Under $100: Greenport, N.Y.

Located on Long Island’s North Fork, Greenport is a quaint historic seaport town perfect for a quick summer getaway. Easily accessible via the Hampton Jitney or Long Island Railroad, travel is easy for New Yorkers and other visitors.

Start your day with a walk or jog through downtown. There are many great vantage points along the waterfront, making for a pleasant morning. Make your way to The Cheese Emporium by Bruce & Son for breakfast. Choose from lighter options like an egg white omelet and granola, or heartier dishes like lemon ricotta pancakes and steak and eggs. Spend $8–12 on breakfast.

Kontokosta Winery, Greenport, Long Island, New York © Peter Titmuss | Dreamstime

Greenport is known for its chic shops and boutiques. Browse the stores on Main Street and get lost in the specialty shops hidden on the side streets. You’ll find everything from antiques and clothing to books and sporting goods. Next make your way to Little Creek Oyster Farm & Market to test your skills. The raw bar offers a “shuck yourself” option for their oysters — lesson included. Enjoy a dozen fresh oysters for $16. Keep in mind: If you would prefer to have them shucked for you, the price is almost doubled.

Enjoy a wine tasting at Kontokosta Winery. Opened in 2013, the tasting room is open daily. Tastings start at $15. Continue your boozy tour of Greenport at Greenport Harbor Brewing Company. Sample from the rotating brews on tap. A pint costs $5.

Grab a pie for dinner at 1943 Pizza Bar. Try one of their specialty pies — The New Haven white pie with mashed potatoes, bacon and garlic is a standout. If you’re more particular, create your own from the list of toppings. Spend $10–20. For a nightcap, stop next door at Brix & Rye. Specializing in cocktails, sample a classic drink like a Sazerac or a New York Sour. Cocktails start at $10.