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.

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

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


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.


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


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



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


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



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

Travel tips, resources, & musings on Italy

From The Blog

best places to visit in italy

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

best places to visit in italy

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!



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