Guess Where Trips
Overview
Guess Where Trips is a company that creates curated mystery road trip itineraries with surprise destinations revealed the day of your adventure.
Timeframe
3 months - Currently ongoing
My Role
UX Researcher, UI/UX Designer
The Problem
Hesitation
Some users hesitate to purchase a mystery road trip due to uncertainty or lack of clarity about what's included
Need More Details
Others want more assurance (distance, difficulty, cost, accessibility, etc.) without spoilers
Unclear
The product's "mystery"
element is exciting but can also be a conversion barrier
The goal is to improve the UI/UX of Guess Where Trips so more users:
1. Book mystery road trips
2. Understand what to expect from the experience
3. Retain the “mystery” element that makes the product unique
Research
I conducted 18 survey responses from potential and past users, and 6 task-based usability tests using the current site
18
survey responses from potential and past users
72%
were interested in mystery trips but said lack of clarity was a barrier to booking
33%
wish there was a sample trip preview feature on the website
67%
expressed some level of anxiety about not knowing what they were paying for
44%
of usability testers hesitated on the trip selection screen, unsure of what they were choosing
User Personas
Sarah (29)
The Careful Planner
🤔 Goals
-
Try new experiences with her husband
-
Take a break from planning every trip detail herself
-
Find getaways within a 3-hour drive
😤 Frustrations
-
Doesn’t feel she can trust a product without knowing what she’ll get
-
Needs to know if there are long hikes or hidden costs
-
Worries about being disappointed if expectations aren’t managed
Isha (34) and Ravi (36)
The Family Oriented Budget Travelers
🤔 Goals
-
Introduce kids to nature and new places
-
Spend screen-free family time together
-
Avoid logistical surprises or long drives
😤 Frustrations
-
Not knowing if all stops are kid-friendly or accessible
-
Fear of meltdowns if the trip isn't engaging
-
When logistics are not planned out in advance
Josh (25)
The Spontaneous Traveler
🤔 Goals
-
Impress friends with something unique
-
Avoid the work of planning a trip
-
Stay within budget and time constraints
😤 Frustrations
-
Doesn’t want to read walls of text
-
Gets overwhelmed with too many options
-
Concerned about cost but doesn’t want to seem cheap
-
Sticking to a rigid itinerary
“I want to be surprised, but I don’t want to show up in flip flops and find out there’s a 5k hike.”
Key Findings and Design Opportunities
😟 Ambiguity = Anxiety. Many users want the surprise, but still need logistical assurance to feel confident.
ℹ️ 80% of interviewees mentioned needing some sense of distance or time commitment before booking.
🤔 Users need reassurance to trust the experience
🗺️ Previews build confidence
🔧 Design opportunity: Add icons or general labels to give clues without revealing specific stops.
🔧Design opportunity: Improve trust with visual credibility (e.g., “What You’ll Receive,” testimonials, professional trip teasers)
🔧Design opportunity: Feature a sample trip to let users know what to expect.
Information Architecture
Below is the design's IA which condenses various elements into three sub-pages allowing users to:
-
Understand how Guess Where Trips works
-
Browse and Purchase trips
-
View a sample trip along with all information provided up front
The Solution
Home Page
Efficiency and minimalism, two key drivers in Guess Where Trip's design, are heavily reflected on the home page. Here, users can:
-
Easily navigate to View Trips or See a Sample Trip
-
See a simplified overview of how Guess Where Trips works
Sample Trip Page
Gives the user a preview into what is included in a Guess Where Trips mystery road trip
-
The Before You Go section condenses key information
-
Each stop is explained along with recommendations similar to how a real trip would be
-
CTA to book trip at the end
View All Trips Page
Concisely view all trips
-
Filter through different options such as city, theme, season, etc.
-
Trips are separated by region for ease of navigation.
-
If the user is unable to decide, they can take a quiz to help narrow down options
View/Purchase Trip Pages
Gives the user a preview into what is included in a Guess Where Trips mystery road trip
-
Users can see all available trips from their region/state
-
Icons have been added to each trip for a quick filter
-
Once a trip is selected, user has the option to purchase it, view necessary details in the "Before You Go" section and see a preview of each stop without revealing too much
Functional Prototype
I created a functional prototype within Figma. Check it out here!
Current State and Conclusions
As a Type-A individual who also thrives on adventure and exploration, I was genuinely excited to dive into the Guess Where Trips project. Designing for a company that curates surprise travel experiences felt like the perfect intersection of structure and spontaneity.
This project has challenged me to think critically about how to capture the magic and mystery of the Guess Where Trips brand while ensuring the digital experience remains clear, intuitive, and engaging. I’ve spent significant time refining the visual identity by experimenting with playful yet clean typography, a warm and welcoming color palette, and thoughtful microinteractions that reflect the excitement of a surprise trip.
As the project continues to evolve, the next important step will be conducting in-depth usability testing with real users who are actively planning trips. This will help validate design decisions, uncover pain points, and provide insights into the emotional journey users experience as they interact with the product. I also plan to explore motion-based prototypes to better communicate key interactions and transitions, especially around moments of surprise and discovery.
So far, working on this project has given me a deeper understanding of how to balance creativity with user-centered thinking. It’s been an exciting and rewarding process, and I’m looking forward to continuing to iterate, refine, and push the design even further.