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Located a few blocks from Courthouse Square and Whiskey Row in downtown Prescott, about 100 miles north of Phoenix, the Motor Lodge is ideal for a retro road trip. The 13-room lodge began life around 1910 as summer cabins. After a century of serving as all manner of accommodation, it was purchased in 2008 by Joe Livingston and Brian Spear, who set out to prove it had at least one more life as a modern boutique hotel, complete with comfy beds, tastefully eclectic decor, flat-screen TVs, and free Wi-Fi. One of the few hints that this is no longer an old-fashioned motor court is the bright yellow exterior doors and other splashes of color that suggest a more modern era. Still, there are throwbacks—some delightful (the room porches which are close enough together, and few enough in number, that chats with people who might otherwise remain strangers seem the neighborly thing to do) and some not so much (the tiny bathrooms in most of the rooms that would have passed without comment in earlier decades). Mostly, though, the two hosts seem to be striving for, and achieving, a hospitality that often becomes a guest’s strongest memory.

With only a couple of exceptions, you can’t soak in Yellowstone’s thermal features (this is for numerous reasons, not the least of which is that most are so scalding hot they’d burn the flesh off you). North of Gardiner, Montana, though, in the no-stoplight community of Pray, Chico Hot Springs has welcomed soakers to its spring-fed hot pools since 1900. Spend the night in one of the quirky rooms in the historic main lodge, originally built as a boardinghouse for miners, or in a refurbished caboose from the Northern Pacific Railroad. If at all possible, plan to be at Chico on a Sunday morning, when it serves the best brunch in Montana.

When the Art family bought the struggling Chico Hot Springs Resort in 1972, some of the earliest improvements they made were to its dining room. The idea was to create one of the best restaurants in the state; if guests came for the food, maybe they’d spend the night. The family succeeded. Today the Chico Dining Room is so beloved it spawned a cookbook, A Montana Table: Recipes from Chico Hot Springs Resort. While ingredients are as fresh as can be—with produce from on-site greenhouses, meat from local ranchers, seafood flown in overnight from the coast—the menu includes some dishes that have been around for more than 40 years. The classic Chico meal is beef Wellington (service for two) and, for dessert, a Flaming Orange, which is exactly what it sounds like.

It may be only 22 miles west of San Juan, but Dorado Beach, a Ritz-Carlton Reserve feels a world away. The resort has a spectacular location on a three-mile stretch of beach on Puerto Rico’s north shore, where Clara Livingston once ran a sugar plantation—and Amelia Earhart visited before departing for her fateful world tour. In 1958, Livingston sold the property to Laurance S. Rockefeller, who turned it into the first of his legendary Rock Resorts. Known for his green streak, he designed the hotel to respect the local beauty, mandating that buildings could not be taller than the surrounding palm trees.

The Ritz-Carlton—which reopened in October 2018 after a meticulous restoration following Hurricane Maria—pays homage to that original vision. Here, every room is beachfront, with floor-to-ceiling sliding doors that disappear into ocean views, plus deep soaking tubs, outdoor showers shaded by gardens, and either spacious balconies or private plunge pools. As part of the property’s renovation, rooms were refreshed with a color palette that amplifies the natural beauty just beyond the doors. Additionally, the grounds showcase 3,000 new plant species, the spa is offering new locally inspired treatments and cuisine, Encanto Beach Club Bar & Grill features a refreshed dinner menu, and the Positivo Sandbar debuted an omakase and ceviche bar directly on the sand. There’s even an entirely reimagined signature restaurant, Coa, which serves farm-to-table fare cooked on the grill. Still standing strong on the verdant, 1,400-acre grounds are the five 18-hole championship golf courses. The biggest challenge is pulling yourself away from the luxury of the resort to tee up a shot.