Montreal’s recently augmented cultural offerings make this summer the perfect time to take a food-loving family on a foreign escape just a two-hour flight away. Among the city’s wealth of new attractions, you can experience a simulated archaeological dig at the new Mariners’ House pavilion at Pointe-à-Callière Museum of Archaeology (514-872-9150, pacmusee.qc.ca/en); explore the just-opened Rio Tinto Alcan Planetarium (espacepourlavie.ca), which is like an artful space station with its shiny conical theatres jutting into the sky; or catch the Festival International de Jazz de Montréal from June 28 to July 7 (montrealjazzfest.com; tickets from $20). When you’re ready to eat, go to Olive + Gourmando (514-350-1083, oliveetgourmando.com) for a fun breakfast, La Croissanterie Figaro (514-278-6567, lacroissanteriefigaro.com) for a bistro lunch, and Venti (514-284-0445, osteriaventi.com) for a casual yet excellent Italian dinner. Call ahead for a table at Le Club Chasse et Pêche (514-861-1112, leclubchasseetpeche.com), where you’ll want to complement the fabulous haute cuisine with a ginger martini. Flop down at LHotel (877-553-0019, lhotelmontreal.com; from $180), a bank-turned-boutique-hotel with an impressive art collection, both owned by the jeans mogul Georges Marciano.

The sophisticate of the Twin Cities, Minneapolis has emerged as an epicenter of Upper Midwest hipness, home to cultural attractions designed by Frank Gehry, Herzog & de Meuron, and Jean Nouvel. But it’s the dining scene, supplied by the fertile fields encircling the metro area, that has made this northern city a must-do. Start your progressive feast at the Bachelor Farmer (612-206-3920, thebachelorfarmer.com), inspired by immigrant Scandinavians and seasonally sourced from an extensive roof garden. Move on to the meatcentric Butcher & the Boar (612-238-8888, butcherandtheboar.com) for wild boar head cheese and bourbon. Save room for chicken with Parmesan Malt-O-Meal and preserved truffles at Tilia (612-354-2806, tiliampls.com). Wind down over sexy French lounge fare at La Belle Vie (612-874-6440, labellevie.us) from uber-chef Tim McKee. Then waddle back to your contemporary-art-filled hotel, Le Méridien Chambers (612-767-6900, lemeridienchambers.com; from $249), for a dose of zero-calorie sleek.

Alongside 70 miles of coastline, San Diego has a craft-brewing scene running amok recently: 18 of the city's 66 breweries opened just last year, with 20 more expected to join the scene by the end of 2013. Pick which ones to visit by taking a tasting tour at Bottlecraft Beer Shop & Tasting Room (619-487-9493, bottlecraft.myshopify.com), where friendly experts curate flights of the local art. Nearby, the Mike Hess Brewery (619-786-4377, hessbrewing.com), is scheduled to open in June and will offer creamy, flavorful pours and a tours from a 50-foot sky bridge over the shiny new facility. Next grab a bite to eat at Toronado (619-282-0456, toronadosd.com), a pub known for its tremendous rotation of local drafts. Drive north, stopping at Ballast Point Brewing Company (858-695-2739, ballastpoint.com) for its Calico Amber Ale and specialty scotch ales, before reaching the beautiful, sprawling Rancho Bernardo Inn (877-517-9340, ranchobernardoinn.com; from $169). Spend the next day visiting North County standouts: Start at the immense brewery and gardens at Stone Brewing Co. (760-471-4999, stonebrew.com); check out Plan 9 Alehouse (plan9alehouse.com), the brand-new Kickstarter-funded nano-brewery expected to open this month; and finish with tastings at the Lost Abbey (lostabbey.com), which recently bagged awards for its Belgian- and French-style ales.

Chicagoans don’t need much of a reason to drive the scenic route up the eastern side of Lake Michigan through Harbor Country. But foodies might love an excuse: Since 1991, Julee Rosso, the coauthor of The Silver Palate Cookbook, has owned the Wickwood Inn (269-857-1465, wickwoodinn.com; from $229), where you can barely turn a corner without encountering one of her delicious homemade treats. In fact, the inn’s entire menu—brunch items, happy hour hors d’oeuvres, and sweets—seems like a time machine back to the extravagant 1980s style of entertaining that Rosso’s seminal book (written with Sheila Lukins and now in its 100th printing) translated for home cooks. Rosso offers three-hour classes to weekend guests interested in getting their hands dirty—but not during the summer, because, she says, everyone would rather go to the beach. You’ll just have to return in the offseason.

The relatively untouristed Willamette Valley, within half an hour’s drive of downtown Portland, is producing well-regarded Pinots—Noir and Gris—from winemakers known to muck around vineyard tasting rooms in Wellingtons and pour the wines for you themselves. Start your tour at one of the area's pioneering wineries, Sokol Blosser (5000 NE Sokol Blosser Ln., Dayton, 503-864-2282, sokolblosser.com), with its organic vineyards and LEED-certified cellar; its brand-new tasting room, designed by the acclaimed local architect Brad Cloepfil, is set to open July 1. Then pay a visit to the dozen “garagiste” tenants—small producers so named for their tendency to blend wines in their garages—at the nearby Carlton Winemakers Studio (801 N. Scott St., Carlton, 503-852-6100, winemakersstudio.com). Drink local while eating local at Thistle (228 NE Evans St., McMinnville, 503-472-9623, thistlerestaurant.com), from the farm-to-table-focused chef Eric Bechard. Sleep it off at the cosseting Allison Inn & Spa (2525 Allison Ln., Newberg, 503-554-2525, theallison.com; from $330), where the “Pinot therapy”—relaxing grape-seed scrubs and facials—goes to your body, not your head.