How to Use These Itineraries
These are starting templates for someone testing destinations rather than running a deliberate tax-avoidance rotation (see Sample Rotation Circuits in the Tax-Residency Rotation section for that version, which includes detailed day-count math). These itineraries prioritize depth of experience at each stop over maximizing time efficiency.
Itinerary 1: Single-Country Deep Test (3 Months)
For someone seriously considering one specific country and wanting a real seasonal test rather than a quick visit.
- Month 1: Settle into a furnished rental in the primary city under consideration (e.g., Lisbon). Establish routines — grocery shopping, local transit, a regular café or two.
- Month 2: Take 1-2 short trips to secondary cities or regions within the same country to compare against the primary location, while keeping the home base.
- Month 3: Return to full daily-life mode in the primary location, this time tracking budget and comfort more deliberately to inform a real decision.
Stays comfortably within Schengen's 90-day allowance if the destination is in Europe.
Itinerary 2: Two-Country Comparison (4 Months)
For someone choosing between two specific countries, splitting time evenly.
- Months 1–2: Country A, ideally including both a primary city and one secondary location
- Months 3–4: Country B, same structure
If both countries are in Schengen, this requires careful day-count planning — two months each likely exceeds 90 days if done back-to-back without a non-Schengen gap. Consider pairing a Schengen country with a non-Schengen one (e.g., Portugal then Mexico), which sidesteps the visa math entirely while still allowing a real comparison.
Itinerary 3: Seasonal Split (Ongoing, Year-Round)
For someone not looking to relocate at all, but wanting a recurring seasonal rhythm — e.g., winters somewhere warm, summers somewhere temperate, home base the rest of the year.
- Winter (Dec–Mar): Mexico or Costa Rica, both offering warm-weather dry seasons during the US winter
- Spring/Fall: US home base
- Summer (Jun–Aug): A European destination during its most pleasant shoulder-season weather window, timed to avoid both peak summer crowds and Schengen day-count pressure if repeated annually
Note on repetition: an annual recurring pattern like this is exactly the scenario flagged on the Slow Travel vs. Moving Abroad page — worth periodically checking whether a repeating seasonal stay has started to resemble something closer to residency in the eyes of any of these countries, particularly if the same housing is used each year.
Where to Go Next
→ Slow Travel Destinations database — build a custom itinerary using the full comparison data.
→ Tax-Residency Rotation section — if any of these patterns start shifting from "testing a place" toward "deliberately avoiding residency everywhere."