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While there’s much to do in Milan, there’s also a lot to do outside the city. Hop on a train and enjoy lunch by a lake, see a contemporary art collection in an 18th-century villa, and dine at a Michelin-starred restaurant. Then take a stroll in a walled city, go winetasting, or climb a tower. All you need is an adventurous spirit.

When Domingo Ghirardelli immigrated to the United States in 1849, he planned to strike it rich in the California Gold Rush. Unsuccessful, he opened a store in Stockton selling supplies and some confections to other hopeful miners. Flash forward a few years (and failed businesses), and Ghirardelli opened another confectionary company called Ghirardely & Girard, which would lay the foundation for today’s Ghirardelli Chocolate Company.

Chocolate was made on San Francisco‘s northern waterfront for many years but eventually moved out of the city. Luckily the buildings still stand, including the historic power plant with clock tower. Two floors were added to a warehouse in 1923, and atop those the famous 15-foot-high letters spelling out “Ghirardelli.” Though the company continues to make chocolate, it is no longer owned by the Ghirardelli family.

Still, there are plenty of reasons to visit the brick buildings that have been transformed into a thriving marketplace with restaurants—including our favorite, an upscale dim sum restaurant, Palette Tea House—, art galleries, shops, a winetasting room, and of course, a place to taste and buy Ghirardelli chocolate, a true San Francisco original. The square also hosts some popular San Francisco events, including an annual Christmas tree lighting and a chocolate festival held each September.

Set on a steep hillside overlooking vineyards and the Silverado Trail, Stuppa Estate Napa Valley manages to be both secluded and well positioned for exploring Napa Valley’s wineries and towns. The suite-only property has five poet-themed rooms—refreshed in 2021 by Erin Martin Design and embellished with hand-painted murals by artist Michael Duté.

Each suite is themed after a literary icon, such as Emily Dickenson, and includes a private patio, a soaking tub, and an outdoor shower—including a few oriented toward the valley. Sunset is a highlight: All rooms face west, giving guests unobstructed evening views of the valley and vineyards below.

Breakfast is a lavish spread with dishes like seasonal pancakes or shakshuka—served either in-room or on the open-air patio. A small outdoor pool and on-site spa treatments add to the quiet atmosphere, and staff can arrange private tastings at Sullivan Rutherford Estate, a boutique winery under the same ownership. Service is a defining feature; the team handles everything from sunset cocktails to dinner reservations with a level of care that consistently elevates the stay.

At Boschendal, guests can slow down and savor “Le Pique Nique,” a pre-packed picnic basket that you can order in advance of your visit to the vineyard. When you arrive, collect your wicker basket filled with sweet and savory treats, pick up a bottle of wine to pair with your snacks, and find a spot under the pine trees to sit for the afternoon, relaxing and enjoying the sunshine.

Boschendal is right on the edge of Stellenbosch, about an hour’s drive from Cape Town through the beautiful hills and valleys of the winelands. The owners transformed several farm laborers’ cottages into luxury accommodations, should you wish to spend the night after a day of vineyard tours, winetastings, and dining at the estate’s several restaurants.

If you’re seeking a quirky yet educational winetasting experience in South Africa, look no further than Warwick Estate’s “Big Five Wine Safari.” While you won’t see any lions in Stellenbosch, your guide may help you spot a falcon or two while you cruise around the vineyard. Here, the Big Five refers to the five types of wine grapes planted on Warwick’s farm, from cabernet sauvignon and sauvignon blanc to pinotage, merlot, and cabernet franc. Board Warwick’s safari-style vehicle and leave the driving to your guide as you enjoy the views—and the wine. Advance bookings are recommended.

The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.

American entrepreneur Michael Evans and Argentine winemaker Pablo Gimenez Riili joined forces to create an unparalleled viticultural paradise for wine lovers from around the world. Set on 1,500 pristine acres in the heart of the Uco Valley, the Vines Resort & Spa is a haven of laid-back luxury with a robust offering of culinary and wellness activities, winemaking endeavors, and outdoor adventures. Every aspect of the hotel is designed to share Mendoza’s natural beauty, superior wines, and Argentina’s warm culture through a tailored guest experience provided by the resort’s “Gauchos”—personal concierges and tour guides who curate one-of-a-kind itineraries for visitors.

The resort’s 22 spacious villas have ample indoor/outdoor living space, with wood-burning fireplaces, open-air fire pits, plunge pools, hot tubs, and private rooftop terraces with 360-degree views. Siete Fuegos, the resort’s signature restaurant, showcases open-flame grilling techniques mastered by Argentina’s acclaimed chef Francis Mallmann. The fitness center and yoga studio look out to the Andes, while three miles of running trails weave through the property’s vineyards. There’s never a dull moment at the Vines, with horseback riding, hiking, biking, cooking lessons, and winetasting at your fingertips—unless lounging is your preferred activity, in which case a cabana next to the 1,000-square-foot infinity pool will be calling your name.

Visiting Santiago Achaval and Manuel Ferrer’s boutique winery Achaval-Ferrer is a requisite visit while in Mendoza to sample Argentina’s most awarded wines. Their malbec wines and blends consistently earn high scores from Robert Parker, Wine Enthusiast and Wine Spectator. Started by a group of Argentine and Italian friends, Achaval-Ferrer’s Italian winemaker Roberto Cipressois specializes in small production wines that yield a high concentration of flavors, colors and aromas. Their beautiful 60-acre vineyard, Finca Bella Vista, offers free wine tours and tastings daily. You’ll sample three of their red wines, a sweet dessert wine and homemade olive oil. Chances are you won’t walk out empty handed. Calle Cobos 2601, Pedriel, Mendoza; +54 9 261 553 5565

Wind through the Santa Monica Mountains to Malibu Wines, a grassy garden retreat with gorgeous views for picnicking and sipping wine with friends. The space is accented by Instagrammable features like the metal WINE sculpture that emulates the iconic LOVE sculptures by artist Robert Indiana that are found in cities around the world. Entry is free; just order wine from the farmhouse-style tasting room and enjoy the live music and festive atmosphere on the weekends. (Weekdays are more mellow.) Table reservations, including one inside a vintage school bus, are recommended for groups—but if you’re more flexible, simply bring a blanket and some food, find a spot to spread out on the lawn, and explore the grounds.

This refined 28-acre resort set in the rolling hills between downtown Sonoma and downtown Napa makes guests feel relaxed the moment they check in. The vistas are unobstructed from the resort’s pool areas, and many of the property’s 94 stand-alone cottages with private balconies and six private homes offer views of the open space, too. By day, lawn games are usually underway on the grassy expanse called the Town Square, while in the evenings, a pavilion provides an unparalleled backdrop for stargazing. This is a hotel that values fresh air, as evidenced by the walls in the common areas, which retract to bring the outdoors in. There are other reasons to fall in love with Carneros—namely, the on-site restaurants. The casual Boon Fly Café is famous for breakfasts, with spicy bacon Bloody Mary drinks and tiny made-to-order doughnuts. FARM, on the other hand, is more formal, with menu items such as braised oxtail terrine and smoked Sonoma duck breast. While the hotel offers in-room massages, it will also reopen its spa after a full-scale renovation later in 2018.

On this week’s episode of Travel Tales by AFAR, the food-obsessed host of the podcast eats, drinks, and shops along the 400-mile Vallée de la Gastronomie.