Steven Callas

I plan extended stay luxury travel for professionals who need to keep working while they are abroad. A month in Buenos Aires, six weeks in a staffed villa in Bali, a full summer in Lisbon. The trip works only if the infrastructure works. I handle the logistics so your days run on a reliable routine and your evenings actually feel like you are somewhere worth being.

Infrastructure is everything
The most critical amenity on a working trip is not the pool. It is the internet. A digital nomad might be fine with a cafe signal. My clients are not. I vet luxury vacation rentals specifically for fiber optic connectivity, dedicated workspaces, and backup generators in regions like Costa Rica and Bali where power can be inconsistent. Upload speeds get verified before anything is confirmed, because running a board meeting from the tropics only works if the connection does.

The Americas: Argentina and Costa Rica
For professionals based in the US, time zone alignment matters more than anything else on a long stay. Argentina and Costa Rica both keep you on a schedule that works with your team back home.

In Costa Rica, you work a full day and by 5pm you are in the Pacific. I source private estates in Guanacaste with legitimate connectivity and total seclusion.

In Argentina, a high-end apartment in Buenos Aires's Recoleta or a vineyard estate in Mendoza gives you a pace of life that feels nothing like home but keeps you fully operational during business hours.

Europe: The "Morning Shift" advantage
The six or seven-hour time difference with the US means your mornings in Europe are free. You spend them however you want, and by late afternoon you log on to sync with your team back home. Portugal and Spain have the best infrastructure for this kind of stay. I source apartments in Lisbon and fincas in Mallorca that feel like a home rather than a hotel, with the connectivity to run your workday without compromise.

Asia: Bali and Japan
Bali's reputation for wellness is earned, but quality varies wildly. I source luxury private villas in Bali near Ubud and Uluwatu with full staff, including private chefs. You work from a dedicated office with the jungle below your window, and your household needs are handled for you.

Japan works differently. A serviced apartment in Tokyo gives you a week of focused, high-intensity work. A ryokan in the mountains afterward gives you the decompression. The contrast between the two is part of the point.

Concierge support for long stays
Living abroad for a month is not the same as a week-long vacation. The daily logistics, housekeeping, grocery runs, a doctor when you need one, a dry cleaner when you do not want to figure out the local system, are the things that wear you down if nobody is handling them. My local partners take care of all of it so your focus stays on the work and the downtime.

Q: How do I plan a month-long trip while working?
A: Do not try to move every two days. Pick one or two locations and stay put long enough to build a real routine. Adventures go on the weekends, just like they would at home, but the scenery is considerably better. A stable base is what makes the work side functional and the travel side feel like more than a string of hotel lobbies.

Sabbaticals and career breaks
If you are taking a real break, the pacing changes entirely. A sabbatical trip is not a long vacation. I build itineraries around learning something, cooking in Bologna, surfing in Bali, or simply spending enough time in one place that it starts to feel familiar. The goal is to come back with something that lasts longer than a tan.

YOUR EXTENDED STAY STARTS WITH THE RIGHT SETUP

If you have a destination in mind and a work schedule to protect, reach out and I will tell you what the infrastructure looks like and how to build the trip around it.