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The warm, handsome dining room at Terra is situated high enough for sweeping Santa Fe sunsets and glorious mountain silhouettes. Helmed by chef Andrew Cooper, the food is contemporary American and Southwestern, from tortilla soup to pan-seared scallops to a zesty green chili braised short rib. After your meal, visit the mod, circular outdoor fire pit and wind down with a nightcap. The cool inside bar has a great wall of old black-and-white photos, including one with visiting actor and cowboy Robert Redford.

A landmark property perched between the city and the ocean, the El San Juan blends Old World elegance with tropical vibes. The famed hotel reopened on December 14, 2018 after a full restoration following Hurricane Maria and now features updated guestrooms, public spaces, and landscaping. Thankfully, the original feel was left intact, and details like the iconic chandelier and hand-carved mahogany ceiling in the lobby remain. Guests can still sip Champagne under sparkling crystals at the Chandelier Bar or party the night away at BRAVA, but now they can also sample Puerto Rico’s national spirit at rum bar 1958, grab a glass of vino at Wine Bar, or refuel with locally roasted Alto Grande coffee at El Cafecito. Also new to the property is Caña, a locally minded restaurant from Puerto Rican chef Juliana Gonzales, and Chico Cabaret, a hotspot off the lobby featuring live entertainment.

Ranging from guestrooms in the grand tower to villas surrounding the pool and beach, the 388 rooms all feature floor-to-ceiling windows with city, ocean, or pool views, as well as modern conveniences like sensor-activated air-conditioning, large HDTVs, and complimentary Wi-Fi. When not lounging on their Lovell Plush mattresses made exclusively for the hotel, guests can take a dip in one of four pools, sunbathe on the two-mile-long Isla Verde Beach, or visit the brand-new, tri-level Well & Being center for balancing spa treatments and fitness classes on the open-air rooftop.

Located in Park City‘s renovated Masonic Hall on historic Main Street, the Riverhorse caters to a high-end fine-dining crowd. Seth Adams, the executive chef and co-owner who drives the seasonally appropriate creative menu, has brought home prestigious awards, including a few that were firsts in the state of Utah. While the Riverhorse has a great selection of wine, it does allow patrons to bring in their own bottles for a $25 corkage fee. The restaurant is family friendly, with healthy selections on the kids’ menu. Dress is “mountain casual,” and reservations are strongly encouraged.

In December 2017, one of the country’s oldest Ritz-Carlton properties was rebranded as The Whitley, and though the name may have changed, the property’s high standard of elegance endures. The 507 stately guest rooms—which start at a spacious 720 square feet—are currently undergoing a refresh (but still include comforts like high-thread-count sheets and Nespresso machines), and the restaurant and bar have been reimagined as Trade Root, a Mediterranean-meets-Southern lounge featuring house-made pastas, an extensive selection of cheese and charcuterie, and craft sodas and cocktails. Guests can avail themselves of the indoor lap pool—a top-floor beauty with a stunner of a glass roof—as well as a fitness center and spa, or indulge in a little retail therapy in the neighboring shops of Buckhead. No doubt further renovations will ensure that this hotel remains an icon well into the next generation.

Leading the charge for independent bookstores since it opened in 1970, Book People is legendary for creativity and a strong calendar of events. The store holds frequent author signings—and we’re talking big authors—and book club meetings for all manner of book genres. Those who can’t get to Austin can sign up for a subscription service called Trust Fall in which a new book, handpicked by the staff, arrives in the mail a few times a year. Kids are a special focus here: The store publishes a blog written by its own “teen press corps” and collaborates with librarians around the state to hold the annual Texas Teen Book Festival. Book lovers should not miss visiting this stalwart home of literature, and handily, it’s open a lot: 9 a.m.–11 p.m. every day but Thanksgiving.

Fans of Georgia O’Keeffe should definitely book a stay at this quaint adobe hotel in her old painting grounds. Not only is there a well-stocked gift shop where you can buy O’Keeffe prints and books, the property arranges tours of her home and studio, and is located near the Ghost Ranch retreat center and the White Place rock formations, both of which the artist loved to paint. Wood-beam ceilings and New Mexico antiques adorn rooms. Request one of the cottages with wood-burning Kiva fireplaces, or if you come in winter and book economy like I did, you’ll likely get upgraded to a nice room with a gas fireplace. My best meal in New Mexico was also enjoyed here. I ordered trout stuffed with corn pancakes and a chardonnay from nearby Black Mesa winery. My partner’s chili rellenos with green chili and Monk’s Ale—brewed at the Christ of the Desert Monastery about an hour away—were also tasty. It was a lovely introduction to the beautiful state.

The Freedom Trail is the artery connecting most of Boston’s key Revolutionary War sites, from Boston Common to the USS Constitution—16 stops in all. Besides providing you with some history, following the red stripe around town also delivers an easy self-guided tour of the heart of Boston, including the lively North End and Charlestown. The Common, Old North Church, the Paul Revere House, and the site of the Boston Massacre are obvious and obligatory stops, but the trail also leads to three legendary cemeteries, the 1718 Old Corner Bookstore (now a Chipotle restaurant, of all things), the 1713 Old State House, and the unmissable Bunker Hill Monument, whose cornerstone was laid by Lafayette to mark the 50th anniversary of the bloody battle between British troops and patriot militias in June 1775.

Nature may have spent 12 million years creating the rock formation that is the centerpiece of this 1,300-acre Hilton Curio Collection resort in the foothills of the Sonoran Desert, but late-coming humans have done a commendable job of adding the finishing touches. Although the Boulders, with its casita accommodations blending into the landscape, its championship golf courses, and its upscale shops, is as luxurious as any resort in the Scottsdale area, it’s also where guests are most likely to feel they are truly in the desert. An early-morning walk along groomed paths, when the first rays of light are turning the landscape golden, is as likely to produce the sounds of woodpeckers or owls calling from their nests in saguaro cacti as it is the whack of a ball against club or racket.

Despite its size (10 square miles) and population (fewer than 170 permanent residents), Little Cayman enjoys a worldwide reputation among serious divers. The island is renowned for its exceptional underwater visibility and vertigo-inducing walls, especially north-shore Bloody Bay. Dive boats flock to Three Fathom Wall, where bulbous coral heads teeming with fish rise to within 10 feet of the surface. Snorkelers are likely to encounter schools of blue tang and stoplight parrot fish, as well as hawksbill turtles and nurse sharks.

At Lizard Island, luxurious amenities meet an ecologically diverse island paradise. The sole resort on the island, the exclusive spot features 40 rooms as well as 24 private beaches, all but guaranteeing your own pristine sliver of paradise. Accommodations range from posh villas set apart from one another (including the two-bedroom, cliff-top villa, with its 26-foot pool and endless views of the Coral Sea), to garden-view rooms with private terraces and pathways leading directly to Anchor Bay beach. Furnishings follow a tranquil white-and-gray color scheme, while amenities include LCD smart TVs and Apple docking stations. Guests also receive their own motorized dinghy, standup paddleboards, clear-view sea kayaks, and snorkeling gear for exploring Giant Clam gardens and the schools of brightly colored fish in the surrounding waters. The more adventurous can even arrange for private deep-sea dives to locations accessed exclusively by the Lizard Island Marine & Dive team, ensuring you’ll have the coral reefs all to yourself.