Here's the repeatable process I follow every single time to build trip itineraries that actually work, from research to checkout day.
The System
1. Build a day-by-day plan in Google Sheets with 7 columns.
This is the backbone of every trip I plan. I create a spreadsheet with these columns: Date, Destination, Accommodation, Transportation, Activities, Reservations, and Extra Notes. Each row is one day. Here's what it looked like for French Polynesia:
| Date | Destination | Accommodation | Transportation | Activities | Reservations | Extra Notes |
|---|---|---|---|---|---|---|
| 05/11 | Moorea | Airbnb | 9:00am AirTahiti | Tamea Beach | Avis, 7:00pm-Rudy's | |
| 05/12 | Moorea | Airbnb | Lagoon tour | Tiki Tours | ||
| 05/13 | Bora Bora | Hotel | 10:00am flight | Matira Beach | Scooter rental |
I can glance at any day and know exactly where I'm sleeping, how I'm getting there, and what I've already booked. It also makes it dead simple to share with a travel partner. No back and forth about "wait, which hotel are we at on Tuesday?"
2. Collect every reservation screenshot in a single Google Doc.
Every confirmation email, booking receipt, and QR code goes into one Google Doc in chronological order. I screenshot it and paste it in. This is my backup plan. If I lose Wi-Fi or my email is slow to load, I've got everything in one place. Make the doc available offline before you leave.
Research
3. Use AI to draft a starting itinerary, then tear it apart.
I'll ask Claude something like "Make a 14-day very detailed itinerary for Japan covering Tokyo, Kyoto, Osaka, and Hakone" and use the output as a rough draft. It won't be perfect. AI tends to over-pack days, underestimate transit times, and miss local favorites. But it gives you a skeleton to rearrange and customize in 10 minutes instead of two hours. I treat it like a first draft, not a final plan.
4. Search Reddit for real itineraries from real travelers.
Blog posts give you the polished version. Reddit gives you the honest version. I search for things like "10 days Japan itinerary site:reddit.com" and read through what actual travelers did, what they'd skip, and what surprised them. Pay attention to the comments more than the original post. That's where people say things like "skip that temple, it's a tourist trap" or "add an extra day in Kyoto, two isn't enough."
5. Check Kimkim for realistic pacing between cities.
Kimkim has multi-day itineraries built by local travel specialists. I don't copy them, but I use them to gut-check my own plan. If Kimkim gives three days in the Algarve and I've only planned one, that's a signal I'm rushing it. They're especially useful for countries I haven't been to yet where I have no intuition for distances and transit times.
6. Flip through the books that started it all.
Two books I keep coming back to: 1000 Places to See Before You Die by Patricia Schultz and Lonely Planet's Ultimate Travel List. The first helps me catch locations I might be overlooking, and the second is great for identifying must-see spots in a region.
Building Your Map
7. Use top-rated.online to find the best spots on Google Maps.
Top-rated.online surfaces the highest-rated and most-reviewed places in any city on Google Maps. Type in "Seville" and you'll get a ranked list of restaurants, attractions, and bars sorted by rating and review count. It cuts through the noise fast and helps you find the spots locals actually go to, not just what's marketed to tourists.
8. Cross-reference restaurants on Wanderlog.
Wanderlog aggregates restaurant mentions across travel blogs. If a restaurant keeps showing up in post after post, it's probably worth your time. I use this alongside top-rated.online. One gives you the crowd favorites, the other gives you the blogger favorites. The places that show up on both lists are almost always great.
9. Save everything to two separate Google Maps lists.
I create two lists: one for things to do and one for restaurants. Keeping them separate means I can toggle each layer on and off, so when I'm looking for dinner I'm not scrolling through museums. By the time I land, my Google Maps looks like a custom travel guide with dozens of pins across the city. This is probably the single most useful thing I do on every trip.
10. Book your restaurants before you land.
Once my Google Maps restaurant list is built, I start making reservations for every night of the trip. For most places, Google Maps has a "Reserve a table" button that links to the restaurant's booking system. If that's not available, I check the restaurant's Instagram or website for a booking link. Some cities rely on specific platforms (Resy and OpenTable in the US, TheFork in Europe), so it's worth checking what's standard for your destination. I try to lock in reservations at least two weeks before departure. The best spots fill up fast, especially on weekends, and having dinner sorted every night means one less decision to make after a long day of walking. If plans change, you can always cancel, but you can't always get a table last minute.
11. Download offline maps for every region before you leave.
Open Google Maps, search for the city or region, tap the three dots, and hit "Download offline map." Do this for every destination on your itinerary.
On the Ground
12. Take a walking tour or boat tour on your first day.
A guided tour on day one gives you a mental map of the area, highlights neighborhoods you want to return to, and comes with local recommendations from the guide. In Moorea, a boat tour on our first day helped us understand the island better and our guide pointed us to restaurants we never would have found on our own. Every day after that feels more efficient because you already have a feel for the layout.
13. Use Google Maps to check walking distances before committing to a day plan.
Before I finalize any day's activities, I plug the locations into Google Maps and check the walking and transit times between them. If three things I want to do are on opposite sides of the city, I'll rearrange them across different days and group nearby activities together. This sounds obvious, but it's the difference between a relaxed day and an exhausting one. Ten minutes of route-checking saves hours of unnecessary backtracking.
A great itinerary is about building a system tight enough that you never waste time figuring out logistics, and loose enough that you can say yes to something unexpected. Build the spreadsheet, do the research, pin the map, and then go enjoy it.