If you come to my restaurant you will often hear me saying that the free activities in Drake Bay are better than the paid tours located in other parts of Costa Rica. I also always say that the tours in Drake Bay are worth their value. To those few visitors that have time for a horse riding tour, I can recommend two options for day trips.
The reasoning behind these 2 suggestions is based on the actual value of having a tour guide and horse. I have found from horse backers that a good tour is generally when you needed either the horse or the tour guide. A bad tour is when neither was needed and then finally a great tour is when both are needed. This makes complete sense to me.
The other main concern of travelers considering a horseback riding tour in Drake Bay, is the behaviour of the horses. Luckily, the problem of poorly behaved horses is an easy fix here. The small village of Drake Bay contains about as many people as I had in my graduating class, everyone knows everyone and everyone knows which families have pride in their horses. The horseback riding guides that I suggest have a well trained lead horse and the rest are docile followers. The tourist has full capability to turn left or right, speed up or slow down, but the horse is trained to always stay reasonably close to the lead horse. Both of my suggestions can be comfortably experienced by ages 8 and over even if the tourist has no experience.
This large Tico family owns a property that is both close to the Drake Bay center and rarely visited. It has many steep inclines and some spots are inaccessible even by quad bike. The numerous trails are only known by the family members and thus, a guide is absolutely necessary. The high elevations reached produce many great views but the best opportunity is at the point that overlooks all of Drake Bay and Cano Island. the tour also usually includes a canter along Agujitas Beach. In summary: primary jungle, swimming holes under beautiful waterfalls, completely off the beaten track. I would estimate that this family does less than 10 tours per year.
The second recommendation is a further distance from Drake Bay Center and horses are used for transportation just as much as the horseback experience itself. The morning begins with a short taxi ride where the horses will be waiting. The journey from there is on a trail made up of red clay, river crossings and hills. The trail passes a number of tiny farms and the jungles which surround them. After 5 river crossings you will arrive at Tamandua Biological Station. This property is owned by a Tico construction worker and his lovely biologist Tica wife. They have created Tamandua with the intention of being harmonious with their surrounding natural paradise.
You could stay in Tamandua for months and never traverse all of their trails. The primary jungle borders Corcovado National Park and is as if humans never happened. Only the family members know this area and very few of them could direct people through all of the waterfall trails.
Once at Tamandua, the horses are left next to the river and the adventure continues on foot. One of the trails will be explored and at least one waterfall with swimming hole will be enjoyed before having lunch. The horses are then used to return to the Drake Bay center. This is a full day with a little less than 4 hours of horseback riding and a few hours of pristine primary jungle hikes. I would never suggest more than 4 hours on a horse and the hike is a great break between rides. It is possible to get to Tamandua on a quad bike but I have found the experience better when riding a horse. The trail is beautiful and worth enjoying at a slower speed.