Places you'll visit
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Tailor-made Tuscany trip
Turn a dream of Italy into a tailor-made reality with this Tuscany trip that curates authentic moments just for you. Choose private wine tastings, hands-on pasta classes, and quiet hilltop views guided by locals who reveal hidden corners.
Act now to shape an itinerary that reflects your tastes, pace, and passions. Book a consultation, request custom dates, and secure small group or private options designed around your desires. Let this Italy trip be crafted, personal, and unforgettable. Start your custom planning today and step into Tuscany with intention and joy.
Tuscany trip highlights
- Curated Chianti wine experiences: Savor private tastings at family-run wineries, guided to your tastes.
- Bespoke truffle hunts and cooking: Join local truffle hunters, then craft personalized meals with a chef.
- Hidden medieval villages: Wander charming hilltop towns off the tourist trail with private guides.
- Luxury farmstay immersions: Stay at family-run agriturismos where hosts personalize activities.
- Tailored cultural and scenic routes: Custom drives through vineyard lanes and panoramic viewpoints.
| Day | Location | Activity | Overnight |
|---|---|---|---|
| 1 | Montepulciano (Tuscany) | • Arrival in Rome and transfer to your hotel in Tuscany • Free afternoon in Montepulciano | Montepulciano |
| 2 | Montepulciano | • Private Montepulciano tour • Authentic Tuscan lunch with wine | Montepulciano |
| 3 | Siena / San Gimignano / Chianti | • Private tour of Siena, San Gimignano and the Chianti countryside • Winery lunch with wine tasting • Explore San Gimignano’s towers and artisan shops | Montepulciano |
| 4 | Florence | • Private transfer to Florence • Guided Florence walk • Accademia Gallery visit (David) | Florence |
| 5 | Florence | • Pasta and gelato cooking class in Florence • Free time for exploration | Florence |
| 6 | Florence | • Florence Duomo tour with exclusive terrace access • Relaxed evening in the city | Florence |
| 7 | Florence → Rome | • Transfer to the train station for your journey to Rome • Departure from Rome | — |
Day01
Arrival in Italy
Arrive in Rome, where your private driver will welcome you and transfer you to your hotel in Tuscany, where you will begin your Italy travel.
Enjoy a free afternoon in Montepulciano to relax, wander medieval streets, visit a local enoteca, and taste regional wines for a true sense of place.
Day02
Montepulciano wine experience
Stroll Montepulciano's streets on a private, tailor-made tour and savor panoramic views and historic charm. Visit boutique wine cellars producing world-class reds, including Nobile di Montepulciano (DOCG).
Finish with a lunch of authentic Tuscan cuisine paired with local wines in a spectacular underground cellar. This Tuscan itinerary element enriches your experience with intimate local insight and exclusive tastings.
Tips from Martina
Italy
Travel Expert
Ask to taste a Vino Nobile di Montepulciano Riserva. It's usually tucked behind the counter, but worth the ask; locals know it’s the bottle they keep for special dinners.
Day03
Private tour around Siena, San Gimignano and Chianti
A private English-speaking driver will tailor this day to your interests, starting in Siena to wander its medieval streets, soak in art and history, and admire the Piazza del Campo.
Enjoy a leisurely lunch at a Chianti Classico winery with local wine tasting and vineyard views, an indulgent pause that echoes the flavors typically highlighted on a Tuscany food tour, while still keeping the day entirely your own.
Then end in San Gimignano exploring its towered skyline, artisan shops, and gelato spots for a truly authentic Italian experience.
Day04
Florence guided tour and Accademia Gallery
Begin with a private transfer to Florence. In the afternoon, enjoy a guided walk through Florence from Roman origins to the present, visiting Piazza della Signoria, the Duomo, and Ponte Vecchio.
Skip the line at the Accademia to admire Michelangelo's David and his unfinished works with an expert English-speaking guide who brings Italy's art and stories to life.
Day05
Pasta and gelato cooking class in Florence
Join a hands-on pasta and gelato cooking class in Florence. A skilled chef guides you through kneading, shaping, and churning so you master classic techniques and regional flavors.
At the end, receive a recipe book and a certificate to celebrate your new skills and take home a delicious memory from your Tuscany tour.
Day06
Florence Duomo tour
Skip the lines on a guided visit to Santa Maria del Fiore in Florence. Climb Brunelleschi’s dome for breathtaking panoramic views and a tailor-made, authentic Tuscany trip experience.
Explore normally restricted terraces, study Paolo Uccello’s intricate clock and Vasari’s frescoes, and enjoy behind-the-scenes access to the cathedral complex for an intimate, expert-led cultural journey.
Day07
Private transfer and departure
Relish a relaxed final morning, savoring local coffee and leisurely strolls through village lanes curated to your tastes. A private transfer will take you to the train station for your comfortable ride to Rome.
On arrival, you will be met and taken to Rome’s airport, ensuring a seamless end to your Tuscany trip. Leave with beautiful memories and the confidence that every detail was crafted for a smooth, stress-free farewell.
