The first destination will be the large town of San Isidro de el General located to the west of the peak and national park. To reach San Isidro from San Jose, take one of the hourly (seven days a week) buses to San Isidro from the bus terminal at Calle Central and Avenida 22. It's a three hour ride.
From San Isidro, you must take another bus to San Gerardo de Rivas. The bus takes two hours and leaves at 5 AM and 1 PM each day. Get off the bus at the Parque National Chirripo ranger station.
Cerro Ventisqueros from Chirripo.
The first day is a long one. It is recommended that you arrange permits the day before in order to get an early start the next morning. At the very latest, a 6 AM (earlier is better) start is recommended. It is much better to do the first section of the trail in the cool of morning as it can be very hot later in the day. Make sure you carry enough water along for the first 7.5 kms as none is available. Most of the hostels and lodges can arrange transport early in the morning to the trailhead. It's about 2 kms from the ranger station to the trailhead.
The first day to the Base Crestones (hut) is 14.5 kms with 2200 meters elevation gain. From the ranger station, follow the signs to the trailhead. The trail immediately begins its steep climb to the "Water Ridge". You will pass some cleared land for cattle grazing before you enter the rainforest. Keep an eye out for Quetzels (birds) along the way. After 7.5 kms of steep walking, you will reach "Water Ridge" which is a picnic area and a water tap. Stock up with water here, as there is no more available until you are near the Base Crestones. Keep an eye out for both spider and white face monkeys in the area; we saw several just below the lunch area on our return trip.
After enjoying a well deserved break, continue of the steep trail. The three uphill sections have names. The first is Cuesta de Agua (Water Hill), the second Monte Sin Fe (mountain of no hope), and the third is La Cuesta de los Arrepentidos (repentance hill). The first and last hills are the longest and steepest. At the top of Monte Sin Fe, you reach the Paramo. A few kms after that you will cross a stream on a bridge. From here its one long steep section to the Base Crestones Hut.
After spending the night in the hut, follow the trail posted for Cerro Chirripo and Cerro Ventisqueros. After a short distance, you will reach another junction with a sign pointing left and to the trail to Cerro Ventisqueros. Turn left onto this much less used trail. It climbs steeply to the crest of the ridge and to a false summit. After the false summit there is some minor scrambling that brings you to the summit of Cerro Ventisqueros. The summit is 3.1 kms from the base Crestones. The views from the summit are spectacular. If the weather is exceptionally clear (rare) you can see both oceans. There are many rugged glacier-carved peaks all around including a great view of Cerro Chirripo, the highest peak in Costa Rica. Between Cerro Ventisqueros and Cerro Chirripo are the Lagos Chirripo. The largest one is the highest lake in Central America.
If you're feeling up to it, you can also climb Chirripo on the same day. This requires spending another night at the Base Crestones. Since it is assumed that most people climbing Cerro Ventisqueros also plan to climb Cerro Chirripo, spending at least two nights at Base Crestones hut is recommended. There are other peaks in the area to climb as well (see the page on Crestones-Cerro Terbi, and there are more peaks to choose from), so some may want to spend a third night. The trip can be done in two long days if you plan on just climbing Cerro Ventisqueros.
Cerro Ventisqueros is the peak to the left. Photo was taken from the trail just above Base Crestones.
A good pair of boots, warm clothing, rain gear, and a sleeping bag is needed.