Seeking authentic, deeply engaging travel experiences often means bypassing generic high streets and chain-filled shopping malls for avenues brimming with local character. To guide explorers toward these coveted destinations, Time Out’s global network of editors and city experts has curated and ranked the world’s “coolest streets,” evaluating them based on crucial metrics: dining, nightlife, cultural vibrancy, community spirit, and overall fun factor. This year’s list highlights unique, localized arteries, with Rua do Senado in Rio de Janeiro taking the top spot and several other dynamic Asian locations making a strong showing.

The 2025 list celebrates streets that encapsulate the true spirit of their respective metropolitan areas, focusing on independent businesses, distinctive architecture, and palpable local energy. While Hong Kong streets did not feature this year, neighboring Asia boasts two high-ranking contenders within the top five, offering enticing short-haul excursions.

Osaka and Chengdu Offer World-Class Charm

For travelers planning a trip to Japan, a compelling detour awaits in Osaka. Orange Street, situated just off the bustling Shinsaibashi district, was officially named the second coolest street globally.

Once known primarily as a hub for hype culture and high-end streetwear in the 2010s, Orange Street has recently rediscovered its foundational appeal as a treasure trove for vintage enthusiasts. Today, it’s a premier destination for those seeking unique antique furniture and pre-loved sartorial finds. Thrifters can unearth everything from designer housewares to one-of-a-kind fashion samples at accessible prices. Beyond shopping, the street provides ample respite for weary explorers, hosting numerous cafes, authentic Osakan street food vendors, and modern neo-izakaya establishments.

Further solidifying Asia’s presence in the global ranking is Fanghua Street in Chengdu, China, which secured a top-five position. This alleyway offers a striking fusion of Chengdu’s traditional, quiet charm and a bold, youthful, design-forward aesthetic. Low-rise residential blocks frame an evolving urban canvas, where casual coffee shops transform into sophisticated wine bars at night, sitting alongside design studios and the city’s beloved, time-tested hole-in-the-wall snack stalls.

The Global Vanguard of Urban Cool

Claiming the title of the world’s coolest street for 2025 is Rua do Senado in Rio de Janeiro. Located in the bohemian heart of downtown Rio, this historic area masterfully retains its architectural heritage—featuring beautifully preserved townhouses and traditional, long-standing bars—while simultaneously integrating vibrant, newer restaurants and energetic nightlife venues that inject a continuous stream of fresh vitality into the locale.

Rounding out the list’s top tier were two distinct European and North American contenders: Rua do Bonjardim in Porto, Portugal, ranked highly for its cultural richness, and Sherbrooke Street West in Montreal, Canada, praised for its engaging community focus.

For those looking to expand their travel itineraries beyond the usual tourist routes and immerse themselves in truly localized culture, examining the full list of the 31 Coolest Streets in the World for 2025 offers abundant inspiration. Several other engaging Asian locales have also earned spots, promising discovery and delight for the seasoned urban explorer. Choosing a street from this curated selection is an excellent way to ensure your next trip literally goes off the beaten path.