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The head winemaker at Eikendal in Stellenbosch, Nico Grobler has been producing award-winning wines for more than nine years. An innovator in the Western Cape wine industry, he makes mostly single varietal wines like chardonnay, using an “old world” approach that focuses on terroir to produce the fruitiest vines possible.

The whole family is welcome at Eikendal. While adults enjoy a pizza and wine pairing, children can partake in a juice tasting of their own. On a nice day, visitors can also take a 1.5-mile self-guided walk around the vineyards to learn more about the winemaking process and the farm itself.

One look at this hilltop fort, perched over the Port of Kingstown, and you know the British built it to fight the locals rather than to meet any threats coming by sea—all the cannons face the island’s rugged interior, where the Caribs lived. Inside the fort, you’ll find a series of murals depicting the bloody Carib wars. Kids will love exploring the old buildings, and everyone will enjoy the views.

The waters surrounding Bequia beckon scuba divers with everything from brilliant sponges, colorful fish, and deep-water corals to shallow reefs, sheer walls, caverns, holes, and wrecks. While the area is home to 30 or so easily accessible diving sites, you should head to the designated marine park, which occupies seven miles along Bequia’s leeward coast. Family-run outfitter Dive Bequia (located on Belmont Walkway in Port Elizabeth) offers three dive trips to the park each day, along with instruction, certification, and rental gear. Divers must be at least 8 years old, but snorkelers of all ages are welcome as well.

This handsome resto-bar on Boulevard Saint-Laurent trades in a fantastical aesthetic reminiscent of old timey circuses featuring mustachioed acrobats in striped leotards. The interior is panelled wood with a stuffed dear head and a long pale-wood bar, with disparate chairs around small tables for intimate get-togethers. Their curvy emblem glasses are filled with house cocktails or good beer, and the plates filled with delights conceived by chef Charles-Antoine Crête, of Toqué! fame. Try their Sunday brunch every week starting at 11 am, featuring a salmon feuilleté that will make your day.

The recipe for the delicious, tiny truffle-cream sandwiches at atmospheric old Procacci is a guarded secret but, oh boy, are they good, especially when accompanied by a glass of prosecco. Smart Florentine ladies-who-shop flock here for a pit stop between purchases, but it’s also popular for an early-evening aperitivo. Procacci is additionally one of the few places to buy just-harvested truffles in Florence: look out for them in November and December. Heap truffle shavings over fresh, buttered taglierini pasta or a simple scrambled egg—after only one bite, you’ll understand the attraction to these precious, musty-smelling delicacies.

At this speakeasy-inspired cocktail bar near Chiesa Nuova, hipster bartenders pour and shake American classics like Manhattans, Sazeracs and Old-Fashioneds in a smoky lounge. To gain admittance, make a booking and come armed with the secret password, a clue to which can be found on the venue’s website. Once you enter, you’ll be shown to a table or barstool, handed a menu, and asked to fill out a membership card. Service can be slow and snarky, but drinks are worth the wait. Cash only.

If there’s a better way to start your day in London than with an Arnold Bennett omelette at the Delaunay, I don’t know it. The Delauney is the latest in elegant, old-fashioned glamour from the group that created The Ivy, Caprice, and The Wolseley, and it’s a beautiful, relaxing place to break your fast. The coffee is fantastic, the tea fragrant, and the omelette a rich eggy treat that will see you through to lunch and beyond.

“What wisdom can you find that is greater than kindness?” So said local philosopher and writer Jean-Jacques Rousseau, a statue of whom oversees his namesake island, a wee, romantic spot in the middle of the Rhone where it empties into Lake Geneva. The island-park may be served by two bridges, but it feels like a universe of its own and is a favorite of many visitors and locals in Geneva. The tranquil tree-lined island was once a 16th-century fortification that protected the city, then the site of a bustling shipyard before finally being transformed to a peaceful sanctuary in 1832, when the Pont des Bergues bridge was constructed. (The Pont des Bergues ends across from the 1834 Hotel des Bergues, which was the first meeting place of the United Nations and is now a Four Seasons Hotel.)

A UNESCO World Heritage site, this hotel was the home of Hispaniola’s first governor, Nicolás de Ovando, and one of the first colonial structures built at the top of cobbled Calle Las Damas (the first paved street in the Americas). Built in 1502 and connected in 1974 during a reconstruction ordered by then President Joaquín Balaguer, the three stone buildings retain their original coffered ceilings, massive arches, tile floors, and brick and stone walls. In addition to 92 rooms and suites, including a dozen Imperial Club rooms overlooking the Ozama River and Don Diego Harbor (Room 4015 has a particularly stunning view and gorgeous bathroom), you’ll find a lovely reading nook, gourmet restaurant, lobby mojito bar, and tranquil garden, which features herbs and fruit trees used by the hotel kitchen.

Tannersville’s Deer Mountain Inn looks more like a gigantic personal home than it does a hotel, but therein lies its charm. Set on 168 acres in the Catskills, the gorgeous property features six rooms in an Arts and Crafts-style summer home dating back to 1880, along with a couple of cottages for groups or those seeking extra space. Each room is individually decorated with details like big stone fireplaces, wood-paneled ceilings, and wainscoating, and most have lovely views of the surrounding lawn and forest. There’s no shortage of hiking trails on and around the property and the hotel can arrange bicycle rentals on request. For something a bit more relaxed, there’s a cozy game room with an antique pool table, and regular outdoor painting sessions for the artistically inclined.

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.

Tokyo’s first design hotel, Claska is a fitting choice for creative types. Not only is it located on a street known for its second-hand furniture stores, its 20 individually decorated rooms—all masterminded by architect Tei Shuwa, who also designs furniture and home appliances—fall into four categories: midcentury-style Modern, traditional Tatami, minimalist Contemporary, and Story, which feature ever-evolving aesthetics carried out in collaboration with Japanese artists and designers. French-influenced dishes take centerstage in the ground-floor restaurant, and the hotel has a shop for Japanese artisanal home products and a gallery with monthly exhibits, as well as a dog-grooming salon and a fleet of custom Tokyo bikes for exploring the cafés of the nearby Nakameguro neighborhood.

This family-run micro-village in Valais offers 36 rooms across six separate chalets. Huddled together on a hill above the popular ski resort of Zermatt, the buildings reference the area’s traditional architecture, from the timber frames to the hunting-themed decor.

Have dinner on the hotel’s terrace in the summer, when clear skies afford a picture-perfect view of the Matterhorn. The modern menu pulls inspiration from traditional Swiss cuisine.

All the rooms have balconies or terraces to make the most of the superlative views. Rent a whole chalet to accommodate up to 10 people. These come with separate living and dining rooms, and wellness areas (sauna, massage room) as well as open fireplaces.

Le Rêve rises up like a dollhouse from a street lined with bars and restaurants in the leafy neighborhood of Providencia. Completely renovated in 2011, this pretty boutique hotel works on a B&B basis, the idea being that guests make the most of the surrounding eateries. However, tea, coffee, and snacks are always available, and there is an open kitchen so guests can poke their head in the fridge when peckish. This gives the hotel a unique, homey feel.

Behind the white shuttered windows, communal areas include a lounge area with an honesty bar and a library stocked with international books. The dollhouse feel continues inside with details such as an elegant green velvet sofa, blue and white ceramics, and waitresses dressed in French maid outfits. Rooms are equipped with wireless Internet access.

Stretching high above Fifth Avenue, the Peninsula is a glamorous, classic hotel. Formerly the Gotham Hotel (built in 1905), this building is at the heart of prestigious Midtown Manhattan with neighbors like the Museum of Modern Art and Rockefeller Center. It has a convenient location for Fifth Avenue shopping and exploring Central Park. The Peninsula is a favorite of New Yorkers for its rooftop bar, Salon de Ning, with its mesmerizing views of the city skyline. Rooms are polished and inviting, designed to resemble a luxurious New York City apartment. Kick off your stay with a classic cocktail in the Gotham Lounge, followed by a locally sourced meal at the elegant Clement Restaurant and Bar.