The best travel experiences…
The best travel experiences have a way of pulling us out of our routines and reconnecting us with what feels exciting, inspiring, and completely present.
Whether it’s a helicopter ride over rolling wine country, a luxury safari in Africa, a yacht day along the Mediterranean, or a laidback escape to the beaches of Mexico, every Skinny Dip journey is thoughtfully designed around how you want to experience the world.
From exceptional hotels and insider access to seamless logistics and elevated details along the way, each itinerary is created to feel effortless, immersive, and deeply memorable.
Meet Kylie Osmundson
FOUNDER OF SKINNY DIP TRAVEL
Travel has always been more than a vacation to me — it’s the feeling of being completely immersed in a place, discovering something unexpected, and stepping outside of everyday life. Some of my favorite moments have come from wandering unfamiliar streets, staying in unforgettable hotels, sharing incredible meals, and experiencing destinations in ways that feel deeply personal and connected.
What I love most about designing travel is that no two journeys should ever feel the same. The same destination can become a completely different experience depending on what inspires you. That’s why every Skinny Dip itinerary is thoughtfully curated around your travel style, priorities, and the moments you want to remember long after you return home.
WHY SKINNY DIP
Skinny Dip Travel was inspired by the feeling great travel creates — freedom, exhilaration, spontaneity, and stepping outside of your everyday routine. There’s something incredibly powerful about letting go, embracing adventure, and doing exactly what lights you up without overthinking it. The best journeys reconnect us with the most present, confident, and alive versions of ourselves. That feeling became the inspiration behind Skinny Dip Travel.
The Journey behind skinny dip
My love for travel started with large family trips to Mexico growing up, where I quickly realized how deeply travel connects people and creates lifelong memories.
During college, I spent a semester abroad in Sweden and traveled throughout Europe whenever I could, often booking last-minute flights to somewhere completely new.
A few years later, I took a leave of absence from my corporate career to complete yoga teacher training in Costa Rica, which completely shifted my perspective on life and travel.
Eventually, I took a leap of faith and moved to an island in the Caribbean, where I spent a year working at luxury resorts, aboard yachts, and immersed in the hospitality world that would later inspire Skinny Dip Travel.
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.
