DreamTrips Responsive Website
DreamTrips Responsive Website

Travel Together: Strategic Redesign with Increased Retention and Engagement

As Lead Designer, I was tasked with addressing key opportunities to enhance the way our members interact and travel together.

Sector

Socially-connected Travel Community

Results

Improvements led to a 125% increase in bookings (8,079 to 18,151 in best month)

My Role

• Lead Designer • Research Partner • Established Design System

DreamTrips Desktop and Mobile Homepages
DreamTrips Desktop and Mobile Homepages

Bringing the Social Heart Back to Travel: The DreamTrips Redesign

The Challenge: When Adventure Meets Loneliness


"I wish I could stay in touch with the amazing people I met on my trip to Bali..."

"How do I find other members who want to go to Japan next spring?"

"I'd love to see what the DreamTrips community is really like before joining..."

These were the voices of our members and potential members that kicked off our journey to transform DreamTrips from a travel booking platform into a thriving social community. As Lead Designer, I was tasked with reimagining how our 500,000+ members connect, share experiences, and plan adventures together.

Why This Project Mattered


DreamTrips had always been more than just another travel site – it was a community of adventurers seeking authentic experiences together. But our digital platform wasn't living up to this promise. Members were booking trips but struggling to maintain the connections they made. Meanwhile, potential members couldn't see the vibrant community that made DreamTrips special.

The stakes were high:

- Member retention was suffering due to limited engagement between trips

- Conversion rates for new members were below target

- Our search experience lagged behind competitors

- Shopping cart abandonment was higher than industry standard

Discovery: Going Beyond Standard Research


To truly understand our community's needs, I took an immersive approach to research:

  1. The Community Deep Dive

Instead of just running standard user interviews, I:

- Attended actual DreamTrips events to observe member interactions firsthand

- Hosted virtual coffee chats with members from different countries

- Shadowed our customer service team to understand common pain points

- Created a member advisory board for ongoing feedback

2. The Competition Analysis

I analyzed not just travel sites, but successful community platforms:

- Studied how Strava builds community around fitness

- Examined how Meetup facilitates group formations

- Investigated how Airbnb Experiences creates trust through content

3. The Data Story

Partnering with our Data Science team, we uncovered crucial insights:

- 78% of members who formed connections during trips were more likely to book again

- Detailed trip content with rich media led to 45% higher conversion rates

- Members who joined pre-trip social groups had 89% lower cancellation rates

The Big Insight: Connection is the Key to Conversion

Through our research, one truth became crystal clear: successful trips weren't just about the destination – they were about the connections made along the way. This insight led to our core design principle: "Every interaction is an opportunity for connection."

The Solution: Building Bridges Between Adventures
1. Reimagining Search

Before:

Generic Search with basic filters


After:

- Social-first search showing who else is interested

- Rich content including member stories and photos

- Smart recommendations based on community interests


2. The Social Layer

We introduced:

- Trip Groups: Automatic social spaces for each upcoming trip

- Interest Communities: Spaces for members to connect based on travel styles

- Story Sharing: A platform for members to showcase their experiences

- Member Matching: AI-powered suggestions for travel companions


3. Unified Shopping Experience

- Combined retail and travel carts into one seamless flow

- Added social proof elements throughout the booking process

- Integrated community content into product pages


Authenticated User View of a spotlighted DreamTrip
DreamTrip Product Page
Mobile App Screens

The Results: Numbers Tell the Story

The impact exceeded our expectations:

- 125% increase in search conversions in our best month post launch (8,079 to 18,151 bookings)

- 32% boost in retail shopping conversions

- 67% increase in member-to-member connections

- 45% reduction in post-trip member churn

- 89% of members reported feeling "more connected to the community"

Key Learnings & Growth
What Worked Well

1. Immersive research approach gave us deeper insights than traditional methods

2. Cross-functional workshops helped align stakeholders early

3. Regular member feedback loops caught issues before they became problems

What I Would Do Differently

1. Start A/B testing earlier in the process

2. Include more international members in initial research

3. Build a more robust analytics framework from the start

Looking Forward

The DreamTrips redesign taught me that great UX isn't just about usability – it's about creating spaces where human connections can flourish. This project pushed me to think beyond traditional e-commerce patterns and consider how design can foster genuine community.

Today, DreamTrips isn't just a travel booking platform – it's a thriving community where adventures begin long before the trip starts and connections last long after it ends.

Lindsay K.

UX Designer, Amira Learning

With Mike as my manager I felt empowered to express my ideas and encouraged to lead workshops as he created an accepting, respectful environment where all team member's ideas were valued. His positive mindset and trust in our team was motivating and kept stress at bay.

Lindsay K.

UX Designer, Amira Learning

With Mike as my manager I felt empowered to express my ideas and encouraged to lead workshops as he created an accepting, respectful environment where all team member's ideas were valued. His positive mindset and trust in our team was motivating and kept stress at bay.

I've had the pleasure of working closely with Mike, an experienced design leader with a deep commitment to customer satisfaction. Mike's approach to design is rooted in empathy—he believes in understanding the customer's perspective by immersing himself in their experience. … Mike excels in inspiring his teams to deliver high-quality work while maintaining an enjoyable work environment. His expertise in design processes, workshops, and facilitation, combined with his collaborative nature, fosters innovation within cross-functional teams. Mike's proficiency in A/B testing and guiding design through validation processes demonstrates his dedication to delivering top-notch user experiences.

Mia L.

Principal Researcher, RealPage