The Berkshires

When I first learned about Tourists Welcome, a converted motel in the tiny town of North Adams, Mass., I tried hard not to roll my eyes. Despite being a reference to the signs once donned by the area’s roadside inns, the name pained me, and the fact that it was owned by Wilco’s bassist and his friends made me skeptical of how it might deliver on anything other than Instagram bait. But I was curious, and a location within driving distance—plus last-minute availability over the Fourth of July—made it ideal for baby’s first vacation.

It took less than an hour for me to toss aside my assumptions and start drinking the Kool-Aid. Tourists Welcome brims with summer camp conviviality: Between outdoor cookouts, an indie-folk soundtrack, and a canteenlike front desk, it’s chill in all the right ways. It fosters an atmosphere where it’s oddly easy to strike up conversation with total strangers—and where families with kids of all ages can coexist seamlessly with weekending couples and celebrities. (In the spirit of the place, I’ll stay mum on which major TV star we ran into.) The service was unbuttoned but not slow; the design was comfortable but endlessly photogenic; and the saltwater pool was so warm, I watched my 2-month-old fall asleep in it (while lounging in a flamingo-shaped baby float, natch). Plus, there’s loads to do. We hiked a section of the Appalachian Trail one day and ogled giant Sol LeWitt murals at Mass MoCa the next.

It’s no wonder this single hotel became the must-visit spot of the summer for anyone within driving distance. The appeal is undeniable; it just happens to look good on Instagram, too.

Mallorca (and Barcelona)

While I initially thought a destination in a nearby time zone would make sense for our first big trip as a family of three, my desire to expose our daughter to Spanish—my first language­—and love for Europe set us on a more ambitious track. Now Mallorca is the place I can’t get out of my head. Its rocky, Tramuntana mountain range cuts along the northwest coast, and within its craggy peaks are nestled tiny, cobblestoned villages that look like Van Gogh paintings washed in Mediterranean light.

We split our time between Deia, a picturesque speck of a town where the spectacular Belmond La Residencia is based, and Port Soller, a slightly larger coastal village that’s especially popular with German beach-going families. At the former, we took lazy walks through olive groves and bought orange jam from a woman’s front porch—made with fruit from her own citrus trees. At the latter, we spent pool days at the cliff-top and family-friendly Jumeirah Port Soller, ate paella by the sea, and watched a particularly charming, 100-year-old tram pass by the boardwalk a few times a day.

The trip also marked baby’s first missed flight, thanks to an hourslong weather delay on our return flight to New York. And yet, getting stranded in Barcelona may have been the biggest blessing of all. We’d already spent a few days there at the beginning of our trip, happily cocooned in luxury at the spectacular new Almanac Hotel. But our delay coincided with the city’s biggest annual holiday, La Mercè, and all of the bustling streets we’d strolled were shut down to car traffic and filled with all sorts of festivities from concerts to parades. In a stroke of serendipity we witnessed competitions for traditional sardana dancing and gigantic human pyramids outside the city’s namesake cathedral—one of the coolest cultural experiences I’ve ever seen. For a planning-obsessed new mom, it was a refreshing reminder that the best things in life are often unscripted—and fully left to chance.

This article was provided by Bloomberg News.

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