Alternative cool

    Want to holiday with the cool, creative crowd, away from the tourist masses? Stacey Lane checks out five trendy havens for the hip.

    Lisbon, Portugal

    A great base for exploring Lisbon is Baixa – charming and historical, it’s the heart of the city. The street art in Lisbon is as strong as the coffee evolution, and the hipster staple of vintage stores are overflowing. In fact, Lisbon boasts the most vintage boutiques in the world at 78 per 100,000 people.

    Hit up The Decadente for a value feed before the evening festivities. The Bairro Alto may seem sleepy by day, but it’s home to more than 250 bars, and as the sun sets the area becomes one giant street party.

    In Cais do Sodré, Pink Street – the former red-light district lined with pink carpets – is home to heaving clubs and cocktail bars. Superclub Lux Frágil, housed in a giant old warehouse by the river, boasts a massive dance floor and when you’re all danced out, there are giant armchairs beneath disco balls to kick back in.

    On the way home, blast the beginnings of a hangover with a juicy bifana (pork bun), something Lisbonites have developed a culinary affinity for.

    Portland, Oregon

    Portland is the original cool hipster city that inspired the namesake parody TV show Portlandia, in which characters with high-maintenance beards live in a utopia of free-range chicken and single-origin coffee.

    If you’re keen to catch the vibe, book a room at the Ace Hotel, where you can wake up and sip cortados at Stumptown Roasters in the morning. Whether you want to mix with locals at live music venue Doug Fir Lounge (above) or head to Dig A Pony to play drinking games, the Ace is a great starting point for exploring the city.

    Portland is #5 for the most microbreweries per capita in the US. Head east to gastropub Produce Row Cafe to satisfy your craft beer cravings, or Laurelwood where everything on the menu is certified organic. Many breweries are family friendly, with play areas for children and excellent pub food for all ages.

    Speaking of food, you’ll be spoilt for choice, with plenty of baked goods and wellness bowls at hotspots like Harlow and Rontoms, while Le Pigeon serves experimental dishes (grilled pigeon anyone?). Don’t miss Pip’s Original Doughnuts – these fried morsels are made to order and are OMG good. The cool kids get around via the cycle sharing system, and so should you.

    Brighton, UK

    This 1950s UK holiday town has been transformed, with an eclectic mix of residents roaming the cobblestone streets – think drag queens (Britain’s biggest gay scene lives here!), skater girls, DJs and yes, hipsters. Together with a hefty number of cafes, vinyl stores, coastal yoga classes, beachfront markets, vintage shops and boutique hotels, they’ve elevated Brighton’s cool factor.

    Stop in at Small Batch Coffee with its industrial chic interior for a decent brew. Shop at Snoopers Attic for timeless treasures and some shabby chic sold to you by chatty staff covered in ink – most likely from neighbourhood tattoo parlours Blue Dragon or Blind Pig.

    The North Laine boho district is overflowing with eye-popping street art, offbeat designers, flea markets housed beside slick restaurants and cosy cocktail bars.

    Medellín, Colombia

    Once a place famed for drug kingpin Pablo Escobar, Medellín is now earning a reputation as a tech capital and urban innovator. Today, the capital of the Antioquia province is teeming with trendy cafes (Pergamino is a great spot for single-origin coffee), breweries, boutiques and co-working spaces – a big draw for the millennial start-up community.

    Stay at the chic Charlee Hotel or the industrial-style Art Hotel, and on Friday nights, mix with locals at the Museo de Arte Moderno’s free outdoor film screenings – the food trucks are worth a visit, too. For fine dining, El Ciel will wow you with its local produce.

    A great way to absorb the city is from above in a cable car – a new addition to Medellín’s transport system that services the steep Andean mountainside barrios.

    Marfa, Texas

    Seemingly in the middle of nowhere is this mini mecca (population 2000) for art darlings, road warriors and alt musicians. While you’ll find man buns and moustaches aplenty, there are also cowboys and other curious characters at every turn.

    Book into a vintage trailer at kaleidoscope campground El Cosmico, or check out the Thunderbird Hotel where minimalist digs and a pool will satisfy tired travellers of all persuasions. If that’s not your style, visit Hotels.com for other fun options.

    Art lovers usually make their first stop the sprawling Chinati Foundation, but our tip is Ballroom Marfa, a 1920s dance hall transformed into a space for film, sculpture and more.

    Just don’t leave dinner too late, or you might find the town’s kitchens have all shut up shop. Head out as the sun sets over the desert landscape to restaurant Cochineal’s fairy-lit courtyard. Or saunter over to the Hotel Paisano – once home to Elizabeth Taylor and James Dean, who shot 50s flick Giant here – for homemade burritos, pistachio-crusted sirloin steak or the Black Angus Giant burger, as well as delicious cocktails.