Day 1
Welcome to Uruguay, South America’s best kept secret. After customs, begin your journey east along the coast to the Maldonado province. Bearing a small city with the same name, the Maldonado province sports pristine beaches with plenty of Uruguayan rugged charm mixed in. Outside the seaside resort of Punta del Este, turn towards the hills. Visit a young winery project focused on Merlot, Tannat, Cabernet Franc, Syrah and the white Viognier. Meet the youthful, enthusiastic owners to understand this unique microclimate and place in a private tasting from their sundeck with sweeping views.

Drive into upscale Punta del Este, a glamorous seaside playground often compared to St. Tropez in the summer months. This ritzy beach town marks where the Rio de la Plata meets the Atlantic Ocean with miles of golden, sandy beaches framed by green, rolling countryside inland. Anchor in the Marina for a brief walk out to the “punta” to the historic lighthouse and where these bodies of water meet. Stop at “Los Dedos”, an impressive hand sculpture that rises out of the sand.

Continue east over the funky bridge connecting the area of La Barra, rippled like a wave. Turn inland towards one of the most exclusive and exquisite projects in the area. Located in the middle of a stunning property with roaming cows and distant views of the river, sink your fork into a gourmet lunch experience that sources all local fresh ingredients with international touches.

Check into your boutique hotel, located off a quiet side road in La Barra. With a facade of rusted corrugated iron, hodge-podge interior, and eclectic mix of vintage furniture, books, and knickknacks, the property’s aesthetic reflects the passion of its owner, a local designer and antiques dealer. Traditional milk jugs and vintage apothecary bottles sit atop old medical filing cabinets. Worn but comfy blanket-covered chesterfield sofas are the perfect place to curl up with a book. Breakfast is served at a communal table until the afternoon. Retreat to one of the funky six rooms like arquitecto, airy and spacious, decorated with the restraint of a Bauhaus-trained architect. (Casa Zinc)

Day 2
Today is yours to explore Punta Este. Speed off on the house bikes along the shoreline. Camp out on the gorgeous sandy beaches like Manantiales to work on your tan—or finish that novel. Relax. (Casa Zinc)

Day 3
From the coast, drive a half-hour drive inland from José Ignacio to gaucho country. Here, there’s nothing but grassy, rolling hills, sheep and ñandúes grazing. Perhaps, you’ll pass an old-fashioned gaucho on horseback wearing flared bombachas de campo riding pants, with a felt beret and dagger stuck in his embroidered waistband.

Visit a new olive oil project nestled in the folds of the hills producing some of Uruguay’s finest extra virgin olive oil. Understand the process of making the oil and head out into the plantation for sweeping views of the countryside. Afterwards, sit down to a guided tasting of the different oils, along with snacks and tasting of their excellent new wines.

Head to the dusty, village of Garzón—population 200. This place is the definition of bucolic where long siestas and the word hurry doesn’t exist. Step into another world at the delectable restaurant of Argentina’s best known celebrity chef occupying the town’s old general store. Dine in the elegant dining room, or on the balmy terrace, where the theme is a seasonal menu of meat, fish, and vegetables, all cooked on an iron grill in Andean infernillo style, with a very hot eucalyptus-wood fire both above and below. Homey yet sophisticated. Simple, clean, mesmerizing flavors. Such is Uruguayan country life.

Arrive in the chic village of José Ignacio, nestled among the wind-blown dunes and crystalline waters. Located on Playa Mansa in the middle of town, this destination hotel is housed in bunker-like villas constructed from untreated cement with gardens planted on the roof. Tastefully decorated with hammocks, rustic yet modern furniture, and sisal rugs, the center of the property is the space-age pavilion where the infinity pool melds into the sea with jaw-dropping vistas of the Uruguayan coastline. It’s the perfect spot to contemplate life. Napping, reading, swimming, or dining under the stars are the du jour. If you feel the need to leave the compound, the cool town of José Ignacio is only a few steps away. (Playa Vik)

Day 4
Today, there’s nothing on the agenda. Other than the beach—and hanging out. It’s a blissful world where the day starts with a walk on the beaches, La Mansa or La Brava, stopping to gaze at the postcard-perfect lighthouse on the rocky point. Maybe after go for a bike ride up to the hamlet of Manantiales with its chic antique shops, peddling along the azure coast with the constant breeze. Stop to lunch at Parador La Huella and linger till sunset sipping your clericó, the local sangria. Simple. Perfect. (Playa Vik)

Day 5
Enjoy a leisurely morning and day at leisure in José Ignacio. Transfer to the Punta del Este or Montevideo airport for your departing evening flight.