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It’s hard being number two—just ask Guadalajara, Mexico’s second-largest city. Although Travel + Leisure gave Guadalajara the first runner-up spot on its 2016 “Best Places to Travel” list (Bocas del Toro, Panamá took top honors), the landlocked city remains a secondary destination within Mexico, where it simply can’t compete with hot spots like Cancún, Mexico City and Puerto Vallarta (the latter being about a 5-hour drive to the west). Always a bridesmaid, never a bride.

RELATED: 7 worthwhile Mexico destinations that aren’t Cancun

Guadalajara’s got plenty of charms, of course, from the old town scattered around its 15th-century cathedral, to hipster ‘hoods whose coolness rivals those down the road in CDMX (aka Mexico City), to being within day-trip distance of the birthplace of tequila. Here’s how to make the most of 3 days in Mexico’s proverbial second-fiddle city.

Day 1

Fiddle or violin, as it were. As you traipse around the Guadalajara Cathedral and other old-city attractions, including the Rotonda de los Jalisciences Ilustres monument and sprawling Mercado San Juan de Dios, it’s almost certain that you will come across a mariachi band.

Photo courtesy of Robert Schrader

Even if you’re not the one being serenaded by the street symphony of trumpets, guitars and, yes, violins, there are few better introductions to Guadalajara than hearing its de-facto theme music. Mariachi became a staple in Guadalajara in the 19th century, having migrated into the city center from the surrounding countryside.

Apart from this, Guadalajara’s old city is a wonderful place to try the food of Mexico’s Jalisco state. Or, rather, to re-acquaint yourself with it. Dishes like flautas (rolled tacos made with chicken or pork) and hearty pozole hominy soup are staples of Tex-Mex cuisine, which has become synonymous with “Mexican food” north of the border. Restaurante La Chata is an authentic spot to sample Guadalajara’s flavors, and a convenient one too—it’s just steps from Hotel Morales, a heritage five-star that makes for a classy, luxurious home in Guadalajara.

Speaking of class, there’s also Guadalajara’s bountiful culture to contend with. Whether you go back in time—way back in time—at the archaeology-focused Regional Museum of Guadalajara, or see what sort of performance is on at the Roman-inspired Teatro Degollado, Guadalajara has plenty of substance to back up its style.

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Day 2

Guadalajara might only be 25% as populous as Mexico City, but don’t think it’s only got a quarter of its cool factor. Wake up on your second day in Guadalajara and have your hotel call you a taxi to the Providencia neighborhood, which is perhaps the hippest of the city’s hipsters hang outs.

Indeed, you might run into the governor of Jalisco state here, although that has more to do with happenstance—his official residence is here—than hipness. Whether or not you manage to see el gobernador, immerse yourself in the Providencia lifestyle with coffee and a light meal at CAPPUCINO 96, a preview into your post-trip scrapbook at Papeleria Mony stationery shop or retail therapy at Conspiración Moda, where a dozens-deep team of stylists will help you fine-tune your look.

Photo courtesy of Robert Schrader

Another place to be among Guadalajara’s coolest residents is Zapopan, which serves a secondary purpose, as well—it’s home to almost as much heritage architecture as the center of Guadalajara proper. From the 17th-century Basilica of Our Lady of Zapopan, to the dramatic Arcos Vallarta, to a Japanese garden that might have you thinking you’re in Honshu rather than Jalisco, Zapopan effortlessly expresses the timelessness and timeliness that co-exist in Guadalajara today.

Day 3

You could easily spend three full days in the center of Guadalajara—or you could spend day three in the birthplace of tequila. Wasn’t that an easy decision?

To be sure, making a day trip to Tequila (original name, right?) is as much about how you go as what you do there. While public buses are affordable and frequent, arranging a taxi through your hotel allows you to stop whenever you want. And you will want to stop: The rolling fields of blue agave that carpet the countryside between Guadalajara and Tequila are a selfie lover’s dream. Alternatively, ride the Tequila Express train, which among other advantages allows you to drink en-route.

Photo courtesy of Robert Schrader

Tequila isn’t just about distilleries, though, even if you could occupy your entire day with tours from big-name tequila producers like Cazadores, Cuervo and Herradura—and some small names as well. It’s a small town that’s dripping in charm as much as your margarita glass will drip with sweat, whether you stay in town and traipse around Parroquia Santiago Apostol church and its plaza, or make an excursion to the gorgeous Cascada los Azules waterfall. (Pro tip: Sober up before you jump in!)

If you’re drunk in the first place, that is. The tequila you find in the spirit’s birthplace is so fine you might prefer to sip, which is an apt metaphor for Guadalajara in general. It might not be as intoxicating as the Yucatán or as strong as the country’s capital, but the taste of three days in Mexico’s second city will linger with you a way that’s second to none.

Featured image courtesy of Robert Schrader

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Tagged: Destinations, International, Mexico, Types of Travel

Robert Schrader

Robert Schrader

Robert Schrader

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