Owner Howie Mallowes set up shop across from the Martha's Vineyard ferry terminal, where his restaurant specializes in infusing New York–style pies with gourmet ingredients such as shrimp, gorgonzola, and steak. Amongst the fresh harbor air, staffers shuttle whole pizzas and single slices to tables of visitors and regulars until the wee hours of 2 a.m. every night. The menu plays host to more than a dozen specialty pizzas such as the Pizans "Soon to be Famous" Clam Pizza, which just signed a three-picture deal with DreamWorks. Pizzas share stomach space with pastas, oven-baked grinders, footlong subs, beer, and wine.
The family who owns One Horse Pizzeria and Saloon crafts a pizza for every palate, with options ranging from traditional thin-crust pies to the inventive Tom The Turkey pizza with turkey, cranberries, and gravy sauce. Those pizzas share table space with fresh salads, pastas with housemade sauces, and sandwiches. Located in a quaint red bungalow with white trim, the restaurant also features a wooden bar where patrons can sip wine and more than 30 types of cold beer.
The menu offers seafood, veal, pasta, and chicken prepared from time-tested family recipes. Rev an appetite engine with coconut shrimp ($11) or homemade fennel-sausage antipasti ($9) and a glass of wine, such as Beringer Pinot Grigio ($6.50) or Trivento Pinot Noir ($7). Traditional Italian entrees include lobster, shrimp, and scallop cannelloni gratineé ($16); chicken campagnolo (egg-battered medallions with prosciutto, mozzarella, sherry, and mushroom demi-glace, $19); and veal bella Napoli (sautéed veal, shrimp, asparagus, portobello, tomatoes, and buffalo mozzarella, $23). Point Judith clams with shrimp and your choice of white, red, or fiery fra diavolo sauce over linguine ($22) and shrimp and scallop della casa ($22) will make any fisherman fondly remember his finest seafood- or mermaid-catching sprees. The trattoria experience would be incomplete without dessert, so sweeten endings with crème-brûlée cheesecake, tiramisu, or spumoni (all desserts are $7).
Cavalieri's Wood Street Pizza is a family-owned-and-operated cookery that has been serving up house favorites and custom creations for 18 years. While the basic variety of pizza exists ($6.75 for 10" to $16.25 for a full sheet), Wood Street's pizza menu shines with exotic topped discs, such as buffalo chicken pizza, taco pizza fiesta, and a lasagna pizza pie. Specialty pizzas are $9, $18, or $27 (or $18.25 for thin crust), depending on size. If you prefer your pizza folded into a crescenty pocket of flavor, opt for one of the 20 varieties of calzones ($2.75 for single up to $27 for a 25" giant). Wood Street also whips up appetizers, grinders ($5.75–$6.75), a soup of the day ($4.25), salads ($2.50 for a side salad, others $4.50–$7.25), and pasta creations ($6–$9.95). Check the menu for changing specials for lunch, dinner, sandwiches, soups, and pizza, such as June's chicken Caesar.
A family-owned sustenance staple for more than 60 years, Leo's Ristorante's homey redbrick exterior greets families to generous portions of homemade Italian and American comfort-food dishes culled from fresh ingredients. Leading off a stacked menu is the hearty New England clam chowder ($4.59 cup, $5.59 bowl), which sets the table for wholesome, heavy-hitting handhelds such as the chicken parmesan sandwich ($7.99 small, $8.99 large) and the Big Red meatball sub ($6.99 small, $7.99 large). The tortellini a la Carolina ($15.99) surrounds its tricolored, circular cheese pasta with grilled chicken and a light butter sauce, while the spaghetti a la Gina's ($12.99) savory red-sauced noodles send forks into a pasta pirouette. Enjoy a large, one-topping pizza ($12.99), adorned in culinary confetti such as pepperoni or olives, or wrap taste buds around the Milano panini ($8.99), containing grilled eggplant, smoked mozzarella, fresh tomatoes, and garlic olive oil.
It would be impossible for just one chef to handle the entirety of Siena's massive menu of Italian eats. That's why Executive Chef Nick Jankowski works in close collaboration with his sous chef, Jill Sanger, to create the restaurant's hearty Old World flavors. Those run the gamut from handmade eggplant parmesan to italian meatloaf stuffed with provolone, spinach, and roasted red pepper. Before 16-inch pizzas go into the brick oven, they get topped with ingredients such as homemade meatballs, toasted garlic, and candied walnuts.
To accommodate all types of diners, Nick also alters many of his dishes for gluten-free and vegan patrons. Selections from a handpicked wine list can complement any meal, as can an extensive selection of classic and original cocktails. After meals, guests can settle their stomachs with specialty coffees, dessert martinis, or an 18-year Macallan single-malt scotch, the last chance for patrons to drink it before it goes off to college and stops calling.