Once dubbed the “friendliest town in America,” Sayville is one of the most popular areas on the South Shore to shop and dine. Visitors can walk the tree-lined streets and explore the Maritime Museum, Loughlin Vineyard and the weekly farmer’s market. Unique shops, fabulous restaurants and seasonal festivals make Sayville the perfect day trip destination for any duo looking for a nice way to spend time together.
The Sayville Inn
One of the oldest restaurants in town, Teddy Roosevelt used to arrive here on horseback. Reopening under new ownership this past fall, The Sayville Inn is a lively hotspot for locals. This historic venue with comfortable seating and nautical vibes serves up great chowders, seafood and steaks. Come early or you’ll have to wait to be seated.
Recommended plates: Avocado Toast, Long Island Clam Chowder, Stuffed Quahog and Hot Coffee Burger. Eat here.
Off the Block Kitchen & Meats
This meat lovers’ paradise, a finalist for Pulse’s Great Burger Battle, is one of the most exciting new places to dine in Sayville. Part butcher shop, part eat-in restaurant, couples rave about the locally sourced meats and produce. The modern, rustic décor is both simple and chic with open views to the kitchen to watch meals be prepared. The dining room is often packed, but diners can eat at the bar or order dinner to go to enjoy at home.
Recommended plates: Apple Glazed Brussels Sprouts, The Duck Buns, Smokehouse Burger and Steak Au Poivre. Eat here.
La Tavola Trattoria
Where do you go when you’re in the mood for Grandma’s meatballs, but you don’t want her interrogating your new date? La Tavola, a cozy restaurant known for serving delicious “country Italian food with flair.” The hidden outdoor patio is a favorite dining spot, but the inside accommodations are lovely too. Gluten-free options available.
Recommended plates: Watermelon & Feta Salad, Black Mission Fig Pizza, Pan Roasted Diver Sea Scallops and the Life Changing Doughnut. Eat here.
Sometimes, you’re not in the mood for a big date night meal. When this happens, visit American Cheese. Touted as being “comfortable in all the right ways,” this artisanal cheese shop boasts a beautiful “eatery” with a rustic, farmhouse feel. Enjoy a delicious cheese and meat plate paired with a glass of wine or craft beer. Hours and menus change often, so check the website before visiting.
Recommended plates: 3 Cheese Platter with fig spread and toasted nuts, American Onion Soup, Hawaiian Flatbread, Chutney and Cheese Panini. Eat here.
This welcoming European style bistro is run by the same owners as Pasta Pasta in Port Jeff. Offering an eclectic New American menu, Café Joelle is a very popular date night spot. The décor is simple, but creative soups, innovative daily specials and a diverse menu ensure that there’s something for everyone. Reviewers exclaim that “every town should have a place like this” and it’s great for “brunch dates” too.
Recommended plates: Grilled Calamari, Grilled Turkey and Brie Sandwich, Chicken Panzanella and raspberry almond cheesecake. Eat here.
The Cull House
When you want a casual beachy atmosphere, The Cull House is the place to be. Located off the beaten path, this diamond in the rough is located right by the ferries. Meals are served on paper plates with plastic utensils, but the nautical vibe and “outstanding” food keep bringing people back. Couples should grab a seat outside on the patio for great food without all the fanfare.
Recommended plates: Lobster Bisque, Baja Fish Tacos, Lobster Grilled Cheese and Summer Bread Pudding. Eat here.