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- đ What Makes This Italian City Ideal for Remote Work
đ What Makes This Italian City Ideal for Remote Work
Discover a slow-living Sicilian city worth working from and a new AI companion built to ease the digital nomad mind

Hereâs whatâs inside todayâs issue:
This slow, sun-soaked Sicilian city might be your ideal base for balancing work and play
How Tolan, a gentle AI âalien,â is supporting remote workers without the pressure
Nomad reading picks on finding quiet workspaces, navigating invisible disabilities, and a remote role at HappyCo
Some of the links featured in this issue are affiliate links. If you buy through them, we may earn a small commissionâat no extra cost to you.
â Why Syracuse Sicily Is a Surprisingly Great Base for Digital Nomads
Sicily might not be the first place you think of for remote work, but Syracuse quietly checks a lot of boxes for digital nomads. With its blend of ancient ruins, crystal coastlines, and laid-back piazzas, itâs the kind of place where you can jump between focus time and exploration without ever needing a car.
A good way to get your bearings is through a street food walking tour across Ortigia. Youâll nibble on cannoli, granita, and just-caught seafood while weaving through vibrant markets and sun-soaked alleys. As this guide to Syracuse shows, the city naturally supports a slower, more integrated pace of work and play.
For remote work breaks, thereâs no shortage of open-air tables and energizing espresso. Caseficio Borderi inside Ortigia Market is a standoutâknown for its giant sandwich boards, friendly vibes, and laptop-friendly setup.
Whatâs most compelling is how seamlessly history fits into everyday life. One moment youâre answering emails, the next youâre staring up at a Greek temple or ducking into a Baroque cathedral. Even the archaeological park feels like a peaceful place to think, not just a tourist stop.
Syracuse isnât trying to be the next nomad hotspotâbut thatâs part of the charm. Itâs a place where work can feel lighter, routines more flexible, and daily life genuinely inspiring. For those craving cultural depth and calm energy, this underrated city just might be your next favorite base.
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Ruins, cooking classes, and coastal townsâGreece never disappoints. This deal packs in the value with top hotels and guided experiences. Get the details
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See Bangkok, Phuket, and the mountains of Chiang Rai in one epic itinerary. Flights included, and every day comes with something wow-worthy. Book your adventure
đ€ This AI App is Helping Burnt Out Digital Nomads

Tolan is a new AI chatbot gaining traction for its mental health-friendly design and low-pressure vibe. Built to be a âfriendly alienâ rather than a virtual lover, itâs already racked up 100,000 monthly users and is proving popular with solo remote workers, especially young women navigating life on the move.
What sets Tolan apart is its focus on balance. Instead of mirroring human behavior or getting too emotionally intense, it encourages users to go outside, check in with friends, or take breaks. For digital nomads, that kind of gentle nudge can go a long way in unfamiliar cities or when juggling isolation and productivity.
Backed by $20 million in funding from major names like Khosla Ventures and GitHubâs former CEO, the team is investing in long-term stability and privacy-first design. This is especially reassuring for travelers who want support tools that wonât turn into data farms or intrusive trackers.
Users describe Tolan as calming, even uplifting. It doesnât pretend to replace real relationships but offers a consistent, pressure-free space to think out loud. For nomads, that might mean a morning check-in before heading to a co-working cafĂ© or a quick chat after a long travel day.
In a sea of overstimulating apps, Tolan stands out by doing lessâand doing it well. Itâs not trying to be your best friend or therapist. Itâs a steady companion that helps digital nomads stay grounded while always on the move.
đOn Our Nomad Reading List
Need peace and privacy on the road? This guide covers hot desks, phone booths, pods, and private office options to help you stay focused in quiet spots wherever you go.
One traveler shares how they navigate getting non-obvious disability support while traveling, with tips for documenting needs, self-advocating, and improving the system.
HappyCo is hiring a US-based remote ops lead to improve support systems, workflows, and metrics. Salary ~$68â80k, with a focus on tooling, BPOs, and service quality.
Until next time,
The Nomad Cloud Team â
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