10 Day Itinerary: Tuscany and Italian Riviera


“You may have the world if I may have Italy” — Giuseppe Verdi


There are so many beautiful places to visit in Italy that I'm convinced you could return year after year and never tire of it. No matter where you go, you're in for a treat. On our most recent trip to Italy we dedicated most of our time to exploring central Italy, specifically the Tuscany Region. While Tuscany is home to the iconic capital city of Florence, it's the region's smaller and lesser-known hill-top towns and villages that I think are even more special. This is where you'll find the quintessential experience of Italian culture, history, and slow-living.

We also tacked on three extra days to explore the Italian Riviera which borders Tuscany in the northwestern region of Liguria. It's a short 2.5 hour drive away and was such a special way to round out our trip. We stayed in Portovenere which is a lesser-known stunning seaside town located just south of the famous Cinque Terre. Here we got the opportunity to experience some stunning coastal views and enjoy a less-crowded home base for exploring Cinque Terre.

We flew in and out of the Florence airport and had a private driver reserved for the entirety of our trip. We shared our planned itinerary ahead of time and our driver picked us up each day and got us from place to place as a group. This gave us the ability to customize our own itinerary and gave us the flexibility to pivot along the way if we wanted. This is a must, especially if you're staying somewhere more privately tucked away in the countryside (like most of the Villas in the region).

Below is the ten-day travel itinerary we followed. So much time and energy (and love) was put into planning this trip and we came up with just the right mix of iconic sites, immersive experiences, and time to appreciate the Italian's slower way of living. Here she is:

Day 1 - Free day Villa il Colto in Arezzo, Tuscany (side note: very thankful we had this free day to recharge after some major travel woes getting to the Florence airport).

Day 2 - Day trip to San Gimignano and lunch/wine tasting at Tenuto Torciano Winery

Day 3 - Half-day trip to Montalcino and Pienza

Day 4 - Half-day trip to Siena and Cooking Lesson at Villa

Day 5 - Day trip to Florence

Day 6 - Free day at Villa

Day 7 - Half-day trip to Lucca, then to Grand Hotel Portovenere

Day 8 - Full-day private boat ride and tour of Cinque Terre with a stop for swimming and in Vernazza for lunch and exploring

Day 9 - Hike and explore the the villages of Cinque Terre

Day 10 - Free morning in Portovenere before return trip home

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