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This particular area of the Gold Coast is jokingly nicknamed the Viagra Triangle, but the Thompson Chicago doesn’t discriminate by age. The 247-room hotel is dark and moody, drawing artists of every generation to its swanky lobby bar at the back, peppered with colorful canvases and couples sneaking a snuggle in a booth. The whole town is awaiting the opening of Tavern on Rush, a reboot of the beloved steak house that used to reside just up the block. Rumors say this hangout will become a dining destination, what with its cocktail lounge, main dining room, patio, and private rooms spread across 16,000 square feet and multiple levels.


Set among all the best shopping in the Midwest, the Thompson’s midcentury-style guest rooms with hardwood floors provide the perfect minimalist location to unbox those favorite finds from Michigan Avenue around the corner. Digital nomads can book their work meetings in one of the rooms named after the Chicago Seven: countercultural anti-war protesters charged by the U.S. federal government with conspiracy and intent to incite a riot to stop the Vietnam War. The Abbie Hoffman room is a favorite.

The entire north side of Santa Fe’s downtown plaza is taken up by the 1610 Palace of the Governors, the oldest continually occupied public building in the United States. Its front adobe facade is completely shaded, and in this “portal,” the Native American Vendors Program has been operating for over six decades. A daily lottery ensures a rotating selection of artisans from the various pueblos throughout New Mexico. Yes, there might be some “finer” pieces available in the chic boutiques elsewhere in Santa Fe, but here, in the shade of a four-century-old adobe building, you can meet the artists and even haggle a bit. Be respectful, though—these are not cheap trinkets made in a sweatshop abroad: The crafts and the jewelry are usually made by the person with whom you’ll be conversing. (An interesting side note: The Palace was taken over in 1680 and occupied by Native Americans during the Pueblo Revolt until 1692, when the Spaniards returned. This is the only government seat in the U.S. to have ever been taken over by Native Americans. It then served as the residence of the governor during the Spanish, Mexican, and U.S. territorial regimes, until 1907. In 1912, New Mexico became a U.S. state. Today, the Palace serves as a museum.)

This landmark inn has been around since 1936, when it was known as the Hotel Martin—and the adobe homes that comprise the property date back even earlier. Originally built in the 1800s, the structures are clustered around a central plaza that, today, serves as the hotel lobby. The largest residence is now the restaurant Doc Martin’s, named after its onetime owner, Dr. Thomas Paul Martin, the county physician as well as an avid supporter of the arts. In fact, the Taos Society of Artists was founded in his dining room in 1912, and he later bought the neighboring houses to rent out to writers and artists. When the only hotel in town burned to the ground, Doc bought the Tartleton House (the last on the square and now home to the Adobe Bar) and he and his wife Helen opened for business. The property has been maintained and upgraded over the years (most recently in 2006), but the look (Spanish colonial antiques and brightly patterned bedspreads) hasn’t changed much since then—and that’s part of the charm.

The Aubrey sits at the edge of Barrio Bellavista, a few steps from Santiago’s bottle-green 1925 funicular (which takes visitors up to Cerro San Cristóbal) and just below the zoo (sometimes guests can hear the animals when they’re lying by the pool). Open since 2010, this 15-bedroom boutique hotel is housed between two 1920s mansions built by the same architect. The larger of the two houses once belonged to famed Chilean railway magnate Domingo Durán. Today, the hotel is owned by a Brit and an Aussie who spent $3 million and several years transforming it into its current state.

The bedrooms are split between the two mansions, and there’s also an outside block housing a few pool suites. A cobbled terrace runs between the restaurant and piano bar. The interiors are inspired by the early 20th-century art deco movement and feature statement art deco furniture, printed fabrics, and elaborate wallpaper.

It is really hard to walk past a cute bakery like Ovenly without going in. Pretty decor plus shelves and glass jars filled with homemade treats just catch my curiosity everytime. Plus, there is something very comforting about biting into a scone with a just-right crust or a gooey cookie with a hint of salty and sweet. So imagine my delight when I discovered Ovenly, on a quiet, industrial street in Greenpoint, Brooklyn. I tried a Cheddar Mustard Scone baked with locally-made wholegrain mustard and sharp cheddar, a Chocolate Truffle Cookie enhanced with sea salt, and Salted Chocolate Chip Cookies. Next time I’ll be sure to try the Apricot Thyme Scone, Black Caraway Bread, and Spicy Bacon Caramel Popcorn, which sounds so wrong it must be right. Ovenly was just named Best New Bakery by Time Out New York. Owner/bakers Agatha Kulaga and Erin Patinkin are young Brooklynites who infuse their treats with traditions from their Eastern European backgrounds. Grab some pastries, then stroll around the other independently owned boutiques and cafes in downtown Greenpoint.

Montauk State Park sits at the head of the Current River, where seven springs converge to form a breathtakingly beautiful area. The park is popular with anglers who come to fish for rainbow trout in the cool waters, but also offers ample opportunity for hiking, biking, and picnicking in shady groves. Visitors can even learn a bit of history during tours of the old gristmill, built in 1896 at the center of what was once a thriving community. For a relaxing day in nature, follow the locals to the river, where they float in canoes with coolers of cold drinks in tow, then spend the night at one of the modern campgrounds, rental cabins, or motel rooms that dot the park grounds.

One of the most recognizable sites in Hawaii, this volcanic ash cone overlooks Waikiki’s coastline—a tectonic memory from an explosion half a million years ago, measuring almost 3,500 feet across. British sailors named it Diamond Head in the 1800s, mistaking calcite crystals in the crater’s soil for jewels. Despite its volcanic grandeur, the ascent takes most hikers an hour or so, clocking in at 560 feet of elevation gain and 1.6 miles round-trip. At the top, on a clear day, you can see all of Oahu’s south shore, from Koko Crater and Waikiki to the mountains of the Wai’anae Range.

Take a riverboat up the Wailua—which translates as the “river of the great sacred spirit"—fed by the Mount Waialeale shield volcano, one of the wettest spots on the planet. Seven temples once stood along Hawaii’s longest and only navigable freshwater passage. Today, the remains of four are still visible, alongside petroglyphs and rocks where the island’s alii (royalty) would give birth. Stretch your legs at the stunning Fern Grotto: Verdant plants blanket the roof of the volcanic-rock cave there. Smith’s offers 80-minute tours there on open-air boats, which include the songs and stories of ancient Hawai’I, plus a bonus hula lesson (smithskauai.com).

The description may sound daunting: a 2,000-vertical-foot gain in less than a mile. OK, it is a little daunting—but the trick is to take your time. This nearly mile-long wooden stairway was converted from a funicular railway that washed out in a rock slide in 1990. Averaging a 24-degree slope, it has a few “false summits,” where it looks like you’re about to get to the top only to discover there’s still more to go. The reward for this effort is an incredible view looking out from the foothills over Colorado Springs. Up for the speed challenge? The current record was set on Sept. 25, 2015, by U.S. mountain-running team member Joseph Gray, who did it in 17 minutes, 45 seconds. Good luck.

Vintry is a small, cozy bar and restaurant in lower Manhattan. It provides a welcome counterpoint to the larger gathering spaces in the Wall Street area - it has the vibe of a discreet speak-easy. Vintry specializes in artisan producers of whisky and wine - they have carefully selected an interesting group of handcrafted libations. There are 80 wines from France, Italy, Spain, and the U.S. available in a “tasting” size, glass or bottle, plus hundreds of other wines by the bottle. There are also 100 whiskeys. Vintry’s specialties are cocktails from the house mixologist featuring homemade bitters and syrups. I don’t consider myself a whiskey drinker, but I absolutely loved the Gingerade, a shaken cocktail made with 13 Jameson black barrel Irish whiskey, fresh ginger extract, fresh squeezed lemon juice, fresh lime, Peychaud’s bitter, cane solution and ginger ale. It was ice cold, crisp, slightly sweet with a subtle twist of ginger and lime. DELICIOUS. This warm, dark, welcoming bar is easily the type of place where you can pass a good amount of time before realizing it. Vintry also has nicely prepared food - along the lines of veal meatballs and lamb ragu - to accompany its wine and whiskey list.

Before cotton reigned supreme in the South, tobacco was the money-maker. Planters channeled their profits into increasingly ornate homes, and one of the best examples of this post-Revolutionary architecture can be found in the Harrisburg district of Augusta, Georgia. Between downtown and the Augusta National Golf course (where The Masters takes place every April) is the Ezekiel Harris House, dating from the 1790’s. In later years, the area around the Harris House would become known as Harrisburg, before becoming incorporated into Georgia’s second-oldest city. The South’s first industry grew up nearby after the Augusta Canal was dug in the 1840’s. While the neighborhood is awaiting renewal today, the house remains as a relic to the society and tastes of a fledgling United States. The house is open for tours every Saturday and by appointment during the week. The Smithsonian has called it ‘the finest 18th-century house surviving in Georgia.’

Since everything seems bigger in Texas, it’s no surprise that the Texas State Capitol holds the title for largest state capitol building in the union (360,000 square feet of floor space in the main building!). The building is also quite beautiful and houses some historical paintings. The inside of the capitol dome, with a lone star at the apex, is an impressive sight. Stroll the grounds to see fountains, old trees, and sculptures of historical Texas figures. The capitol grounds also offer a great view of downtown to the south and the University of Texas to the north. The Texas landmark is definitely worth a visit on a trip to Austin.

Though the DR isn’t traditionally known for its surfing, the little town of Cabarete (a 30-minute drive from the Puerto Plata airport) is fast becoming a hot spot for newbies and those wanting to take their board skills to a new level. Cabarete boasts several surf camps including SWELL, “a purpose-built surf camp” that attracts surfers and wannabe surfers from all corners of the globe. A cross between a hostel and a just-the-basics boutique hotel, the camp has co-ed quad dorms and private rooms accommodating some two dozen travelers of all ages — a healthy mix of singles and couples, mostly urban professionals. Days here start really early, but what does it matter when you’re on the water catching waves? (There’s always the rest of the day to make up for that lost shut-eye.) Once you’re done with your surfboard, wander into Cabarete to grab a cerveza and a bite. Be sure to check out the town’s other favorite pastime, kitesurfing. Just look to the sky.

Perched on stilts above its own patch of sand, Sound View Greenport is a peaceful retreat, offering a variety of rooms and apartments with up to two bedrooms. Bright and airy, accommodations come with either shared or private sea-facing decks, which provide direct access to the hotel beach. Other amenities include a pool deck with plenty of loungers for guests to sun themselves, plus a bocce court, putting green, and multi-purpose sports court. For meals, Sound View’s gorgeous seafront restaurant, The Halyard, features gourmet dishes inspired by sea and land. There’s also a charming piano bar, decorated with wood-paneled walls and nautical oil paintings. Adding substance to style, the hotel hosts a smattering of cultural events, including musical performances and educational talks.

The Cloisters, a museum devoted to medieval art and architecture, is a delightful respite from the hustle and bustle of NYC. This tranquil treasure is definitely worth a half day (or more) trip on your next visit. A branch of the Metropolitan Museum of Art, The Cloisters opened in 1938 and is located in Fort Tryon Park in northern Manhattan. Perched on a towering cliff, the museum offers commanding views over the Hudson River to New Jersey and the George Washington Bridge. The buildings include elements from medieval sites from Europe (primarily France) and renowned artwork includes the Unicorn Tapestries and the Annunciation Triptych, but the heart of the museum is the cloistered garden. This lush space consists of an interior courtyard surrounded by covered walkways. The flowering garden within invites contemplation and appreciation of a different time. The Cloisters includes a broad terrace with expansive views across the Hudson. The view is so prized that in 1901, J.P. Morgan purchased 12 miles of the New Jersey coastline to protect it from excessive quarrying and in 1933 John D. Rockefeller, Jr. donated 700 additional acres of NJ to preserve The Cloisters’ view. Be sure to include time in your visit to explore beautiful Fort Tryon Park.