You’ve saved the Reels. You’ve bookmarked the blog posts. You’ve told yourself you’ll “plan it properly this weekend.” But you didn’t. Because trip planning is tedious, scattered, and somehow always takes an entire Sunday afternoon. Wingman’s itinerary creator exists to make that Sunday afternoon last 25 seconds.

What is the Wingman Itinerary Creator?

It’s an AI-powered trip planner built into the Wingman app that generates a full, multi-day walking itinerary for almost any city in the world. You tell it where and how many days. It does the rest.

The result isn’t a vague list of “top 10 things to see.” It’s a structured, day-by-day plan with mapped walking routes, realistic distances, time estimates between stops, and detailed information about every sight along the way. If Wingman has audio tours in that city — and it currently covers over 155 cities — they’re woven directly into your itinerary at no extra cost.

The entire feature is free. No paywall, no premium tier, no trial period. Every itinerary you generate is yours to keep, edit, share, and walk.

How It Works: 5 Taps, One Complete Trip

What’s Inside Every Itinerary

A Wingman itinerary isn’t a skeleton plan you need to fill in yourself. It’s a comprehensive travel companion that covers everything from daily walking routes to tipping etiquette. Here’s what’s included:

Day-by-Day Walking Plan

Every itinerary is broken into realistic daily routes with mapped stops, walking times between each sight, total daily distance, and a clear overview of what you’ll see each day. No guesswork, no overloaded 14-stop days that leave you exhausted by noon.

Sight Information

Every stop in your itinerary comes with background information — what makes it worth visiting, what to look for when you’re there, and practical details. It’s the kind of context that turns a building into a story.

City Intelligence

Beyond the walking routes, every itinerary includes a full city guide packed with the things you’d normally spend hours Googling:

Every itinerary also includes a city photo gallery and emergency information — hospital locations, police numbers, embassy contacts.

Built for Planning Together

Travel is rarely a solo decision. Wingman’s itinerary creator is built for collaborative planning from the ground up.

Invite friends to your itinerary with a single tap. Everyone can view the full plan, add or remove stops, rearrange the schedule, and leave notes for each other in a shared notes space built right into the itinerary. No more WhatsApp threads with 47 links nobody clicks. No more “I’ll make a Google Doc.” It’s all in one place, and everyone can edit in real time.

When your itinerary is ready — or even while you’re still tweaking it — you can share it to Wingram, Wingman’s community feed for travelers. Other users can discover your route, save it, and walk it themselves. Found someone else’s itinerary that looks perfect? Save it as your own with one tap and customize it from there.

Turn Social Media Into Real Trips

Here’s where Wingman does something no other travel app does.

You know that folder of saved TikToks and Instagram Reels — the one with the hidden Rome street food spot, the Kyoto temple walk, the “you HAVE to go here in Lisbon” video? Wingman turns those saves into actual walking itineraries.

Copy the link from any TikTok or Instagram Reel. Paste it into Wingman’s Import trip feature. The AI analyzes the video, extracts the locations, and builds a complete, walkable itinerary from the content. Walking times, mapped routes, sight information — everything, generated from a 30-second video you saved at 2 AM.

If Wingman has audio tours in that city, they’re automatically integrated into the imported itinerary. A Reel about Trastevere becomes a walking route through Rome with professional audio narration at every stop.

650+ Audio Tours, Included Free

Wingman isn’t just a planner — it’s a walking companion. The app includes over 650 self-guided audio tours across 155+ cities, created by real travel professionals, local guides, and storytellers who know the difference between a tourist fact and a story worth hearing.

When you generate an itinerary for a city where Wingman has audio content, those tours are woven into your plan automatically. You don’t search for them, you don’t pay extra, you don’t download separate files. They’re just there, ready to play as you walk.

Available cities with audio tours span six continents — from Amsterdam to Auckland, from Istanbul to Mexico City, from Tokyo to Toronto and everywhere in between.

Fully Customizable, Fully Yours

Every itinerary Wingman generates is a starting point, not a locked document. You can add stops, remove them, rearrange the order, change which day a sight falls on, and add personal notes to any point in the plan. The AI gives you structure. You make it yours.

This matters because no algorithm knows that you hate museums, that you need a coffee stop every two hours, or that you promised your partner you’d find that specific bookshop from a TikTok. Wingman builds the framework. You shape it into your trip.

Free. Actually Free.

There’s no premium tier. No “unlock full itinerary for $9.99.” No paywall after three trips. No feature that suddenly requires a subscription when you need it most.

The itinerary generator, the audio tours, the collaborative planning, the social import, the city guides, the Wingram community — all of it is free. Wingman is built on the belief that better trip planning shouldn’t cost anything. The app is free to download, free to use, and free to share.