We’re planning a trip to Chile for two weeks in mid-May, targeting Santiago, Valparaiso, wine country, Lake District and Atacama. Would like to consider Torres del Paine but wonder if weather will be against us? Would appreciate thoughts on best order for the trip and when to use rental car versus possibly seeking tour organizer. Gracias.

May is not good for the lake district. You are likely to encounter a lot of rain and cold days. You could wait until you arrive to check the weather but then bus would be the best option as prices for flights rise the closer you get to a date. You can visit Torres del Paine but you need to do a lot of planning as a lot of lodging will be closed and transport is less frequent. It would actually be preferable to the lake district if you want to head south but you really need a week.

You don't need a tour operator for Santiago. Take one of the free for tips walking tours or the hop on/off bus. Then return to what interests you. Valparaiso can also be done without a tour. If staying overnight then you could go on one of the free for tips walking tours there. But a good alternative would be a driver to take you from Santiago, stop at a couple of vineyards in Casablanca on the way and drop you in Valparaiso. You could spend a night there and return via one of the frequent intercity buses back next day. A car is a liability in both Santiago and Valparaiso.

A car is a big plus if visiting the Colchagua wine valley about 3 hours south of Santiago. You could take route 5 there and return via Pichilemu on the coast and Melipilla at the end. Taxis are cheap around Santa Cruz and most lodging will arrange wine tours. But a car is useful for exploring the area around Santa Cruz.

San Pedro de Atacama, Atacama is the entire desert and contains other places, involves a flight to Calama and a shuttle from the airport to the town. Three full days are ideal.

So, if you have 3 days in San Pedro (excluding travel time), 2 days each Santiago and Valparaiso that is a week. You just need to decide what to do with the second week. Don't try to connect a domestic flight to Santiago the same day you have an international flight.

Thanks so much for your thoughtful reply. We'll reconsider Torres del Paine in lieu of the Lake District.

I would recommend March being the latest to visit TDP if you want to do extensive hiking.

We loved visiting the lake district and were advised to go early in March rather than later as we originally had planned. Weather was perfect.

Huge difference between March (Chile's best kept secret) and May. It is quite possible to visit Patagonia in May, it has a lower rainfall than somewhere like Puerto Montt. The winds die down as winter approaches. What you do need to do is careful planning. Not all lodging is open but enough is to enjoy the views and do some day treks. Multi-day treks are often not possible or have to be done with a guide. That still leaves plenty to see in this huge park.