"Local Beer, Wine, and Vodka One of the most popular spots on the island, Cisco Brewers began as a winery 25 years ago and has now grown into a destination that showcases offerings from the Nantucket Vineyard, Triple Eight Vodka, and the Cisco Brewers beer label. Summer weekends there is a lively crowd listening to music and taking advantage of the food carts and raw bar. For a tour and a more intimate view of the production, visit during the week. There is a seasonal shuttle available and the new bike path makes Cisco all the more accessible."

"Classic Cocktails in Slick Setting The Pearl is one of the most highly polished restaurants on Nantucket and their slick bar is a worthy stop even if you don't want to eat. Attracting a glitzy crowd, you’ll find unusual and classic cocktails as well as a carefully curated wine list. For the ultimate evening, reserve the chef’s table on the back deck and have champagne and cocktails beforehand."

"Cocktails and Oysters with Superb People-Watching Cru is a spectacular location for a drink, with the harbor and Billionaires Row as its backdrop. The outdoor patio is great for people-watching, as is the silky-smooth stone-topped bar. The tart and refreshing Crucomber is the signature cocktail: a mix of bison grass vodka, lemon, cucumber, and toasted sesame. If you want to snack, the cocktail pairs well with any of the delightfully fresh crudos and oysters on the menu. After a few, take a walk along the pier and fantasize about life aboard a luxury yacht."

"Cocktails on the Beach Galley Beach has one of the best locations on Nantucket. With views out over the ocean from the dining room and tables spilling onto the beach, there’s not a bad seat in the house. It's a popular spot with a stylish crowd, and the martinis flow freely. Come early to snag a seat for sunset, one of the best shows in town, and as the evening gets underway enjoy the breeze on your face and scrunching your toes in the sand while tiki torches light up the night."

"Drink in the Friendly Party Vibe Award-winning Nautilus offers seasonal cocktails, over 20 wines sold by the glass, and an extensive list of mezcal, beer, and sake. Warm and friendly, this is the kind of place where you’ll no doubt meet the folks sitting next to you at the bar. Owned by a threesome who know their way around the industry, the lively, hip scene almost feels like you're at a cool friend's cocktail party."

"Coffee and Connection The Handlebar Café communal space was opened by the same folks that run Nantucket Bike Tours. Offering a great coffee selection and light bites, it’s a spot where people come to hang out and meet friends. They often have events showcasing local talent in the evenings. Behind the café is an outdoor area, dubbed the Secret Garden, with additional seating."

"Scenic Drinks at the Summer House For an especially scenic drink, try the umbrella-shaded Beachside Bistro at the Summer House. Down a flight of stairs into the gentle dunes, you can't get much further east unless you want to go swimming. A full bar is available and you can snack on the likes of lobster salad or crab cake. Come at sunset, and even though you won't see the sun itself, the entire sky glows pink and dreamy as the waves roll in."

"Fresh Cold-Pressed Juice It’s easy to stay health-focused, even on vacation, if you stop by the Lemon Press. This adorable space in the middle of town has fresh cold-pressed juices and super smoothies. Liquid Sunshine is a winning combination of mango, peach, and organic apple juice. And if you are looking for damage control from the previous evening, try the Scenic Root or Georgia Green. Both will help you get back on track. Also on the menu are delicious sandwiches and photo-worthy toasts."

"Coffee Roasted on the Island Located in the heart of the historic district, the Bean is a fixture for both locals and visitors. Serving drinks made with Nantucket Coffee Roasters beans, the French press brews are rich and satisfying and the espresso is the best I’ve found on the island. There are also teas, pastries, sandwiches, and soups on the menu."