Insight Vacations  ·  Country Roads of Tuscany & Central Italy  ·  10–18 May 2026
Piazza del Campo Siena with Torre del Mangia
Day 5 Thu 14 May Perugia · Siena · San Gimignano
Siena & San Gimignano
From the most beautiful medieval piazza in Italy to the world-champion gelato maker — this is one of those days where every stop feels like the best one yet.
Meals: ☕ Breakfast 🍽 Included Dinner ✓ Gelato Tasting Included ★ Insight Choice
Weather · Siena / San Gimignano · 14 May
25°C
Warm sunshine — perfect Tuscan spring day
High 25°  ·  Low 12°  ·  UV high — sunscreen advised  ·  Light breeze
‹ Day 4 · Assisi Day 6 · San Gimignano ›
⏰ Morning Departure — Important Times
06:45
Breakfast & Bags
Early breakfast at the Sangallo. Luggage outside your door — you check in to a new hotel tonight.
07:45
Coach Departs
Please be onboard and ready. We leave Perugia behind and head into Tuscany.
09:30
Arrive Siena
Walk to Piazza del Campo and meet your Local Expert for the included sightseeing.
🚌 Perugia → Siena → San Gimignano → Cappuccina Resort
Full Day Schedule
06:45
Breakfast
Breakfast & bags — Sangallo Palace Hotel
Early start. Bags outside your door before 07:45. This is the last morning in Perugia — you move to San Gimignano tonight.
07:45
Depart Perugia
The coach heads west across Umbria and into Tuscany — roughly 90 minutes of beautiful scenery with the crete senesi hills announcing Siena ahead.
09:30
Included
Arrive Siena — Piazza del Campo with Local Expert
Walk into one of the great public spaces in the world. Your Local Expert brings the piazza, the Palazzo Pubblico and the Torre del Mangia to life — and then presents you with a choice.
10:00
★ Insight Choice
Your Choice: Siena Cathedral OR Panforte Tasting
Two equally wonderful experiences — choose the one that speaks to you. See the Insight Choice card below for the full details of each option.
11:30
Free Time
Free time — lunch & shopping in Siena
Explore at your own pace. Siena's medieval centre is small enough to walk entirely in an hour or easily spend three. Try the local pici pasta, browse the ceramic shops on Via di Città, or simply sit in the Campo with a coffee.
13:30
Depart Siena for San Gimignano
A scenic hour north through the Chianti hills, past vineyards and cypress-lined roads, into the heart of Tuscany.
14:30
Included
Arrive San Gimignano — luggage to hotel
The driver takes your bags directly to the Cappuccina Resort. You're free to explore the medieval town immediately.
14:45
🍦 Included
Gelato tasting with Maestro Sergio Dondoli
The world champion gelato maker waits for you in his famous parlour on Piazza della Cisterna. This is not an optional. This is a life event. (Time to be confirmed with supplier.)
16:30
Depart San Gimignano
Short transfer to the Cappuccina Country Resort — just 1.5 km from the medieval towers.
17:00
Check In
Arrive Cappuccina Country Resort — check in
Your new home for the next few nights. Art Nouveau villa, pool with panoramic views of San Gimignano's towers, spa and gardens.
19:30
Included Dinner
Included dinner at the hotel
Your first dinner at the Ristorante La Cappuccina — Tuscan cuisine, local Vernaccia di San Gimignano wine, and the towers of the medieval city lit up in the distance.
Today's Highlight
Siena Cathedral Duomo with striped campanile
Insight Choice Option · UNESCO World Heritage
Siena Cathedral —
The Marble Masterpiece
Few buildings in Italy stop you in your tracks the way the Cattedrale di Santa Maria Assunta does. Its façade — an extraordinary riot of white, green and red marble inlay — is one of the most extravagant in the world, begun in 1215 and worked on by the greatest craftsmen of the age for nearly two centuries.

The interior is just as arresting. The floor alone took over 600 years to complete and consists of 56 inlaid marble panels depicting biblical scenes and allegories — a Renaissance artwork you walk on. Above, the black-and-white striped columns rise to a gilded ceiling of deep blue and gold stars.

The Piccolomini Library inside the cathedral shelters a complete cycle of 10 frescoes by Pinturicchio (1502–1508), painted in colours so vivid they look freshly done. Nicola Pisano's great pulpit (1265–68) is considered the first piece of true Renaissance sculpture — predating Giotto, predating Donatello, predating everything.

The unfinished nave to one side was meant to make this the largest cathedral in Christendom — abandoned when the Black Death halved Siena's population in 1348, leaving a haunting shell that stands as one of the most poignant monuments to lost ambition in Italy.
★ Insight Choice · Guided Visit Included
★ Your Insight Choice in Siena
Both experiences are included — choose the one that calls to you. Let Carmela know your preference on the coach.
Option A
⛪ Guided Visit — Siena Cathedral
A deep dive into one of Italy's greatest buildings — the marble inlay floor, Pinturicchio's frescoes, Nicola Pisano's pulpit and the story of the city that tried to build the biggest cathedral in the world.
Option B
🍎 Panforte Tasting with Carmela
Siena's famous spiced fruit cake has been made here since the 13th century. Carmela leads a tasting of different varieties — a delicious, deeply local experience and a wonderful way to understand Sienese food culture.
San Gimignano — Don't Miss This
🍦
Included · San Gimignano · Piazza della Cisterna
Gelato Tasting with Maestro Sergio Dondoli — World Champion
Sergio Dondoli has won the Gelato World Cup — the most prestigious competition in the industry — and his parlour on Piazza della Cisterna in San Gimignano is pilgrimed by gelato lovers from across the globe. His creations go far beyond the classics: think Crema di Santa Fina with saffron, or a champagne and grapefruit sorbet that stops people mid-sentence.

This is a fully included tasting experience — not a shop stop, a proper event. You'll taste alongside the maestro himself and understand why San Gimignano is considered the gelato capital of Italy.
✓ Fully Included · World Champion Gelato Maker
Tonight's Hotel — New Base for Tuscany
Cappuccina Country Resort San Gimignano
Nights 5–7 of 9  ·  3 Nights in San Gimignano
Cappuccina Country Resort & SPA
Loc. La Cappuccina 46/A, San Gimignano, Tuscany  ·  Pool · Spa · Panoramic Views
📍 Google Maps 🌐 Hotel Website
Live Exchange Rates
💶
Live Exchange Rates
Euro — Today's Rate
Italy uses the Euro (€). Enter any amount to see the equivalent in US, Canadian and Australian dollars.
€ EUR
🇺🇸
$54.50
US Dollar
🇨🇦
CA$74.50
Canadian Dollar
🇦🇺
A$83.50
Australian Dollar
Indicative rates · Check with your bank before spending
Language Helper
🗣️
Language Translator
English → Italian
A few words go a long way in Siena and San Gimignano. Try a phrase — the locals will always appreciate the effort.
🇬🇧 English 🇮🇹 Italian
Quick phrases
Hello! Best gelato ever! What a beautiful square! Thank you Where is the cathedral? A coffee please How much? Cheers!
‹ Day 4 · Assisi Day 6 · San Gimignano ›
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