TripUp

Redesigning group travel planning to reduce friction and keep friends aligned.






User research

TripUp is a mobile app designed to help groups organize trips together.

While early adopters appreciated the concept, research revealed recurring friction points:

  • Group decisions happened spontaneously.

  • Users abandoned complex flows and moved conversations to WhatsApp.

  • Expense management became frustrating at the end of trips.

  • Participants wanted to contribute without feeling overwhelmed.

The redesign focused on creating a faster, more collaborative experience for planning, voting and settling expenses.

Main insights

User research

TripUp is a mobile app designed to help groups organize trips together.

While early adopters appreciated the concept, research revealed recurring friction points:

  • Group decisions happened spontaneously.

  • Users abandoned complex flows and moved conversations to WhatsApp.

  • Expense management became frustrating at the end of trips.

  • Participants wanted to contribute without feeling overwhelmed.

The redesign focused on creating a faster, more collaborative experience for planning, voting and settling expenses.

Main insights

  • Two primary user types:

    The Organizer creates the trip, invites participants, keeps plans moving.

    The Partipant wants to contribute, prefers lightweight interactions and needs visibility without complexity

  • Spontaneous decision making

    Most decisions happen during the trip.

    The experience must support quick actions and real-time collaboration.

  • Shared ownership

    Everyone wants input on:

    • Restaurants

    • Activities

    • Expenses

  • Low tolerance for friction

    If an action takes too many steps, users move to WhatsApp.

  • Two primary user types:

    The Organizer creates the trip, invites participants, keeps plans moving.

    The Partipant wants to contribute, prefers lightweight interactions and needs visibility without complexity

  • Spontaneous decision making

    Most decisions happen during the trip.

    The experience must support quick actions and real-time collaboration.

  • Shared ownership

    Everyone wants input on:

    • Restaurants

    • Activities

    • Expenses

  • Low tolerance for friction

    If an action takes too many steps, users move to WhatsApp.

  • Two primary user types:

    The Organizer creates the trip, invites participants, keeps plans moving.

    The Partipant wants to contribute, prefers lightweight interactions and needs visibility without complexity

  • Spontaneous decision making

    Most decisions happen during the trip.

    The experience must support quick actions and real-time collaboration.

  • Shared ownership

    Everyone wants input on:

    • Restaurants

    • Activities

    • Expenses

  • Low tolerance for friction

    If an action takes too many steps, users move to WhatsApp.

Key design decisions

Replacing chat chaos with lightweight polls

Problem

Group decisions often became fragmented across different channels.

Solution

A lightweight polling system allows users to:

  • Create polls directly within the trip

  • Suggest options quickly

  • Vote in real time

  • Automatically update the itinerary

This creates a reduced coordination effort and created a shared source of truth.

Making expense splitting flexible

Problem

Not every expense should be shared equally. In the scenario, some participants joined dinner but not wine.

Solution

Users can:

  • Add expenses quickly

  • Exclude participants when necessary

  • Update balances automatically

Reducing settlement complexity

Problem

Settling expenses between multiple people creates unnecessary transfers.

Solution

TripUp consolidates debts automatically and calculates the minimum number of payments required.

The whole process

Structuring a complex travel experience

Trip planning involves several interconnected activities:


  • Coordinating people

  • Making decisions

  • Managing itineraries

  • Tracking expenses

  • Settling balances


One of the main challenges was creating an information architecture that kept these activities connected without overwhelming users.

User Flows and Wireframes

Based on the research findings, I mapped the complete end-to-end experience to identify moments where users were most likely to abandon the app and move conversations elsewhere.

Particular attention was given to three critical flows:

Creating and voting on a poll

Users needed to suggest options and reach decisions quickly while on the go.

Logging shared expenses

The process had to support both simple and more nuanced scenarios, such as excluding specific participants from selected costs.

Settling balances

The final settlement flow focused on minimizing effort by consolidating debts and reducing unnecessary transactions.

To validate navigation and task completion, I created a detailed wireflow covering the entire scenario from trip planning to final settlement.

User Testing

Evaluating clarity and efficiency

After defining the architecture and workflows, I conducted usability testing with users representing both primary personas:

  • Organizers

  • Participants

Participants were asked to complete realistic travel-related tasks based on the project scenario.

Key tasks
  • Create a poll and vote on a restaurant

  • Add a shared expense

  • Exclude selected users from a cost

  • Understand their balance

  • Complete debt settlement

User Testing key findings

Poll creation was intuitive

Users quickly understood how to create options and participate in decisions.

Expense splitting required additional clarity

Some participants initially expected expenses to be split equally by default. To address this, I improved visibility around participant selection and exclusion.

Balance information was highly valued

Users consistently appreciated having a clear overview of who owed what and why.

Settlement generated the highest satisfaction

Participants responded positively to the debt consolidation approach, which reduced the number of required payments.

Insights from testing led to several improvements:

  • Simplified expense management flows

  • Clearer balance summaries

  • Stronger hierarchy between trip balances and overall balances

  • Reduced cognitive load during settlement


These refinements helped create a faster and more intuitive experience aligned with the project's goal of minimizing friction.

Thanks vor visiting.

© Antonino De Stefano 2026. All Rights Reserved.

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