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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.

Former British prime minister Harold Wilson, who loved the Isles of Scilly and visited every summer (his wife, Lady Wilson, now 100, still does), is buried at the pretty Old Town Church in its atmospheric graveyard. The grave is modest compared to the grander tombs belonging to distinguished Scilly families, but not nearly as modest as the Wilsons’ nearby summer house, which is inconceivably tiny for a residence of one of Britain’s most important 20th-century statesmen.

At the top of Little Cottonwood Canyon, above the town of Sandy, Utah, the Alta Resort offers 2,200 skiable acres and an average of more than 550 inches of snowfall a year. While the steep slopes of the Wasatch mountains draw expert skiers, there is plenty of terrain for intermediate skiers and a number of programs within the ski school to get beginners and first-timers out and enjoying themselves. As for families, even those with little ones as young as two months old, day care is available all day long and into the early evening through Alta Children’s Center, and on Fridays and Saturdays until 6:30 p.m. with its Après-Ski Care. To get tykes skiing and on the slopes, Alta partners with the ski school.

The main branch of the New York Public Library is one of the country’s grandest Beaux Arts buildings, a temple to learning on Fifth Avenue between 40th and 42nd streets. At the end of the 19th century, John Bigelow, who oversaw the Tilden Trust, decided that as New York was becoming a global financial capital, it required a grand public library. When the Astor and Lenox libraries faced financial difficulties, he convinced them to merge and, with the Tilden Trust, underwrite the library that now stands next to Bryant Park. The firm of Carrère and Hastings was entrusted with the design, and construction began in 1902 on the building that would be the largest marble structure built up to that time in the United States. The elegant main reading room with its soaring carved-wood ceilings is the highlight of its interiors. The library hosts temporary exhibitions related to literary and cultural topics that draw on its extensive collection of books and other printed materials. The two beloved lions in Tennessee marble—Patience and Fortitude—have stood at the entrance to the library since it opened in 1911 and were created by sculptor Edward Clark Potter.

This lovely state park stretches along the rugged volcanic shoreline of western Maui, three miles from Hana. It’s best explored on the 2.2-mile hike that starts at the black-sand beach and follows the dramatic coast, passing lava tubes, rock arches, blowholes, and Polynesia’s largest heiau (an ancient Hawaiian temple) along the way. Avoid standing too close to the geysers as well as the lava benches near the ocean, which can crumble easily, and watch out for high surf. If you’re looking to cool down after your trek, take the loop trail to the park’s freshwater caves, where you can explore two separate chambers (the first tends to be clearer and more inviting).

A stay at this resort offers the best of many worlds: easy access to San Antonio and its airport, proximity to scenic Hill Country and its wineries, and plenty of on-site amenities to encourage you to hang around. Spread over 600 acres, the property includes an 18-hole golf course, a nine-acre water park (with a winding lazy river and 650-foot rapid river ride), hiking trails, and a 30-room spa, where treatments incorporate Texas-grown ingredients like lavender and sassafras. The facilities fan out from the LEED-certified main building, which houses 1,000 warm, comfortable guestrooms, many of which look out onto the main pool. There are also enough restaurants to warrant a multi-day stay, from an organic-focused spa bistro and a sports bar with local brews, to a Texas-inspired main restaurant and a fine-dining steakhouse set among the golf greens. Each spot uses ingredients sourced within a 150-mile radius of the hotel, and aims to highlight Texas wine and beer. While the kids are off enjoying the water park or video game arcade, adults can take a tequila tasting class or settle into a rocking chair with a good book—then everyone can meet around the indoor or outdoor fireplaces to trade stories.

The historic Crazy Mountain Inn is a great place to stop while cruising through Montana, especially if you arrive with a growling stomach. The Inn’s legendary chicken-fried steak will set you right (and put you in the mood for a 10-mile trek, or a fireside nap, depending on your constitution). The Sour Cream Lemon Pie is qually famed, though lighter breakfasts, lunches, and dinners do come out of the kitchen from time to time.

Even though Butcher’s is a nice steak house (“elegance without arrogance” is the owner’s motto), with one of the most appealing bars in town (a full wall of gleaming bottles behind the bar, views of the Town Lift just outside the door), they double as a great place to go and watch the game. The late night menu is offered until midnight. Order the housemade potato chips topped with melted Monterey Jack and aged blue cheese.

One of the oldest restaurants in Park City, the “Double E,” as locals call it, opened in 1972. When I first lived in town in the mid-1980s, they’d have $1.95 breakfast specials of eggs and bacon. Can’t beat that. They serve breakfast, lunch, and dinner, but the stick-to-the-ribs breakfasts are what they’re really famous for. Try the signature Miner’s Dawn, seasoned potatoes with melted cheddar cheese, topped with basted eggs and served in a skillet with wheat toast.

Casual wood-fired pizzas are the specialty in this popular, contemporary-styled restaurant owned by longtime locals Deb and David Harries. This place is always busy, so expect a short wait. It’s worth it. The V salad, with arugula, prosciutto, olive oil, lemon and shaved Parmesan is to die for, as is the Tutabella pizza with housemade sausage, caramelized onion, fresh tomato, roasted pepper, fontina, and fior di latte mozzarella. Don’t skip the housemade gelato for dessert.

Seek, and antiquers shall find that New York is a paradise of flea markets, vintage shops, and emporia like this one offering up all kinds of goods. The Manhattan Art and Antique Center is in Midtown East, near the tony Sutton Place enclave. Its individual shops and galleries feature everything from Egyptian antiquities to classic toys from the golden age of American manufacturing.

With soaking tubs and smart TVs in every room, Hotel Ivy is sleek and sophisticated. In addition to the stylish rooms, the subterranean cocktail bar (Constantine) and coastal Italian restaurant (Monello) are hip destinations in themselves, with renowned local chefs and bartenders from Borough and Parlour at the helm.

Built in 1863, Magnolia New Orleans is classic in decor—especially in the marbled lobby with its antique furnishings and Renaissance murals—but with all the up-to-date amenities you’d expect: Rooms and suites have flat-screen televisions and Nespresso coffeemakers, and there’s a small but well-equipped gym on-site and a rooftop sundeck with a Jacuzzi.

Just 12 miles north of Santa Fe, this picturesque spot is perfect for table-side, made-to-order guacamole and a cold margarita (or two) on a spacious, relaxed scenic patio full of flowers and stunning high-desert mountain views. You might not want to leave.