It’s tempting to call Rosario’s most overwhelming monument, which pays tribute to the Argentine flag and its designer Manuel Belgrano, a colossal failure or even a shrine to kitsch—the outline of architect Angel Guido’s design represents a ship whose symbolic mast is a 78-meter tower on its bow.

Alfredo Bigatti and José Fioravanti sculpted the patriotic statues that adorn it, while Eduardo Barnes carved bas-reliefs depicting the country’s diverse geography.

Historic Harberton dates from 1886, when missionary Thomas Bridges resigned from Ushuaia’s Anglican mission to settle at his new estancia at Downeast, later renamed for the Devonshire home town of his wife Mary Ann Varder. Thomas Bridges, of course, was the author of the famous English-Yámana dictionary, and their son Lucas continued their literary tradition with The Uttermost Part of the Earth, an extraordinary memoir of a boyhood and life among the indigenous Yámana and Ona (Selk’nam).

A short distance from the intersection of Mexico 19 and Mexico 1, modern-day El Triunfo (pop. 350) makes an intriguing stop on the drive from Los Barriles to La Paz or Todos Santos.

You’ll know you’ve arrived at this ghost town when you reach the only bend in the road lined with aging brick structures and a few small businesses hoping to catch travelers passing through.

Originally platted by Pedro de Valdivia’s surveyor, Pedro de Gamboa, the colonial Plaza de Armas is the center of a zona típica national monument. Until 1821, when the central market moved north to the Mapocho’s banks, it was also the city’s commercial center.

On its west side, the plaza’s oldest surviving landmark is the Catedral Metropolitana, begun in 1748 but, because of setbacks including earthquakes and fires, not completed until 1830. Italian architect Joaquín Toesca designed its neoclassical facade, since modified with late-19th-century Tuscan touches.

After 1609, the Real Audiencia housed Chile’s colonial supreme court, but earthquakes destroyed its quarters in both 1647 and 1730. Architect Juan José de Goycolea y Zañartu designed the current neoclassical building (1808), but its clock tower dates from Mayor Benjamín Vicuña Mackenna’s late-19th-century term.

Three years later, during the independence struggle, the first Congreso Nacional met here, but royalists restored the Real Audiencia from 1814 to 1817. After the battle of Chacabuco that same year, the Cabildo of Santiago met here to make Argentine general José de San Martín head of state, but San Martín declined in favor of Bernardo O’Higgins. After President Manuel Bulnes moved government offices to the Casa de la Moneda, the building became municipal offices and then a museum.

Never intended as the seat of government, the neoclassical Moneda became the presidential palace in 1846, when Manuel Bulnes moved his residence and offices to the former colonial mint. It made global headlines in 1973, when the Chilean air force strafed and bombed it in General Pinochet’s coup against President Salvador Allende, who shot himself to death before he could be taken prisoner.

Pinochet’s regime restored the building to Italian architect Joaquín Toesca’s original 1780s design by 1981, but it’s no longer the presidential residence. Shortly after taking office, President Ricardo Lagos (the first Socialist elected since Allende) opened the main passageway for one-way public traffic from the Plaza de la Constitución entrance to the Plaza de la Ciudadanía exit, 10 a.m.–6 p.m. weekdays only.

South of the Alameda, dating from 1618, the major landmark is the Iglesia y Convento de San Francisco (Alameda 834), Chile’s oldest colonial building and a survivor of repeated fires and earthquakes; the former convent is also home to the Museo de Arte Colonial, an ecclesiastical colonial art collection.

Until the early 1920s, the Franciscans controlled much of this area, but a financial crisis forced them to sell 30,000 square meters to developer Walter Lihn. Lihn demolished several buildings and patios, and their gardens, but architects Roberto Araya and Ernesto Holzmann created an intimately livable neighborhood of meandering cobbled streets in their place.

South of Providencia and east of Santiago Centro, middle-class Ñuñoa has few obvious landmarks, but the vigorous cultural life on and around Plaza Ñuñoa, thanks partly to nearby campuses of the Universidad Católica and the Universidad de Chile, has made it a growing attraction. There are good but unpretentious restaurants, bars, and dance clubs.

With the Andean front range as a backdrop, Ñuñoa’s sole unforgettable landmark is the Estadio Nacional (National Stadium, Av. Grecia 2001). First famous for the 1962 World Cup, it became infamous after the 1973 coup, when Pinochet’s regime incarcerated some 7,000 Allende sympathizers (and suspected sympathizers) in an impromptu prison camp here.

Santiago’s most accessible winery is a short subway ride from downtown—at its creation in 1875, though, Luis Pereira’s Viña Santa Carolina was puro campo (countryside). Santiago gradually enveloped it and there are no more vineyards here, but the original house, a national historical monument with galleries and patios, and impressive subterranean vaults where the wine ages in French oak casks remain.

Santa Carolina’s main white varietals are chardonnay and sauvignon blanc, while the reds include cabernet sauvignon, carmenere, merlot, and syrah; there are also blends of both whites and reds.

Parque por la Paz (in the 8300 block of José Arrieta, 11 a.m.–8:30 p.m. daily except Monday, admission is free) is the most subtly eloquent memorial to the Pinochet dictatorship’s victims.

During General Pinochet’s 17-year dictatorship, when more than 3,000 people were murdered or disappeared and as many as 400,000 others were detained and tortured, no single site evoked more fear than Villa Grimaldi, the largest detention and torture center.

Before the 1973 coup, Villa Grimaldi, in a then-isolated neighborhood, was a retreat popular with leftists and intellectuals. Appropriated by the dictatorship, between 1973 and 1980 it saw the deaths and disappearance of well over 200 people — though no bodies have been found there — and more than 5,000 detentions.