Is Venice still relevant? That’s the question lingering on the edge of this year’s Biennale as it prepares to open on 11 May. The art world’s annual calendar has become so crowded with must-visit events – the Art Basels, the Friezes, the TEFAFs, the art weeks, the blockbuster exhibitions – that the Biennale, with its ban on art sales and scattershot, nation-based approach, is risking obsolescence.

Ralph Rugoff, the director of the 2019 Biennale, is well aware of the danger – and he is rising to the challenge with the caustic wit and fearless élan that he has brought to exhibitions on both sides of Atlantic over the past decades. The title of this year’s event, “May You Live In Interesting Times”, is a provocative reference to a British political speech and a Chinese curse (Rugoff neatly sums it up as a “counterfeit curse”) and it also refers, of course, to our contemporary politics, the subject to which so much art now seems to be trending.

“Perhaps art can be a kind of guide for how to live and think in ‘interesting times’,” explains Rugoff, who was born in New York and who has run the ascendant Hayward Gallery on London’s South Bank since 2006. “The exhibition will focus on the work of artists who challenge existing habits of thought and open up our readings of objects and images, gestures and situations.”

It’s a bid for relevance that is being aptly echoed across the national pavilions. A few countries are giving space to established artists at the peak of their powers: France with Laure Provost, the US with Martin Puryear and the UK with Cathy Wilkes. While the pioneering and remarkable works of Isuma, an Inuit art collective, are the focus of the Canada pavilion, and equally new to the global spotlight are Shoplifter, whose multi-coloured hair-based works will cover the walls of the Iceland pavilion, and Naiza Khan, whose paintings will adorn the inaugural Pakistan pavilion. Also keep an eye out for the Ghana pavilion (designed by architect David Adjaye with works by El Anatsui and John Akomfrah, among others) as well as those of Japan, New Zealand and Taiwan.

That there is only the most tenuous connection between these pavilions and artists is precisely Rugoff’s intention. The true joy of the Biennale has always been about happenstance and coincidence: the juxtaposition of artists who have nothing in common and the fleeting encounters with other visitors in the heritage-inflected spaces. Our circuitous wanderings through the most timeworn of cities remind us of something essential about art and about us – they remind us, as Rugoff says, that “human happiness depends on substantive conversations”.

There is another, essential side to the Biennale: the satellites. And this year’s crop in La Serenissima might be worth the trip themselves. A few galleries are holding selling shows, and many of these are emphatic in their emphasis on putting works in dynamic conversations. Carpenters Workshop Gallery (carpentersworkshopgallery.com), for instance, has responded to the Biennale’s title with a exhibition that also characterises our politics: “Dysfunctional”. The gallery, which focuses on collectible design, is presenting an array of works by 17 artists that straddle the bounds of art, design and architecture. As co-founder Loïc Le Gaillard told NetJets, “The exhibition initiates a dialogue between the stunning architecture of Ca’ d’Oro, its impressive collection of Italian masters, and the best of contemporary collectible design.” By way of an example, he cites Fragile Future by Studio Drift, a contemporary work that “will form a frame of light around the painting St Sebastian by Renaissance artist Andrea Mantegna, which is the centrepiece of Ca’ d’Oro’s collection.”

A similar time-crunching ethos will be found at Colnaghi (colnaghi.com), the venerable Old Masters gallery that will be taking over the Abbazia di San Gregorio to create what it calls “the home of a 21st century traveller”, which transforms the medieval abbey with an infusion of Old Master paintings as well as vintage and modern furniture and design.

Up on Murano, there is an ongoing conversation with Venice’s history taking place at what has become one of the Biennale’s signature satellites, Glasstress (glasstress.org), now in its sixth edition. Pairing contemporary artists with the city’s heritage medium, glass, is “like a magic trick”, says Glasstress founder Adriano Berengo. Working with a host of artists like Ai Weiwei, Erwin Wurm and Tony Cragg in his glass furnace, celebrating its 30^th anniversary this year, Berengo is ebullient about the artistic spirit that is unleased by introducing artists to a new medium: “Not having preconceptions really helps an artist to have a free, experimental approach that challenges the limits of the medium and the techniques known so far,” he says. “I find that this liberates glass from its traditional role and brings the artist’s and glass masters’ best work to the fore.”

If Berengo’s optimism and enthusiasm are echoed across this year’s Biennale, it will make the city an apt counterpoint to our interesting times – and will make it a place that reminds us of all the reasons we love art.