Extended Stay & Remote Work Travel

Work from anywhere with verified high-speed Wi-Fi

The line between living and traveling has blurred. You no longer have to quit your job to see the world. I specialize in planning extended stay luxury travel for professionals who need to remain connected. Whether you want to spend a month in a Buenos Aires apartment or six weeks in a staffed villa in Bali, I handle the logistics. My goal is to set you up with the infrastructure you need to work effectively, so you can spend your evenings and weekends immersing yourself in a new culture.

Infrastructure is everything
For a working vacation the most critical amenity is not the pool, it's the internet. A "Digital Nomad" might be fine with a cafe signal. My clients are not. I vet properties specifically for their connectivity. I look for luxury vacation rentals with fiber optic internet and dedicated workspaces. I ensure the villa has backup generators in regions like Costa Rica or Bali where power can be inconsistent. I verify the upload speeds so you can run your Zoom board meeting from the tropics without anxiety.

The Americas: Argentina and Costa Rica
For Chicago-based professionals, remaining in a friendly time zone is crucial. Working from Argentina or Costa Rica allows you to keep your normal office hours.

In Costa Rica, you wake up, work a full day, and by 5:00 PM you are surfing in the Pacific. I secure private estates in Guanacaste that offer total seclusion but enterprise-grade connectivity.

In Argentina, you get the culture of Europe with the convenience of the Americas. I find high-end apartments in the Recoleta neighborhood of Buenos Aires or private vineyard estates in Mendoza. You enjoy world-class steak and wine without the jet lag.

Europe: The "Morning Shift" advantage
Working from Europe offers a unique lifestyle benefit. The six or seven-hour time difference means your Chicago morning starts in the European afternoon. You can spend your mornings exploring Roman ruins or hiking the Alps, then log on in the late afternoon to sync with your U.S. team. I recommend Portugal and Spain for remote work because of their excellent infrastructure. I find apartments in Lisbon or fincas in Mallorca that feel like homes, not hotels.

Asia: Bali and Japan
For those who need deep focus or restoration, Asia is unmatched.

Bali is the ultimate location for wellness, but quality varies. I avoid the crowded tourist zones. Instead, I secure luxury private villas in Bali near Ubud or Uluwatu. These properties come with full staff, including private chefs. You work in a dedicated office overlooking the jungle, and your household needs are managed for you.

Japan offers high-efficiency work environments. I can position you in a Tokyo serviced apartment for a week of high-intensity business, followed by a quiet Ryokan in the mountains to decompress.

Concierge support for long stays
Living in a foreign country for a month involves different logistics than a week-long vacation. I act as your local fixer. I arrange housekeeping, grocery stocking services, and private drivers. If you need a doctor or a dry cleaner, my local partners handle it. I remove the friction of daily life so you can focus on your work and your downtime.

Q: How do I plan a month-long trip while working?
A: The key is "Slow Travel." Do not try to move every two days. I recommend a "Basecamp" strategy. We choose one or two primary locations to minimize checking in and out of hotels. This gives you a stable routine. We then schedule your adventures for the weekends, just like you would at home, but with much better scenery.

Sabbaticals and career breaks
If you are taking a true break from work, the pacing changes. A sabbatical travel planner looks for transformation, not just relaxation. I build itineraries that allow you to learn a new skill, like cooking in Bologna or surfing in Bali. We pace the trip to prevent burnout. You return to your career refreshed and with a new perspective.