Create Once In a Lifetime Memories

Curated Travel

Relax. We'll Handle Everything

Royal Treatment

See The Best of the World Stress Free

Impactful Experiences

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.

Learn More About Us Schedule Discovery Call

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!

Dream Trip Planning

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

Let's Make It Official!

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

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.

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!)

Bon Voyage!

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

Pick a Date

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

Pick a Time

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

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 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

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

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

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