FOUNDER & TRAVEL ADVISORMeet Michelle
Some people find their passion early. Michelle found hers the moment she watched her daughters' eyes light up on their first trip to Italy, and she never looked back.
Michelle has built Olivia Blaire Travel on a simple conviction: that extraordinary travel should feel effortless. Through her affiliation with Departure Lounge, a Virtuoso member, she brings insider access, preferred relationships with the world's finest properties, and a level of personal attention that no booking algorithm can replicate.
Michelle's approach begins with listening. Every itinerary she designs starts with a conversation — understanding not just where you want to go, but how you want to feel when you get there. From securing suite upgrades and curated welcome amenities at exclusive properties to crafting private experiences in destinations most travelers never discover, she handles every detail so her clients simply arrive and enjoy.
Italy remains her greatest love and deepest expertise, though her passion for discovery extends across every continent. Whether you're planning a solo escape, a romantic journey, or a family adventure your children will talk about for the rest of their lives — based in Central Wisconsin and supporting clients nationwide, Michelle is ready to make it unforgettable.
Departure Lounge
A Virtuoso member agency with preferred access worldwide
Italy Specialist
Deepest expertise in Italy, with reach across every continent
Central Wisconsin
Based locally, serving clients nationwide
We were so pleased with our trip to Puglia. You did an outstanding job!Laura T.