The question of when to book in advance versus when to show up and book in person has different answers by region and season.

Book well in advance: popular destinations in peak season (Dubrovnik in July, Santorini in August, any European Christmas market city in December). Specific overnight trains or buses with limited seats (India Rajdhani Express 60+ days out, Chiang Mai to Bangkok overnight). Budget airlines 6-10 weeks ahead for cheapest fares.

Book a day or two ahead: most Southeast Asian destinations outside peak season. Eastern Europe year-round outside of specific festivals. Most cities in Central America.

Show up and book in person: many small towns and villages in Southeast Asia, Central America, and the Balkans have guesthouses not listed on any platform. The walk-in rate is often lower than online platforms by 20-30% because the host avoids the commission. This works best for stays of 3+ days where your negotiating position is stronger.

The hybrid approach I use: book the first 1-2 nights of accommodation in a new country or major city online to eliminate arrival-day stress. From there, let the trip evolve based on what other travelers are doing and what looks good in person.

The risk of pure spontaneity: it works beautifully in off-peak seasons and fails spectacularly when you arrive in a sold-out city in high season. Learn which destinations have genuine capacity constraints and pre-book those specifically.