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Tucked away in Cartagena’s Old Town, Casa de Indias combines colonial architecture with vibrant eclecticism. Though the villa dates to 1693, when it was owned by the then-governor of Cartagena, its purchase in 1979 by the family of famed Colombian figurative artist and sculptor Fernando Botero set the tone for its current iteration. His interior designer daughter Lina Botero redecorated the guesthouse and opened it to travelers in 2013, keeping old-world features like terra cotta–hued stucco walls and black-and-white marble tile floors while adding colorful textiles and pottery, rough-hewn wood furniture, and works by her father to create an artsy lived-in feel. Individually decorated rooms are likewise warm and distinctive, some showcasing original brick walls and all offering iPod docks and flat-screen TVs. The 16-guest maximum capacity helps ensure a quiet atmosphere where you’re free to roam between palm-shaded patios, lounge around the outdoor pool, or take in panoramic city views from the rooftop terrace and hot tub.

Carmen lies at the crossroads where quality, creativity, and sustainability (plus every other big-city culinary trend) meet. The namesake proprietress, alongside musician husband Rob Pevitts (both San Francisco Cordon Bleu graduates), is the genius who imported the restaurant’s California-sybarite style to Cartagena. She also brought a passion for everything that comes from the sea, and even imported her father, who’s responsible for serving up crab, lobster, fish, and octopus in line with standards he picked up on his many travels in New York and Japan.

This dockside restaurant has a charming historic patina, as it is part of an actual fishing club headquartered in an 18th-century military Cartagena fortress, San Sebastián del Pastelillo. Sit at outdoor tables with views of the city, the bay, and the club’s private marina and pier (some of your fellow patrons arrive by boat!), and dine on freshly caught seafood. On weekends, live music—jazz, bossa nova, and flamenco—animates the scene.

Restaurante Celele in Cartagena’s hip Getsemaní quarter sits right at the cutting edge of contemporary Colombian cuisine. Chefs Jaime Rodríguez and Sebastián Pinzón see research as part of their endeavor and have dedicated years to exploring the region’s flavors, especially in indigenous communities. The bottom line is a well-thought-out menu, beautiful presentation and a celebration of the local in a warm, welcoming ambience.

With the temperature sitting pretty around 75 degrees at all times, walking around Medellín is pure pleasure. To get a deeper understanding of the history of and life in Colombia, don’t miss the Museo Casa de la Memoria, which recounts Colombia’s brutal civil war. After, head to the Parque de los Pies Descalzos, where you get to kick off your shoes and, like all the other kids and adults, run through fountains. For a stellar view, hop a Metrocable car to the neighborhood of Santo Domingo.

Discover things to do and where to stay in Tofnio, an island getaway in British Colombia, Canada.

The seven-room Tcherassi Hotel and Spa is an ode to modernism set in a renovated 250-year-old mansion. Colombian-born fashion designer Silvia Tcherassi named each room after a fancy fabric (the trilevel penthouse is called the Gazar). After a chocolate-particle scrub at the spa, head to the rooftop Aquabar for a champagne-and-cognac Silvia Royale cocktail beneath the stars. —Milena Damjanov From $432. Calle del Sargento Mayor N 6-21, 57/5-664-4445, tcherassihotels.com. This appeared in the March/April 2011 issue.

Behind a discreet blue door in Cartagena’s walled historic zone, La Passion maintains its low-key ambiance with just eight rooms and a maximum of 16 guests. The distinctly decorated 19th-century building was designed by French film producer and theater designer Thierry Forte, who owns the property with his Colombian wife, and balances original elements like black-and-white-tile flooring with such antiques as brass gramophones and heavy wooden chests. Brightly painted accent walls, abstract art, and colorful decorative objects keep things from feeling too fusty, as does an indoor garden of tropical flowers, vines, and trees that soars through an interior courtyard. Best of all, the standout rooftop pool and restaurant are typically uncrowded, making the surrounding panoramic city views all the more stunning.

Colombian fashion designer Silvia Tcherassi took the design world by storm when she transformed a 250-year-old mansion in the center of Old Town Cartagena into a contemporary refuge that honors both past and present. Mansion Tcherassi’s seven rooms blend fashion-forward decor (think sparkly gold throw blankets) and original features such as restored stone walls and private balconies, but the vibe is much more understated, with ethereal fabrics, soft colors, and natural wood, in the 42 neutral-hued rooms at sister property Tcherassi Hotel & Spa. You can order fresh-caught seafood and icy raspaos (traditional drinks made with fruit and condensed milk) at the restaurant, while carpaccios, pizzas, and ceviches are on the menu on the rooftop lounge; the Italian restaurant at the mansion extends to a cozy patio facing a plunge pool and vertical garden made with thousands of local plants. After a day spent exploring Old Town’s historic buildings, relax with a Chinese medicine–inspired treatment in the spa, or take a dip in one of the property’s four pools.

The 19th-century residence that houses this restaurant by chef Juan Felipe Camacho presents a subtle maritime vibe. The gustatory offering highlights a little bit of everything, but seafood and local shellfish—in generous portions—are the stars of an unpretentious international menu that’s anchored by a celebrated dish of sautéed snapper in coconut-shrimp sauce. Also available: exquisite carnivore dishes like grilled beef shoulder with blood sausage and piquillo peppers.

Occupying three whitewashed colonial buildings sheltered from the bustling streets of Old Town Cartagena, Casa San Agustín sits on the site of a former aqueduct and channels its heritage with a swimming pool that tunnels through its stately remnants. Inside, common spaces feature a mix of Colombian art and artifacts with contemporary wicker furnishings and marble floors. The 20 rooms and 10 suites are cozy and a bit more polished than those found at other historic properties nearby: Units feature 200-year-old wood-beamed ceilings and iron canopy beds topped with Frette linens; some have patios with hot tubs or brick terraces with views of surrounding buildings. But there’s plenty of space to unwind throughout the property, namely a library with original frescoes and a lounge with a long wooden bar and ceiling-high wine cabinet. It’s a good idea to make reservations in advance for dinner at Alma, considered among the city’s best restaurants, where the upscale international cuisine includes fresh ceviche and dry-aged beef cured on-site.

A short walk from the city sits imposing Castillo San Felipe de Barajas, covering almost the whole of San Lázaro Hill, 135 feet above sea level. The castillo bit is something of a misnomer, as the structure is not technically a castle but a fort; it happens to be one of the most impressive the Spanish ever built, resisting a number of land and sea attacks. Allegedly its tunnel system was engineered so that the slightest sound anywhere within it would reverberate a warning of approaching danger or attempted escape. Audio guides, available in English, Spanish, and other languages, recount the full story. The castle also happens to be one of the best spots in the city from which to watch the sunset.

Beyond the beach, the billboards, and the freeways, there’s a city of neighborhoods waiting to be explored.

Whether or not you’re planning a trek to the Lost City, a visit to the starting point of the hike, Santa Marta, and Barranquilla, also part of Magdalena Province, should be. The coastal towns feature carefully-prepared fresh seafood, the nearby Tayrona National Park, museums, and much more.

The peak called Monserrate towers over central Bogotá and lends its name to the church that tops it. Perched more than 10,000 feet above sea level, the sanctuary—dedicated to the Passion of Christ—has beautiful gardens showcasing marvelous highland vegetation, and the city views from here are spectacular (sunsets are especially recommended). Ascend Monserrate by cable car, via railway, or on foot (this last is only for the fittest and those already acclimated to the altitude). That beautiful white house on the mountainside is Casa Santa Clara restaurant, a better-than-expected, special-occasion-suitable venue at which to try traditional Bogotá favorites like ajiaco, a thick potato-and-chicken soup.