Get quick Asian-influenced takeout fare—including hot and sour soup, teriyaki chicken, and spring roll wraps—at The Kitchen (249 Prune Alley, 360/376-6958, 11 a.m.–7 p.m. Mon.–Sat. in summer, 11 a.m.–4 p.m. Mon.–Sat. in winter, closed Sun. year-round, $13). Another good spot for finger food is The Lower Tavern (Langell St. at Orcas Rd., 360/376-4848, 11 a.m.–10 p.m. Mon.–Sat., 11 a.m.–9 p.m. Sun., $12), where the tasty bar meals include the best fish and chips in town, along with burgers and soups. The television has sports on most afternoons, making this a good rainy day retreat.
For Mexican meals, Bilbo’s Festivo (360/376-4728, 11:30 a.m.–3 p.m. and 5 p.m.–9:30 p.m. daily, $28) is a local legend. It has distinctive handcrafted furniture and large servings of tasty Mexican/Southwest favorites, mesquite-grilled meats, seafood, and fresh-fruit margaritas. Crab enchiladas are especially good, and the chips and salsa are house-made. Outside dining is available in the courtyard. The setting is fun and friendly, but meals are surprisingly expensive; it’s easy for two people to drop $60 with drinks. Bilbo’s stays crowded even in the winter months, so reservations are advised.
Get pizzas by the slice or pie at Portofino Pizzeria (A St., 360/376-2085, www.portofinopizzeria.com , 11:30 a.m.–8:30 p.m. Mon.–Sat., 4 p.m.–8:30 p.m. Sun., $18). The deep-dish pizza is your best bet. This is a fine place to take kids and offers a view across Eastsound from the second-floor deck.
Enjoy the great outdoors on a sunny summer day by sliding into one of the picnic tables set in the garden courtyard at Sunflower Café (Prune Alley at A St., 360/376-2335, 7:30 a.m.–3:30 p.m. daily, $9). Housed in a cute little cottage right on the main drag, this acclaimed eatery serves up healthy and hearty breakfasts and fresh deli foods for lunch.
Inn at Ship Bay Restaurant (326 Olga Rd., 360/376-5886, www.innatshipbay.com , $22), just east of Eastsound, is the best place to taste fresh oysters in the San Juans. This spacious old farmhouse overlooking Ship Bay attracts both visitors and locals for a variety of fresh-from-the-sea daily specials; try the Pacific rim hot pot: salmon, rockfish, and mussels in a hot and sour broth with udon noodles. The appetizer list always includes fresh oysters from Buck Bay, prepared in a multitude of ways.
Set inside the historic Outlook Inn New Leaf Café (171 Main St., 360/376-2200 or 888/688-5665, www.outlookinn.com , call for reservations, $22) has a great view of East Sound and is conveniently located right in the hubbub of town. The New Leaf menu focuses on free-range meats and seafood, offering smaller-size dishes à la carte to encourage family-style eating.
Enjoy excellent Northwest cuisine at the acclaimed Christina’s (located on Main St. upstairs and directly behind the gas station, 360/376-4904, www.christinas.net , reservations 5–9 p.m. daily, $30). The menu changes daily, and there’s a patio out back overlooking the sound. Christina’s has been here for more than two decades, so you know it’s doing something right. Diners will appreciate the cozy atmosphere, attention to detail, and excellent service. It’s a great special-occasion spot, and children are welcome. Stop by 4–6:30 p.m. for lighter and more reasonably priced meals off the bar menu.