If you’re in Norwalk, there’s always Barcelona, naturally. BUT: a nice place to stop in is also Strada 18. Valentine’s Day just works well with Italian, and this place is perfect for anyone interested in a variety of pizza toppings—they have gluten-free—as well great stuff from oven. You can also wander into a warm spot, such as Match, nearby, for a drink afterward, or LOCAL, if you’re looking for a craft brew.
On the other side of Norwalk, there’s Fat Cat and Bar Sugo—excellent pizza, a good variety of drinks, and cozy environs. Around the way, Paella is perfect for a large, shared dish of Spanish cuisine—the chef will always visit your table—and for a cocktail or beer before/following, BJ Ryan’s is near, as is its informal BANC House.
For Italian in New Canaan, go with Cava Wine Bar—good lighting, great food and a cavernous setting make it a special choice. You also can’t go wrong with South End; while it can get noisy, with its wide array of (cheerful) spirits and scotches/whiskies, you can prep the meal with—or finish with—a drink and dine on superb gastropub cuisine. If you’re just after nibbles, charcuterie and cheese, also try Barolo.
You can’t go wrong with The Restaurant in Rowayton. OK, technically it’s “The Restaurant at Rowayton Seafood,” but if you want to canoodle over seafood locally, essentially, this is the best spot for it. Sails is another great Rowayton locale, as its wine menu is extensive, and the dishes you can sample from are extremely inventive—foie gras fries? Yes, please!
Ten Twenty Post is a perfect Darien spot for the big night: a fine bar, and an eclectic variety of eats, both unpretentious and more “refined.” Darien Social’s also a hip spot—maybe you start there with drinks and small plates? The warm interiors at The Goose also provide a nice dine-and-drinks stop-in, as you can’t beat a fireplace with inglenooks. While not so many would nominate a “cold meal” at this time of year, if you are in search of good sushi, then Darien has some of the best at Matsuri, with its smooth, ambient atmosphere, as well.