Villages of Tuscany
Duomo di Orvieto, Umbria, Central Italy
10 Days | 12 Cities | Roundtrip Rome, Italy | Small Group Tour
Sun-drenched hillsides, medieval stone towers, and the rich aromas of local wine and pecorino cheese, Tuscany is a region that feels entirely frozen in time. While many only see its major hubs, the true heartbeat of this iconic region lies hidden away in its quiet, fortified hill towns and volcanic ridges.
Trafalgar’s Villages of Tuscany tour is a beautifully paced 10-day roundtrip itinerary from Rome designed to escape the crowded tourist tracks. What makes this trip truly seamless is Trafalgar's signature knack for unlocking local life, matching you with expert Travel Directors who handle all the transit and logistics behind the scenes while introducing you to the people who give this region its soul. From wandering through the dramatic, tufa-carved streets of Pitigliano to enjoying a home-hosted Be My Guest dinner at a local countryside agriturismo, every day is built around effortless, genuine connection.
What Your Journey Looks Like
Dine at a Countryside Agriturismo Settle in for an exclusive Be My Guest experience at a local Tuscan estate, where regional history, culture, and homemade wine come together over a traditional dinner
Explore Medieval Siena Discover Siena's historic districts with a Local Specialist, browse one of Tuscany's largest weekly markets, and gain exclusive entry into a traditional contrada museum
Taste Authentic Pecorino in Pienza Tour the UNESCO-listed Renaissance town of Pienza, learn about its Papal history, and sample the signature, sharp pecorino cheese the town is famous for
Walk the Tufa Lanes of Pitigliano Wander through "Little Jerusalem," a spectacular hill town carved directly into volcanic tufa rock, and explore its striking lanes, arches, and deep Jewish heritage
Your Itinerary
-
Step into the Eternal City for an evening orientation tour and a classic Italian welcome dinner.
Arrive in historic Rome, a capital shaped by centuries of ancient emperors and papal power. Meet your Travel Director and fellow travellers before heading out on an evening orientation tour of the city's legendary landmarks. Walk past the ruins of the Roman Forum and toss a coin into the spectacular Baroque waters of the Trevi Fountain. Afterward, gather with your small group for a welcome dinner to toast the start of your Italian adventure.
Guided Orientation of Rome's Ancient and Baroque Treasures
See the Historic Roman Forum and the Trevi Fountain
Welcome Dinner and Drinks with Your Small Group
Included Meals Dinner
-
Ride a funicular up to an Umbrian cliffside town before entering the iconic wine country of Tuscany.
Leave Rome and head north to Orvieto, where you will ride a funicular up to the volcanic-rock old town. Explore its labyrinth of medieval streets and admire the city's famous cathedral facade before enjoying a free lunch. In the afternoon, journey deep into Tuscany's vineyard-draped hills to the medieval town of Montepulciano. Take an orientation walk through the village with your Travel Director and cap off the day with a tasting of the region’s celebrated local wines.
Funicular Ride up to the Volcanic-Stone Hill Town of Orvieto
Leisure Time for Lunch and Independent Exploring in Orvieto
Orientation Walk of Hilltop Montepulciano with Your Travel Director
Premium Local Wine Tasting in the Heart of Tuscany
Included Meals Breakfast
-
Explore Renaissance architecture in Pienza and savor world-class pecorino cheese and local pici pasta.
Spend your day discovering two of southern Tuscany's most beloved hilltop gems. Start with an orientation in Montalcino, leaving you free time to sip a cappuccino while gazing over the panoramic Val d'Orcia. Next, move on to the UNESCO-listed Renaissance town of Pienza. Learn about its papal history, sample the sharp, local pecorino cheese the town is famous for, and enjoy a relaxed lunch. Return to Montepulciano for a free evening to relax or hunt down a local plate of pici all’aglione pasta.
Panoramic Views and Free Time in the Fortified Village of Montalcino
Guided History Walk of the UNESCO-Listed Renaissance Center of Pienza
Local Tasting of Pienza's Renowned Pecorino Cheese
Free Evening in Montepulciano to Try Regional Culinary Specialties
Included Meals Breakfast & Dinner
-
Browse a massive weekly market, taste local panforte, and dive into Siena's medieval historic districts.
Drive through the rolling Tuscan countryside to Siena, a stunning medieval city famed for its Gothic Duomo and shell-shaped main square. Time your arrival with the Mercato delle Merci, one of Tuscany's largest weekly markets, where you can browse stalls alongside the locals. Try a slice of traditional panforte (fruit and nut cake) before joining a Local Specialist to tour the city's historic districts and step inside an exclusive contrada (neighborhood) museum.
Morning Visit to the Bustling Mercato delle Merci Weekly Market
Sampling of Traditional Sienese Panforte Cake
Guided Tour of Siena's Piazza del Campo and Gothic Duomo with a Local Specialist
Exclusive Insider Visit to a Historic Sienese Contrada Museum
Included Meals Breakfast
-
Walk the medieval walls of Certaldo and enjoy an authentic Be My Guest dinner at a Tuscan estate.
Begin your morning in Certaldo, a hilltop town steeped in medieval history in the heart of the Val d'Elsa. Walk along its ancient defensive walls, look out across the Chianti hills, and enjoy a coffee in the main square. Continue to San Gimignano, a UNESCO World Heritage site legendary for its skyline of soaring medieval towers. In the evening, head into the countryside for a signature Trafalgar Be My Guest Experience at a local agriturismo (farm estate) for a home-cooked dinner, wine, and local storytelling.
Walk the Ancient Medieval Walls and Square of Certaldo
Explore the Tower-Filled Skyline of UNESCO-Listed San Gimignano
Be My Guest Experience: Traditional Dinner and Wine at a Local Tuscan Agriturismo
Included Meals Breakfast & Dinner
-
Uncover Etruscan mysteries, Roman ruins, and the ancient art of alabaster sculpting.
Travel to Volterra with your Travel Director to discover a spectacular hill town with deep Etruscan roots. Wander through the historic core to see the ancient Roman Theatre, the Cathedral, and the 13th-century Palazzo dei Priori, the oldest town hall in Tuscany. During your explorations, watch local artisans carry on a centuries-old tradition as they skillfully carve and sculpt native Volterra alabaster.
Guided Exploration of Volterra's Etruscan and Medieval Center
View the Ancient Roman Theatre and the Historic Palazzo dei Priori
Live Artisan Demonstration of Volterra's Ancient Alabaster Sculpting Craft
Included Meals Breakfast
-
Visit a roofless gothic abbey and explore a historic fortress city enclosed by Medici walls.
Enjoy a slow morning to shop, explore, or relax in Volterra at your own pace. In the afternoon, head south to the hauntingly beautiful Abbey of San Galgano, where the massive, roofless ruins of a 13th-century Gothic church stand solitary in the countryside. Continue into southern Tuscany to the walled city of Grosseto. Join your Travel Director for an orientation walk to admire the impressive star-shaped defensive walls built by the Medici family.
Free Morning for Independent Sightseeing in Volterra
Visit the Striking, Roofless Monastic Ruins of the Abbey of San Galgano
Orientation Tour of Grosseto's Historic Center and Star-Shaped Medici Walls
Included Meals Breakfast & Dinner
-
Witness cascading natural thermal pools and explore a striking town carved into volcanic rock.
Make a morning stop at the famous Cascate del Mulino in Saturnia, where steaming, mineral-rich thermal waters cascade down natural white limestone pools. Afterward, continue to Pitigliano, an extraordinary town dramatically carved straight out of a tufa volcanic rock cliffside. Known as "Little Jerusalem" due to its rich Jewish heritage dating back to the 16th century, you will walk through its ancient stone arches and narrow lanes before enjoying free time to explore independently.
View the Steaming Natural Limestone Pools of the Saturnia Thermal Baths
Guided Walk Through Pitigliano, the Cliffside Town Built on Volcanic Rock
Discover Pitigliano's Fascinating Jewish History and Architecture
Free Afternoon for Independent Exploration and Photography
Included Meals Breakfast
-
Walk through a vibrant, oversized mosaic sculpture garden before a grand farewell dinner in Rome.
Journey to the enchanting hilltop village of Capalbio, often called "Little Athens" for its artistic charm. Visit Il Giardino dei Tarocchi (The Tarot Garden), a dazzling outdoor art park where massive, colorful mosaic sculptures by artist Niki de Saint Phalle pop against the Tuscan landscape. In the afternoon, return to where it all began in Rome. Gather with your small group for a festive farewell dinner to celebrate your unforgettable journey through Tuscany.
Visit the Picturesque Hilltop Village of Capalbio
Admission to the Whimsical, Colorful Tarot Garden Mosaic Sculpture Park
Scenic Return Drive Through the Italian Countryside to Rome
Farewell Group Dinner to Celebrate Your Tuscany Journey
Included Meals Breakfast & Dinner
-
Bid a fond farewell to Italy as your small group vacation comes to an end.
Savour your final Italian breakfast at the hotel this morning. Say goodbye to your Travel Director and your newfound friends as your tour through Rome and Tuscany officially concludes.
Complimentary transfer from the hotel to Leonardo da Vinci airport
Included Meals Breakfast
-
An expert Travel Director and professional Driver
Cherry-picked hotels, all tried and trusted
All porterage and restaurant gratuities
Private air-conditioned vehicle
All hotel tips, charges and local taxes
Breakfast daily and up to half of your evening meals
Must-see sightseeing
Audio headsets for flexible sightseeing
Optional Experiences and free time
On occasion, hotels of similar standard and location may be utilised
Take advantage of the Early Booking offer*, and save 10% on selected small group tours when you book by 30 September 2026
From $8,006* per person, save $889
San Gimignano, Siena, Tuscany
Terms & Conditions *From price is based on the departure date 04 April 2027*Early Bird Offer Sale is only valid on new bookings made by 30 September 2026; not valid on existing bookings. Deposit is due at time of booking to lock in savings; full payment is due 120 days before departure or at time of booking if within 120 days. Prices are per person, land or river cruise only, based on double occupancy, are subject to availability, and Trafalgar reserves the right to withdraw or amend this offer at any time. Bookings made and confirmed before this offer is withdrawn or amended will be honoured at the price advised at the time of booking confirmation. Where reasonably practical, we will endeavour to provide advance notice of any withdrawal or material changes to this offer on our website. A minimum number of guests is required to operate departures. If guests change to another tour or date not on sale, they are responsible for paying the difference and adhering to different payment conditions; discounts are not transferrable.
Offer is combinable with 5% Global Tour Rewards loyalty discount available to eligible past guests only but cannot be combined with: any other promotional offer or discount code; Future Travel Credit carry-forward discounts or any other special offer, unless expressly stated otherwise. All bookings are subject to confirmation of availability following your booking request.
Interested in this experience? Mention this Deal Code: 1217 when speaking with your travel agent. Don't have an agent? Click here to connect with one of our experts.
