Almost every difficult Costa Rica itinerary we are asked to rescue has the same problem, and it is not a lack of research. It is sequence. People book flights before choosing a route, pick lodges before knowing how long the drives are, and leave national park tickets until last — and by then the tickets are gone and the route has to bend around a hotel that is three hours from everything.

Here is the order that works. Eight decisions, and only three of them have real deadlines.

Everything downstream depends on this, because season changes price, weather, and how far ahead you must book. Dry season runs roughly December to April: reliable Pacific sun, the highest prices, and lodges filling two to three months out. Green season, May to November, means afternoon rain, noticeably lower rates and far fewer people. The shoulder months — May and November — are quietly the best value of the year.

One regional exception matters: the Caribbean coast runs on its own weather. September and October are the driest months in Puerto Viejo and the wettest almost everywhere else. Our month-by-month guide has the detail.

Costa Rica has two international airports and they are on opposite sides of the country, about four hours apart. San José (SJO) is central, serves the volcano–cloud forest–central Pacific routes, and is the right choice for most first trips. Liberia (LIR) is in the northwest and puts you 40 minutes from the Guanacaste beaches — the Playas del Coco transfer is just 40 kilometres.

Pick the wrong one and you spend a day correcting it. Also price open-jaw flights — into SJO, out of LIR — which removes an entire repositioning day from longer routes.

Then plan roughly one base per three days, with a two-night minimum in each. We wrote a whole piece on this: how many days you actually need. The short version is that seven days is the practical minimum for a touring trip and ten is the sweet spot.

Choose your regions and their order first. Order matters more than people expect: put the long-haul or remote leg early while everyone is fresh, and finish somewhere easy, because the last three days of a trip should be slower than the first three. Start from a skeleton — our itinerary library has eleven, from a weekend to three weeks — and adjust from there. Only once the route is settled should you look at lodges.

Three categories genuinely sell out, and they are the only things you must move fast on:

• National park entries with quotas. Manuel Antonio is online-only, capped at 600 visitors a day, and closed Tuesdays — read our tickets and hours guide before booking anything in Quepos. Corcovado requires a certified guide and permits.
• Monteverde lodges in dry season. They fill earlier than anywhere else on the classic route — two to three months ahead for December to April.
• Turtle nesting season. Tortuguero's green turtle walks run roughly July to October and are permit-controlled.

This is the decision people leave until last and should make third or fourth, because it changes which lodges make sense. The honest comparison: a rental car plus mandatory local insurance and fuel costs about the same as private transfers on a one-week trip, and hands you the driving. Private transfers are door-to-door, fixed-price and include car seats — our route list publishes every price, so you can do the arithmetic yourself. On a three-week trip a hybrid usually wins: transfers for the hard legs, a rental for the flexible coastal stretches. We lay out both sides in local planner vs. big agency.

With route, dates and transport fixed, lodges become straightforward — you now know exactly which town, how many nights and what time you arrive. Pick places with pools if you are travelling with children; in green season the pool is your afternoon insurance policy.

Finally, and this is the step everyone skips: leave one unscheduled day per week. Not a spare day at the end — a genuine gap in the middle. It absorbs a rained-out morning, a missed connection or a place you liked more than expected, and it is reliably the day people describe when they get home.

If you would rather hand the sequencing to someone who does it every week, that is literally our job. Send us your dates and we will come back with a real proposal — lodges we know personally, honest prices, and a route that respects the drive times. Start with custom planning.