48 Hours in Montevideo: The Ultimate Itinerary

Day 1: Morning

10 a.m.: A 45-minute Uber from Carrasco International Airport will place you at your lodging, the Alma Histórica Boutique Hotel. A renovated mansion on Plaza Zabala, each of the Alma’s 15 rooms were inspired by different Uruguayan culture figures, like the feminist poet Delmira Agustini and the tango singer Julio Sosa. When not cruising around the city, take a nap on Egyptian cotton sheets or head to the rooftop terrace for unobstructed views of the plaza. Ask for early check-in, but if that isn't possible, store your bags with the concierge.

11 a.m.: Walk to breakfast at Jacinto. Run by Lucía Soria of MasterChef fame, the restaurant's attached café has espresso-based beverages, fluffy croissants, creamy pavlovas, and creative salads like kale with mole eggs and almonds. Afterwards, wander Cuidad Vieja's alleyways, or go straight to Plaza Independencia. Take a picture with the Puerta de la Ciudadela (City Gate), the last remaining structure from the original wall around Montevideo. Check out the Tango Museum in Palacio Salvo or visit the mausoleum of national hero General José Artigas. Stop by Teatro Solís, Uruguay's premiere theatre, and purchase tickets for that evening’s show.

Day 1: Afternoon

2 p.m.: Walk three blocks from Teatro Solís to the Rio de la Plata to meander along the Rambla, the longest sidewalk in the world. Running 13.7 miles, strolling it offers the perfect introduction to Montevideo, as everyone comes here to bike, laze on the beach, and meet with friends. Drinking mate (a highly caffeinated tea) while overlooking the river is a quintessential Montevidean activity. (Locals will generally share mate if you ask politely, but be sure to finish the whole cup since only taking a sip is considered rude.) Walk about 40 minutes until you reach El Tinkal, a bar with beachfront views and one of the best chivitos (steak mozzarella sandwiches) in town.

4 p.m.: If you want to walk more, continue along the Rambla to Ramírez Beach, then on to Punta Carretas Lighthouse for one of the best views of the city's shoreline. Afterwards, walk to The Lab Coffee Roasters for specialty coffee expertly prepared in a chemex or siphon. Alternatively, take an Uber to Pittamiglio Castle, the former home and passion project of the mysterious architect Humberto Pittamiglio. With 23 towers, 54 rooms, extremely narrow passageways, and stairways to nowhere, the castle has many legends surrounding it. Take a tour to learn about its history, symbols, and tales—including one that claims it once contained the Holy Grail.

Day 1: Evening

6 p.m.: Hop in an Uber and head to the Espacio de Arte Contemporáneo (Contemporary Art Space), an exhibition center housed in what was formerly Uruguay’s oldest prison. The EAC contains multimedia installations, graffiti murals, and rotating exhibits in cells-turned-mini galleries. Some of the works incorporate pieces of the old prison, like the giant yellow hands mural that reaches skyward from a cellblock window.

7 p.m.: Return to your hotel to change before heading to Teatro Solís (wear semi-formal attire). Admire the theatre’s Neoclassical architecture and lush inner trappings, like the 50-bulb Baccarat glasswork chandelier and ornate ceiling moldings. Whatever the show—a concert, opera, ballet, or play—expect it to be of the highest caliber, not only because of the theatre’s international prestige, but also because of its highly discerning audience. (Italian tenor Enrico Caruso was supposedly once booed here after not delivering a high note on pitch.)

10 p.m.: Revel in your post-show memories as you walk to dinner at La Fonda. Highlighting local and regional ingredients, the menu changes daily, though you can expect dishes such as house-made pasta, risotto with asparagus, grilled fish, and lamb. Pair your meal with a wine cocktail, like a sparkling white with passionfruit juice. From La Fonda, it’s only a two-block walk back to your hotel and a sound night’s sleep. However, if you want to check out the nightlife scene, head to Baker’s Bar for creative cocktails. If you prefer tango and celebrity sightings, go to Tango Bar El Haucha, a bar older than the country of Uruguay itself.

Day 2: Morning

9:30 a.m.: Wake up, pack a beach bag, then walk to breakfast at La Farmacia Café. Formerly a pharmacy, the eatery serves gouda pesto panini, parfaits with apple and kiwi, avocado toast with microgreens, and specialty coffee from local roaster Seis Montes. Take your time while eating, and enjoy the sights and sounds of Cuidad Vieja in the morning.

11 a.m.: Head to Full Sailing at Carrasco and Punta Gorda Nautical Club to rent a kayak, SUP or windsurfing board, or a small boat. Spend an hour on the water, then sunbathe on the white sands of Playa Verde. If you only want to relax by the water and prefer a closer beach, go to Pocitos instead. Just over a mile long and lined with skyscrapers, this beach is wide with fine sand. You'll have plenty of space to place a towel down without being too close to your neighbors. Read your favorite book, jump in the water, or join a volleyball game.

Day 2: Afternoon

1 p.m.: Have lunch at Sinergia FoodSpot, a sleek industrial-style food court, co-working office, and cultural space all under one roof. Order Chepi’s fondue bread bowl as an appetizer, and La Vaca Negra’s succulent secret pork with lemon cream as a main. Pair them with a fresh-squeezed juice, then finish with a coffee from Café de Vita and alfajores from La Petite Patisserie de Flor. Afterwards, head to one of Montevideo’s many museums. If you're interested in how marijuana became legalized here, check out the Museo del Cannabis. If you prefer art, go to the Blanes Museum to admire the work of Juan Manuel Blanes, Uruguay’s most famous portrait artist.

4 p.m.: Depending on which museum you’re coming from, walk or take an Uber to Avenida Tristán Narvaja for the most famous street fair in Montevideo. Only happening on Sundays, it’s a great place to pick up unique souvenirs like antiques, curios, books, and vintage clothing. If you're here another day of the week, go to the Mercado del Puerto instead to browse leather goods and handicrafts, see street performers, and admire the market's historic wrought iron structure.

Day 2: Evening

6 p.m: Learn about Uruguay’s wine by doing a tasting at Montevideo Wine Experience, a small wine bar with an English-speaking sommelier. Try their wine-based cocktails or ask them to recommend different reds or whites based on your preferences. Though the owners have a list of credentials to their names—one of them comes from a family of pioneering Uruguayan winemakers and another is a nationally-known sommelier—the place has no pretension. Take advantage of their well-priced bottles and purchase a few gifts to take home.

7 p.m.: Drop off your purchases at your hotel, then go to the Palermo or Barrio Sur neighborhoods to experience live candombe music. Originally started by enslaved people in Uruguay to celebrate and remember their roots, candombe is now an art form, played and danced to throughout the country and recognized by UNSESCO as an intangible cultural heritage practice. Comparsas (troupes of candombe drummers) practice each weekend in these neighborhoods as a testament to Uruguay’s past and in preparation for the city's two-month-long Carnival celebrations.

9 p.m.: For dinner, treat yourself to one of the country’s signature experiences: asado (barbeque). Dine at La Otra, a classic parilla (steakhouse), and begin your meal with grilled provolone cheese sprinkled with oregano and an order of crispy sweetbreads with a hint of lemon. Bite into a juicy bife de lomo (tenderloin steak) or a bife de ancho (prime rib) complemented by buttery mashed potatoes. Have a final glass of wine, then it’s off to bed and onto the next destination.