Your Go-to Italy Trip Planner


Meet caitlynN

Ciao, mi chiamo Caitlynn! I’m a travel guide, writer, mother, and lifelong learner. I’ve lived in Cortona, Perugia, Rome, and Alberobello. I’ve travelled to 19 of the 20 Italian regions (Sardinia, I’m coming for you!). And I can’t get enough. Italy has gotten under my skin, and now it’s my mission to visit as often as possible and share my love and knowledge with others who also might wax poetic about drinking a glass of Sagrantino while the sun slinks behind undulating Umbrian hills.

How’d I get here?

My Love For Italy...

My love for Italy began when I majored in Classics in university, learning about ancient Roman emperors and declining Latin verbs. Or perhaps it was even earlier: I distinctly remember being obsessed with Minerva and Neptune when studying mythology in Grade Six. In 2009 I first stepped foot in the bel paese, embarking on a semester abroad in Cortona, Tuscany. It changed my life.

Even now I can recall those January scents of pruned olive branches burning on the hillsides and fragrant orange varieties I had never before encountered in a Canadian grocery store. That semester I learned about the innovative Mannerist painters of Renaissance history, the English obsession with writing about Italy, and the political motivations of gladiatorial spectacles. 

Turned into...

My universe had expanded tenfold by travelling to Italy, and I was enthralled. From then on, it was travelling to Rome spontaneously for birthdays, planning my wedding in Umbria, acting as travel guide for my extended family and friends, enrolling in language classes at Università per Stranieri di Perugia, moving to Italy for a year, and writing a travel memoir about the peninsula. 

"I’m not Italian, but I’m a great mix of two worlds: Italy expertise and an instinctive understanding of what non-Italian travellers are looking for..."



With every trip, my knowledge and appreciation for all things Italian deepens. Over 14 years I’ve learned how to avoid the tourist traps and find authentic, economic osterie. The meals I ate in 2009 are not those I enjoy now with my husband and toddler. I’ve learned how to eat seasonally, which specialties to order in which regions, and how the Italian table is governed by a series of unwritten rules.

Having eaten couscous in Trapani and fumbled over my German in Bolzano, I’ve travelled from the deep south to the steep north, and now have a good sense of the different atmospheres of the Italian regions and the unique experiences they offer.

I’ve validated innumerable Trenitalia tickets on railway platforms, navigated bus routes from Tuscany to Umbria to Lazio, and reversed Fiats down hills on the Amalfi Coast when two cars just wouldn’t fit, so I’m comfortable with all modes of travel.

The week before my wedding, I shepherded my family and friends on an epic sightseeing itinerary that included the Colosseum, the Capitoline Museums, and the Uffizi Galleries, with as few lines as possible.



I want to pass on all my learning and experience to you, so your next trip to Italy is customized to your individual desires, and you feel a deeper connection to the people, places, customs, and food of this incredible country.

I’m not Italian, but I’m a great mix of two worlds: Italy expertise and an instinctive understanding of what non-Italian travellers are looking for and struggle with in their trips.

I understand the shock at discovering that most Italians don’t drink cappuccini after 11am and many frown at the idea of sipping one after lunch. I understand how long it will take a non-Italian traveller to order a caffè at the bar if they mistakenly think there’s some sort of silent queuing system. I understand some travellers will not quite know what that towel is for near the bidet. 

Let me nip some of these cultural misunderstandings in the bud, teach you some Italian to endear you further to this country’s warm citizens, and get you hyped before your next trip!

I'm All About

Passionate People

And that includes you! We’ll bond over our shared zest for Italy, I’ll really get to know you, and I’ll become your matchmaker, pairing you with the Italy that is most well-suited to your unique needs and desires.

Curiosity & Learning

I am driven by a genuine love for Italy and an interest in understanding its complexities. It is this thread of curiosity and learning that creates the most thoughtful and respectful travellers—people I want to work with, like you!

Dolce Far

Literally, the sweetness of doing nothing. It is people-watching in the piazza or really tasting that tomato on your bruschetta. Italy inspires you to slow down, live in the present, and realize what’s actually important in life: family, friends, food, and beauty.

Get to know me

Fun facts

People Are Surprised That

I made my friends and family
walk 33 km (20.5 miles)
around Rome’s centro storico
one day during my wedding week.
What? I love Rome!

My Friends Know Me As

The one who won’t let them order a cappuccino after lunch.

Polenta or Paccheri?

I’m a sucker for the south, I must admit. Paccheri!

Think we’ll get along?

Let's Get Planning

It’s casual, it’s easy, and there are no strings attached. What are you waiting for?