Making Your Itinerary

Once you have a sense of what your trip will look like, it is always a good idea to have an itinerary to keep all the information in one place. In our opinion, a good itinerary is essential for every type of trip, from weekend getaways to epic voyages.

Here are some of our favorite resources in crafting a great itinerary from scratch if you don't want to keep it all in a Word or spreadsheet document.

How to Start

There are a few ways to get started, and they depend on how comfortable you are with the internet, word processing, spreadsheets, and AI.

If you are most comfortable using word processing & spreadsheets, use your favored software.

All the mainstream packages offer travel/ trip itinerary templates.
Sometimes, it's easier and faster simply to write up your own.

If you want help, here are some options:

Need a quick AI draft? → Check out Layla or Wonderplan
Need tight logistics & reservations in one place? → TripIt
Traveling with friends? → Wanderlog for collaboration
Going cross-country by car? → Roadtrippers
Exploring offline or on spotty data? → Sygic Travel
Just want Google to do the lifting? → Google Travel/Maps

Free Itinerary Planning Sites

Please note that these recommendations are based on our personal experiences and in no way guarantees that they will be helpful to you or that they will provide exactly what you want.

Google Travel / Google Maps “Explore”

Built into Google Search, Flights and Maps, it now surfaces AI day-by-day suggestions for whole cities, regions or countries, lets you save them to a trip board, and can even read location text in your screenshots to pin spots automatically. Great if you already live inside the Google ecosystem and want something quick and shareable.

Layla (incorporating Roam Around)

Type a few lines (“5 days in Kyoto with nature and food focus”), and Layla’s AI returns a complete schedule with transit links, photos, and booking buttons in seconds. You can regenerate or tweak parameters on the fly. Ideal for inspiration sprints and last-minute planners. Layla: AI Travel PlannerLayla: AI Travel Planner

Sygic Travel (Tripomatic)

Another AI-driven option that asks budget and interest questions up front, then builds an editable plan you can download for offline use. Particularly handy if you want PDF or map exports without paying for premium tools. Wonderplan

TripIt

The veteran “inbox-parser.” Forward any booking email (air, hotel, rail, restaurant) and TripIt auto-builds a unified timeline you can view offline, export to calendars, and share. Its Pro tier adds real-time flight alerts and check-in reminders, but the free version handles the core aggregation perfectly.

Wonderplan

Wanderlog

A map-centric planner that layers AI suggestions, budgeting, checklists, and group chat onto a draggable day-by-day timeline. Everything syncs across web and mobile; collaborators can vote or comment in real time. Offline access and expense splitting make it popular for backpacking or multi-city trips. WanderlogGoogle Play

Road Trippers

The go-to for US & Canada road trips. Plot a start and finish and it auto-suggests quirky stops, national parks, hotels, and gas stations along the way; premium unlocks multi-stop optimization and RV-friendly routing. Roadtrippers