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This leather atelier off a leafy boulevard in the Porta Romana district is the epitome of chic. The only way to buy its coveted handbags and accessories, regularly spotted on celebrities, is to visit this white-hued, mirrored store. Designer Roberta Giacobbe crafts understated, heirloom-quality pieces including totes, iPad cases, and men’s carryalls using the finest quality leather. Each one is handmade in her workshop above the boutique. One of the most popular items is the zippered pochette (an envelope-shaped handbag), which can be custom-made in any color.

Poschiavo is one of the last stops along the UNESCO-listed Rhaetian Railway before it descends towards Tirano, Italy. It’s also one of the few Italian-speaking villages in Switzerland outside of Canton Ticino. The seemingly untouched medieval town is a jolt back in time, with a full-on baroque piazza boasting a stone campanile and a museum stuffed with 16th-century furnishings and antiquities. Don’t leave without stopping for a nibble at its Wednesday market: Local specialties include pizzoccheri (a buckwheat pasta), burrata, local truffles, anise-flavored bread, wine from Campascio in the surrounding valley, and cheese from Caseficio Valposchiavo, a nearby organic dairy. The market is held every Wednesday on Poschiavo’s main piazza.

Netta Bottone, the force behind this rustic eatery, is everyone’s favorite Italian nonna. The cuisine at Cumpa’ Cosimo—enjoyed by celebrities from Gore Vidal to Mariah Carey, as well as locals and travelers—is straightforward and made with heart (and fresh ingredients). The day’s selections will be rattled off to you in place of a written menu and likely will include fresh soups, pasta, and grilled fish. An enormous platter of several different pastas, perfect for sharing, is a perennial favorite. The pizza oven turns out pies with both traditional and special toppings, such as shavings of white truffles.

The façade may be classic, the doormen crisp, and the location tony, but once inside Le Royal Monceau, you’ll feel an independent, unexpectedly edgy spirit running through this luxury hotel. Opened in 1928, the historic spot, now part of the Raffles collection, underwent a complete renovation in the mid-2000s, overseen by interiors master Phillipe Starck, who—true to form—filled the spaces with contemporary style, dramatic flair (like oversized lobby sculptures and a stairwell adorned with dozens of chandeliers), and over 350 pieces of art, many culled from the hotel’s private collection. Art is a big focus here overall: along with a well-stocked art-library-cum-bookstore (which draws a lot of gift-seeking locals) and an on-site showroom curated by local gallerists (recent shows have spotlighted street artists, from Basquiat to Banksy), there’s a resident Art Concierge—the first in Paris—who can create bespoke itineraries for guests and arrange for special access, studio tours, and VIP experiences (including, with enough notice, an after-hours visit to the Louvre).

The royal family has made this intimate hotel their home-away-from-home since Otto Goring first opened its doors in 1910—which is why it’s the only hotel to hold an official Royal Warrant for hospitality services, bestowed in 2013 by Queen Elizabeth II, who has been enjoying lunches and teas here since she was a child. Set on a quiet Belgravia side street, just a few blocks from Buckingham Palace, the elegant hotel also hosted nobility, both foreign and domestic, during the coronations of King George VI and the current queen, and—as the first hotel in the U.K. with en suite bathrooms—often served as a convenient place for dignitaries to freshen up prior to an audience at the Palace.

Today, the 69-room spot—which is still owned by the same family—caters to a devoted (and primarily American) clientele, who love the intimate feel, central location, and excellent service, not to mention the rare perks like a back garden. Rooms are cushy and comfortable, with traditionally English décor (silk wallpaper, vintage-inspired headboards, Italian linens, and oversized armchairs) and playful details (pops of color, giant stuffed sheep mascots peeking around corners, and an in-room lighting switch with choices like “Bright,” “Cozy,” and “Oooh”). Upgrade to a suite to enjoy more room and dedicated service from one of the legendary footmen, identifiable by their gold-embroidered scarlet coats. (For even more perks, check in to the gorgeous, two-bedroom Royal Suite, which boasts four-poster beds, a grand piano, a six-seat dining room, antique glassware, and a life-sized portrait of Queen Victoria in the shower.) A steady stream of locals of all ages join hotel guests for lunch on the garden terrace, drinks around the gleaming wood bar or in the fireplace lounge, and the famous Afternoon Tea—just book early for the latter, as there can be a months-long wait list.

Opened in 1946 as a restaurant (where the famous regulars included Churchill and Hemingway), La Maison Arabe later expanded to a small hotel, then grew again under its current French-Italian owner. Today, it features 26 garden- or patio-view rooms and suites, individually designed in either a traditional or slightly more modern Moroccan style. All have air-conditioning and heating (a must for the varied desert temperatures) as well as Wi-Fi, satellite TVs, and marble-and-granite bathrooms stocked with aromatic toiletries. Also available to guests is an idyllic swimming pool, around which the hotel serves a home-cooked breakfast each morning, and the clubby, 1930s-inspired Piano Bar, where guests can enjoy live jazz and pre-dinner drinks by the fireplace. When it’s time to unwind, head to the cozy spa for an array of face, body, and hamman treatments, all performed with products made exclusively for the hotel.

Much like in the past, La Maison Arabe revolves around food. Guests can choose between Le Restaurant, where a gorgeous fountain and hand-painted ceiling set the stage for authentic Moroccan fare, and the intimate, lantern-lit Les Trois Saveurs, which serves a sophisticated menu of French, Moroccan, and Asian dishes. Additionally, the hotel offers some of the city’s best cooking classes, which are open to outside guests. Led by a dada (a traditional Moroccan cook), the lessons take place either at the main hotel or the Country Club—a satellite property located 15 minutes away by complimentary shuttle, where students can also find a larger pool, lush gardens, a restaurant, and a bit of calm away from the bustle of the medina.

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.

Built on the ruins of an ancient seaside villa, La Posta Vecchia has a long history of noble ownership. The estate-turned-hotel was originally laid out in the 17^th century. Then, in the 1960s, American billionaire J. Paul Getty purchased the property and turned it into his seaside home. During Getty’s residence, the palace was outfitted with ancient works of art, as well as original works and furnishings from the 15^th through 17^th centuries. The estate now belongs to the Sciò family, who have transformed it into one of the Leading Hotels of the World. The 19 rooms, including 8 suites, are spacious, and many offer views of the Tyrrhenian Sea. Each is outfitted with antique furnishings, while bathrooms are clad in precious marbles.

Although La Posta Vecchia is only 30 miles northwest of Rome (about a one-hour drive, traffic permitting), it should be treated as a destination hotel rather than a home base for day trips to the Italian capital. To make the most of the luxurious accommodations, tack a dedicated stay onto the beginning or end of a visit to Rome.

Described by Napoleon as the “Drawing Room of Europe,” Venice’s principal public square is dominated by Saint Mark’s Basilica and the Doge’s Palace—as well as its famous pigeons. Wander the framing porticos, have coffee at Quadri or Florian’s and just take it all in. Even on the most crowded days, there’s a feeling of calm in the eddying whirls of people who gather in this impressive space.

Famous for its long history of handblown glassmaking, Murano sits just a few minutes’ ferry ride offshore in the Venetian Lagoon. The main attraction is the Glass Museum (Museo del Vetro), which recounts the history of glass through the centuries, with the largest focus on important pieces of Murano glass produced between the 15th and 20th centuries. You can also join a guided tour and catch a glassmaking demonstration here. When finished, do a bit of shopping for locally produced glass at some of the boutique shops. Also check out the Romanesque-style Church of Santa Maria and San Donato, which may or may not house the bones of a slain dragon under its boldly hued mosaic floor.

We were offered the chance to visit Pompeii or Herculaneum when we docked at Sorrento. People rave about Pompeii because it’s absolutely huge and gives you a great sense of just how sophisticated Roman civilisation was. Herculaneum, by contrast, was a Roman seaside town, a sort of holiday resort, and doesn’t offer the same kind of scale. Still. I remembered my Latin lessons, and how we’d learned that while Pompeii’s buildings were smashed and burned by the falling volcanic ash, Herculaneum was actually preserved in the thick mud that engulfed it. And it’s true: wandering around the archaeological remains of the town, you feel like you’re in a place that’s only recently been abandoned. The wine shop (above) still has its amphorae stacked to the side, the houses have beautifully preserved frescoes and mosaics. What it lacks in size it more than makes up for in detail.

Since opening in 2001, the Frist Art Museum has hosted an inspiring—and continuous—slate of exhibitions from both nearby and around the world in its Art Deco digs. Visit on a Thursday or Friday night to catch “Music at the Frist,” when a wide range of musicians perform live in the museum café. The shows are free to attend with the purchase of admission.

Right in the center of town, Capri Tiberio Palace mixes la dolce vita glamour with a globe-trotting sensibility that’s equal parts quirky and elegant. Wanderlust-inducing knickknacks such as globes, vintage trunks, and an eclectic collection of art stud the public spaces, and bookshelves are stocked with coffee-table tomes from the publisher Taschen. A white baby grand provides the soundtrack for aperitivo hour at the Jacky Bar, where wicker poufs, striped blue-and-white banquettes, and Panama hats repurposed as wall decor signal vacation vibes; things are slightly more reserved at the terrace restaurant, a formal space whose brightly colored dishes (think seared scallops with almond sauce and beef tartare with chestnut cream as well as kosher fare) are rivaled only by the panoramic views of the island’s craggy peaks coast and azure sea. And the indoor-outdoor swimming pool, though small, is a savior in the summer heat.

Often called the Spanish Steps, Rome‘s famous scalinata (monumental staircase) is the centerpiece of Piazza di Spagna. Built in the early 1700s, the steps connect the piazza (now a busy shopping area) with the Trinità dei Monti church on the hill above. The area became a hangout for models and artists and one of Rome‘s most photographed sites. Head to the top to see the sunset, or make like Hepburn and Peck in the film Roman Holiday and stroll around the piazza.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.