40 under 40

Ashley D'Aristotile, Flyway Travel

Last updated: 12:40 PM ET, Tue October 27, 2026
Ashley D'Aristotile

Ashley D'Aristotile.

Bio

Ashley D'Aristotile started in the world of group sports travel before launching her own agency, Flyway Travel, in 2022. Through deep local partnerships and a love of Italy’s many distinct identities, Ashley designs journeys that invite travelers to experience Italy, rather than simply sightsee through it. And recently she's carved out a highly focused niche within bespoke Italy travel: language immersion tours. As the travel coordinator for Vero Viaggio, she helps take over 100 people to Italy every year with the goal of helping them improve their spoken Italian, while making meaningful and authentic connections along the way.

She's partnered with an Italian-language "influencer" to help market the trips to her followers, who are actively interested not only in traveling to Italy, but specifically traveling there to speak Italian. This has proven so successful that she's been invited to speak about this marketing tactic at her host agency's annual conference for luxury advisors (TPI Platinum Symposium).

D'Aristotile loves training advisors on how to use "The Influencer Advantage" to grow their group travel sales and her earnest desire is to help other advisors grow. She wants to see other advisors find the spark to grow their own business into new and interesting niches.

D'Aristotile is 37 years old.

"Being named to TravelPulse’s 40 Under 40 is an incredible honor and a reminder of the importance of building a business that truly reflects who you are," said D'Aristotile. "I believe in finding your niche, leaning into what you love, and letting your personality shape the way you work. When you build a business around what genuinely excites you, that passion carries through to the experiences you create for your clients."

Industry References

"In addition to serving as Ashley’s ASTA Mentor, I have had the opportunity to know her and observe her growth in my role as CEO of Signature Travel Network, representing a community of approximately 15,000 travel advisors. From that perspective, I can say with confidence that Ashley stands out as one of our best. She possesses the professionalism, entrepreneurial spirit, client focus, and business acumen that distinguish the very best advisors in our industry," said Alex Sharpe, CEO, Signature Travel Network.

"She is thoughtful, curious, highly motivated, and genuinely committed to improving her business. She combines those qualities with a strong understanding of the business side of travel, and that combination has fueled impressive growth," added Sharpe.

"Ashley is also simply a wonderful, professional travel advisor. She cares deeply about her clients and consistently approaches her relationships with enthusiasm, integrity, and attention to detail. She represents the very best qualities of our profession and is exactly the kind of emerging leader we want to see recognized and encouraged."


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Lacey Pfalz

Lacey Pfalz

Senior Editor, News & Features

Lacey Pfalz is Associate Editor at TravelPulse. She's a passionate advocate of responsible travel and believes the best travel experiences happen outside of a planned itinerary. Lacey currently lives in rural Wisconsin. She can be reached at [email protected].

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