Creating your first trip
Walk through the create-trip questions step by step — destinations, bookings, dates, travelers, and preferences — and what to expect while Plannery builds the itinerary.
Plannery builds a trip from a short series of questions. Only a few are required; the rest sharpen what it plans for you, and each of those can be skipped. At the end, Plannery generates a day-by-day itinerary you can edit.
Starting a trip
On the home page, tap Create Your First Trip (or Create new trip next to My Trips once you have one).
A progress bar runs along the top of the screen. At the bottom of each step, Back returns to the previous question and Next moves on; steps that are optional also show Skip. On the first step, Back reads Cancel and exits without saving. Pressing Enter also moves you forward.
Your answers are saved in the browser as you go, so you can leave and come back — with one exception: files you upload on the bookings step are dropped if the page reloads. You'll need to add them again.
Where would you like to go?
Search for a city or region and tap a result to add it. Add as many destinations as you like; each appears as a chip you can remove.
Below the destinations, Add a day trip? suggests nearby places you can visit for the day without changing where you sleep. A day trip is not a destination — pick it here rather than adding it to the list above.
Then answer Where are you traveling from? If you've set a home location on your account, it's already filled in. Plannery uses it to reserve travel days at the start and end of the trip.
You need at least one destination to continue.
Already booked anything?
Optional. Drop in flight or hotel confirmations — PDFs or screenshots — or tap Choose files. Plannery reads each one and uses what it finds to fill in later steps: a booked flight can answer your dates, a hotel booking can answer where you like to stay.
If a hotel booking doesn't show its check-in and check-out dates, you'll be asked to add them so the Stay lands on the right days. Two screenshots of the same booking are combined into one.
Do you have specific dates in mind?
Choose Yes, I know my dates or Not yet — still flexible. Picking one moves you on automatically.
If your uploaded documents already show the dates, this step says so — you can still change the answer if the documents only cover part of the trip.
What are your travel dates?
Shown only if you know your dates. Tap your departure date, then your return date on the calendar.
How long in each place?
This step spells out every day of the trip. What it asks depends on your earlier answers:
- One destination, flexible dates — set how many days you want there.
- Several destinations — split the days across the cities, and drag rows to reorder them. You can also add a destination between two others here.
- Dates already chosen — the same, shown as real dates. Adding a day to one city pushes the cities after it later and the trip runs a day longer.
Travel days appear as their own rows. One Plannery inferred from distance can be waved off; one backed by an uploaded flight is fixed.
Who's coming?
Optional. Add one row for each traveler, then enter their name or invite them by email. You can also add past travelers or people from Contacts.
The From your trips section shows chips for past travelers you can tap to fill open rows or create an adult row, with a More option for additional people. You can always invite people later from trip settings.
What matters most to you?
Optional. Pick up to five interests — Food, History, Nature, and so on. Tapping a selected interest reveals more specific choices underneath it, like Street food or Hiking.
Anything else?
Optional. Tell Plannery anything in your own words — dietary needs, a special occasion, things to skip.
How should we set up your itinerary?
Optional. Choose how much Plannery plans for you:
- Plan it for me — every day is filled with stops you can swap or edit.
- I'll plan it myself — days are left empty, and suggestions go to Want to go for you to place yourself.
Picking one moves you on. You can still change any individual day afterward.
Budget, stays, and getting around
Three more optional steps:
- What's your budget level? — one of $ — Budget, $$ — Moderate, $$$ — Upscale, or $$$$ — Luxury.
- Where would you like to stay? — pick every type that fits: Hotel, Hostel, Airbnb / rental, Boutique, Resort, Camping. A type you've already booked is pre-selected.
- How do you want to get around? — pick whatever you'd actually use: Rideshare, Metro, Walking, Rental car, Taxi, Bicycle.
If you've set travel preferences on your account, these steps start with those answers filled in. Changing them here only affects this trip.
Look good?
The last step summarizes everything: your Destinations with their days or dates, The basics (duration, dates, travelers), and Your preferences.
Next to each destination, a curated badge means Plannery has a guide for that city. AI picks means it doesn't yet, so suggestions for that city will be generated rather than drawn from a guide.
Tap Create trip.
Building your itinerary
Plannery now generates your days. This usually takes 30–45 seconds. While you wait, you may see a few cards of trivia about your destinations.
When it finishes, your trip opens on the itinerary. Photos and details for each stop keep filling in for a short while after you land.
If generation fails, you'll see Couldn't generate the itinerary. Your trip and its days were saved either way. Choose Try again to generate once more, Open trip to look at it as it is, or Skip for now to add stops yourself.