Tour · Trafalgar Tours · 9 nights

Villages of Tuscany - Small Group

Expert Travel Director and professional Driver
All porterage and restaurant gratuities included
Visit the thermal baths of Saturnia

$6,615 pp twin share

9 nights

Enquire

Sunset over Pitigliano, Tuscany, Italy

Hilltop Villages of Tuscany Guided Tour Map 2027

Departs 4 April 2027 Returns 9 November 2027

Duration9 nights

OperatorTrafalgar Tours

StyleTour

HighlightDiscover the timeless charm of Tuscany's hill towns, vineyards, and medieval heritage on this small-group journey

Sip Vino Nobile in Montepulciano. Gaze across the stunning Val d'Orcia. Uncover Volterra's Etruscan past

Travel from Rome into the heart of Tuscany, where hill towns and sun-drenched vineyards hold centuries of tradition. You'll get to sip Vino Nobile in Montepulciano, gaze across the Val d'Orcia, wander Siena's bustling market and uncover Volterra's Etruscan past.

$6,615

pp twin share

Enquire

Refundable until 90 days before departure. No pressure.

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When & how much

Departures & Pricing

Departs

4 April 2027

Returns

9 November 2027

Duration

9 nights

From pp twin share

$6,615 pp

04 Apr 2027 - 13 Apr 2027
from $6,615 pp twin share *
18 Apr 2027 - 27 Apr 2027
from $7,350 pp twin share *
02 May 2027 - 11 May 2027
from $6,727.50 pp twin share *
16 May 2027 - 25 May 2027
from $7,475 pp twin share *
30 May 2027 - 08 Jun 2027
from $7,475 pp twin share *
13 Jun 2027 - 22 Jun 2027
from $7,475 pp twin share *
27 Jun 2027 - 06 Jul 2027
from $6,705 pp twin share *
11 Jul 2027 - 20 Jul 2027
from $7,450 pp twin share *
25 Jul 2027 - 03 Aug 2027
from $6,705 pp twin share *
08 Aug 2027 - 17 Aug 2027
from $7,450 pp twin share *
22 Aug 2027 - 31 Aug 2027
from $6,705 pp twin share *
05 Sep 2027 - 14 Sep 2027
from $7,475 pp twin share *
19 Sep 2027 - 28 Sep 2027
from $7,475 pp twin share *
03 Oct 2027 - 12 Oct 2027
from $7,475 pp twin share *
17 Oct 2027 - 26 Oct 2027
from $7,475 pp twin share *
31 Oct 2027 - 09 Nov 2027
from $7,295 pp twin share *

* Prices and category availability are subject to change without notice.

Cabin grades, balcony upgrades and pre-cruise hotel options are quoted on enquiry — call 1300 414 198.

Day by day

Itinerary

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.
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.
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 location. Then taste the pecorino cheese the town is known for before free time for lunch. Later, return to Cortona, where the evening is yours to relax before you head out with your small group for a dinner in town.
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.
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.
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.
7
South through Tuscany
Enjoy a morning a leisure in Volterra with time 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.
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.
9
Etruscan Legacies and Return to Rome
This morning make your way to the enchanting hilltop village of Capalbio, also known as "Little Athens". Visit Il Giardino dei Tarocchi, where large-scale sculptures by Niki de Saint Phalle bring colour and character to the Tuscan landscape. This evening, you’ll gather for dinner with your small group and raise a glass to your journey through Tuscany.
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.