Trip planning has a problem: it creates chaos. Someone sends a link in the group chat. Someone else drops a Pinterest board. Another person is frantically Googling walking distances. By the time you’ve got an itinerary, it’s scattered across WhatsApp, Google Docs, Maps, and three different apps nobody will actually use together.

Wingman consolidates all of that into one place. And it does it in a way that actually makes planning enjoyable.

The Wingman Trinity: Generate, Import, Customize

Everything starts with your itinerary. Wingman gives you three ways to create one.

Full Customization, Your Way

Whether you generated your itinerary or imported it, Wingman gets out of your way and lets you build exactly what you want.

The philosophy is simple: Wingman does the structural work (routing, timing, distances) so you can focus on the creative work (what you actually want to see).

Plan Together, Actually Seamlessly

Travel planning gets messy when you add people. Different opinions, different preferences, different communication channels.

Wingman’s collaborative planning eliminates that friction entirely.

Real-Time Group Editing

Invite friends to your itinerary with a single tap. Everyone can see the plan, add stops, remove things, rearrange days, and leave notes — all at the same time. Changes sync instantly. No “did you get my latest update?” no competing versions, no decision paralysis.

Shared Notes Space

Built right into your itinerary, not in a separate chat or document. “We need to be here by 2pm,” “Can we skip this?” “Love this spot,” — all connected to the exact moment in your trip. Context lives with the decision.

Clear Ownership

See who suggested what, who made changes, and who added notes. You know the trip’s history and reasoning. This matters when you’re trying to understand why something’s on the schedule or who’s championing a particular stop.

Walk With Purpose: Comprehensive City Guides

Your itinerary isn’t just a list of stops. It’s a complete city guide that answers every question before it becomes a problem.

What’s Actually Included

Every itinerary also includes emergency contacts, hospital locations, police numbers, and embassy information — practical safety net for wherever you’re going.

650+ Professional Audio Tours, Included Free

Wingman isn’t just a planner. It’s a walking companion.

The app includes over 650 audio guides created by professional travel guides, local historians, and storytellers who understand the difference between a fact and a story worth hearing. These aren’t voiceovers read by robots. They’re created by humans who know these cities.

When you generate or import an itinerary for a city where Wingman has audio tours, they’re automatically woven into your plan. Walk down a street and a story plays. Arrive at a monument and context appears. The audio enriches what you’re seeing in real time.

Available across 155+ cities on six continents — from Amsterdam to Auckland, Istanbul to Mexico City, Tokyo to Toronto.

Share With the World (Or Just Your Friends)

You created something great. Maybe it’s worth sharing.

Wingram: The Social Travel Feed

Wingman has a built-in community called Wingram. Post your custom itineraries, watch other travelers discover them, and let your planning inspire real trips.

See an itinerary you love from another traveler? Save it with one tap. Modify it to fit your dates and interests. Thousands of user-created routes, ready to customize.

It’s not a rating system or a social media algorithm trying to make things go viral. It’s travelers sharing what worked, and other travelers learning from that. Authentic, useful, human.

Private Sharing

Or keep it private. Share with your group, never publish to Wingram, keep it just for you. Your itinerary, your rules.

Everything Your Brain Needed Someone Else to Handle

Trip planning involves a lot of decisions:

How far is too far to walk in a day? Wingman calculates realistic daily distances based on your stops.

What’s the optimal route? Wingman maps the walking order that makes sense geographically, not just chronologically.

How much time per stop? The app estimates realistic time at each location based on what it is and how far you’re walking next.

What time should we start each day? Wingman factors in your stops, walking distances, and restaurant hours to suggest realistic timing.

What if someone has different pace/interests? Fully customizable. One person wants museums, another wants food — build different routes on the same trip.

These are the decisions that make trip planning take hours. Wingman handles the framework. You handle the preference.

Built for Travelers Who Care

Wingman has a philosophy that shapes every feature: travel should make you a better person, not just take pictures for Instagram.

That’s why we emphasize walking over driving. Why we highlight local businesses over chains. Why we include audio tours from real humans instead of algorithm-generated content. Why we make it free and don’t try to upsell you on premium features.

Travel slower. Stay longer. Actually talk to people. Support local. That’s not our marketing slogan — that’s baked into how Wingman works.

One Itinerary, Infinite Possibilities

Generate a trip to Barcelona. Import a TikTok about Greek islands. Create one from scratch in Prague. Customize it with friends. Share it with the Wingman community. Keep it private. Use the audio tours or skip them. Add your own stops. Change the whole route midway through your actual trip if inspiration strikes.

Wingman doesn’t constrain you. It enables you.