Polynesian party at Three Dots and a Dash

Chicago winters can be punishing, so what better way to stave off the northern hemisphere chills than with a Painkiller No 3, loaded with two varieties of rum and the tropical bouquet of summer? Award-winning watering hole Three Dots and a Dash has Polynesian mixology down pat, with a heady menu of cocktails that will blast away the winter blues.

Named after a famous cocktail created to celebrate the end of World War II (in Morse code it stands for ‘V’ and, in the 1940s meant ‘victory’), Three Dots and a Dash serves up 20 cocktails and 250 varieties of rum. Park your behind under the thatched canopy at the bar, get both hands around a decorative tiki mug, and try not to be intimidated by the big dudes carved into the decor.

The Harrison Speakeasy

Argentina may be known for its big, bold reds, but expertly crafted cocktails are on the rise, and the best are hiding in Buenos Aires. It will, however, take some work to find them. Concealed behind a nondescript cellar in the back of a sushi restaurant called Nicky New York, The Harrison Speakeasy transports guests from the Palmero Soho neighbourhood to the sultry world of the 1920s Big Apple.

Entry into this land of crystal decanters, champagne and bourbon is exclusive, so unless you’re a member or rub shoulders with the right people, you’ll need to book a meal at the restaurant out front and do your best to charm the waiters. Your efforts will be more than rewarded once you’re sipping a creation poured by one of Argentina’s best bartenders, Seba Garcia.

Rooftop views at Suite 700

If you enjoy views with your Veuve it’s hard to pass up this westside beauty. Ensconced within the beachfront Hotel Shangri-La, Suite 700 blends old Hollywood glamour with modern chic, and is the only public open-air rooftop bar and lounge in Santa Monica.

The art deco lounge is sleek and inviting but, on a balmy night, it’s the rooftop that rules. Feel the Pacific breeze tousle your hair as you take in the 360-degree views. Chomp into a Korean BBQ slider, washed down with a signature lavender crush cocktail, and watch the sun set over the famous Santa Monica Pier.

Retro drinks at The King of Ladies Man

Want to know a secret? Getting to The King of Ladies Man is like opening a Russian matryoshka doll inside a time machine. Within The Breakfast Club, a 1950s all-day cafe and brunch bar, is a kitsch, bamboo-clad ’80s launderette complete with a fake wall. Slide back the faux panel and – voila! – you’ll be stepping inside a ’70s-style bachelor pad to snag a date with The King. Think pink flamingos, bronzed mirrors and vintage Playboy mags. In the glow of a stained-glass window etched with, well, a penis, bartenders rocking Hawaiian shirts and porn-star moustaches serve up ‘disco drinks’ like Pina Coladas and Mai Tais. For something less sweet, order from the rotating list of craft beer and pair with a toastie fit for royalty.

Play it cool at JuJu

Sidle up to this trendy inner London bar expecting a quaint English pint and you’ll be sorely disappointed. JuJu is one of London’s hippest cocktail bars, whose extensive drinks menu is a roll call of Stolichnaya and Laurent Perrier, not stout and lager. Make sure you dress to impress; this upmarket venue is owned by celebrity couple Lee Chapman and Leslie Ash.

Perch yourself on one of the dark leather lounges, soak up the candlelit ambience and check yourself out in the mirrored ceiling. The porn star martini is to die for, darling, and the Asian tapas will delight your tastebuds.

Overwater drinks at Baba Nest

With a panoramic view of the Andaman Sea, Baba Nest is one of the world’s most impressive rooftop bars. Open to only 20 guests at a time, it’s also one of the most exclusive; the bar occupies an island deck smack bang in the middle of a wraparound infinity pool. It’s the perfect place to watch the sunset blaze across the peninsula, or take in a sunrise – if you can last. Beanbags and low tables provide a home to park your rear and your glass while you cool off with your feet in the water and a sake mojito in hand.

Washaway Cafe: The Pacific Honesty Bar

Possibly the last remaining honesty bar on the planet, the Washaway is a Niue institution. Open only on Sundays, this open-air watering hole has an anything-goes dress policy and a laid-back, help-yourself attitude. Locals, expats and visitors who have crossed the 2,400 kilometres of ocean between New Zealand and this coral atoll congregate around the circular bar, decorated with hanging buoys and other trinkets washed up on the beach. Beer and wine lubricate the conversation, as the sun sinks into the Pacific. Help yourself to the fridge, write down what you take on the bar’s notebook and fix up owner Willie before you go.

Bohemian hangout at Hannekes Boom

It may be constructed from salvaged materials, but this beer garden is as cosy as they come. It’s a bohemian hotspot with a beachy vibe, live music and an up-close view of Amsterdam’s busy waterways. You can even moor your boat right out front. Try their organic food or the evening barbecue.

Depending on the day, you might be able to join a craft workshop or yoga class, or scour the onsite vintage market. Chill out in a hammock on the rooftop terrace or claim an armchair by the fire when it’s frosty outside.

La Zebra Cantina Caribbean beach bar

Nothing says beach bliss like a straw hut sitting beneath palm trees and overlooking one of the Caribbean’s white-sand beaches. La Zebra Cantina is part of a hotel, but you’re welcome to come and enjoy the setting, even if you’re not a hotel guest. Every day the bartenders press sugarcane juice to use in the bar’s full range of cocktails, and they go oh-so-well with dishes prepared using freshly caught seafood, local vegetables and homegrown herbs from the hotel’s garden.

Make your way through the cocktail list developed by award-winning mixologist Jasper Soffer and take a run at the extensive range of tequilas available, or order a cucumber mojito and watch the sunset. A salsa band gets busy after dark on Sundays, with staff leading impromptu dance lessons. The vibe is laid back, the staff are friendly and the view of the Caribbean Sea is picture perfect.

All-day affair at Theros Wave Bar

Situated away from the rows of beach clubs that are most commonly associated with Santorini, Theros Wave Bar is the perfect place to kick back and escape the crowds. With the spectacular sandstone formations sparsely dotted with shrubbery, you could be forgiven for thinking you’ve arrived on the set of Star Wars.

This is an all-day affair, with lounges along a private beach servicing sun seekers. Take a dip in the sheltered bay or organise a massage between cocktails. There’s a casual-chic restaurant and bar area overlooking the sea that, at night, is beautifully lit and primed for romance. For those who like things a bit more lively, Theros organises a killer full-moon party.