🌞 What Makes This Italian City Ideal for Remote Work

Here’s what’s inside today’s issue:

• This slow, sun-soaked Sicilian city might be your ideal base for balancing work and play

• How Tolan, a gentle AI “alien,” is supporting remote workers without the pressure

• Nomad reading picks on finding quiet workspaces, navigating invisible disabilities, and a remote role at HappyCo

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☕ 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, it’s 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. You’ll 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, there’s no shortage of open-air tables and energizing espresso. Caseficio Borderi inside Ortigia Market is a standout—known for its giant sandwich boards, friendly vibes, and laptop-friendly setup. 

What’s most compelling is how seamlessly history fits into everyday life. One moment you’re answering emails, the next you’re 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 isn’t trying to be the next nomad hotspot—but that’s part of the charm. It’s 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.

🌏 Explore These Global Itineraries This Summer! 

9-Day Spain & Portugal Escape | Save $1000 per Couple
From Barcelona to Lisbon, this tour hits all the highlights. It is culture, coastlines, and comfort in one bundle. Explore this trip

7-Day Greek Escape | Off-Season Tour
Ruins, cooking classes, and coastal towns—Greece never disappoints. This deal packs in the value with top hotels and guided experiences. Get the details

12-Day Thailand Explorer Tour | Save $200 Per Person
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

🤖 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 “friendly alien” rather than a virtual lover, it’s 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 GitHub’s 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 won’t turn into data farms or intrusive trackers.

Users describe Tolan as calming, even uplifting. It doesn’t 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 café or a quick chat after a long travel day.

In a sea of overstimulating apps, Tolan stands out by doing less—and doing it well. It’s not trying to be your best friend or therapist. It’s a steady companion that helps digital nomads stay grounded while always on the move.

📚On Our Nomad Reading List

💼 How to find a private space to work as a digital nomad 

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.

♿ I have an invisible disability - getting travel accommodations is tough 

One traveler shares how they navigate getting non-obvious disability support while traveling, with tips for documenting needs, self-advocating, and improving the system.

📣 Remote Customer Support Operations Lead at HappyCo 

HappyCo is hiring a US-based remote ops lead to improve support systems, workflows, and metrics. Salary ~$68–80k, with a focus on tooling, BPOs, and service quality.

Until next time,
The Nomad Cloud Team ⛅️