.
Why we love it: Indoor-outdoor dining, cozy fire pits, and a menu that hits all the right notes.
Client Tip: The Truffle Risotto is rich and comforting, and the Spicy Margarita is a crowd-pleaser with just enough heat. Perfect for warming up a new connection.
3. Terra – Italian Warmth with a Wood-Fired Soul
📍 156 Greenwich Ave, Greenwich, CT
🌐 zhospitalitygroup.com/terra-greenwich
Terra is date-night gold. Between handmade pastas, a wood-fired grill, and an atmosphere that’s both cozy and sophisticated, this is where meaningful conversation and good food meet.
Why we love it: Great for a romantic-but-laid-back evening. Think wine, laughs, and “wow, we really clicked.”
Client Tip: The Wild Boar Tagliatelle is unforgettable. Pair it with the Smoked Old Fashioned—served with flair and a hint of fire.
4. Valbella – Old-School Italian Glamour in Riverside
📍 1309 E Putnam Ave, Riverside, CT
🌐 valbellaristorante.com
Valbella is the grand gesture of Greenwich date night. Think white tablecloths, impeccable service, and candlelight that flatters everyone.
Why we love it: This is where you go to celebrate someone—or impress them right out of the gate.
Client Tip: Order the Lobster Ravioli or Veal Milanese. Finish with their house-made Tiramisu and an after-dinner glass of vin santo. (It’s giving cinema.)
5. The Cottage – Seasonal, Thoughtful, and Cozy
📍 49 Greenwich Ave, Greenwich, CT
🌐 thecottagegreenwich.com
The Cottage is relaxed, refined, and full of heart. With a seasonal American menu and candlelit interiors, it’s a great place for genuine connection—without the pressure of a “fancy” setting.
Why we love it: It feels like dining in a chef’s dream kitchen. Unfussy, but incredibly well done.
Client Tip: Go for the Duck Breast with cherry glaze or the Ricotta Gnocchi. Ask your server about the rotating seasonal cocktails—they always have something surprising and delicious.
6. Homestead Inn – A Quiet, Storybook Setting in Belle Haven
📍 420 Field Point Road, Greenwich, CT
🌐 homesteadinn.com
Hidden in a leafy, elegant corner of Belle Haven, Homestead Inn offers fine dining with the feel of a private country house. It’s the most intimate spot on this list.
Why we love it: You feel like you’ve stepped out of time. The perfect place for quiet, intentional conversation.
Client Tip: Start with the Foie Gras and end with the Crème Brûlée. If it’s warm outside, don’t skip a slow stroll through the garden.
💘 Final Thought
The best dates don’t just happen—they’re curated.
So whether you’re planning a first impression, a reconnection, or anything in between, these restaurants set the stage for the kind of chemistry you can’t fake.
Need someone to enjoy these beautiful moments with? That’s what we’re here for.
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