Villages of Tuscany – Small Group

SAVE up to $905 per person!

Travel from Rome into Tuscany on a small group journey through hilltop towns, vineyard-covered landscapes and historic cities rich in local character.

Along the way, enjoy Vino Nobile in Montepulciano, take in the beauty of the Val d’Orcia, browse Siena’s weekly market and uncover Volterra’s Etruscan and medieval heritage. You’ll also visit San Gimignano, Orvieto and Pitigliano, plus enjoy a Be My Guest countryside experience before returning to Rome.

Pricing

10 days

from

$8,005*

per person, twin share

Based on 4 Apr 2027 departure.

Highlights

• Explore Rome, Orvieto, Pienza, Siena, Volterra, Grosseto and Pitigliano. 
• See Roman Forum, Piazza del Campo and Duomo, Roman Theatre, and the Palazzo dei Priori. 
• Visit a Contrada museum in Siena, the hilltop village of Orvieto and a local weekly market in Siena.
• Discover winemaking traditions in Montepulciano, the town of Orvieto by funicular, the timeless art of carving alabaster, the local traditions of the Sienese during the Palio and the importance of pecorino cheese in Pienza.

What's Included

Your Small Group Tour with Trafalgar includes:

• 9 nights in handpicked hotels
• Daily breakfast; select dinners
• Private air-conditioned vehicle
• Expert Trafalgar Travel Director
• Be My Guest experience
• MAKE TRAVEL MATTER® experience
• Porterage at hotels

Day to Day Itinerary

Day 1: Welcome to Rome

Arrive in Rome, a capital built on the legacy of the ancient empire and the power of the papacy, then meet your Travel Director before heading out on an orientation. You’ll see the Roman Forum, where public life once unfolded in the heart of ancient Rome, and the Trevi Fountain, a Baroque landmark that shows a later chapter of the city at full scale. This evening, sit down to dinner with your fellow travellers as historic Rome sets the scene for the journey ahead. (D)

Day 2: Head into the Tuscan Countryside

Travel to Orvieto and ride the funicular up to its hilltop old town, where your Travel Director introduces you to this Umbrian city of volcanic stone, cathedral facades and streets built high above the valley below. Take time to explore at your own pace and find somewhere local for lunch. Continue through Tuscany’s wine region, a landscape shaped by vineyards and long-standing wine traditions, before arriving in Montepulciano for an orientation of the village with your Travel Director. Later, you’ll enjoy a tasting of local wines and discover the character of one of Italy’s best-known wine regions. (B)

Day 3: Views and Tastes of Tuscany

Spend the day in two of southern Tuscany’s best-known hilltop towns. In Montalcino, join your Travel Director for an orientation, then take time to explore and pause for a cappuccino with views over the Val d’Orcia. Continue to Pienza, the Renaissance town created under Pope Pius II, where your Travel Director introduces the layout and history of this UNESCO-listed centre. Then taste the pecorino cheese the town is known for before free time for lunch. Later, return to Montepulciano, where the evening is yours to relax or head out with your small group for a plate of pici all’aglione in town. (B,D)

Day 4: A Day in Siena

Drive through the Tuscan countryside to Siena, a medieval city best known for the shell-shaped Piazza del Campo and its Gothic Duomo. Spend time at the Mercato delle Merci, one of Tuscany’s biggest weekly markets, where locals come to shop for everything from food to everyday goods. Browse the stalls, step into Siena’s small stores and perhaps try panforte, the dense fruit and nut cake closely tied to the city. Later, join your Local Specialist to explore Siena’s historic districts, see the Piazza del Campo and Duomo, and visit a contrada museum. (B)

Day 5: Walls of Chianti and on to San Gimignano

Start in Certaldo, where your Travel Director introduces a hill town with strong medieval roots in the heart of Val d’Elsa. You’ll have time to walk the walls, look out across Chianti and perhaps settle into the square for a cappuccino before exploring the shops and museums. Continue to San Gimignano, the UNESCO-listed town that rose to prominence on the Via Francigena pilgrimage route and is still known for its skyline of medieval towers. Later, head into the Tuscan countryside for your Be My Guest experience at a local agriturismo, where wine, history and local culture come together. (B,D)

Day 6: Crafts of Volterra

Head to Volterra with your Travel Director to explore a hill town known for its Etruscan roots and medieval streets. In the historic centre, see the Roman Theatre, the Cathedral and the Palazzo dei Priori, the oldest town hall in Tuscany. You’ll also get to witness the ancient local tradition of alabaster sculpting, one of Volterra’s best-known crafts, and for which the town is still renowned today. (B)

Day 7: South through Tuscany

Enjoy a slow start in Volterra, with the morning free to explore more of the town at your own pace. Then head south to the Abbey of San Galgano, where the roofless church and monastic ruins make a striking stop in the Tuscan countryside. Continue to Grosseto, a walled city in southern Tuscany, for an orientation with your Travel Director. As you get your bearings, see the layout and landmarks of a historic centre shaped by Medici rule and still enclosed by its star-shaped walls. (B,D)

Day 8: Thermal Baths and Hilltowns of Tuscany

Stop at Cascate del Mulino, part of the thermal baths of Saturnia, where mineral-rich waters flow through the white limestone pools. Then continue to Pitigliano with your Travel Director and explore one of southern Tuscany’s most distinctive hill towns. Built into tufa rock and known as Little Jerusalem for its long Jewish history, Pitigliano stands out for both its setting and its story. As you walk through the town, take in its lanes, arches and views before time to look around further at your own pace. (B)

Day 9: Etruscan Legacies and Return to Rome

Visit Il Giardino dei Tarocchi, where large-scale sculptures by Niki de Saint Phalle bring colour and character to the Tuscan landscape. Then continue to Cerveteri with your Travel Director, one of the key cities of the ancient Etruscans and home to a necropolis that reveals how this civilisation buried its dead. This evening, you’ll gather for dinner with your small group and raise a glass to your journey through Tuscany. (B,D)

Day 10: Arrivederci Roma

Your journey through Tuscany comes to an end today as you say goodbye to your Travel Director and fellow travellers. Take with you the hilltop towns, local flavours and moments shared along the way. (B)

Terms and Conditions

Save 10% on select Small Groups as featured on Trafalgar.com as "Early Booking Offer". Valid on new bookings made between April 20, 2026 and September 30, 2026; not valid on existing bookings. Deposit is due at time of booking to lock in savings; full payment is due 120 days prior to departure or at time of booking if within 120 days. Prices are in NZD, are per person, land or river cruise only, based on double occupancy, are subject to availability and we reserve 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. Minimum number of guests are required to operate departures. If guests change to another tour, river cruise, small group or date not on sale, they are responsible to pay the difference and adhere 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. The availability shown on our website is indicative only and may not reflect real-time capacity. In some instances, departures which have recently become fully booked may continue to display as available for a brief period. All bookings are subject to confirmation of availability following your booking request. Other conditions apply. We reserve to correct any errors, inaccuracies or omissions and to change or update information at any time without prior notice. Professional service fees apply.