Jennifer Pearson-Smith packs a few vital tools when she embarks on a road trip: a vintage Pendleton blanket, a soft-sided cooler, a corkscrew and a cheese plane. “We’ve dined al fresco in such destinations as Sedona, Lake Tahoe and Napa,” says the Costa Mesa-Calif.-based social media consultant. “It’s so much fun to discover local markets when selecting picnic eats.”

One of her favorite picnic cities—San Diego, where she has dined above the crashing waves at Sunset Cliffs— is also a favorite of Travel+Leisure readers. In the annual America’s Favorite Cities survey, readers ranked 38 cities on such urban qualities as luxury shopping, cocktail lounges and cool food trucks. But to calculate which cities offer the best grassy dining, we looked at the more outdoor-feast-friendly rankings: parks and gardens, gourmet markets, epic sandwiches, accommodating weather, and perhaps the lovely accompaniment of wine.

With or without a fine bottle, there is something magical about a picnic while traveling: picking up sandwiches, local tacos, or just some fresh bread and cheese (assuming you packed that cheese plane) and settling in for a fresh-air meal and people-watching in a city park. In some winning cities, the best picnic spots offer uniquely local settings, whether you’re next to a natural spring, in front of an iconic band shell, or in the shade of an 80-foot-tall shuttlecock.

Picnicking can also make you feel more like a local—though it’s also important to know the local rules. Pearson-Smith, for instance, has learned that there’s no glass permitted in San Diego’s Balboa Park. “No picnic in San Diego would be complete without sampling a brew or two from the local craft beer scene,” she says, “so I stock up on versions from local breweries like Saint Archer and Ballast Point—in cans.”

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