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A winery with an enviable view, Tokara is considered one of the best in the region for its cabernets, sauvignon blancs, and premium olive oils. As compelling as the wines are, though, people flock to Tokara for its restaurant, led by chef Carolize Coetzee. Here, in a stunning building made of glass, steel, and stone, diners enjoy contemporary cuisine, award-winning wines, and dramatic views over Stellenbosch and False Bay. Before sitting down for your meal, enjoy a drink at the bar, which offers views of the kitchen as well as the sun setting through a picture window. Then dig into creative dishes like roasted beef with lemon-glazed shimeji mushrooms, and pork belly with carrot-ginger sauce. The menu changes seasonally, but guests can always expect a life-changing meal.

A refined yet rustic restaurant and guesthouse nestled into the rural landscape of Mendoza’s Uco Valley, Finca Blousson is a hidden treasure for wine lovers seeking life’s simplest pleasures. Pair the Bistro’s blend of Argentine and French Provencal fare with wines sourced from the region’s top local boutique wineries, and you’ll be treating yourself to an unforgettable experience. The intimate country guesthouse has three cozy rooms overlooking the vineyard or a spectacular view of the mountains. Owners Victoria Jones and her French partner, Patrick Blousson, will look after you like a member of their own family. Route 94, km 14, on the road to The Manzano Histórico, Tunuyan, Valle de Uco, Mendoza; +54 9 261 15 655 3382

The metal-and-glass ribbon structure of this Frank Gehry−designed hotel—not too far from Bilbao—creates an ethereal silhouette that contrasts dramatically with Elciego’s medieval landscape. Opt for a guided tour to learn more about the history of winemaking in the Basque countryside.

On the North Fork of Long Island, Shinn Estate Farmhouse Inn is tucked away on a peaceful vineyard. Rooms are in the estate’s historic 1880s homestead, and guests get to experience life on the vineyard—and taste the final product in the winery’s tasting rooms. There is also a lovely front porch and gazebo for kicking back with a glass of wine. A cozy wood-burning stove in the reception area is an ideal spot on a chilly day. Breakfast here is a slow and civilized affair, starting with hot coffee and finishing with a full farmhouse hot breakfast from chef David Page, made from farm-fresh ingredients. This is the pastoral North Fork at its best, designed for lazy afternoons, sleeping in, and one too many glasses of wine.

Around since 1692, Spier is one of the oldest and best-known wineries in Stellenbosch. Not only does this historic estate continue to receive accolades for its wine, it’s also become a hot spot for travelers thanks to its family-friendly atmosphere. Visitors can easily spend anywhere from a couple hours to an entire day enjoying all the activities Spier has to offer, from picnics on the lawn overlooking the Eerste River to self-guided walking tours of the property. There’s also a farm-to-table restaurant on-site, as well as an outdoor playground for children. For something unique, book the “Eagle Encounter” program to learn how the estate rehabilitates wounded birds and uses them for natural pest control, or take an evening Segway tour of the vineyards, followed by a sunset tasting among the vines.

Secreted away on Giudecca Island is the glamorous, lagoon-facing Belmond Hotel Cipriani, originally opened in 1958 by Giuseppe Cipriani, founder of the infamous Harry’s Bar and the creator of that ubiquitous brunch cocktail, the Bellini. The peach-hued 15^th-century palazzo is styled with Murano glass chandeliers and Fortuny and Rubelli fabrics and has a Michelin-starred chef in house and several knockout restaurants all set on manicured grounds. The hotel is kept safe from the prying eyes of paparazzi behind a castlelike wall. No wonder it’s the luxury hideout of choice for celebrities (Mick Jagger is a fan) and the jet set.

If guests do feel like venturing out, the hotel offers one-of-a-kind outings with expert local guides such as a nighttime photography stroll, a visit to area wineries and farms via boat, and a kayak paddle on the lagoon.

There is a reason why renting a villa in Tuscany is so popular - rustic farmhouses, rolling hills filled with olive and plum trees, golden sunsets, locally-harvested wine, creamy cheeses, and cool evenings spent with friends and family. Renting a villa provides a relaxing base for your sightseeing in the region. Almost all Tuscan towns allow easy day trips to the main sights: - Florence‘s art and Renaissance history (Duomo, Uffizi Gallery, Michelangelo’s David) - Cortona’s steep, narrow streets and medieval walls - Siena’s cultural city center, now a UNESCO World Heritage Site - San Gimignano’s fortified towers set amidst picture-perfect Tuscan hillsides - Montelpulciano’s world-famous wineries and more This offers the best of both worlds - after a dusty day of sightseeing, you can relax at your villa with a jump in the pool and a glass of wine. Watch the sun go down in a purplish haze, unwind with friends, and enjoy the lovely moment. I recommend YourTuscany.com, which is where we found Villa Coloniale (above) in the town of Pergine Valdarno. The infinity pool and covered patio are guaranteed to put you in a relaxed, Italian frame of mind!

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.

Posada Borravino is tucked away along one of Mendoza’s oldest poplar-lined streets in the city’s Chacras de Coria neighborhood. The country inn has eight distinct guestrooms that offer a peaceful respite in a quiet Mendocenean neighborhood. The hotel’s design is simple but elegant. Rooms feel clean and refreshing with rustic yet stylish furniture, patina walls, and high, white-washed wooden ceilings.

A boutique hotel experience in every sense, here guests frequently mingle in the sun-drenched living room and cultivate friendships over bottles of malbec and long evening asados (barbecues). The back garden provides an inviting place to enjoy a good book, dip in the small swimming pool, or simply soak up the tranquil atmosphere. The staff is friendly and knowledgeable about what to do and see in Mendoza—from winery tours to adventure activities. In the evenings, Posada Borravino is lit up by dozens of scented candles, creating a magical ambience that casts a rosy glow on your entire stay.

Fans of Georgia O’Keeffe should definitely book a stay at this quaint adobe hotel in her old painting grounds. Not only is there a well-stocked gift shop where you can buy O’Keeffe prints and books, the property arranges tours of her home and studio, and is located near the Ghost Ranch retreat center and the White Place rock formations, both of which the artist loved to paint. Wood-beam ceilings and New Mexico antiques adorn rooms. Request one of the cottages with wood-burning Kiva fireplaces, or if you come in winter and book economy like I did, you’ll likely get upgraded to a nice room with a gas fireplace. My best meal in New Mexico was also enjoyed here. I ordered trout stuffed with corn pancakes and a chardonnay from nearby Black Mesa winery. My partner’s chili rellenos with green chili and Monk’s Ale—brewed at the Christ of the Desert Monastery about an hour away—were also tasty. It was a lovely introduction to the beautiful state.

If you want to get away from the crowds in Santorini, try Megalochori - one of the prettiest, quietest little villages on the island. The town’s location further inland, away from the caldera cliffs, removes it from the typical tourist itinerary. A beautiful bell-tower archway frames the entrance as you drive into town, which is easily accessible by a short car, taxi or bus ride from any part of Santorini. Megalochori features a maze of extremely narrow cobblestone streets passing by hundreds of traditional white-washed houses and churches with accents of bright blue. Let yourself get lost. At the the center of Megalochori is a sleepy town square, with two tavernas and bougainvillea-covered patios. Sit in the welcome shade and order a vibrantly-hued Santorini tomato salad, grilled souvlaki and sesame & honey-coated feta. Try Restaurant Raki (above) in the town square, where the locals go. (Live Greek music at night.) And since Megalochori is the heart of Santorini’s wine industry, be sure to visit a winery, where you can meet the local vintners and sample their goods. If you are looking for a very quiet village and a low-key, relaxing day, this is a wonderful place to visit. Sometimes a really lazy day is just what the doctor ordered. www.santorini.com/villages/megalochorivillage.htm

Why I was so surprised to find a food truck in the village of Volcano outside of Volcano National Park, I’m not sure. All I know is that it was one of the many culinary surprises on the Big Island. This truck was packed with all kinds of wonderful things, and almost all of it was healthy too. If you can find it, and I have no way of telling you where they will be parked, ask for the special drink they mix up daily, I think it has ginger it in, but they’ll know what you mean. The company is called Higher Taste Vegetarian Cafe, and this truck was parked outside of the Rainforest Gallery at Niaulani near Volcano Village. That’s the best I can do, but then again, finding the truck is half the fun!

Ontario has another wine destination, Prince Edward County, affectionately named “The County.” This cluster of towns, about 2.5 hours east of Toronto, is home to some of Ontario’s best wineries. But never was there a great place to stay until summer 2015 when Jeff Stober, the hotelier behind Toronto’s stylish Drake Hotel, opened a rural clone, the Drake Devonshire. It’s the ideal retreat for travelers wanting their Drake by Lake Ontario. Once a 19^th-century foundry, the building is now a contemporary farmhouse-cottage, decked out with 11 individually-designed hotel rooms and two suites in the quaint town of Wellington. The property offers coziness all year round in the communal living room and out back over a lakeside fire pit and s’mores. Guests can hang in the barnlike Pavilion for musical performances, sommelier seminars, seasonal events, or just to gawk at the floor-to-ceiling mural by Brooklyn artist FAILE. It doesn’t hurt that Sandbanks Provincial Park—known for its 60-foot sand dunes—is practically the backyard of the Drake Dev.

I love all of the McMenamins properties I’ve stayed at over the years on travel through the Pacific Northwest, but I may have a new favorite: McMenamins Edgefield in Troutdale, right at the western mouth of the Columbia River Gorge. As always, the hotel honors the past of the building it now resides in, it has great food and drink, and every inch is covered in whimsical art that demands you have a good time. Historic Edgefield was built in 1911 as the county poor farm, and it’s now a 74-acre hotel and playground, home to award-winning farm-to-table cuisine, a winery, a brewery, three pubs, movie theater, golf course, you name it. With 100 guest rooms and hostel accommodations, the instant you step on the grounds you’ll be able to tell that community and creativity are cherished here. If you’re traveling solo or out on a long trip and looking to save some money on the hotel part, I’d encourage you to look at their rooms that don’t have a private bathroom en suite. Instead, you head to the large, comfy, and private communal restrooms to get cleaned up. Brilliant. This is a great spot to launch your explorations along the Columbia River Gorge, and if you live in the Portland area, it’s a great place to gather for a weekend bike ride, grub with fellow friends, and a few cold pints around the outdoor fire pits when things get cold. With films and live music nightly, it’s hard not to want to just live here forever.

On a hilltop perch overlooking 8,000 acres of grounds designed by famed landscape architect Frederick Law Olmsted, the Inn on Biltmore Estate’s 210 rooms and suites evoke traditional 19th-century manor houses, with dark mahogany beds and desks, billowing window treatments, and comfortable overstuffed chairs; book a room with a balcony to breathe fresh mountain air while appreciating views of rolling hills—or simply take in the vista from the hotel’s veranda. The formal dining room showcases seasonal specialties using estate-raised cattle and lamb, vegetables from the on-site garden, and wine from the property’s own winery, where you can participate in a free tasting, then ride back in a complimentary shuttle. If you’re looking for something more casual, the lobby lounge and library bar offer salads and sandwiches—and no dress code. But the main attraction is the 250-room Biltmore château, the Gilded Age mansion George Vanderbilt built here in the late 1800s, and its 16th-century tapestries, Renoir and Sargent originals, and 65 fireplaces.