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About Windward + Crown

Kim McCardell, Owner and Travel Advisor,

I always dreamed of traveling for work. So it is not difficult to say that starting a travel company is indeed my dream job. As an advisor, I take great care and joy in getting to know my clients in order to curate personalized and refined itineraries that fulfill their travel dreams. My goal is to exceed client expectations and eliminate the stress of planning and managing your own travels.
I have always had a passion for learning about and exploring the world. In my first career I was a middle school social studies teacher. I immersed my students in global cultures and geography. I envisioned traveling the world to the places I taught about. I carried that love of teaching and learning into planning and managing our extensive family travels. As a family we have gone inside glaciers and volcanoes in Iceland, taken part in beach cleanup and sea turtle patrol on beaches in Hawaii and watched the sunset from the top of the Eiffel Tower.
My professional travels have taken me to many more places around the globe including Costa Rica, South Africa, Mozambique, Mexico, Italy, Greece, Paris and beyond. These business travels help me gain first hand understanding of new destinations while forging relationships with regional travel partners, all in the name of best serving my clients.

When I am not working or traveling, I like to relax at home with my husband, 3 children and 2 dogs. I enjoy cooking, spending time with friends, taxiing my kids to school, sports and social events and playing with my favorite furbabies.

I look forward to connecting with you and planning your next amazing adventure.

Virtuoso Certified Travel Advisor

Sherry Proctor, Travel Advisor, 

Of the memories created with my husband and 2 children over the years, our favorites have been while traveling. Whether learning to surf in Costa Rica, horseback riding in the mountains of Colorado, or cruising in the Bahamas, our adventures have brought us closer together, while taking us far from home. I spent 13-years in a successful career in the pharmaceutical industry before choosing to focus on raising my family full-time.
During this time, I focused on my passion and talent for event planning by serving in a fundraising auxiliary for a local charity; and volunteering as class mom, team mom, and PTA president. I learned much from these experiences and loved meeting and working with everyone from administrators to parents, coaches, teachers, and students to improve our community. These experiences and relationships, paired with my background in pharmaceutical sales and marketing, provide a strong foundation of skills applied daily in my role as a travel advisor.
What I love most about travel is its extraordinary ability to transform the traveler. Sometimes a simple change of scenery is all that is needed to gain understanding, perspective, and inspiration. In the fall of 2022, my husband and I went on an incredible journey through Italy for our 20th wedding anniversary.
This experience, planned by Windward and Crown, is what led me to pursue becoming a travel advisor. In this role, I strive to provide the same seamless and special experiences for clients as I experienced first-hand. I take the time to get to know my clients, their needs, and their vision. I then leverage this collective knowledge and expertise with our extensive, curated network of suppliers to create a custom experience that brings to life a truly unique, and memorable adventure.

Outside of work and travel, I enjoy reading, cooking, exercising, having cocktails and charcuterie with friends, and playing with our yellow lab, Drake.

Press and Accolades

Articles we've been featured in across the web.

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Best of Baltimore Weddings Readers Poll

 We are proud to share that Windward and Crown has been named as a finalist in the Best of Baltimore Weddings Reader's Poll for 2023. This prestigious acknowledgment is featured in the Travel Agencies category, where our dedication to creating dream wedding travels has been recognized by the vibrant Baltimore community.

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Baltimore Magazine

We are thrilled to announce that Windward and Crown has been featured in Baltimore Magazine’s "Women Who Move Maryland 2023" section. As an integral part of the community that propels Maryland forward, Baltimore Magazine has shined the spotlight on the female professionals leading the way in Baltimore and beyond..

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6 Splurges That Turn Trips From Good Into Great - GoBankingRates.com

There are always ways to cut corners when planning a vacation, but sometimes it’s worth paying a little extra to make your trip that much more unforgettable.

The Trip of a Lifetime Awaits You.Are You Ready?