About us

Welcome to the When Women Fly community where we celebrate women who dare to pursue their dreams and fly - metaphorically and literally. In a world that gives a lot of feedback about what women 'should' do, look, and say, it's easy to feel boxed in.

Ashleigh Thompson, guest from episode 056, rock climbing.

We are here to change the narrative. 

Every woman harbors the spirit of flight and in our podcast, we explore what happens and what we become when we fly, one story at a time.

The worlds needs more women who fly. Be bold, be brave and fly.

Guest: Ashleigh Thompson • Episode: 056

Sylvia Winter


Journey into Flight

Sylvia Winter first took to the sky to better see the ground. As a landscape architect with a passion for the design of landscape and public space, aerial photography proved to be an invaluable resource during her design work. The process of seeing the world from above, once a means to an end, soon became an obsession that launched her on an unexpected personal journey of discovering flight.

She is never far from an airstrip and a trail network, with husband, daughter, and two sons. When not in the cockpit or traveling the globe, she can be found creating art, playing the fiddle or taking long runs in the woods. Depending on the ever-shifting winds of the last few years, Sylvia and her family have most recently lived in Switzerland, Vermont, and Cambridge.

She grew up in rural Illinois where the natural horizon, the place where the sky and earth meet, was both an ideal and an invitation. Although she found solace in open spaces of the Midwest a burning curiosity to explore in other lands pulled her out into a life of seeking and learning through travel and engagement.

 

Bio

Sylvia’s love of art and design and mobility flourished in her impressionable 20s. She holds a Visual Arts from Brown University, and a Master of Landscape Architecture and a Master of Design Studies from the Harvard’s Graduate School of Design. During these years, she studied one year at Rhode Island School of Design, the Pacific Northwest College of Art and an impressionable two terms in southern France at L’Ecole des Arts in Lacoste. The peripatetic nature of these years fed a deep curiosity of places and people and the spaces that define them. It led to work and design research in mountain cities: Bariloche, Kyoto, Bilbao, Lausanne and Palmer, Alaska, and others, where the landscape plays a role in the character of the place and spirit of the people.

At every scale, Sylvia’s approach to design draws from an understanding of the cultural formation of landscapes and the reciprocal influence of landscape on culture. Sylvia’s approach to design that values public places and serenity designed in everyday spaces attracted her to work with nonprofits like the Arnold Arboretum and the Nature Conservancy. At the core of all her art and design is a curiosity and reverence toward the environment and people that create the character of a place.

FLIGHT

Sylvia’s romance with flight began during the magical moments as a passenger in small aircrafts accessing remote wilds of Alaska, Mexico, Kenya, and Costa Rica in her 20s. She felt that there was more to flying than being a passenger and learning to fly became a goal. Combining a passion for adventure and a love of vistas, Sylvia applies her desire to see the world from above in her creative projects.

Sylvia launched the independent podcast When Women Fly to profile stories of adventurous women finding flight and busting paradigms.

Sylvia is an instrument-rated single engine land private pilot and flies a Cirrus SR22. She is also a 200hr Certified Yoga Instructor, an amateur photographer, and avid runner. Sylvia’s many hours of flight have inspired creativity, taught lessons of resilience, and fueled her soul.

 
Host Sylvia Winter in the cockpit flying her plane
When Women Fly host Sylvia Winter seen here with her Cirrus SR22 plane
 
When Women Fly Podcast Art
 

About the Podcast

When Women Fly is a celebration of the journey to flight with an ultimate goal of building a unique community of women who reach amazing heights in the literal and metaphorical sense. In these weekly recorded conversations, Sylvia explores the roots of passion, the quest for prominence, and the challenges of excelling often in the face of uncertainties, glass ceilings and other limitations.