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Field Notes

When to go where

Timing is the single biggest lever on how good a trip is, and it's the thing most people get wrong. This is our working calendar — where we'd send someone each month, and why.

MonthWhere we'd goWhy
JanuaryDominican Republic · Los CabosWarm, dry, and clear — 83°F, low humidity, and the golf is at its best. The correct answer to a Northeast winter.
FebruarySonoran Desert · ArizonaCool mornings, 65–70°F days, and almost no rain. Desert singletrack in its short perfect window.
MarchAtacama · Southern SpainAtacama's shoulder season opens — clear skies and manageable temperatures. Andalusia begins to green up.
AprilMallorca · UmbriaThe Mediterranean wakes up. Green hills, cool mornings, no crowds. Riding is excellent and hotels aren't full.
MayMallorca · Lake Como · ScotlandThe best month we know. Late May in Mallorca is the island at its most balanced — warm days, deep blue water, green hillsides before the heat.
JuneLake Como · Iceland · VermontComo settles into summer with long days. Iceland opens up. The Northeast trail networks dry out.
JulyLake Como · DolomitesHot on the lakes but the water is the point. High Dolomites accessible, though busier than September.
AugustLitchfield · Vermont · DolomitesEurope is crowded. This is micro-adventure season — one or two nights close to home, no flights.
SeptemberDolomites · Umbria · ScotlandThe alpine month. Clear days, quiet trails, warmer tones before winter. Umbria's harvest begins. Highlands still in season.
OctoberUmbria · Tuscany · Rome60–70°F, dry, clear. Truffle season in Umbria. The best month in Italy and not close.
NovemberAtacama · Morocco · UAENorthern Europe closes. The desert opens — Atacama's second window, Morocco cools to comfortable.
DecemberAlUla · Oman · New ZealandArabian desert at its best. New Zealand's summer begins, which makes it a long-haul option worth the flight.
Late May in Mallorca. Late September in the Dolomites. October in Umbria. Everything else is negotiable.
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and what a good day looks like.

That is genuinely the whole brief. We come back with a shape for the trip — or for the year — within a few days.