The Columns Hotel

New Orleans, Louisiana

As the humidity drops and temperatures cool, it’s New Orleans’s time to shine. Visitors who stay at the Columns, an iconic and eclectic Victorian mansion in the Garden District, will take a front row seat overlooking St. Charles Avenue’s centuries-old oaks. It’s wholly possible to hang on the veranda all day, but it behooves you to visit the bar, which draws a crowd. In the bedrooms: antique furniture, Parachute linens, and Aesop by the sink. While you’re here, hit N7 for biodynamic wine and bistro food, Bacchanal for the best backyard party in town, and Preservation Hall for jazz.

What to bring: October in New Orleans feels like summer most everywhere else, so flowy dresses and whisper-weight skirt sets that hover off the body are the move. (Bonus points if they match the lushness of the courtyard or the color palette of your room.) Practical shoes—ones that can handle a walking tour of the historic homes in the area—are a must, as is a compact crossbody that goes everywhere you do.

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The Inn at Mattei’s Tavern, Auberge Resorts Collection

Los Olivos, California

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  Photos courtesy of Auberge Resorts Collection

Photos courtesy of Auberge Resorts Collection

It’s harvest season in central California, which means it’s prime time for Angelenos to take an easy couple-hour drive up the 101 to Los Olivos, where Auberge just opened its newest wine country resort, the Inn at Mattei’s Tavern. (It’s a longer trip for San Franciscans but worth it for those who have seen enough of Napa and Sonoma.) The bright, airy farmhouse cottages are outfitted with gas fireplaces, cushy four-poster beds, and claw-foot soaking tubs. Settle in, then let yourself take on the pace of the place: leisurely. When you do venture off-site, let it be for excellent food. On Saturdays in Los Alamos, Priedite Barbecue pops up behind the Michelin-starred Bell’s. Bar Le Côte is number one for oysters and uni, and Bob’s Well Bread makes the best pastries in the Santa Ynez valley.

What to bring: A pretty dress for wine tasting, casual denim separates for a horseback trail ride or a tour of the local llama farm, and a striped bikini, should a private cabana at the pool call your name. If you’re tight on space, you can get away with bringing only one pair of shoes for all these outfits. You know the ones—after all, this is California.

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The Lygon Arms

Broadway, Cotswolds, United Kingdom

Picture this: an old hunting lodge in the cutest, tiniest town set on the edge of the Cotswolds, where the restaurant is helmed by a renowned chef and after-dinner drinks in the lounge are not to be missed. That’s Lygon Arms. It’s a great spot to kick back on a weekend away from London—remarkably cozy, with gorgeous gardens and easy access to town. The staff is attentive and warm. The spa isn’t the main draw here, but it’s worth spending some time at the indoor pool, which is in a pretty atrium.

What to bring: You’ll need a couple of well-chosen woolen knits, plus black jeans, cashmere socks, and some lace-up boots to wear with them. For outerwear, we recommend a quilted cocoon coat (in case you get lucky with the weather) and a waxed-cotton field jacket (in case you don’t). Finish with a gleamy signet ring, which adds a tiny dose of glamour to any look and—practical bonus—takes up zero room in your suitcase.

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