With panoramic views overlooking the Newport Harbor, 22 Bowen’s encompasses a casual-chic atmosphere. Excellent service enhances meals on the wraparound deck or inside the bustling yet cozy main dining area. Across the cobblestone path on the wharf's other side sits Portside, a seasonal bar that offers refreshing cocktails and bar snacks during summer months.

7a Foods redefined the packed beach lunch game when it opened in 2011. Located mid-island in West Tisbury, this eatery proves that there’s no such thing as a simple sandwich; the menu rotates, but there are always house-baked goodies and you can’t go wrong if you order something involving their freshly-baked foccaccia. It’s a wonder no one discovered the genius combination of asparagus, lemon aioli, pickled onions and dried blueberries until these guys slapped them between two slices of bread.

A good option for a romantic night out, Alchemy serves elegant but unfussy cuisine in a beautiful two-story setting. New American dishes take center stage, and the varied venue offers a main dining room, alfresco veranda and lively upstairs pub, each with modified atmospheres but the same reliable cuisine.

Just a few blocks beyond Nantucket’s downtown fringe, American Seasons has the air of a longtime classic but the cuisine of a hip new spot. Foodies delight in the farm-to-table dishes, which may include such tastes as carrot soup with cream cheese falafel and bulgar wheat risotto with farm egg and fried pickled ramps in a baked potato broth. With a wine list with over 500 titles, American Seasons is the perfect spot for a romantic evening, especially when dining in the garden patio.

A local favorite for decades (it opened in 1943 as the Captain St. Clair Brown Diner), the Art Cliff, one room in a simple white cottage, is located off busy Beach Road in Vineyard Haven near the ferry terminal. Owner Gina Stanley, who took over the kitchen in 2000, whips up such delectable breakfast fare as almond-crusted French toast and “Drunken Sailor” pancakes with pecans and rum raisins. It can be tricky during high season to score a table in the dining room, which seats 39; your best bet is to arrive early (it opens at 7 a.m.).

This local favorite, open year-round, is located in an old mansion and serves an innovative mix of Mediterranean, Asian and Middle Eastern dishes. While the main floor is home to a formal dining room, the cellar bar has a legendary burger menu. Live music is performed on most summer nights.

A spanking fresh raw bar and casual South End scene make B&G Oysters a good choice for gourmet versions of New England specialties. From fried Ipswich clams to buttery lobster rolls and the to-die-for lobster BLT, the food is fresh, well prepared and served by a gracious, attentive staff. The restaurant sits in a chic subterranean space in the heart of the Tremont Street restaurant row and boasts an open kitchen, a minimalist design and a pretty backyard patio. Although B&G’s pint-sized space tends to fill quickly, the long rectangular bar provides plenty of extra spots for singles or couples who don’t mind dining side-by-side. (A corner seat at the bar will work for parties of three as well.)

For an early morning sugar rush, islanders head to Martha’s Vineyard Gourmet Café & Bakery, Oak’s Bluffs’ baked goods mainstay. While the signature treats are available at the main store, the real secret lies behind the shop at the back door, where the kitchen doles out freshly baked donuts for a late-night treat (7:30pm-1am) during the summer season. The goods are delicious in the morning, but a piping hot donut—especially the substantial apple fritter—satisfies in an entirely different way.

An urban clam shack with incomparable views of the skyline, the restaurant sits on Fort Point Channel across from the financial district and has an authentic New England atmosphere, complete with gruff service, rough picnic tables and a smattering of tough locals. On a warm afternoon or evening, this is a classic spot to pass the time over messy lobster rolls and ice-cold beers. In the summer, some diners arrive by boat, the small sails contrasting with the soaring skyscrapers across the channel. But even in the winter, the Crab remains open. When the wind dies down and the sun comes out, a February afternoon may suddenly feel like springtime.

Less than a mile from the Beach Plum Restaurant lies its main supplier, Beetlebung Farm, a five-acre spread where owner and Beach Plum chef Chris Fischer hosts the occasional pop-up supper. Elegant evenings are spent in the farm’s intimate greenhouse, outfitted with a long picnic table and soft lighting. When the farm is literally beneath the table, you’re guaranteed quality ingredients—and a unique menu; as Fischer says, “Every [meal] is different. It depends on what we have and what the people want to do.”

Helmed by a vet of Alice Waters’s famed Berkeley restaurant Chez Panisse, Behind the Bookstore is a charming local favorite for an alfresco breakfast, lunch or dinner.

Beloved by Newport weekenders and locals for breakfast and brunch, this spot on the water offers beautiful outdoor dining and delicious fare. Even New Yorkers rave about the lox bagels.

While some prefer the ice cream at Mad Martha’s, Ben & Bill’s is far more consistent when it comes to quality. The creamy flavors are reliably excellent, and Ben & Bills also stocks an impressive selection of chocolate confections sure to induce a sugary haze.

Located on Charles Street in Beacon Hill, Bin 26 is a chic, simple wine bar, an ideal place to cozy up with some friends over a great bottle of vino. Owned by the same family as Lala Rokh, the restaurant also serves a simple Italian menu, but I recommend instead choosing from a selection of charcuterie and cheese and pairing your choice with one of the more than sixty wines available by the glass or the two hundred options to be had by the bottle. Pours come in 100-, 250- and 500-milliliter sizes and are priced starting at five dollars.

Situated on the bustling Bannister’s Wharf, this waterfront-dock-turned-fine-dining establishment is known for its award-wining New England Clam Chowder. Sip on a cocktail and people-watch at the outdoor patio bar or enjoy freshly caught lobster tail and Nantucket Bay scallops inside The Commodore’s Room. For a more casual ambiance, snag a table at the Tavern.

There’s still no easy way of getting into this island favorite—reservations are accepted only for dinner—but locals and longtime visitors have accepted the fact that lining up in front of the unassuming restaurant is part of the experience. Opened in 1992 by chef Jeff Worster and Susan Handy, the BYOB restaurant has a small dining room with white-washed walls and green copper chandeliers, as well as a lovely outdoor dining space. The hearty breakfast, served until 1 p.m., is the most popular; arrive early and be prepared to wait.

Baseball fans should not miss stopping at the Bleacher Bar, a watering hole built inside Fenway Park’s famed Green Monster. Part of the wall has been cut out so that patrons, who enter from Lansdowne Street rather than through the ballpark itself, can look directly onto the field. You’ll save yourself the cost of a ticket if you want to watch part of a game from here. Bleacher Bar is a bit of a dive, but that’s part of the draw.

Bricco occupies prime real estate on the North End’s main drag, Hanover Street. Lively almost any night of the week, this welcoming trattoria is a popular local meeting spot for dinner and drinks. The menu offerings, which noted food critic John Mariani has called “among the finest Italian cooking in the country,” include traditional antipasti, homemade pastas and a selection of hearty tenderloins for meat lovers. Service can be a little slow, especially on crowded weekend nights, and the noise levels rise to earsplitting when the bar area is packed. Nevertheless, be sure to request a table downstairs, not one on the quieter mezzanine level, and ask to be seated by the window that looks onto Hanover, especially on a snowy evening. It may be loud, but the fun of being swept up in the scene overcomes the restaurant’s minor flaws.

Though he now calls New England home, Chef Karsten Hart originally hails from New Orleans and grew up with one German and one Italian parent. Hart's menu emphasizes seafood and many dishes, such as the fluke and lobster etouffee and a delicious muffaletta, celebrate his background.

The best dishes on the menu are the double-stuffed lobster roll, steamed littleneck clams and Jonah crab stuffed quahogs. The Dining Room and Lawn have the same menus, but very different atmospheres. Whereas the Dining Room is more formal and popular with an older crowd, during the summer months, the Lawn is the place to be, overlooking the water and a lawn covered with white Adirondack chairs.

Chilmark’s general store may not be as pretty as Alley’s in West Tisbury, but it’s a popular spot for a slice of pizza (there are twenty-five kinds on the menu) and island gossip. If you’re on your way to the western beaches and Aquinnah, it’s a great place to stop for a picnic or grab takeout. The green rocking chairs on the large porch out front are wonderful for a lazy afternoon snack.

Chilmark Tavern celebrates the Vineyard’s natural bounty with fresh seafood and produce from local farms and markets. The chef refers to the endeavor as an American Tavern and serves dishes such as Martha’s Vineyard oysters, Allen Farm lamb cooked two ways, fluke fillet with a Meyer lemon beurre blanc and warm rhubarb cobbler.

Indagare Tip: There’s a bar menu with delicious tastes, which is perfect for a quick dinner if you arrive late on the island.

An institution in Newport, the Clarke Cooke House is as famous for its dining options as it is for its late-night revelry. The 18^th-century building on Bannister's Wharf houses multiple dining rooms but favorites are the traditional Porch, with white tablecloths and green-painted bamboo chairs, and the main, ground level Bistro, which is largely open-air during warm months. Cuisine is typical to Newport, highlighting Rhode Island seafood specialties and sushi is offered in the summer. The SkyBar (at the top) and basement-level nightclub Boom Boom Room are the hottest post-dinner drinks and dancing spots in town.

A longtime reliable takeout place in Siasconset, Claudette prepares hearty—and pricey—sandwiches to go for visitors en route to the local beach. You can also eat on the petite patio in front of the cute storefront with its red-and-white-striped awning.

Just minutes from artisan market Formaggio’s and The Buttery, Toro’s sister restaurant is arguably one of Boston’s best restaurants since opening in 2009. Helmed by experienced restaurateurs Ken Oringer and Jamie Bissonette , Coppa serves Italian-style tapas and superb pizzas. My mom loved a zucchini bruschetta so much that we developed our own recipe at home, but nothing compares to the original. It is hard to get a table for a reason; the food is fabulous, the restaurant is small and cozy, and it doesn’t take reservations. It’s hard to pick what to recommend because it is all so delicious, but a few inventive items are the bone marrow pizza topped with beef tongue and horseradish and a twist on the traditional spaghetti carbonara, which steps things up a notch with sea urchin speckled throughout. The menu isn’t only for culinary daredevils, however, with equally delicious margherita pizzas, simple pastas and a long list of stuzzichini, small Italian bar snacks.

Located within the Nantucket Culinary Center, this cheery café welcomes guests with plenty of natural light and comfortable banquette seating. In addition to excellent coffee, pastries, sandwiches and salads, the menu features a selection of goodies created by chefs in town. Locals swear that these cookies are the most delectable treats on island.