Montevideo

Dear Eva,

Montevideo is a place of pentimento, reflecting layers of history, architectural styles, ethnicities and cultural fragments, as seen in the gracefully faded buildings in the Ciudad Vieja, the oldest area of the city. Over the last quarter century, parts of Montevideo have fallen into disrepair, and the city has suffered an unfavorable comparison to Buenos Aires, which is located just a ferry ride across the Rio de la Plata. But Montevideo has always appealed to me, and these last few years have seen a distinct reinvigoration of the city’s heart, the Ciudad Vieja.

For you, Eva, I have combined my long-time love for Montevideo, your love of art, architecture, literature and luxury, and the city’s recent rejuvenation, to design a custom escape that makes the most of this beautiful, vibrant city.

Day 1: Montevideo luxury

A perfect example of the city’s resurgence is the French styled palace that was the Hotel Casino Carrasco. After nine years of construction, the hotel opened in 1921 as the ultimate in glamour for Montevideo’s elite. For decades, the hotel remained a mecca for luxury-loving tourists and locals, but by the 1990s, the building had fallen into such disrepair it had to be closed down. Twenty years later, it was renovated, restored to its former glory, and, in March 2013, reopened as the Sofitel Montevideo Casino Carrasco and Spa, where you will be staying for the next three nights.

You will arrive in late afternoon, and be ushered up to your suite, where a light meal and chilled champagne will transition you from the hard corners of regular life into a softer, more sensual vacation state of being. After that, you will probably want to explore the hotel’s library. I highly recommend trying Eduardo Galeano (1940-2015), a literary giant of Uruguay who once said, “I am a writer obsessed with remembering, with remembering the past of America and above all that of Latin America, intimate land condemned to amnesia.” His most noteworthy books are “Memory of Fire Trilogy,” “Football in Sun and Shadow,” and my favorite, “Mirrors: Stories of Almost Everyone.”

Once you’ve savored time in the library, you will take whatever delicious new book you’ve selected to the spa, where I have arranged a block of time for you to choose a la carte treatments from the hotel’s premium spa services. After you’ve been pampered to your heart’s content, you can choose to dine on French cuisine in the hotel’s impeccable restaurant, or have food brought up to your suite, where you can eat overlooking the glimmering Rio de la Plata.

Day 2: La Ciudad Vieja

Your driver and guide for your stay, Diodoro, will meet you in the lobby, and take you for short drive along the lovely curved coastline of the Rio de la Plata into the heart of the Ciudad Vieja.

Your day begins with a guided tour of Palacio Salvo, Montevideo’s undisputed architectural icon since it opened in 1928. This 27-floor, Italian-designed building is an unexpected but magnificent marriage of Neo-Gothic and Art Deco that must be seen firsthand to be fully appreciated.

Next, Diodoro will take you to El Bajo, a formerly down and out part of the Ciudad Vieja. The area has seen a renaissance since 2013 due to a collective of inspired artists who have breathed new life into the beautiful, formerly abandoned colonial houses, transforming the area into a haven for visual art, underground theater, and trendy boutiques.

Perusing the boutiques and galleries will no doubt consume the rest of the afternoon. I think you will particularly enjoy Tienda Rara, a haberdashery that creates chic, sustainable garments made from reused materials.

Day 3: La Vie Boheme

After a long, luxurious morning at the spa, and a lovely lunch at the hotel, Diodoro will show you to La Casa Wang, an area which a collective of muralists have turned into a workshop and exhibition space for graffiti. I recall our conversation about Banksy and other street artists you admire, and I’m sure you will agree that the art of La Casa Wang is not to be missed.

In this artistic frame of mind, Diodoro will take you to the Museo Nacional de Artes Visuales, which houses the country’s largest collection of paintings. Wander and while away the rest of the afternoon drinking in masterpieces by great Uruguayan artists such as Gurvich, Cúneo, Blanes, Figari, and Torres García.

For dinner, I have made reservations at Jacinto, one of Montevideo’s premier restaurants. Lucia Soria, a protégée of Francis Mallmann, opened Jacinto in 2012 in La Ciudad Vieja to great acclaim. The menu offers a range of elegant fare, from simple but delectable soups and fresh baked bread, to sophisticated dishes influenced by both Spanish and Italian cuisine. The homemade aguas saborizadas (spring water infused with fresh fruits and herbs), are a not-to-be-missed refreshment.

Day 4: Wine and song

Today you will take a decadent journey into the wineries of Uruguay, which is one of the largest producers of wine in South America. In particular, it is known for red wine made from tannat grapes, which make a rich, bold wine, but your day will include more delicate and refreshing white wines as well.

You will visit two wineries to tour the grounds and facilities, one of which is on a gorgeous French estate, and indulge in wine tastings accompanied by scrumptious snacks of cheese, crackers, and nuts.

You may choose to return to your hotel for a rest after your tour, or head into the city for an early dinner—whatever your preference, Diodoro will make it so.

After nightfall, you will head over to La Ronda Café and Bar. A meeting place for artists and musicians, La Ronda will give you an authentic taste of the Montevideo hipster scene. Wallpapered floor to ceiling with vintage album covers, this laid-back hangout is used as the headquarters for The International Uruguayan Film Festival. It is also a venue for live music and poetry readings. Uruguay has a hugely literate population and has produced, it is said, more writers per capita than any other country.

Day 5: A fond farewell

Today concludes your first visit to Montevideo, but I’m sure it won’t be your last. I so enjoyed planning this getaway for you, Eva. Please call me at any time if I can be of service.