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The JP Morgan Library’s grand, old-world elegance immediately transports you to turn-of-the-century New York. And at that time, there was almost no one more powerful than financier JP Morgan. He launched U.S. Steel and even served as the unofficial central bank of the U.S. for a time. Though some considered him a national hero, his tight control of banks, corporations and railroads led others to label him one of the original “robber barons.” Morgan was an avid collector of art and books with holdings so vast they were housed at multiple locations in New York and England. Eventually, he decided to consolidate his holdings in a huge library next to his mansion in NYC. Designed by renowned architect Charles McKim and completed in 1906, the Italian Renaissance palazzo-style library holds a staggering collection of illuminated books, historical manuscripts, and old master drawings. The library is rightfully considered McKim’s masterpiece—a majestic, soaring space which is both intimate and warm. It features 30-foot ceilings, three tiers of bronze and walnut bookcases, stained glass, a huge marble fireplace and grand tapestries. Also visit Mr. Morgan’s study, with its red silk damask walls and antique wooden ceiling brought over from Florence. The library is off the typical tourist’s radar. Imagine yourself as Morgan in your private quarters, reveling in the power and wealth at your command.

Set on the western side of Circular Quay, the Museum of Contemporary Art Australia (MCA) is the country’s leading institution for modern art. While access to touring international exhibitions from the likes of Tatsuo Miyajima and Annie Leibovitz incurs an entrance fee, the permanent collection of more than 4,000 contemporary works by Australian and Torres Strait Islanders, from Gary Carsley to Lena Yarinkura—plus a rare collection of artist notebooks, music, letters, and sketches—is always free. Come on Wednesday night when the gallery is open until 9 p.m., or for the adults-only Art Bar on the last Friday of the month. The rooftop café offers occasional live music and DJs plus glittering views of the Sydney Opera House and Harbour Bridge after dark.

Established in 1800, the Library of Congress is the oldest federal institution in the United States. The library was destroyed by British troops just 14 years after its conception, and Congress used Thomas Jefferson’s collection of 6,487 volumes to replace it. Today, the collection of the Library of Congress—housed across three buildings—grows by approximately 12,000 items a day and is the second largest library in the world with 164 million items and 838 miles of shelves (that’s farther than the distance from Washington, D.C. to Chicago!). The library holds the world’s largest collection of comic books and one of only three remaining Gutenberg bibles. The Library of Congress offers daily guided tours to explore its historic collection and famous Beaux-Arts architecture.—Miranda Smith

Want to sleep in Boston’s very first skyscraper? Originally constructed in 1893, the 15-story Ames Building was, for many years, the tallest building in the city. Renowned architect David Rockwell helped reconceive the building as the high-end Ames Hotel in 2009, preserving much of the original detailing. Many celebrities have since stayed in the luxury hotel, that’s now part of the Hilton Curio Collection, a collection of unique hotels steeped in history.

The rooms at the Ames feel more like opulent city apartments, with modernist furniture and eclectic details like feather chandeliers and gold-sequined pillows. The property’s historic roots are reflected in the 13-foot ceilings and Romanesque, floor-to-ceiling arched windows. Other classic elements include decorative marble fireplaces and oak wood floors. Centrally located in downtown Boston, the Ames provides easy foot access to many of the city’s best-known attractions.

Deep in the wilderness about an hour’s drive north of Kingstown, Dark View Falls cascade off a cliff and into a pair of natural pools, where everyone gathers to swim in the crisp, clear water. The hike to the falls takes only about 10 to 15 minutes, but involves crossing a jungle-style bamboo bridge across the Richmond River. After passing through a clearing in a picturesque bamboo grove, you’ll arrive at the first fall, where you’ll find a gazebo, changing room, picnic area, and viewing platform for enjoying the beautiful scenery. Another short, more difficult walk will take you up to the second fall, directly above the first.

A two-minute ferry ride from St. Vincent’s Villa Beach brings you to Young Island—the first of the Grenadines. Here, the Young Island Resort welcomes guests and visitors alike to its beachside restaurant for casual breakfasts, local curry buffet lunches, prix-fixe dinners, and barbecue parties. Seated in an open-air hut surrounded by tropical flowers, you can dine on local specialties like freshly caught fish and lobster while enjoying the ocean breeze. Whatever you order, pair it with the restaurant’s signature bread, which comes in banana, coconut, cinnamon, white, wheat, and raisin varieties and gets sliced tableside right before your eyes. Just know that reservations are required to eat here, no matter the time of day.

Even though it’s just 200 yards off the coast of St. Vincent and accessible via a two-minute ferry ride, Young Island feels worlds away from the cares of mainland life. The resort’s 29 guest cottages, which are outfitted with tropical-chic wicker furnishings, stone walls, and louvered windows, provide a plush landing spot after days spent diving among sea turtles and sea horses, hiking neighboring trails to spot the ruins of Fort Duvernette, and swimming up to the Coconut Bar, located on a floating platform 30 feet offshore. Each week, the on-site restaurant serves up Caribbean barbecue favorites like pigeon-pea-and-pumpkin stew, corn fritters, and molasses-glazed wings, making for a delicious stay.

Dasheene, the restaurant in the award-winning Ladera Resort, is a magical place unlike any other on the island. The open dining room, overlooking the sea, is so close to the Pitons that you feel as if you could reach out and touch the peaks. The menu, which focuses on ingredients sourced from local farms and plantations, puts a creative spin on classic St. Lucian cuisine, including plantain gratin with a coconut rum sauce, and roast conch. The restaurant is open for breakfast and lunch as well, but there’s no beating the romantic atmosphere and sunset views at dinner, which make a meal here well worth the high price.

Vesper Bar at The Cosmopolitan is our favorite spot for a serious Old Fashioned—or Elderfashioned, the house’s riff, which gets a dose of St. Germain.

Milliner Mona Strand makes hats for the rich and famous - and for anyone else who would like one. The Philip Treacy of Oslo, Mona Strand has made hats for the Crown Princess of Norway and regularly holds exhibits in many parts of Europe. Her hats also appear on stage, on TV, and in film productions. She makes bespoke hats (appointments needed) and sells ready-to-wear hats in her shop in cosy area St. Hanshaugen.

Directly off the northern highway is Columbus Park, overlooking the scenic harbor at Discovery Bay, where Columbus was thought to have first anchored—although recent indications are that he sailed there from St. Ann’s Bay. The park is the only open-air museum in Jamaica, displaying artifacts dating back to Arawak times. Take in the glorious views, ideal for a photo op, and step back into a slice of Jamaica’s history.

Along with the beautiful scenery, parents will appreciate the many amenities that make Bermuda’s beaches the perfect place for beach bums of all ages. Lifeguards, gentle water, and nearby facilities are always a welcome sight for parents of small children. Clearwater Beach, on the eastern end of the island, has clear, shallow water and a 36-acre public park with restrooms and a playground. Picnic facilities, shade trees, and gentle water make Shelly Bay a good choice for the smallest of surfers, swimmers, and shell seekers. Horseshoe Bay Beach has lifeguards, showers, restrooms, and a nearby café. John Smith’s Bay, Elbow Beach, and Somerset Long Bay are more great beaches for families with kids.

Contemporary art can sometimes be pretentious or obscure, but DHC/ART adds an edgy sense of wit, with exhibitions ranging from the visual puns of Ceal Floyer to the exuberant portraits of John Currin. 451 rue St.-Jean, (514) 849-3742.

The longest developed rail-trail in the country, Katy Trail State Park snakes across Missouri for 240 miles, from the western edge of the state to the St. Louis metro area. Built on the former corridor of the Missouri-Kansas-Texas Railroad, the well-maintained park closely follows the Missouri River, offering bikers, hikers, equestrians, and everyone in between a scenic way to see much of the state. The section between Cooper and St. Charles counties is an officially designated segment of the Lewis and Clark National Historic Trail, adding an educational aspect to any exploration. Most choose to bike a portion of the trail, though hiking, running, and horseback riding are also great ways to experience the park, all the while surrounded by forests, wetlands, prairies, and abundant wildlife. A favorite stop along the way is the charming town of Rocheport, where you can make a pit stop at the bluff-top Le Bourgeois Winery for fine wine and views of the Missouri River Valley.

Just 33 miles northeast of Avignon, the town of Vaison-la-Romaine is home to some of France’s most significant archaeological finds. The Ouvèze River flows through the village, creating two separate banks. On the left, a medieval town features enchanting fountains, houses built into the sides of cliffs, a towering belfry, and the ruins of a 12th-century castle. On the right, the new town surrounds an ancient Roman village, complete with preserved dwellings, a theater from the 1st century C.E., and a Gallo-Roman bridge. Amid the Puymin and La Vilasse archaeological sites, you’ll also find the imposing Our Lady of Nazareth Cathedral (built in the 11th and 12th centuries) and the St. Quenin Chapel (with an apse dating back to the 13th century). A 9-euro (around $10) pass grants 24-hour access to all the sites with guided tours if desired, but you can also just wander the cobblestone streets for free, discovering ancient doorways, striking facades, and hidden statues as you go.