“The most visited city in the world!” proclaims a slogan painted on the side of a building along Tijuana’s iconic Avenida Revolución, nestled amid the souvenir shops, dive bars, and burros painted to look like zebras. Don’t worry about whether the claim stands up to fact-checking: far better to simply soak in the many quirks, curiosities, and anachronisms of this unusual border town, pushed up against the miles of fencing that scar this desert landscape from the mountains to the sea. Tijuana is a city in constant evolution, from its golden days in the 1920s, when the Hollywood elite slipped over the border to gamble and carouse during Prohibition, to today, when its chef-driven restaurants and design shops are frequently celebrated in the pages of glossy magazines.

This is a city of tremendous economic and cultural diversity, where new and historic communities of Chinese, Haitian, and American immigrants coexist side by side. For a visitor, the city’s essence can seem elusive — you’d never think to look for that craft brewery on the sixth floor of a downtown parking garage — so it’s best experienced with the help of a local guide.

No matter what season you book one of Tijuana’s apartments for rent, you’ll be greeted with nearly perfect weather all year round: pleasantly cool mornings and evenings, and plenty of sunshine-drenched days. Expect some coastal fog in the mornings during the summer — a defining feature of the region’s famous May Gray/June Gloom, and more crowds during late summer and early fall, when the nearby Valle de Guadalupe wine region throws a month-long harvest party that attracts glamorous oenophiles from near and far. Pack layers and a swimsuit — the beach neighborhood of Playas de Tijuana is only a few miles west of downtown, and the notoriously chilly Pacific Ocean is most comfortable for swimming from July to October.

Food & Drink

From street tacos to haute cuisine, Tijuana is a phenomenal destination for epicures. Save your appetite for grilled octopus tacos at a gourmet food hall, bacon-wrapped hot dogs and creamy esquites (corn salad) from a street-corner vendor, and Caesar salad prepared tableside at the legendary restaurant where the dish was invented in 1924. By evening, you can stroll into a beautiful high-end speakeasy, peek in at one of dozens of artisanal breweries, or see what the night holds as you enjoy the peanut-shells-on-the-floor kind of dive on Calle Sexta.

Valle de Guadalupe Wine Country

A scenic 90-minute drive along the rugged Pacific Coast brings you to the Valle de Guadalupe wine country. Drawing inevitable comparisons to both Napa Valley and the South of France, the valley’s sandy soil, temperate climate, and evening ocean breezes make it a tasty place to grow grapes such as Nebbiolo and Cabernet Franc. Dozens, even hundreds, of boutique wineries have sprung up over the last several decades, and innovative farm-to-table restaurants ran close behind, making this a worthwhile weekend detour.

Centro Cultural Tijuana (CECUT)

The iconic sphere of the Centro Cultural Tijuana (CECUT) is an emblem of the city. Inside, find exhibitions on the archaeology of Baja California or the latest works from contemporary Mexican and international artists, along with a concert hall.