(Photos from this trip are located here)
I think we can now officially say this trip has become a permanent fixture on our travel calendar! May 2025 marked the fourth year in a row that we’ve offered this tour—and this time, we ran it back-to-back with two amazing groups. Each week had its own personality, and both were filled with laughter, camaraderie, and that unmistakable Tuscan magic. Next year will be our 5th consecutive year returning to this beloved itinerary—proof that it really has become a tradition!
The itinerary has stayed consistent each year (with a little flexibility, of course!) because it works so well. It’s a week packed with incredible food and wine, breathtaking scenery, historic towns, and those “bucket list” sites many people have only read about or seen in movies until now. Best of all, we spend the whole week based at a beautiful villa just outside of Lucca. Unpacking just once, being able to do a little laundry midweek, and returning “home” each evening to our own pool, gardens, and even a personal chef—this format has become a true favorite.
Here’s how the week unfolded:
Day 1 – Benvenuti in Italia!
We kicked things off with warm Italian welcomes, aperitivi by the pool, and that magical feeling of settling into our gorgeous villa just outside Lucca.
Day 2 – Pisa & Lucca
This first full day always eases us in beautifully. Pisa gave us just enough time for the classic Leaning Tower photos, while Lucca welcomed us with cobblestone charm, a private tour, and some time to shop or wander before gathering for a wonderful dinner at a local favorite.
Day 3 – Siena
With its stunning shell-shaped piazza and medieval streets, Siena was a standout. Our private guide made the history come alive—especially the stories behind the Palio horse race. This evening, we were spoiled by our villa chef with a home-cooked feast. ✨ Side note: I have to give huge credit to the group from our first Tuscany week for their incredible positivity (and sense of humor!) during our drive back to the villa this day. When our vehicle’s flat tire unexpectedly went rolling across the highway, everyone kept their cool—and even turned the situation into a bit of comedy, joking and charming the police team that came to help. Thankfully, no one was hurt, the bus was sorted, and we still made it back in time for a fabulous dinner prepared by our chef. What a story to add to the memories!
Day 4 – Cinque Terre Adventure
Whether hiking the famous Blue Path from Monterosso to Vernazza or exploring the villages by train, Cinque Terre gave us jaw-dropping coastal views and plenty of reasons to linger over an aperitivo afterwards.
Day 5 – Cooking Class & San Gimignano
A highlight every year! We rolled up our sleeves for a hands-on Tuscan cooking class, rewarded ourselves with the fruits of our labor (and generous wine pairings), then headed off to explore the towers and alleyways of San Gimignano.
Day 6 – Florence
Always a favorite. Our private walking tour led us through Florence’s iconic sites, including skip-the-line entry to see Michelangelo’s David. The rest of the day was free for gelato, shopping, or simply wandering the Renaissance streets. Florence never disappoints!
Day 7 – Chianti
We saved something special for the finale: tour and tasting at a family-run olive estate (with incredible views), a farm specializing in balsamic vinegar (paired with regional specialties and wines), and a private estate for a last round of tastings. It was Tuscany at its most authentic—and the perfect way to toast to the week.
Day 8 – Departure
Saying goodbye is never easy, but everyone left with new friends, great memories, and full hearts (and full suitcases, too!).
✨ This trip has become a tradition—so much so that next year will mark our 5th year in a row! The 2026 edition is already fully booked, but we’re excited to announce that we’re now taking reservations for 2027. If Tuscany has been calling your name, don’t wait—spaces always go quickly.
Once again, both weeks were an absolute joy, and it’s clear why this trip has become such a tradition. A heartfelt grazie mille to everyone who joined us this year—you’ve officially become part of our growing Tuscany travel family! Tuscany, we’ll be seeing you again soon!
Please make sure to check out some of the images from this trip in the website photo gallery!