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Skinny Dip Watermark - Travel Design for the Modern Traveler

Let’s face it.

You need a break like yesterday, an opportunity to turn the “hustle” mode off and enjoy a change of scenery. After all, everyone needs an escape from the grind every once in a while.

With Skinny Dip, we can design the trip you’ve been dreaming of. From far-away adventures touring wineries by  helicopter to a laidback week to unplug and reset on the beaches of Mexico. A trip booked with Skinny Dip is perfectly curated and each element of the getaway is elevated with VIP perks. Together, we will choose incredible accommodations and experiences  you’ll never forget.

 
 
 

WHERE SKINNY DIPPERS HAVE TRAVELED

DREAMY GETAWAYS ACROSS THE GLOBE

 
Skinny Dip Travel Client Worldwide Destination Map
 
 
 
Kylie Osmundson on a Yacht in Croatia - Lead Travel Designer - Skinny Dip Travel

Meet Kylie Osmundson

LEAD TRAVEL DESIGNER + FOUNDER OF SKINNY DIP TRAVEL

Travel frees me, both mentally and physically. There’s a shift that happens the second I hop on a plane. As cliche as it sounds, traveling brings me home to myself. There’s nothing more exhilarating than exploring a place I’ve never been before. Around each corner is a surprise just waiting to be discovered. 

I love working with people who want to expand their horizons and  step outside of the daily grind. The most amazing thing about travel? You and I could take the exact same trip - from accommodations to meals to  adventures - and our experiences would still be totally different. We each get our very own story to tell when we travel. I want to help you plan YOUR next amazing travel story.

 
 
Woman lounging in an inner tube in a private pool in the Maldives - Skinny Dip Travel
Couple posing on rooftop looking over Venice Italy - Skinny Drip Travel
Woman standing holding cocktail with palm trees in the Maldives - Skinny Dip Travel
 
 

Fun fact:

My love for travel started when I…

  • Travelled annually to Mexico with my grandparents and extended family (sometimes there were more than 30 of us)! We made so many memories together on these trips.

  • Spent a semester in Sweden and travelled all around Europe. I went wherever Ryan Air had the best weekend deals!

  • Took a couple of months leave of absence from my corporate job to enroll in a yoga teacher training in Costa Rica. 

  • Sold all of my belongings and moved to an island. This was my #1 bucket list item, one I never thought would happen. I spent a year teaching yoga and serving on beaches, yachts, and at luxury resorts in the Virgin Islands! 

 
 
Couple in Bali posing with a monkey on a shoulder - Skinny Dip Travel
Group of friends on a boat looking over water - Skinny Dip Travel
Woman on island doing yoga on a paddle board - Skinny Dip Travel
 
 
 
Skinny Dip Watermark - Learn about the perks and benefits of hiring a travel agent
 

 How We Can Help

There’s a very good chance you’ve never worked with a travel designer before. Let me show you all of the amazing perks and benefits a travel designer can provide you with. I’m here to answer all of the questions you never knew to ask. 

 
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