True luxury in travel isn't about excess — it's about intention.
At Windward + Crown, we believe luxury is deeply personal. It goes beyond star ratings. How well does your trip reflect you? Your pace, your preferences, your passions.
We take the time to understand what inspires you — whether it’s a quiet sunrise in a tucked-away villa, a table at the chef’s kitchen no one else can book, or simply knowing that every transfer, check-in, and connection has been handled without you needing to think about it.
LUXURY IS PERSONAL.

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Authentic + Immersive

A private guide who knows every hidden alley and many shopkeepers in the ancient Medina of Marrakech, providing immersive experiences you would never find on your own.

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Private + Secluded

An upgraded suite with a private plunge pool for a honeymoon that doesn’t just celebrate your story- it provides moments that add to it.

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Elevated Service

Arriving to your hotel after a very long flight and being greeted with a warm welcome and cool hand towel.

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Exclusive Access

Spending the night under the stars in a unique treehouse at a safari camp in South Africa.

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Time + Connection

Unhurried, meaningful moments shared across generations. Thoughtfully designed experiences that center on who you're with, not just where you are.

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Surprise + Delight

A table reservation at a highly sought after Michelin restaurant at the top of the Eiffel Tower...with a special anniversary delight to boot.

Kimberly McCardell

Kim McCardell, Founder + Advisor

Ciao! Bonjour! Konnichiwa! Hello! Glad you are here!

When I’m not helping you plan your next adventure, you can find me in the Pilates studio, cooking, laughing with friends — or dreaming up our next family trip. You might also catch me helping my three children with school work (and these days college applications), in the yard with my two dogs, or scouting the best local restaurants for date night .
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.
I am excited to get to know you, your family, and your travel goals. As your travel advisor, my goal is simple: to eliminate stress, exceed expectations, and redefine convenience, because ...
CONVENIENCE IS A LUXURY.

Learn More About Windward + Crown

Working With Windward + Crown

1

Discovery

The first step toward creating your dream trip is to complete our inquiry form. Once we've received your form, we will reach out to schedule your discovery call. Only inquiries submitted via our website will be vetted. To reduce the risk of missing an important message, we do not accept inquiries via social media or
text message.

2

Consultation

On the discovery call, we will discuss your travel needs and goals and our services at W+C. You will select the planning option that best suits your needs. Once the invoice for the selected option is paid, we will create your custom proposal.

3

Proposal Review

We combine takeaways from the discovery call with our expertise and global connections to create a unique proposal for you to review. Timely and thorough feedback is paramount during this phase to secure the components you desire and deserve!

4

Confirm Your Itinerary

Once you approve your proposal, you will be invoiced for the deposit amount. Deposit amounts and due dates are dependent on the proximity to the trip, as well as the partner that the trip is booked through.

5

Seamless Booking + Logistics

Windward + Crown works hand in hand with our global partners to make sure every detail from tour times to tickets and reservations are confirmed and clearly outlined in your final itinerary. We will connect on a video call to walk through logistics and questions before you depart.

6

Time for Takeoff

You are well prepared for your adventure ...●Personalized Itinerary● Travel App and Documents● In-Travel Emergency Support● Finishing touches that elevate your travel experience 

Learn More About Our Services

Our Global Partnerships Provide a World of Exclusive Access.

When you travel with Windward + Crown, you gain access to a world of insider expertise, exclusive perks, and dedicated support every step of the way. Through our global partnerships with the world’s finest hotels, cruise lines, tour companies, and destination partners, we offer you privileged access to exceptional experiences. Our relationships open doors to bespoke, elevated journeys—crafted uniquely for you, anywhere in the world.
Most importantly, you experience warmer welcomes, deeper connections, and more meaningful moments in the places you visit, plus access to VIP hotel benefits such as:
WELCOME AMENITYCOMPLIMENTARY BREAKFAST FOR TWOROOM UPGRADE (SUBJECT TO AVAILABILITY)EARLY CHECK IN / LATE CHECK OUT (SUBJECT TO AVAILABILITY)
LUXURY IS ACCESS.

Departure Lounge
Virtuoso
Relais and Chateaux
Shangri-La
Jumeirah
Small Luxury Hotels of the World

What Our Travelers Are Saying

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Our family needed a getaway and Kim provided amazing options that checked every box on our wish list. She handled all bookings, excursions, insurance, Covid requirement info, and private transfers to and from the airport. She was accessible the entire time we were planning, and while we were away. When we hit some inevitable travel snags, she was quick to help out! We will definitely use her services again, and recommend her highly!

Maureen M.Family Caribbean Escape

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The trip was awesome, and your expertise really helped make it special. The guide services that you used for both, Sienna and Rome, were fantastic. I’m not a history buff and actually don’t enjoy sightseeing, however, I really enjoyed those tours. The “Crown Jewel” was the boat trip around Ischia. It was a fantastic experience in every way, and our guide, Emanuel, was wonderful.

Robert R.Wedding in Italy

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Kim was absolutely fabulous. Going into the planning phase we had lots of special requests and she was able to capture everything! Our trip was effortless. Kim provided an app that had the agenda with all of the who, what, where, why, when and how to approach each day. Super easy!! We will be using Kim for our next trip!

Danielle T.Lifelong Friends on a Southwest Adventure

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Traveling can be stressful and overwhelming. I’ve always booked my travel on my own, but a last minute trip prompted me to contact Kim. I’m not sure I will want to plan trips again. Kim was so helpful and provided an amazing service. Thank you Kim!!! You sure know how to make a trip more special!

Melinda S.Special Mother Daughter Getaway

Read More Reviews or Leave Your Own!

✔ Reclaim your time✔ Travel seamlessly✔ Embrace every moment
LUXURY IS TIME WELL SPENT.

Submit your inquiry form to begin :

Kimberly McCardell

Phone

+1 (443) 475-0292

E-mail

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Trip Inquiry Form

A Seamless And Stress-Free Experience Awaits

1

Submit Your Inquiry Form


2

Connect On A Discovery Call


3

W + C Takes It From Here