Designing Original Paths Through Italy for Thoughtful Travellers

Enrich your next Italy trip with bespoke advice on crafting your ideal itinerary, language and culture prep, tailor-made Italy travel tips, and get hype resources.

Puglia: a sea lover’s paradise, with whitewashed hill towns that gleam above the plains of olive groves below Read More Umbria: think of it as Tuscany without the hordes—hill towns, Renaissance art, a slice of Apennine drama, and delicious pasta and wine Read More Lazio: eat oxtail in a Roman osteria, visit a less busy Pompeii, and swim next to Emperor Tiberius’s villa Read More

How we’re going to level up your trip

Explore My Signature Services

Travel Consulting

What kind of Italy traveller are you? Let’s deep dive into your interests and personality to design your original path (DOP!) through Italy with a personalized itinerary, restaurant recommendations, and tips on neighbourhoods and sights.

Language & Culture Prep

Up your odds of getting an impromptu invite to an Italian’s house for dinner by embracing their language and customs. Take a language lesson, learn about food culture, and watch doors open to authentic connections with the people and places you’ll encounter on your trip.

Food & Wine
Masterclasses

Enjoy your meals in Italy even more by going to an Italian grocer or wine store in Calgary before you leave to learn about pasta shapes, regional specialties, wine designations, and Italian menus. Hungry for more fun? Tack on a cooking class or wine tasting.

Hey friend!

Benvenut*! Caitlynn Here.

I’m an enthusiastic Italophile ready to hone your next trip to Italy, show you hidden gems, help customize your itinerary, and get you excited and prepared while you count down the days until take-off.

Check out my services, peruse the map to discover which Italian region you should visit next, and drop me a line to chat more!

the elevator pitch

Tailor Your Trip

Italy isn’t a one-size-fits-all country. In fact, it’s as multifaceted as you are. Let’s matchmake you with the itinerary, regions, food, vibe, and experiences you’re most likely to enjoy.

Feel the Joy of Italy Sooner

Extend the magic of Italy beyond your trip dates by diving into the food, music, and beauty of the country before you fly out: master carbonara in Calgary, follow curated IG accounts, and listen to my Spotify playlists.

Feel Empowered

Learning some language and cultural etiquette empowers you to step out of your comfort zone, engage with locals, and have more meaningful connections and experiences when travelling in Italy.

Be a Thoughtful Traveller

Patronizing mom-and-pop shops, visiting some lesser-known places, and learning about Italian customs enable you to appreciate the local way of life and ease the pressures of mass tourism.

Avoid Tourist Traps

The Colosseum is majestic, but don’t eat a meal where you can see it! You only have a set number of days on the ground, so let’s not waste any time eating mediocre food. I have 130+ delicious recommendations.

Navigate Daily Life with Ease

Knowing common phrases and vocabulary in Italian makes daily tasks, such as ordering at a restaurant or asking for directions, more manageable and enjoyable.

Get expert advice

Ready To Start Planning Your Next Trip To Italy?

Have questions about my services? Send me an email.

Risotto or rigatoni?

Discover Which Unique Italian Region You Should Visit Next

Campania

For lovers of Neapolitan pizza and buffalo mozzarella, this is the place. Greek temples, the largest monastery in Italy, and the Amalfi Coast also await.

Piemonte

White truffles, chocolate, and Barolo, oh my. Known for its gastronomic delicacies, Piedmont is the birthplace of the Slow Food movement.

Molise

An off-the-beaten-path region rich in evocative villages, ancient Samnite history, and natural beauty.

Toscana

Plunge into the Renaissance, discover atmospheric hill towns, and drink wine so delicious you too will consider buying a vineyard and fixer-upper farmhouse.

Lombardia

One of Italy’s most northern regions, Lombardy is full of alpine thrills, lakes with glamorous visitors, and the country’s commercial powerhouse: Milan.

Calabria

Welcome to the south: 800km of coastline, fortified hill towns, a surprisingly alpine interior feel, and the spiciest food in the country.

Your travel consultant

Helping You Deepen Your Connection To Italy

Italy Expertise & Experience

Let me harness my 14 years of travelling, living, and/or studying in Italy to help you craft your most ideal trip. As a non-Italian myself, I intuitively understand what travellers are looking for and struggle with in their trips.

Genuine, Authentic Travel

We’re not ticking off sights to say, “I’ve done Rome.” I help travellers to Italy create meaningful connections with the people and places they visit by building a foundation of knowledge and curiosity about local cultures, traditions, and customs.

Not a Big Tour Company

Consider me your Italy-obsessed friend who can give you Italy travel tips, assistance creating your made-to-measure itinerary, and an intro class on culture and language. A perfect match for the savvy DIY trip planner who doesn’t want to break the bank.

How DOP is top!

What Clients Have to Say

I've fallen in love with Italy in a deep-in-my-bones way thanks to Caitlynn. I’ve experienced grape harvest, a late-night walk with an opera blaring from a small speaker, the taste of warm figs, the feel of the sea, strong coffee, and the rush to spot the Pope during Easter. Caitlynn has studied the language, travelled the regions, traversed the back streets, and given me wonderful recommendations: coffee at a rest stop that I'd have driven by, a hilltop town with the best ragù, and a particular stone terrace overlooking the sea to enjoy a glass of regional wine on. This is why I recommend planning your travel with Caitlynn, if you're looking to love Italy as she does.

Caitlynn set an itinerary for my honeymoon in Italy. My wife and I walked the streets of Monterosso al Mare’s “old town” in the Cinque Terre, smelling lemon trees and enjoying the native calla lilies. That was only the beginning of a wonderful two-week adventure which took us through Pisa, Rome, Florence, Cortona, and Venice. If you seek an authentic, off the heavily beaten path experience, Caitlynn is the person you need to speak with! Her ability to advise on everything from regional food specialties to how to use the daunting (yet amazing once you’re schooled) rail system to the best place for cappuccini on the cobblestone streets of Rome to, well, you get the idea, anything! She can help prep you for all the things you fear about visiting the country with the richest history in the world. Her vast knowledge of Italian culture will soon have you counting the minutes to departure, ready to take your own plunge into Italia!

Caitlynn helped me create the most amazing memories in Italy! She had the best advice as to how to plan my travels, in what order to go to which regions, and also brought incredible recommendations to the table that I would have never known to go to!! Her passion and love for Italy and Italian culture and language have been translated to mine now too!! I had the most unforgettable trips to Italy and look forward to traveling there again with her help!! Thank you Caitlynn!!

Caitlynn has a knack for curating a well-rounded and tailored experience to showcase the best of what Italy has to offer, and its unique, less obvious cultural and culinary gems you likely wouldn’t find on your own. I would certainly ask for her recommendations and expertise the next time I visit.

Travel tips, resources, & musings on Italy

From The Blog

What Does DOP Stand For?

DOP Italian Travel. Why the acronym? Though travelling to Italy is dope, or top, as the Italians say, I didn’t choose DOP just for these sonic echoes. To me, DOP is Designing Original Paths through Italy for thoughtful travellers, and was inspired by what DOP means in Italy: Denominazione d’Origine Protetta, or Protected Designation of Origin. In Italy, DOP is

Bitter Greens on the Prairies

I first planted cicoria (chicory) in Canada the spring after COVID hit. I have a thing for bitter greens. My husband and I were squirrelly, pacing the perimeter of our 25’ Calgary lot and pouring boiling water on the iced ground to encourage workability. We moved a shed, built a small patio, and made room for a vegetable garden in

Italy With Kids

I look in fear at the Lufthansa landing page and repeat my mantra: the joy on our one-year-old’s face when she ate her first Italian ragù, the joy on her face, the joy on her sauce-slathered face. The text is in bold: flights confirmed. What have I done? When I found these flights for our next family trip to Italy,

Che bello!