One of the best Boston seafood restaurants (hit them up on Pier 4 in the Seaport) has a Nantucket outpost. The Nautilus, which originated in Nantucket, serves small seafood plates izakaya-style, including meaty crab fried rice, prawns a la plancha, oyster tacos, and a Peking duck that you and your friends should order after a day out on a boat or the green.

If you’re looking to dress up and splurge on dinner in the island’s most idyllic setting, head to Topper's in Wauwinet. They’ve got an ever-changing prix-fixe tasting menu, but the more casual a la carte options are always our pick. Sit outside on the bustling deck and watch the pink sunset over the bay while you wait for a stream of chicken and mushroom crepes with vin joune, steak frites with old bay fries, and a loaded lobster roll. Wash it down with a perfectly boozy and tart Wauwintini.

Right in the middle of town, you’ll find a lovely patio with all the twinkly lights, exposed brick, and heat lamps. Besides just giving good lighting, this spot is a strong pick for a date or a night out with friends. There’s also a cozy indoor space with a few tables and seats at the bar. Order the Korean pork BBQ or duck carnitas for the table, and round out the meal with spicy wings and the crab tostada.

Via Mare is a Venetian small plates spot with a menu of nothing but hits. Start off with fresh bread and whipped butter that’s a pure hit of dairy, and the perfectly funky smoked salmon and everything bagel spice arancini. They always make fantastic use of summer staples and island produce, like the loaded tomato toast using heirlooms grown just a mile or two away. And make sure to order two of the crispy taters loaded with parm crema and prosciutto crumble.

Focus on the small plates at this Asian spot that doubles as a concert venue most summer nights. The blue crab rangoons are the freshest we’ve ever tasted, the baby back riblets are sticky and spicy, and the tuna tartare larb stands out due to the addition of fresh papaya salad mixed in. For entrees, the black cod bento box (with fried tempura vegetables and a tofu and tomato salad) is the best choice on the menu, and the smashburger with black garlic truffle cheese is is reliably tasty.

Claudette's makes some of the island's best sandwiches. The options are simple, and we prioritize the ham and cheese, the veggie, the roast beef, and the turkey salad. Order any of them with the works (cheddar cheese, tomatoes, red onion, shredded carrot, and cucumber) and house sauce (a mixture of mayo, spicy brown mustard, and horseradish). Also, be sure to get it on their whole wheat bread.

Gallery Beach is open all day, but it's really perfect for date night—think amazing views from a space overlooking the beach, or dine on the sand itself. Yes, you can sit with your toes in the sand—either under a tent or the sky—and get down with things like miso-yuzu butter-poached local lobster and a Return of the Rose spritz with vodka, ramazzotti rosato, grapefruit, and rose water.

The last time we hit up Breeze, we ran into local royalty—Patriots coach Bill Belichick—which is probably all the endorsement some of you need. We can’t guarantee you’ll run into the leader of a sports team, but you’ll always find a back patio where you can sample wines by the glass and bottle and order from menu with Portuguese influences. They’re open for breakfast, lunch, brunch, and dinner (brunch standouts include the pork belly cornmeal pancakes and a solid lobster roll).

Nantucket’s most famous brewery has three bars serving Cisco craft beer, wine, and cocktails, and is an essential island hang. There are plenty of picnic tables and food trucks like Big Hug Dumplings and the Lobster Trap Truck. Cisco gets crowded at the height of the season, but it’s pretty much the perfect vacation day drinking situation. Just know that it’s sort of in the middle of nowhere, right off Hummock Pond Road.

Nantucket’s best bagels come from Slow to Rise, a current pop-up that’s at the wildly popular Sustainable Nantucket Farmers & Artisans Market downtown every Saturday morning. And it’s worth getting out of bed early and fighting the crowds for their bagels, spreads, sourdough focaccia, and cookies (especially the brown butter chocolate chip). Most of their food sells out within the first couple of hours.

The word is out on Island Kitchen, so get there early (by 9am or so) for lunch and brunch, unless standing in line and waiting around is something you enjoy. Open for breakfast, lunch, and dinner, this unpretentious mid-island spot does acai bowls, smoothies, crab salads, and fried chicken sandwiches, all in a laid-back space. You can grab one of the cozy indoor seats, but the sprawling patio is where it’s at during summer.

Millie’s is worth the bike ride to Madaket Beach for sunset margaritas, fish tacos, and lobster quesadillas. The restaurant’s coastal dishes are heavily influenced by California cuisine, which basically just means you can get guac or queso and chips for the table along with a fresh lobster roll. They’re first come, first served before sunset, so get there early to hear a hundred or so drunk people on vacation freak out over the sun dipping into the horizon.

After a morning whale watching or golfing, stop by this counter-service deli for some of the best sandwiches on the island. They do pulled pork, grilled chicken, and classic New England-style lobster rolls—all hearty options that will keep you happy until dinner. Walter’s doesn’t have seating, so plan to head to the boat, beach, or wherever you’re staying to eat. You’re going to pass this spot on your way to the ferry—it’s a three-minute walk—so do the smart thing and grab a lobster roll to go.

This chic restaurant and bar pours the best cocktails on the island, and does it all in a space that’s romantic with sexy lighting. Sip a Chai Chai Slide with rye, masala chai, and coconut cream, grab some seats at the bar with your person, and order a spread of arctic char crudo, smoked whitefish tea sandwiches, and red lentil hummus with dukkah.

Get your to-go clambake, lobster rolls, fried seafood, and bags of steamers from this small fish market. Outdoor seating is extremely limited, but the dishes are fresh and come out fast, so if you can't get a table, take a few freshly steamed lobsters and fried clams back to your share house and go to town. Coleslaw, fries, and corn on the cob complete your meal, and while you’re there, grab a filet of cod or swordfish for the grill later.

One of the best things about vacation—besides not being obligated to check your email—is packing a picnic for the day’s adventures, and Something Natural will hook you up with superior provisions. Freshly-baked bread, big sandwiches with roasted meats, and fancy sodas make this sandwich shop a must-stop for a casual lunch. The curry chicken salad sandwich is excellent, but if that’s not your jam, there’s a sprouts, vegetable, and hummus sandwich and even a PB&J.