Hidden Uruguay: Winter Wine Country & Coast

Arrive at the Port of Colonia, where a private transfer with a guide takes you to a hotel in the Historic Quarter. At an additional cost, the transfer can also meet travelers at Montevideo Airport. Set out on a private walking tour of Colonia del Sacramento, a UNESCO World Heritage Site shaped by centuries of Portuguese and Spanish rule. Walk the cobblestone streets and visit Portón de Campo, Calle de los Suspiros, historic squares, and Iglesia Matriz. Explore local museums and finish with a mate tasting, learning about the history and traditions behind Uruguay’s national drink.

Travel into the Carmelo countryside and explore La Calera de las Huerfanas, an archaeological site preserving the remains of a Jesuit estancia dating to 1741. Learn how the Jesuit Missions helped introduce grape cultivation to Uruguay before visiting two family-run wineries. At Bodega El Legado, tour the vineyards, cellar, and production area, then taste three wines with cheese, salami, and olives. Continue to Bodega Cordano for a vineyard and winery tour, a visit to the historic Almacen de la Capilla, and a tasting of three wines with homemade lunch.

Transfer to Granja Jacaranda after breakfast for a hands-on cooking class at a family farm. Work alongside Laura and her family to prepare traditional Uruguayan dishes, including empanadas, locro, and dulce de leche pancakes, paired with local wine and a welcome drink. Enjoy lunch featuring the dishes prepared during the class while learning the stories behind each recipe. In the afternoon, transfer to Puerto Camacho for a 1.5-hour sunset boat ride on the Río de la Plata. Cruise through the Delta islands near the meeting point of the Río de la Plata and Uruguay River, known as kilometer zero of both rivers. Board a classic boat at Club del Faro and hear local stories of coastal legends and shipwrecks while watching the sunset. Return to Carmelo after the cruise.

Travel without a guide to a countryside estancia in Uruguay’s Durazno department, settling in for three nights amid open farmland and natural landscapes. Spend the afternoon exploring the property and choose from activities such as tararira fly fishing, horseback riding, water skiing, birdwatching, or practice at the driving range. Experience rural Uruguay at a working estancia surrounded by diverse wildlife and native habitats. Relax at the property after a day outdoors and prepare for the next two days of countryside activities.

Spend a full day at the countryside estancia in Durazno, surrounded by open fields and diverse wildlife. Choose activities based on interests and conditions, from tararira fly fishing and horseback riding to water skiing, birdwatching, and practice at the driving range. Explore the property at a relaxed pace, experience rural Uruguay, and enjoy the estancia’s natural setting before returning to the lodge for the evening.

Spend another full day at the countryside estancia in Durazno and explore the property at a relaxed pace. Continue with favorite activities such as tararira fly fishing, horseback riding, water skiing, birdwatching, or time at the driving range. Take in the open landscapes and diverse wildlife of rural Uruguay while enjoying the estancia’s peaceful setting. Return to the lodge for a final evening in the countryside before departing the following day.

Transfer without a guide to Montevideo and begin with lunch at Mercado del Puerto, a lively food hall known for traditional Uruguayan parrillas. Meet a local guide for a walking tour of Ciudad Vieja, exploring Plaza Independencia, Palacio Salvo, the Presidential Office, and the mausoleum of José Gervasio Artigas. Continue along Peatonal Sarandí to Plaza Matriz, the Cathedral, and the Cabildo, then visit two museums from the Candombe Museum, Museo Torres García, or Museo Gurvich. Finish at the workshop of Lobo Núñez, a renowned luthier and Candombe percussionist, to learn about Uruguayan Carnival and the African-rooted Candombe tradition. 

Transfer from Montevideo to the hills of Maldonado and stop at Olivos de las Animas, an olive farm in the foothills of Cerro de las Animas. Learn about extra virgin olive oil production, taste local oils, and enjoy an exclusive lunch at the owner’s home while spotting native wildlife such as red and blue cardinals, rheas, and other mammals. Continue to an eco-lodge in the valley and hike through an archaeological site featuring cone-shaped stone structures that have raised new questions about the region’s history. 

Transfer to Pueblo Eden and explore the village chapel and main square before starting an approximately 8 km (5-mile) hike through the surrounding countryside. Follow a local trail once used to reach nearby estancias, passing through gates, native forests, open meadows, grazing cattle and sheep, and a small stream. Walk across gentle rolling hills and take in the rural landscapes of Maldonado before finishing at Vina Eden. Enjoy a wine tasting at the winery, sampling local wines after a day of hiking through Uruguay’s countryside.

After breakfast and checkout, meet a guide for a private tour of Punta del Este and the surrounding coast. Visit Casapueblo, the iconic seaside complex created by Uruguayan artist Carlos Páez Vilaró, then explore Punta del Este’s port and watch for sea lions along the waterfront. Cross La Barra’s distinctive undulating bridge and continue through La Barra and Manantiales, browsing antique shops and local boutiques. Finish at the MACA Museum and Atchugarry Foundation Sculpture Park before transferring to the hotel in La Barra for an overnight stay.

After breakfast, travel with a guide to Garzón, a small village known for its rural setting and growing wine scene. Explore the village square, chapel, and former railway station before continuing to Bodega Garzón, a winery set on a rocky rise overlooking the vineyards. Tour the vineyards and winery, learn about Uruguay’s wine production, and enjoy a premium wine tasting with extra virgin olive oils. Sit down to a wine-paired lunch before returning to La Barra for another overnight stay.

Spend the day at your own pace in La Barra.

Transfer to Montevideo Airport for your departure flight.