Digital Nomad Week, an annual gathering of remote workers, returns to the Mother City from 25–31 January, aiming to become one of Cape Town’s most influential nomad gatherings.
The timing couldn’t be better. With the long-awaited remote-work visa officially active and strong signals from the City of Cape Town that it intends to cement Cape Town's status as one of the globe’s premier remote-working destinations, Digital Nomad Week lands at a pivotal moment for the city’s tourism and innovation ecosystem.
A Cape Town community-first festival
Digital Nomad Week began as a grassroots initiative by local entrepreneur Andrae Smith, founder of Work Wanderers, who started hosting intimate dinners for nomads back in 2021.
These dinner-style meet-ups grew into a thriving WhatsApp-driven community of locals and international travellers - offering a rare blend in the global nomad landscapes that can sometimes feel like foreigner-only "bubbles."
In March 2024, with funding support from the City of Cape Town, the first official Nomad Week launched as a four-day festival packed with workshops, panels, community projects and social events. With an estimated 200 attendees, notably 40% of whom were South African, it's a balance that organisers say they want to maintain.
"Last year was a great first initiative and catalyst to get it going," says Smith. "We did keynote talks, a yacht cruise, special dinners, speed dating and a Winelands Day. It's a different type of conference and it's all about connection."
And this year, she wants to further hone the connection aspect.
Smith has partnered with Matt Gray, founder of Pangea, a fast-growing global platform helping nomads coordinate travel, meet up in new cities and join community-led adventures.
The collaboration brings together Work Wanderers’ education and community-building strengths with Pangea's growing global reach.
"My favourite part of the event last year was the mix of nomads and locals. So many of these programs, while well-intentioned, result in a bunch of foreigners hanging out in a bubble, disconnected from the destination, and NomadWeek was a refreshing change," says Gray, who has spent the last 12 years living, working and travelling in 111 countries across all seven continents.
Pangea’s also just announced acquisition of Overlap, an app that helps frequent travellers see when and where their paths cross with friends worldwide, significantly strengthening this community-driven approach set to underpin Digital Nomad Week 2026.
With Overlap now part of Pangea, Nomad Week’s direct community reaches around 40,000 participants, while overall platform reach expands to 100,000 according to Gray, which is expected to give local entrepreneurs, creatives and nomads access to a considerable network of like-minded travellers.
Gray frames the Overlap move as part of a larger vision to consolidate the fragmented travel-tech landscape into one AI-enabled platform focused on connection and shared experiences, rather than just bookings or logistics.
The Nomad Trend + the local factor
Every January and February, thousands of digital nomads descend on Cape Town to work remotely through the Southern Hemisphere summer.
The city’s beaches, mountain trails, café culture, strong English-language base and entrepreneurial energy certainly make it one of the most desirable places to base oneself. Yet Digital Nomad Week aims to add something the scenery alone cannot: genuine connection with Cape Town’s creative and business community.
Smith and Gray believe that this is what will set Cape Town apart as competition intensifies across the world's best digital nomad destinations, like Spain, Malta or Bali.
This year’s programme introduces new initiatives like an Africa Expo Day. Smith sees it as a launchpad for South African creators and entrepreneurs to connect with nomads, who are not just passing through but genuinely interested in building business bridges for collaborative opportunities with local experts.
The festival will spotlight the Nomad Africa Fund, giving attendees the chance to sponsor a local high school student’s education for a full year.
Beyond networking, their broader vision is to provide local participants with the opportunity to pitch their business ideas directly to visiting professionals - laying the foundation to evolve into a Digital Nomad driven Y Combinator.
And it's a necessary evolution in the global nomad landscape, according to Gray. The collapse of Remote Year, a pioneer in curated travel experiences for digital nomads, is a prime example of the foreigner only "bubble".
Remote Year was initially acquired by Selina, a lifestyle-hospitality brand with locations in over 20 countries, in 2020. The intention was to combine its global property network with Remote Year’s community-focused model. Skift reported that after Selina’s financial collapse in 2024, and following a brief period under new owner Collective Hospitality, Remote Year abruptly shut down in December 2024, leaving a gap in how nomads build long-term community.
For Gray, who formed friendships and early Pangea collaborations through Remote Year, the lesson has been clear: the heart of nomad life isn’t itineraries or logistics, but the human connections that last long after the program ends (noting the relevance of Overlap now in its fold).
“It's always felt like a missed opportunity. People from all over the world arrive in a destination, but if you don’t actually talk and get to know each other, you never discover where you might collaborate," says Gray.
“International teams trying to expand into Africa miss the incredible talent here and local skills don’t get exchanged. And that doesn’t happen in a single day. What we want is for the event to be the catalyst for longer-term connection,” adds Gray.
The run-up: a full season of events
Digital Nomad Week isn’t just a one-week gathering - it’s a summer-long immersive experience, with several happening this December and weekly dinners every Thursday - designed to bring nomads and locals into the same room, beach or co-working space.
- Pre-event - Saturday 13 December, 2025
- Pre-event - Saturday 10 January, 2026
- Pre-event - Saturday 17 January, 2026
- Official Digital Nomad Week: 25–31 January, 2026
How to join and get involved:
You can subscribe for updates and more information at nomadweek.co - with new announcements and speaker lineups set to go live throughout the season.
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