Ordered, because several of these block each other.
Before you get on the plane (this is still day one). Your criminal record and pension or income letters must be obtained and apostilled at home. You cannot practically fix an apostille from a beach town. Book a one-way or flexible flight (Aviasales, Trip.com), book four weeks of accommodation rather than twelve months of lease (Travala), and buy travel insurance that covers the flight itself (Travelex) as well as the medical policy your visa file needs. If your inbound flight gets cancelled or badly delayed, AirHelp handles the claim so you're not doing paperwork on arrival day.
Days 1–3: land soft. Arrange the airport transfer in advance (Welcome Pickups) — arriving at a foreign airport after a long flight is the worst moment to negotiate. If you're viewing flats the same day, park your bags with Bounce or LuggageHero rather than dragging them through appointments. Get a local SIM at the airport or the first proper shop you pass; almost everything below needs a local number.
Days 3–7: connectivity and money. Test your actual internet speed wherever you're staying, at the hour you actually work — the city figures on file (~60 Mbps Puerto Viejo, ~80 San José, ~90 Atenas, ~120 Tamarindo) are averages, and your building is not an average. Get your Wise account working with a local top-up route so you're not paying card fees on everything. Buy a coworking day pass before a monthly one.
Days 7–14: file, or prepare to file. If you're on the nomad route, your file should already be complete — processing is 1–3 months, and that clock only starts once it's in. If you're on Pensionado, the same logic applies harder: 3–9 months processing means every week you sit on an incomplete file is a week added to the end. Get to San José for anything that needs to be done in person; that's one reason to base your first month there whatever town you've fallen for.
What blocks what, plainly:
- No apostilled criminal record → no Pensionado file. This is the long pole; start it first.
- No medical insurance certificate → incomplete nomad file.
- No proof of enrolment → no student stay. Course acceptance comes before everything else on that route.
- No local address and phone number → almost every subsequent errand is harder.
- For Pensionado, CCSS registration is part of the route, so budget for the contribution as soon as you have status — not later.
Days 14–30: sign nothing you'll regret. Only now look at twelve-month leases, and only in a neighbourhood you have slept in on a weeknight. Rent on file runs $650 (Puerto Viejo) to $900 (San José, Tamarindo); if you're being quoted far above that, you're being quoted the foreigner price. Ask what utilities cost in the hottest month — air conditioning is the line that breaks tropical budgets. If you're settling somewhere remote like Puerto Viejo, this is also the week to sort medical evacuation cover (Medjet), because the time to arrange it is not the day you need it.
One note on kit: the nomad route carries an import duty exemption on work equipment, which is a real benefit if you're bringing a full setup. Bring the receipts and the boxes' documentation, and confirm the procedure with Migración — an exemption you can't evidence is not an exemption.