How I Plan My Trips: A Practical Guide

I’ve been asked many times how I plan my trips. Over the years, I’ve developed a system that balances thorough preparation with enough flexibility for spontaneous discoveries. Here’s my complete process.

Phase 1: Dreaming (2-6 Months Before)

Every trip starts with inspiration. I keep a running list of destinations that catch my eye — from travel blogs, Instagram posts, documentaries, or conversations with other travelers. When it’s time to plan, I look at my list and consider:

• Season: What’s the weather and tourist season like?
• Budget: How much can I realistically spend?
• Duration: How many days can I take?
• Energy: Am I looking for adventure or relaxation?

Phase 2: Research (1-3 Months Before)

Once I’ve chosen a destination, I dive into research. My go-to resources:

• Google Maps: I “walk” the streets virtually and pin places that interest me
• YouTube: Watching vlogs gives you a real feel for what a place is like
• Local blogs: English-language blogs by expats living in the destination are gold
• Reddit: City-specific subreddits have honest, up-to-date recommendations

I create a simple spreadsheet with columns: Place, Category (food/culture/nature), Priority (must-do/nice-to-have), Practical Notes (hours, cost, booking needed).

Phase 3: Booking (1-2 Months Before)

I book in this order:

1. Flights — I use comparison sites and set price alerts
2. Accommodation — Central location is worth paying extra for
3. Must-do activities — Any attractions that need advance booking

Everything else stays flexible.

Phase 4: Preparing (1-2 Weeks Before)

• Download offline maps for the area
• Learn 10-20 basic phrases in the local language
• Check visa requirements and travel advisories
• Pack light — I’ve never regretted bringing less

My Travel Backpack

After years of testing different bags, the one I always reach for is the Kapten & Son Bali Medium in Walnut. Here’s why it has become my go-to for almost every trip:

• The right volume. Spacious enough for a full week of travel, but never bulky. I can fit clothes, toiletries, a laptop, and small extras without overpacking.
• Carry-on friendly. It fits within hand-luggage limits, so I skip the check-in queue every time.
• No wheels, no hassle. Unlike a rolling suitcase, nothing drags behind me on cobblestones, stairs, or crowded platforms — both hands stay free.
• Perfect on trains. Slides easily under the seat or onto a luggage rack, and I can grab anything I need without standing up.

• Structured, ergonomic back. The firm back panel keeps the bag’s shape, distributes weight evenly, and stays comfortable even on long walking days.
• Safe for a laptop. A padded interior compartment keeps my laptop secure — important when I’m working on the road.

• Smart organization. Small inner pockets for passport, cards, and documents, plus a separate compartment for cosmetics or anything I want to reach quickly.

If you’re building a capsule travel kit, this is the one piece I genuinely recommend.

The Most Important Rule

Leave room for spontaneity. The best travel experiences are often unplanned — a restaurant a stranger recommends, a side street that beckons, a local festival you stumble upon. Plan enough to feel prepared, but not so much that there’s no room for surprise.