7 days, 6 nights · Best for Wine lovers seeking Tuscany's great estates and medieval hill towns
Independent Tuscany wine tour
Explore Tuscany’s medieval towns, iconic castles, and celebrated wine estates. Enjoy tastings, cooking classes, and authentic local flavors on a guided journey through Italy’s heartland.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Monteriggioni, Tuscany
Monteriggioni
Your fortified village base for the wine roads
We base you in Monteriggioni, the thirteenth-century fortress village whose fourteen towers rise above the vineyards between Siena and the Chianti hills. Your hotel sits within the walls or just outside, a short drive from Siena's Campo, the towers of San Gimignano, and the estates that make Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano. Each morning you set out with a driver for tastings at family cellars and castle vineyards, returning to a village you can walk end to end in five minutes.
We arrange full-day guided visits to two Brunello estates in Montalcino, a tasting with the owners of a Vernaccia property in San Gimignano, and a stop at a Chianti Classico castle where you tour the cantina and Renaissance halls. A cooking class at a nearby villa teaches you pici, ribollita and cantucci, and a walking tour of Montepulciano includes the oldest cellar in town, its vaults carved into Etruscan tufa.
Arranged for you: Six nights accommodation, daily breakfast, private driver for estate visits and town tours, half-day guided tour of Siena with Enoteca Italiana visit, San Gimignano Vernaccia estate tasting with owners, Chianti Classico castle tour and tasting, full-day visits to two Brunello di Montalcino cellars, hands-on cooking class at Tuscan villa with lunch, Montepulciano walking tour and Renaissance cellar visit.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Monteriggioni
-
Private truffle hunt in the Crete Senesi Day Trips · Half day
Walk the clay hills south of Siena with a hunter and his dog, then taste the morning's white truffles shaved over tagliatelle at a farmhouse table.
-
Hot air balloon flight over the Chianti vineyards Day Trips · Half day
Lift off at dawn from a castle estate, drift over the rows and oak forests for an hour, then land for a Prosecco breakfast in the vines.
-
Vespa tour of the Chianti back roads Day Trips · Full day
Ride a vintage Vespa (or ride pillion with a guide) through the hills, stopping at a family cantina and a hilltop pieve before lunch in Greve.
-
Ceramic painting workshop in a Siena studio Day Trips · Half day
Learn the techniques of Sienese majolica from a local artisan, then decorate your own plate or tile to take home.
Day by day in Monteriggioni
Arrive in the enchanting medieval village of Monteriggioni and check in to your hotel, perfectly situated for exploring the heart of Tuscany. Embark on a scenic drive to the historic city of Siena, renowned for its stunning medieval architecture and vibrant piazzas. Enjoy a half-day guided sightseeing tour of Siena, uncovering its rich history, iconic landmarks, and charming local shops. Take time at leisure to indulge in authentic Tuscan cuisine and boutique shopping.
In the afternoon, experience a unique visit to the prestigious Enoteca Italiana, one of Italy’s most celebrated wine cellars, nestled within the Renaissance ramparts of the Medici Fortress. Discover a remarkable collection of over 600 D.O.C. and D.O.C.G. Italian wines, representing more than 2,000 brands from every wine-producing region in Italy. Participate in an exclusive wine seminar led by a professional sommelier, featuring tastings of four distinguished Tuscan wines.
Conclude your first day in Tuscany with a memorable welcome dinner in a medieval restaurant in Siena, savoring local flavors in an atmospheric setting. Return to Monteriggioni for a restful overnight stay, ready to continue your Tuscan adventure.
Start your day with a delicious breakfast at the hotel before departing for the captivating medieval town of San Gimignano, renowned for its iconic stone towers and picturesque hilltop views. Enjoy time to explore San Gimignano at your own pace, discovering its charming streets, artisan shops, and historic landmarks.
Later, immerse yourself in Tuscany’s wine culture with a visit to a renowned local estate specializing in the celebrated Vernaccia di San Gimignano D.O.C.G. white wine. Experience a guided wine tasting session led by the estate owners, paired with authentic local delicacies for a true taste of the region. Savor a light tasting lunch surrounded by the scenic beauty of the Tuscan countryside.
In the afternoon, consider a visit to the nearby ancient town of Volterra, famous for its Etruscan heritage and artisan craftsmanship. Return to your hotel in Monteriggioni in the late afternoon. Enjoy dinner at your leisure and unwind with an overnight stay, ready for another day of Tuscan discovery.
Begin your day with a hearty breakfast before setting out on a scenic drive through the world-famous Chianti region, one of the most beautiful and iconic areas in Tuscany. Travel along the renowned “Road of Chianti Castles,” with the option to visit the historic Brolio Castle, a symbol of Tuscan heritage and winemaking tradition.
Experience an exclusive stop at a charming castle estate, celebrated for producing the prestigious D.O.C.G. Chianti Classico red wine. Enjoy a guided tour of the castle’s impressive interiors and ancient wine cellars, followed by a curated wine tasting led by the estate owner.
After lunch at your leisure, spend a relaxing afternoon exploring the picturesque medieval hamlet of Radda in Chianti, often regarded as the heart of the Chianti Classico region. Wander the cobblestone streets, soak in the authentic Tuscan atmosphere, and discover local boutiques and cafes.
Return to Monteriggioni in the late afternoon. Enjoy dinner on your own and a restful overnight stay at your hotel, surrounded by the timeless beauty of Tuscany.
Embark on an unforgettable journey into the world of Brunello di Montalcino, one of Tuscany’s most celebrated red wines. Today’s tour includes exclusive visits to two of the region’s most prestigious wine cellars, where expert winemakers will guide you through the fascinating process of crafting Brunello wine. Enjoy guided tastings and gain insider knowledge about the unique terroir and winemaking traditions that make Brunello di Montalcino world-renowned.
Take time for lunch at your leisure, then explore the enchanting medieval village of Montalcino, famous for its picturesque streets and vibrant local culture. Continue your discovery with a visit to the historic Abbey of Sant’Antimo, a remarkable Romanesque monastery founded, according to legend, by Charlemagne in 781.
Return to your hotel in Monteriggioni in the evening. Enjoy dinner on your own and relax with an overnight stay, reflecting on your immersive Tuscan wine experience.
Start your day with a light breakfast at the hotel before heading to a picturesque Tuscan villa for an immersive cooking class. Enjoy a hands-on culinary experience as you learn traditional Italian recipes from a local chef, using fresh, regional ingredients. Participate in every step of the cooking process, gaining valuable insights into authentic Tuscan cuisine.
After the class, savor a delicious lunch featuring the dishes you’ve prepared, surrounded by the charm of the Tuscan countryside. Spend the rest of the afternoon at your leisure, relaxing, exploring local shops, or simply soaking in the serene atmosphere.
Return to Monteriggioni in the evening. Enjoy dinner on your own and unwind with a comfortable overnight stay, enriched by your new culinary skills and unforgettable memories.
Discover the Renaissance charm of Montepulciano, often hailed as the “pearl of the Renaissance” and renowned for its world-class Vino Nobile di Montepulciano red wine. Begin your day with a visit to one of Italy’s oldest wine cellars, located in the heart of Montepulciano. Marvel at the Renaissance arches and explore The Etruscan burial chambers carved from the ancient tufa rock beneath the cellar.
Continue your journey with a guided walking tour of Montepulciano’s town center, taking in its elegant palaces, historic squares, and local culture. Next, transfer to a prestigious wine estate, where you’ll enjoy a memorable tasting-lunch in the atmospheric cellars, sampling exceptional Vino Nobile alongside regional specialties.
In the afternoon, take time at leisure to explore the nearby town of Pienza, celebrated for its countryside views and charming Renaissance architecture. Return to Monteriggioni in the evening. Dinner on your own and overnight stay, savoring the flavors and beauty of Tuscany.
Day 7
Monteriggioni
After breakfast, check out from the hotel, marking the end of our services and your unforgettable journey through Umbria. Safe travels and arrivederci!
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
Ready to make it yours?
Send us this adventure with your changes. An Italian-born planner builds the first full draft and calls you to walk through it.
Or call 1-866-464-8259
Questions travelers ask
How will we get around during the vacation?
Transportation is arranged as part of the itinerary, with vehicle and train transfers as the itinerary requires. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
What kind of traveler is this package for?
It suits travelers who want Italy arranged by experts, with guided experiences balanced by free time to explore on your own.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.