Flight to Montevideo. Reception and transfer to the hotel upon arrival.

In the morning, take a three-hour tour of Montevideo, Uruguay's largest city and capital, showcasing colorful street markets, the Gaucho Museum and the historic quarter—its highlights, its architectural nuances and galleries. From there, head to El Mercado del Puerto, an indoor market with small shops that sell books, crafts, clothing and textiles. The market has come to be a venue for local, up-and-coming musicians, a common "meet up" for Montevideanos. Lunch at La Posada Don Tiburon, a good market restaurant, where one can try out some authentic Uruguayan cuisine. After lunch, explore Carrasco, Punta Gorda and Pocitos (all residential neighborhoods) and walk along the Rambla on the coast. Note: One can choose to take the city tour in the morning or afternoon, and, on top of that, it's possible for the tour to be customized to one’s needs.
In the afternoon, head to the outskirts of Montevideo to tour some of Uruguay's finest vineyards, see how wine is produced, visit the wine boutiques and cellars, and taste Tannat as well as some other wines. (Tasting included.) Be sure to check and some of the local boutiques and bring some wine back. Note: Street Markets are only open on Saturdays and Sundays.
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Morning transfer to the bus station, to connect with the bus to Colonia. Reception at the bus station and transfer to the hotel upon arrival.
In the afternoon, explore Colonia's historic quarter—the stone-paved streets, colonial architecture, forts, Spanish and Portuguese museums, the port and last but by no means least, Ferrando Beach. From the beach, follow the Coastal Rambla, an esplanade from the Old City to the "Real de San Carlos," and visit the bullring, the horses' race course and the old port. Lunch at Meso de La Plaza Restaurant.
Rest of the afternoon at leisure. Dinner at La Casa de Jorge Páez Vilaro, a restaurant and art gallery.
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After breakfast, visit the Zubizarreta winery (founded by Pedro Zubizarreta fifty years ago) and The Irurtia Winery (the biggest winery in Uruguay). Tannat, Uruguay's all-star grape, produces deep, herbal red wines made with blackberries (sometimes blueberries) that Time Magazine has aptly described as “marvelously complex” and “beautifully structured."
For lunch, head to Finca Narbona, a farm that makes delicious cheese, cultivates organic fruits and vegetables and produces exquisite wines. Narbona’s restaurant has brick and mud walls, a dividing wall with more than 1,700 wine bottles and a countryside kitchen with a first-rate cheese deposit.
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In the morning, set off on a Gourmet Cheese of Colonia Valdense Tour, visit three local artisan producers and taste some typical homemade cheeses. Later, transfer to Posada La Vigna located in Colonia Valdense. Dinner and overnight stay.
A traditional, 1880s estancia with thirty hectares to its name, La Vigna is set apart by its sustainability, the artists and intellectuals that it tends to draw and, perhaps, above all, its homemade pecorino cheese. The owner is the only sheep milk farmer in Uruguay. Some of the available activities are bike riding, bocce & table games, fishing, horseback riding and trekking.
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After breakfast, private transfer to Punta del Este. Upon arrival transfer to the hotel. After settling in, take a city tour featuring some of Punta del Este's foremost highlights, the port; Juan Gorlero, the main avenue, and some residential neighborhoods, such as the San Rafael, Rincon del Indio, Cantegril and Golf. After that, cross La Barra, an undulated bridge, and visit the Indigenous Park as well as Mansa and Brava beaches and Beverly Hills, one of Punta del Este's most elegant neighborhoods. Last, but by no means least, visit Casapueblo, once the self-designed home of Uruguayan artist Carlos Páez Vilaro's and now an art gallery, museum, hotel and sculpture in its own right. ...read less

After breakfast, private transfer to the Posada. Day at leisure. Take advantage of the surroundings: Bird watch, take a walking tour, or horseback ride. Dinner and overnight stay.

Another day at leisure. Explore or just take it easy. (All meals included.)

After lunch, head to Estancia Guardia del Monte, a private transfer that's worthwhile in it of itself; be sure to look around. In the late afternoon, visit to an ombú forest, one of the few that still exist. Part of the Humedales del Este (declared Biosphere Natural Reserve by the UNESCO) and located on the border of the Castillos Lagoon, the landscapes that surround Estancia Guardia Monte are staggering.
Many outdoors activities are available, such as bird watching, canoeing, fishing, hiking and horseback riding. Dinner and overnight stay.
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In the morning, go for a horseback ride through the palm groves. Rest of the day at leisure. (All meals included.)

After breakfast, head for Cabo Polonio, a small fishing village that's only accessible by horseback or by cars with four-wheeled drive on account of shifting sand dunes—sand dunes that make one feel as if they’re in the middle of the Sahara. Have lunch at La Perla, or The Pearl, a small, local posada, or lodge, that looks out on the sea. After lunch, check out the seals and sea lions on the surrounding islands. (Collectively these islands have one of the largest populations of seals in the world.) Then, continue on to Estancia El Charabon, for an overnight stay. Dinner included. ...read less

Day at leisure to enjoy this beautiful Estancia (all meals included). Overnight stay.
At El Charabon, Fabian, who couldn't be much more attentive, will guide the tours. Guests can opt to lend a hand with rural tasks, learn more about cattle breeding or horseback ride through the countryside toward the beach or just take it easy.

After breakfast, private transfer to Montevideo’s airport to take the flight back home.