Ciao! I'm Olli.
I landed in Rome, sniffed my way through Tuscany, and stormed the Piazza del Campo. The pasta was worth every cobblestone.
Follow a very handsome and opinionated Boston Terrier through 7 weeks of ancient Italian towns, incredible food, and Airbnb stops from Fiumicino to Sicily. Olli rates it all from 1 to 5 Olli Pawps — and his standards are very high.
Fresh from the Boot
New episodes dropping faster than I can sniff a new piazza.
Hidden Stops & Adventures: Orte to Sinalunga
Olli lands at Fiumicino, survives Dad's first drive on the Autostrada del Sole, navigates insanely narrow medieval streets in Orte, sniffs out Bar Centrale, and finally rolls into Sinalunga — his first real Italian home base.
Tuscany, Sinalunga & Wine Tasting in Montepulciano
Olli explores the cobblestone streets of Sinalunga, checks into Appartamento Le Poie, then drives to Montepulciano for a wine tasting at Podere Casanova. He doesn't drink wine — but he definitely judged the charcuterie.
Olli Storms Siena & Il Campo
Olli tackles Fontebranda, climbs Siena's steep medieval streets, reaches the spectacular Piazza del Campo, and is carried through the Museo Civico like a tiny visiting pope. Rainy cobblestones, ancient frescoes, and suspicious Vespas.
I Rate Everything. Seriously. Everything.
The Olli Pawp Rating System is the world's only travel rating system developed by a Boston Terrier. Each destination, dish, and dwelling is scored 1–5 Pawps. My standards are high. My opinions are final.
Appartamento Le Poie, Sinalunga
"Charming Tuscan apartment, excellent sniffing radius, and zero suspicious pillows. Olli approved from the first paw-step."
Podere Casanova, Montepulciano
"Outstanding charcuterie. The humans liked the wine. I liked the cheese. Five Pawps, no notes."
Siena & Piazza del Campo
"Magnificent medieval drama. The pasta at Il Campo was exceptional. Torre del Mangia gets a bonus Pawp."
Orte Centro & Bar Centrale
"Steep medieval streets, iron cinematography art, and my first Italian snack. Docked one Pawp for the parking machine confusion."
Take a Piece of Italy Home
Featuring Olli's face on things he definitely approved.
Set of 5 candy flavored lollipops — cherry, apple, strawberry, lemon and grape. Paw-shaped and Olli-approved.
Set of 6 adorable paw-shaped cake pops decorated with Olli's signature colors. Perfect for any occasion.
12 oz bag of paw-shaped all-natural dog biscuits. Made with wholesome ingredients your pup will go pazzo for.
Olli's Italy — Through the Lens
New episodes every weekDon't Miss a Single Sniff
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