WaySide: Group Travel Planner

You're the one who said "I'll plan it."

WaySide is the group travel planner built for the person who organizes the trip. It handles the shared itinerary, the group expenses, the booking confirmations, all of it. One app. Leave the chaos by the WaySide.

Your flight's delayed? Ask your AI assistant to reschedule your afternoon.

WaySide's AI knows your actual trip, your itinerary, your group, your plans. It's not just a generic chatbot. Ask it to fill in gaps in your day when something changes, check what's coming up, or just suggest an itinerary you might enjoy based on your travel interests. It's the co-planner you didn't know you needed.

Build your group trip itinerary together

Share a single join link with your group. They tap it, see the trip and who's joined already, and join in one tap. If they have the app, it'll launch and they can instantly join the trip.

Book what's missing, right from your itinerary

See a gap in your plan and fill it on the spot. WaySide surfaces hotels for open nights, tours and experiences for empty days, car rentals, and eSIMs.

Chat and plan in the app, so all your plans and details are in one place.

Give family members a view-only link so they can follow along without editing anything. Give other travelers full editing access. Everyone sees the same live itinerary, updated in real time.

Forward your confirmations, skip the data entry

Forward your flight, hotel, restaurant, and activity confirmation emails and WaySide parses them into your shared itinerary automatically like TripIt, but collaborative and alive for your whole group. View everything in list, calendar, or map view. Never miss an uncovered night with automatic lodging gap detection.

Split travel costs without the spreadsheet

Log every group expense in any currency. Choose how costs are split: equally, by percentage, by shares, by custom amount, or just for yourself. WaySide tracks who paid and who owes what across every currency in your trip.

At the end, it works like Splitwise but with a single repayment currency: simplified settlement transactions that clear all debts in the fewest payments possible. Set the settlement currency, confirm the exchange rate, and send your group a clear list of who pays who. Done.

Keep everything else organized too

- Group location sharing, so you can find your friends
- Trip documents, to-do lists, and notes in one place
- Flight monitoring and travel reminders
- Export your itinerary as a PDF or calendar file to share with family or border crossing agents
- Full offline access: view and edit your itinerary and expenses anywhere, even without signal. Changes sync automatically when you reconnect.

WaySide Pro

Upgrade for unlimited AI assistant access and email importing, group location sharing, flight monitoring and custom notification. One Pro member covers the whole group. Pro benefits extend across your whole trip, so your group experiences most premium features even if only one person subscribes.

Plan smarter. Split costs fairly. Leave the chaos by the WaySide.

Terms of Use (EULA): https://www.apple.com/legal/internet-services/itunes/dev/stdeula/
Privacy Policy: https://waysideapp.com/privacy/