September through November (spring) and March through May (autumn) offer pleasant weather and fewer crowds than summer. Winter can be rainy, though it's still mild by most standards. Check before you go for any seasonal closures on island or remote desert tours.

Popular multi-day experiences like the 7-day Casablanca Valley and Easter Island tour or longer north-to-south trips can fill up 2-3 weeks in advance, especially in peak season. Single-day wine tours and city walks are more flexible, but booking a week ahead gives you better choice of departure dates.

Absolutely. A guide handles navigation between vineyards, translates tasting notes, and knows which wineries welcome visitors - you get far more access and context than driving yourself. The Colchagua valley biking tour and Maipo Canyon excursions are particularly rewarding with someone who knows the terrain and producers.

The metro is fast and cheap for city movement. For wine valleys, Atacama, or Easter Island, you'll want a tour operator who handles transport - most multi-day packages include it. Taxis and ride apps work for shorter trips around the city center.

You can absolutely do it in 3-4 days: a walking tour of Santiago, a day trip to Maipo or Casablanca vineyards, and one more regional experience. That said, the 7-day and longer trips are popular for a reason - they let you move beyond wine into desert and island culture without feeling rushed.

City tours and some wine tastings work fine for families and mixed abilities. Longer treks to San Pedro de Atacama and Easter Island involve more physical demands - check specific tour details before booking. The private heritage tours to Valparaíso can often be customized.

Most include accommodation, transport between locations, and guided activities. Wine tastings and meals are often built in, but check each tour's details - some are all-inclusive, others have separate costs for extras. Confirm what's covered before you book.