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The Trip of a Lifetime Awaits You

We design unforgettable travel experiences. Custom. Curated. For You..

Create Once In a Lifetime Memories

Curated Travel

Relax. We'll Handle Everything

Royal Treatment

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See The Best of the World Stress Free

Impactful Experiences

You deserve more than a "trip." You deserve a world-class travel experience.

Good news... that just happens to be our specialty.

Kimberly McCardell

From close-to-home escapes to far-flung adventures, we curate bespoke travels.

Hello, we are Kim and Sherry. The team at Windward and Crown.

At Windward + Crown we pair incredible accommodations with unique experiences to create your custom trip itinerary. Top it off with exclusive perks and peace of mind knowing you are working with trusted travel advisors.  Stop stressing and start packing.

  • Luxury Experts

  • Planning Professionals

  • Satisfaction Guaranteed

Our Travel Services and Specialties

Professional Travel Planning

Our Services

    Detailed, Collaborative Trip Design
    Research, Planning and Proposal
    Final Itinerary (on travel app and PDF)
    Book Accommodations, Ground Transportation, Tours and Activities
    Flight Guidance
    Travel Insurance Recommendation and Quote
    Custom Packing List
    Coordination of Luggage Shipping
    Destination Snapshot and Real-Time Support
    Restaurant and Shopping Recommendations
    VIP Perks, Offers & Amenities

Top Travel Styles

    Family Vacations
    Multi-Generational Travel
    Celebrations + Group Travel
    Romantic Getaways + Honeymoons
    Adventure and Active Travel
    Authentic Local Experiences
    Culture and History
    Volunteer + Educational Experiences
    Sustainable Travel
    Hidden Gems
    Food + Wine
    Beach + Sun
    And More, Just Ask!

Our Process

1

Dream Trip Planning

Together, we'll discuss your vision for this trip. Tell us everything you'd love to have happen.

2

Let's Make It Official!

Once you submit the client agreement and planning fee we can get to work on your incredible trip.

3

Personalized Itinerary

We will develop a customized, highly-detailed itinerary for every stage of your trip. Trust us, every detail will be thought through, with some of our signature perks sprinkled in along the way.

4

Seamless Booking and Logistics

Sit back and relax. Our global team and us will handle every detail of getting you where you need to go. You just need to figure out what to pack next (we can help with that too!)

5

Bon Voyage!

It's here. Enjoy the trip of a lifetime. You deserve it.

Getting Started is So, So Easy

1

Pick a Date

We set time aside to have uninterrupted Discovery Calls. Find a date convenient for you.

2

Pick a Time

Do you prefer morning, afternoon, or evening? We have several options available.

3

We'll Chat!

Our discovery call is the first step to your luxury dream trip, we can't wait to explore your ideas with you!

Our Global Partnerships at Your Service

We have relationships with top luxury travel brands worldwide to benefit you. If you need anything while traveling, our network and we are there 24/7 to make sure that your trip goes off without a hitch!

Why Travelers Choose Windward + Crown

100% Done For You



100%Done-For-You

Tell me what you want, and you're done. I'll handle everything else from start to finish.

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1-Call-AwaySupport

Whether you're on a glacier in the Alps or an island in the Indian Ocean, I'm only one call away.

VIP Treatment Wherever You Go



VIP Treatment Wherever You Go

My global network of partners are on call to give you the VIP treatment you deserve, every leg of your journey.

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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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

Free Travel Trends Guide

Ready to sharpen your travel tastes and discover the world's best-kept secrets? This personalized travel guide will help you broaden your horizons and get inspired for the journey ahead. Plus sign up to our monthly newsletter for travel inspiration delivered right to your inbox!

Never Settle.Get the Travel Expertise you Deserve.

Schedule your free initial Discovery Call or submit your trip inquiry form below to begin the trip of a lifetime today.

Kimberly McCardell

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Why Work With Windward + Crown?

Curated Travel, Impactful Experiences, Royal Treatment