4 days, 3 nights · Best for wine lovers and culinary travelers seeking Tuscany's countryside
A Taste of Tuscany Tour | Vacation Packages for 2025, 2026
Experience Monteriggioni, Siena and Chianti as you savor Tuscan wines, cook local cuisine and explore medieval towns in Italy’s countryside.
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
medieval walls and Chianti cellars near Siena
From your base in a walled village ten kilometers north of Siena, you explore the greatest hits of central Tuscany without changing hotels. We arrange private cellar visits in the Chianti Classico zone, where Sangiovese ages in Slavonian oak and cypress trees mark estate roads. A hands-on cooking class in a countryside villa teaches pici, ribollita and cantucci, followed by lunch at the farmhouse table with the wines you opened. Siena's Gothic center and San Gimignano's tower skyline are each half an hour away.
Monteriggioni itself is a perfect circle of fourteenth-century walls with fourteen towers, a single piazza, and none of the tour-bus crowds that fill larger hill towns by midmorning. You walk the ramparts at dusk, dine on wild boar ragu in trattorias older than the Medici, and sleep in converted stone farmhouses where the only sound is the olive harvest in October.
Arranged for you: Three nights in Monteriggioni, welcome dinner, Chianti winery visit and tasting, cooking class with lunch, daily breakfast.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Monteriggioni
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Private truffle hunt with lunch Day Trips · Half day
Walk forest trails with a trained dog and hunter, then cook your finds over pasta at the farmhouse.
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Guided Palio della Balzana archery Day Trips · Half day
Learn crossbow technique from a contrada member in Monteriggioni's annual medieval tournament tradition.
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Private Siena Cathedral complex tour Day Trips · Half day
Historian-led visit to the Duomo floor panels, Piccolomini Library frescoes and rooftop terrace.
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Vernaccia vertical tasting in San Gimignano Day Trips · Half day
Taste five vintages of the white DOCG with the winemaker at a tower-view enoteca.
Day by day in Monteriggioni
Arrive at your hotel in Monteriggioni, a charming medieval village set in the heart of the Tuscan countryside just a few kilometers from Siena. After check-in, enjoy a welcome drink and some time to unwind, taking in the rolling hills, vineyards, and olive groves that define this iconic region. In the evening, savor a welcome dinner at a traditional restaurant in Siena or nearby Monteriggioni, where you can taste authentic Tuscan dishes paired with local wines. Overnight at your hotel in Monteriggioni.
After breakfast, we recommend starting your day with an excursion into the famous Chianti region, known worldwide for its vineyards, cypress-lined roads, and hilltop villages. Stop at one of the most renowned Chianti Classico wineries for a guided visit of the cellars and a tasting of their signature wines. In the afternoon, head to Siena to explore its UNESCO-listed historic center. Wander through narrow medieval streets, admire the magnificent Piazza del Campo, home of the Palio horse race, and take in the city’s Gothic architecture and vibrant atmosphere. Enjoy dinner on your own at a local trattoria before returning to your hotel in Monteriggioni for the night.
Begin your day with breakfast, then immerse yourself in Tuscan cuisine with a hands-on cooking class in a local villa. Under the guidance of an expert cook, you’ll prepare a complete Tuscan menu using fresh regional ingredients, then sit down to enjoy your creations for lunch, perfectly paired with local wines. In the afternoon, we suggest visiting San Gimignano, a splendid medieval town renowned for its skyline of ancient towers, well-preserved walls, and cobbled streets. Explore the historic center, browse artisan shops, and enjoy gelato or a glass of Vernaccia di San Gimignano while taking in the views. Return to Monteriggioni in the evening; dinner is on your own and you’ll spend the night at your hotel.
Stop 2Montalcino, Tuscany
Montalcino
Brunello cellars and Sant'Antimo in Val d'Orcia
Your final day crosses the Val d'Orcia, the UNESCO-protected valley where every view looks like a Renaissance painting: lone cypress on hilltops, white gravel roads through wheat fields, stone farmhouses framed by morning fog. In Montalcino we arrange a private cellar visit and tasting at a Brunello producer, where Sangiovese Grosso ages five years before release and the estate cellars date to the sixteenth century. You learn the difference between Rosso di Montalcino and its big brother, taste from barrel and bottle, and walk vineyard rows where the clones are older than Napa.
Afterward you climb to Montalcino's fortress for views across the valley, then drive four kilometers south to Sant'Antimo Abbey. The Romanesque church, founded by Charlemagne according to legend, sits alone in an olive grove where Gregorian chant still echoes at vespers. Your Tuscany trip concludes here among the stone columns and afternoon light, though we can arrange onward travel to Rome, Florence or the coast.
Arranged for you: Brunello winery visit and tasting, Sant'Antimo Abbey visit.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Montalcino
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Pecorino tasting at a Val d'Orcia dairy Day Trips · Half day
Visit a sheep farm producing Pecorino di Pienza, taste five ages and watch the cheesemaker at work.
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Pienza and Bagno Vignoni walking tour Day Trips · Half day
Explore the Renaissance ideal city and thermal pool square with a local guide.
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Private hot-air balloon over Val d'Orcia Day Trips · Half day
Dawn flight across UNESCO landscapes with Prosecco toast and farm breakfast on landing.
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Private Tour Excursion to the Heart of Brunello of Montalcino Guided Tours and Sightseeing · Tour in a Day
Experience the ultimate Brunello wine adventure with a private driving tour through the heart of Tuscany’s celebrated wine country.
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The Brunello Wine & Montalcino Small Group Tour from S.Gimignano Food and Wine · Tour in a DaySavor the world-class Brunello wines as you visit renowned wineries in Montalcino, enjoying exclusive tastings and learning about the region’s rich winemaking traditions.
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The Brunello Wine & Montalcino Small Group Tour from Siena Food and Wine · Tour in a DaySip your way through Montalcino, where rolling vineyards and centuries of craft create the legendary Brunello di Montalcino.
Day by day in Montalcino
After breakfast, check out and drive through the iconic Val d’Orcia, a UNESCO World Heritage landscape of rolling hills, vineyards, and cypress trees, to reach Montalcino, home of the world-famous Brunello di Montalcino wine. Enjoy a guided visit and tasting in a historic Brunello cellar, learning about the production and characteristics of this prestigious red wine. Afterwards, we suggest exploring Montalcino’s historic center and fortress, then continuing to the nearby Sant’Antimo Abbey, a peaceful Romanesque church set amid olive groves and vineyards. Your journey through Tuscany concludes here, with the end of our services.
Day 4
Departure
A private transfer to the airport. We stay on the line until you are home.
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.
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Questions travelers ask
Where will we travel on this itinerary?
Over 4 days this journey brings you to Chianti Wine Region, Montalcino, Monteriggioni, San Gimignano, and Siena. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. 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.