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No matter what kind of getaway you have in mind, you can find a guestroom to fit at Castle Hill Inn. Rooms in the main house vary in size and décor, but each is kitted out for romance with a fireplace, a king-sized bed, oversized tubs, and windows looking over the water and expanses of lawn. The Turret Suite, a bi-level space, has a bedroom on the first level; on the top floor, a soaking tub on a raised floor takes advantage of the 320° wrap-around windows. Below the main house, the Harbor House’s modern guestrooms feature front-porch views of Newport Bridge and the hotel’s Grace Kelly Beach. At the far end of the 40-acre property, the Beach Cottages and Beach Houses are set along the private beach, offering views that take in both the mansions along Ocean Drive and the wild Atlantic itself. The cottages, slightly smaller and closer to the beach, have peaked ceilings with rafters. The airy Beach Houses, compactly outfitted with galley kitchens, sunny decks, ceiling fans, fireplaces, and curated shelves of books, cast a kind of never-leave spell.

Tempt fate at the Monkey Paw’s Book-O-Matic machine, where for the price of a toonie you’ll be delivered an archaic tome in the vein of Elementary Arabic, Vol. 3. I’ll let you know how my studying gets on. The Monkey’s Paw is an eclectic vintage bookstore on Dundas with a collection of unique books, vintage maps, and bugs preserved in Lucite.

One of Scotland’s most important stately homes, Scone Palace has a colorful history. It’s believed to have been the capital of the prehistoric Pictish people, who inhabited much of northern Britain in the early centuries B.C.E., and also served as the seat of parliaments and the crowning place of the Kings of Scots, including Macbeth and Robert the Bruce. The palace visitors see today only dates to 1802, though parts of a 17th-century house, erected on top of a 12th-century abbey, remain. The famous Stone of Scone, upon which royalty sat to be crowned, was here until 1296, when it was stolen by Edward I of England (today, it’s housed at Edinburgh Castle).

Visit the castle and tour the main State Rooms, full of everything from porcelain, ivories, and clocks to furniture, paintings, and other important family belongings. Then explore the expansive grounds, home to the Market Cross, the Old Scone graveyard, a 16th-century archway that once served as the grand entrance to the city of Scone, and a pinetum full of giant redwoods and noble firs.

There isn’t a houseware buyer in the world who doesn’t whisper of the treasures that can be unearthed in this Aladdin’s cave of a store spread over several floors and houses in Dar el Bacha. Alas, these days Mustapha Blaoui is probably Marrakech’s worst-kept secret, but it’s no less magical for that. Whether your preference is for a fuchsia-colored juju hat (all the rage for giving a pop of color to a boring old wall), bone-handled cutlery, a silver teapot and engraved glasses, a chrome-plated art deco mirror, giant beaded heads from the Cameroon, or Syrian furniture inlaid with mother-of-pearl, chances are Mustapha has it. Even if it doesn’t, you can easily lose yourself in this labyrinth of rooms for several hours, swept up in the magic of the Orient.

This hip little café in the leafy suburb of Loresho feels comfy and welcoming, with candles flickering on the tables throughout the day and a monthly schedule of open-mic sessions for Nairobi’s budding musicians. The menu includes salads, sandwiches, and snacks as well as cold brew coffee. All the furniture here is handmade by the owners and available for purchase. You can even commission your own designs to be made here. After your meal, swing by the farm shop next door for jams, cups, bags of coffee, and more.

Sitting at the tip of the peninsula of St-Jean-Cap-Ferrat, which juts out into the Mediterranean, the iconic Grand-Hôtel du Cap-Ferrat, is now under the management of the Four Seasons brand. Located halfway between Nice and Monaco in the striking Antibes cape, the beyond-glamorous property first opened in 1908, and remains the epitome of the bonne vie, Jazz-era French Riviera. A destination resort, it has hosted everyone from Winston Churchill to Charlie Chaplin to Pablo Picasso, and is set on multiple lushly landscaped acres full of gardens, pools, and tennis courts that tumble down to the Mediterranean. Rooms are in three buildings. Try for one in the hotel’s original core, as these have soaring ceilings and floor-to-ceiling, sliding-glass-door windows looking out to the sea. The suites are also enormous, but ask for a higher floor for the best ocean views.

In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

The Grand Hotel de Londres (also known as Buyuk Londra) has been open for more than 100 years, and while its interior is immaculately kept, there’s something about it that is charmingly stuck in the past. You can imagine Ernest Hemingway at the bar in 1922, reviewing notes for his story in the Toronto Daily Star. Wander through the lobby with its antique furniture, past the requisite portrait of Atatürk, to the tiny elevator that will take you up to the rooftop. The bar there is scenic without being a scene: no seasonal cocktails or artisanal ice cubes here, just a simple but serviceable menu and gorgeous views of the Golden Horn and the Old City. If you can, try to arrive before sunset to hear the call to prayer echo throughout the streets, then descend the grand staircase back into the noisy nightlife of Pera.

The charming little town of Lynchburg is home to Jack Daniel, the most famous distillery in all of Tennessee. Take a quick stroll around the town square before crossing a short bridge, which will lead you over a creek that flows from the same spring that provides fresh water for Jack Daniel’s delicious whiskey. Upon arrival at the distillery, you’ll find a modern visitor center where you can learn about the history of Jack Daniel’s as well as the process of making Tennessee whiskey, including the extra step of charcoal mellowing that differentiates it from bourbon.

It’s remarkable to consider that every drop of Jack Daniel’s served at bars all over the world comes from this lovely hamlet down in the hollow—in fact, visitors are likely to see delivery trucks carrying pallets of bottles back up the hills to parts unknown. Should you want to dive deeper into the whiskey-making process, take a guided tour through the various stages of production, beginning at the source of the springwater and continuing through distillation and finally the rickhouses, where the whiskey ages for years in oak barrels until it’s ready for bottling.

A fairy-tale town deserves a magical funfair. Tivoli Gardens is one of the country’s most popular attractions, drawing more than four million visitors a year (in a country with a population of around 5.5 million). Youngsters will enjoy the rides, while their parents will appreciate the nostalgic charm and the wide range of dining options, from hot dogs and churros to “New Nordic” gastronomy.

When Berlin was divided, Checkpoint Charlie was the most famous of the border crossings between the eastern and western halves of the city. It was here that Allied soldiers registered before crossing over into the Soviet-controlled sectors. Thanks to its appearances in Cold War thrillers from Bond movies to John Le Carré novels, it has become a symbol of that era in the city’s, and world’s, history. A small museum nearby includes a replica of the guardhouse that once stood here.

When in Kingston, make time for a stop at Devon House, a grand 1891 Georgian mansion that was built for George Stiebel, Jamaica‘s first non-white millionaire. The lovely upright house and its 11 surrounding acres are now protected as a National Heritage Site, but that doesn’t mean that there’s not fun to be had. The sprawling grounds include shops, restaurants, a bakery, and a popular ice-cream shop, I-Scream. House tours can be arranged, but the grounds, landscaped with stately palms and fountains, are the highlight—it’s a great spot to take a stroll, read, shop, or dine. The mansion and its manicured lawns are also used for weddings and lavish events.

Active from the 13th to 15th centuries and considered an influence on the pre-Renaissance movement, the Sienese School of painting is identifiable by its themes—always religious, and usually with a focus on Biblical miracles—and its signature style, a dreamy mix of Roman, Gothic, and Byzantine influences that often feature dazzling gold backgrounds. Opened in 1932, this museum boasts one of the world’s largest collections of Sienese School works, as well as a number of Renaissance and late-medieval pieces from Italian artists. Wander through the impressive building—a combination of two 14th- and 15th-century noblemen’s palazzi—to find works like Duccio’s Madonna and Child, Michelino da Besozzo’s Mystical Marriage of Saint Catherine (celebrating the “calling” of Siena’s native daughter), and Bartolo di Fredi’s expansive Adoration of the Magi. Paired with a visit to Florence’s Uffizi, coming here offers insight into the differences—and longtime rivalry—between the two cities.

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.

With just over a year in business, Green Dot Stables is still new, but owner Jacques and his wife took over a building in Corktown that isn’t. Instead, they took it from abandoned and historical to historical but fresh. The interior still retains its ode to horse racing and is kitschy appeal without being cheesy. An innovative new menu presided over by Les Molnar features more than 20 unusual and classic sliders with a “mystery meat” option that changes often. On the day I visited, the special was Lamb Tongue with Dijon Brown Butter and Fennel Relish. My favorite was the Corned Beef Slider with Wigley’s-Brinery Kraut, Pickle and Mustard Aioli. Local and imported beers anchor the drink list and their soda (or pop as it is known in the Midwest) is mixed in-house with locally made syrup. Optional sides include truffle fries, poutine, chicken and orzo salad, kale & quinoa, or classic mac ‘n’ cheese. Menus items start at an affordable $2 and it is a packed house during the lunch rush so plan accordingly or visit at odd hours to ensure fast service.