DREAM
VACATION
WEEK

WEBSITE

Travel booking products tend to follow a familiar script: search, book, go. But this project threw the rulebook out the window. I was tasked with overhauling an outdated, certificate-based vacation search system that felt more vintage than classic. My approach? Craft a compelling, story-driven introduction that showcased the product’s value before users even logged in. Once they were on board, I introduced a modern, intuitive search-and-booking flow to bring the experience firmly into the 21st century.

Overview

For the Dream Vacation Week website the business asked us to boost booking rates for the Dream Vacation Week site—a platform to offload nearly-expired vacation stays and tempt non-members into a low cost 7-night getaway stay at quality resorts. With a legacy backend system anchoring us, I led a heuristic review, and we quickly realized: most users get one certificate ever, one shot, and they’re out. Our redesign focused on that single-certificate journey, and removing the outdated certificate grid approach, cutting the checkout flow from 8 steps to 4—because no one’s dreaming of extra clicks on vacation.

Goal

The goal? Modernize a clunky, non-responsive booking experience without upsetting the legacy backend system. By tackling the outdated search flow, we aimed to boost booking rates from a dismal 5% to a projected 15-20% year over year with a shorter checkout, better filtering, and a long-overdue room size selector—because who books a mystery-sized room?

A New Vision For The Site

Design for Speed and Simplicity

Eliminate barriers in the booking flow to create an intuitive and efficient process tailored to seasoned travelers.

Empower Decision Making

Make it easy for users to find the right options by improving search functionality with filters for price, dates, and room size.

Work with What You’ve Got

Build a front-end that feels fresh and modern, even if the backend is stuck in the past. Users should never feel the age of the system.

Role

Associate Director of UX & Information Architecture

Tools

Figma, Ludic Charts

Team

1 Product Owner, 1 UX designer, 2 developers

Platform

Web

The Current Site

Problems: The legacy site was like an abandoned theme park—outdated rides, no map to navigate, and no one in charge to explain what was going on. Visitors wandered in, got lost, and quickly left. My mission was clear: bring this digital ghost town into the 21st century with a fresh vision, purpose, and a roadmap people could actually follow.

Tackling Challenges with Creativity
and Context

The booking flow was anything but standard, so I set out to introduce a mental model travelers already knew from top OTAs. On top of that, I had to account for pre-login functionality for resort agents to register certificates on-site and guide users into a smoother login flow. It was complex, but I was ready to roll up my sleeves and refine the experience.

User Flow Diagram

To redesign the booking experience, I created a streamlined user flow for the site, cutting clutter and improving the search and checkout processes. I also worked with the business to ensure the flow seamlessly served both savvy customers redeeming certificates and onsite sales reps activating them.

The user flow diagram highlighted some opportunities to use the same website for the agent-facing features which previously was planned to be

View User Flow Diagram

App Sketches

Wireframes & Prototype

Normally, I never skip wireframes, but with a ticking clock—and the looming layoff—I had to fast-track this prototype. While it’s not as polished as I’d like, it captures the core ideas and hints at the functionality I hoped to expand on.

View Prototype

Wireframe Landing Page

This view shows the create profile view and the pre login landing page.

Onboarding

Here we can see a single view of the 3 step onboarding views which only show the first time the member logs in.

Checkout

The 4th and final step is the check out view which aligns with other popular OTA's from an experience perspective. Payment occurs offsite via Stripe and thus is not displayed.

Wireframe Landing Page

This view shows the create profile view and the pre login landing page.

1/5

Learnings

This project let us tackle big UX challenges head-on. The new search data isn’t just gold for optimizing this product—it’s the gift that keeps on giving for our parent site and other member products. Better insights mean smarter designs, happier users, and, let’s face it, a healthier bottom line.

Next Steps

I wish I’d had the chance to tackle the mobile designs. While I may never know how this project evolved after my role was dissolved, I might just create a mobile version for fun—because who says unemployment can’t spark a little creativity?