From left: Toro Bravo in Portland; The Island Cow in Sanibel Island; Tartine in San Francisco

PENNY POLLACK: Portland, Oregon

The things you do on vacation. Like wait an hour and a half to eat tapas at Toro Bravo, a hipster cute resto nestled in a cozy neighborhood of Portland. Fortunately, the melt-in-your-mouth sautéed spinach laced with pine nuts and raisins followed by grilled spring onions with salbitxada sauce makes it all worthwhile. So many yummy tapas, so hard to stop, but I did—leaving just enough room to bliss out on fresh churros and chocolate dipping sauce.

Andy Ricker won a James Beard award in 2011 for Best Chef-Northwest and shortly thereafter was visited by the Chicago’s Next crew to prep for their Thai menu. A year after I lunched at Pok Pok, I’m still thinking about the zingy Pok Pok salad, sticky fish sauce wings, smoky grilled eggplant, and the mysterious kai krapao khai dao (minced chicken is only the beginning). No white tablecloths at Pok Pok. No problem getting a rez for lunch or dinner—last spring anyway. Unpretentious and ridiculously cheap. Utterly Portlandish.

Bakeries are to Portland what steakhouses are to Chicago. There are gazillions of them, and they are mostly terrific. I loved the macarons and shortbreads at Pearl Bakery and the breads and canelés at St. Honoré, but the almond croissant at Nuvrei made me break my eating-on-vacation rule: Never go to the same place twice.


JEFF RUBY: Sanibel Island, Florida

There are two things everyone talks about in this barrier island on Florida’s Gulf Coast. One is the amazing seashells, which everyone claims aren’t as amazing as they used to be. (I don’t know, 250 different varieties is enough for me.) The other is Pinocchio’s Original Italian Ice Cream, which is apparently as good as ever. The homey place has made more than 100 of its own flavors over the past 30 years, all topped with an animal cracker. People go nuts for the Sanibel Krunch, some kind of chocolate/toasted coconut concoction, but I like the Dirty Sand Dollar, a caramely bomb with chocolate flakes and malted milk balls.

Floridians have a special place in their hearts for fried food. Wait, that came out wrong. But OK, the best place to get it in Sanibel is The Island Cow, a breezy, unabashedly cartoonish place with parrots in cages and lounge chairs on the front lawn. The Cow’s enormous menu is packed with conch fritters, po’boys, and the like—and the free sweet muffins and an order of “frickles” (a huge helping of fried pickles for $7) is probably enough for a meal. But I saw plenty of folks digging into a Holy Cow platter, a deep-fried bacchanal that includes clams, scallops, oysters, calamari, and whatever fish the kitchen deems freshest.

I’ve never been to a restaurant like The Green Flash before, and can’t imagine I ever will again, unless I can find somewhere else on earth where I can eat a crunchy grouper sandwich while watching dolphins and manatees frolic in their natural habitat. The boat-friendly restaurant nestles right up to picturesque Pine Island Sound, and the big windows give you a front row view of all kinds of sea creatures, whose relatives you just might be eating. Or just go around sunset, have a slice of Key lime pie and a couple of Green Flashes (stiff piña coladas topped with melon liqueur). Now that’s a vacation.


CARLY BOERS: San Francisco

I’d happily join the perpetual queue every evening to savor Bi-Rite Creamery’s intensely flavored, house-churned scoops of roasted banana, honey-lavender, and chai-spiced milk chocolate ice cream, and tasty morsels (chopped almond toffee! fudgy brownies! lemon gingersnaps!) from the adjoining bakery. (I suppose it’s for the best that I live 2,000 miles from the Mission.) As if the creamery weren’t enviable enough, there’s Bi-Rite Market—a cute-as-a-button, 70-year-old locavore's paradise—just across the street.

Also in the Mission—and also sporting a line every time I’ve been by—Tartine manages to tick every box from my “dream bakery” checklist: crusty bread (bonus points for being crafted by a James Beard award-winning pastry chef), rustic pastries (I’m still fantasizing about the pain au jambon from my January visit), and soul-warming lattes.

The food at NoPa is seasonal, local, wood-fired, and all things trendy, but this spot stands out from the organic pack. Sure, the ridiculously attractive staff has something to do with it, but NoPa also does dinner until 1 a.m. every night (darn near unheard of in Chicago), executes veggie dishes with as much gusto as meaty ones, and has a wine list that’s stellar even by California standards.


Photography: (Toro Bravo) Flickr; (Sanibel Island) handout; (Tartine) Esther Kang