Today we’d like to introduce you to Kim McCardell.
Hi Kim, so excited to have you with us today. What can you tell us about your story?
Before founding Windward + Crown, I spent over a decade as a middle school social studies teacher, crafting immersive lessons in culture, history, and geography. I later earned a masters in school administration and took on a school leadership role, with the goal of one day becoming a principal.
Motherhood shifted my path, but not my passion. Teaching taught me the power of research, planning, and connection. Motherhood taught me the importance of raising globally minded kids. Both roles deeply influence how I design travel today: with purpose, creativity, and a focus on what matters most to each client.
During Covid I spent my time at home planning all the trips I wanted to take with my family. As I was writing itineraries,I realized I could do this to help other families have amazing travel adventures. I started poking around online and discovered I could be a “travel advisor”. Ultimately, I researched and connected with different people in the industry and in May of 2021 I launched Windward and Crown. I knew I wanted to plan excellent trips for people but beyond that I could not imagine the path that have followed in the past 5 years. Professional development, destination experiences and industry relationships are key to our role. What started as an idea has become a thriving luxury travel company.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Time management. I am always on. I am always working.
Growth management.
As you know, we’re big fans of Windward and Crown. For our readers who might not be as familiar what can you tell them about the brand?
Windward + Crown is a boutique luxury travel advisory specializing in thoughtfully curated, highly personalized travel experiences for clients who value their time and want every detail expertly managed. We believe luxury isn’t defined by a hotel star rating or a price tag—it’s defined by how intentionally a journey reflects the traveler.
We take the time to understand each client’s travel style, priorities, and goals, then design seamless experiences that combine authentic local connections, exclusive access, elevated service, and meticulous planning. Through our global partnerships and industry relationships, we create journeys that are not only memorable but effortless from beginning to end.
Our clients don’t come to us simply to book a trip. They come to us for expert guidance, insider knowledge, VIP benefits, and the peace of mind that comes from having a trusted advisor managing every detail before, during, and after travel. Whether it’s a milestone celebration, a multi-generational family vacation, a luxury cruise, a custom European itinerary, or a once-in-a-lifetime adventure, we transform travel planning from overwhelming to exciting.
At Windward + Crown, we believe convenience is a luxury, time is priceless, and the best travel experiences are deeply personal.
Our ideal clients are successful professionals, business owners, families, and couples who value exceptional experiences but have limited time to research, plan, and coordinate complex travel on their own.
They appreciate expertise and personalized service over endless online searching. They want someone who understands their preferences, anticipates their needs, and advocates for them throughout the entire travel experience. They seek meaningful experiences, authentic connections, and seamless logistics rather than cookie-cutter vacations.
Many of our clients are celebrating life’s important moments—anniversaries, family milestones, destination weddings, honeymoons, retirement trips, or bucket-list adventures. Others simply want to maximize their vacation time and know that every detail has been carefully considered.
The best Windward + Crown clients value a collaborative planning relationship and understand that professional travel design delivers more than reservations—it provides access, expertise, convenience, and peace of mind. They want to spend less time planning and more time experiencing the world.
Do you have any memories from childhood that you can share with us?
Listening to Billy Joel on the record player while my parents played with me in the living room of our first house.
Pricing:
- Planning services fee from $300 per trip
- 4 and 5 star travel
Contact Info:
- Website: https://www.windwardandcrown.com
- Instagram: @windward_and_crown
- Facebook: /windwardandcrown
- LinkedIn: /WCtravel
Image Credits
Personal Photos Only
