Too often I hear of travelers not even thinking there is a Bolivia east of La Paz, or a Bolivia that has a jungle. Bolivia is a HUGE country with many different climates and histories and cultures, and this route will treat you to some rich and exotic experiences that are very different from the routes of the high Andes.
This route I'm recommending is also a bit unusual in that it's neither the most straight or efficient way to get from A to B, and there are many different ways to get to Trinidad.
TALTA - LA SERENA
Start your journey in Taltal, a quaint seaside town that is home to several national monuments from its 19th-century railroad days, giving the town a preserved European flair. Particularly interesting are the old buildings made from Oregon Pine that were built starting in 1882 for the Taltal Railway Company. Visit the Club Taltal to see old historical letters and photos of the region.
Head south for some extraordinary outdoor hiking and/or camping, first hitting Parque Nacional Pan de Azúcar
This is a great bus trip for day trips if you're staying on the beach in Ilo and looking for things to do, or coming across the border from Argentina to get a feel for Peru without going very far. The general climate is desert with wide open skies, and it is also known for its immense wetlands (birding) and vineyards.
In and around Ilo, I would recommend the museum of the Chiribaya people at El Algarrobal just outside of town to the northeast, as this was the foundational culture that inhabited the area
TALCA - CONCEPCION
The central heartland of Chile is rich and fertile farms and vineyards, coastal beauty, cultural and historical charm, and the energy of modern cities with boundless enthusiasm.
We start our tour in Talca, where Chile's Declaration of Independence was signed in 1818. A significant museum , the O'Higgins, offers historical insight into the events of that time as well as exhibits of fine art. But most use Talca as a central and cheap base from which to travel to nearby communities. Like Rari, 69 km to the southeast, which is famous for its preservation of weaving horse hair into spectacular objects of art
SANTIAGO - LOS ANDES
This is a micro-route with macro experiences, a chance to visit the stunning capital Santiago, the romantic and historically illustrious Valparaiso, and finally the staggering mountain beauty of Los Andes.
I won't repeat here a full tour book of what to do in Santiago, but I will tell you my personal favorites. Plan a full day or two half-days to visit one of the best museums in Latin America, bar none, the Museo de La Memoria