Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
4.91,049 reviews9h
from €190
Check availabilityBudget · 7 Days
€490
Mid-range · 7 Days
€1,169
Best months
April to June
Hotel per night (mid-range)
€110
With 7 days in Siena, you'll have time to experience the city's highlights. Beyond the Campo, Siena's Gothic soul is carved in marble and brick. The breathtaking Duomo, with its zebra-striped bell tower and intricate facade by Giovanni Pisano, houses treasures like Nicola Pisano's pulpit and the inlaid marble floor—a masterpiece only fully unveiled for a few weeks each year.
Perfect for art lovers
Perfect for history buffs
Perfect for wine enthusiasts
Day-by-Day Itinerary
Day 1: Arrival & First Impressions
Start your Siena adventure by getting your bearings and exploring the city's most iconic landmarks. Take time to soak in the atmosphere and discover why this destination captures the hearts of millions.
1
Piazza del Campo
Experience Piazza del Campo, one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
2
Siena Cathedral (Duomo)
Experience Siena Cathedral (Duomo), one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
Day 2: Local Life & Neighborhoods
Experience Siena like a local today. Wander through authentic neighborhoods, discover hidden cafes, and get a taste of everyday life in Italy.
1
Torre del Mangia
Experience Torre del Mangia, one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
2
Palio Horse Race
Experience Palio Horse Race, one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
Day 3: Art, History & Discovery
Uncover layers of history that shaped Siena. From ancient remains to modern marvels, today reveals the stories behind the city's evolution.
1
Pinacoteca Nazionale
Experience Pinacoteca Nazionale, one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
2
Chianti Wine Tours
Experience Chianti Wine Tours, one of Siena's beloved attractions that offers a unique glimpse into Italy's culture and heritage.
⏱️ 1.5-2 hours
💡 Tip: Check opening hours online and consider booking in advance during peak season.
Day 4: Explore Terzo di Città
Trade the big landmarks for a neighborhood day in Terzo di Città, one of the best areas to see everyday life in Siena.
1
Terzo di Città
The historic civic and religious center, home to the Piazza del Campo and the Duomo. This is Siena's most monumental and tourist-frequented district, buzzing with energy and architectural grandeur.
⏱️ Half day
💡 Tip: Don't miss: Piazza del Campo, Palazzo Pubblico & Torre del Mangia, Siena Cathedral (Duomo) & Baptistery.
2
Orto de' Pecci
A peaceful, walled public garden and small farm just below the city walls, near Fontebranda.
⏱️ 1-2 hours
💡 Tip: It's a secret green oasis with vegetable plots, farm animals, and a lovely café—a world away from the tourist bustle just minutes from the center.
Day 5: Day Trip to San Gimignano
Leave Siena behind for a day and head to San Gimignano (40 min by bus or car).
1
San Gimignano
The 'Medieval Manhattan' famous for its 14 surviving stone tower houses. A beautifully preserved hill town offering stunning views, Vernaccia white wine, and a step back in time.
⏱️ Full day
💡 Tip: Highlights: Piazza della Cisterna, Climb the Torre Grossa, Sample Vernaccia di San Gimignano, See the frescoes in the Collegiata.
Day 6: Day Trip to Montepulciano
Leave Siena behind for a day and head to Montepulciano (1 hour by bus or car).
1
Montepulciano
A majestic Renaissance hill town renowned for its noble Vino Nobile red wine. Explore its steep main street lined with elegant palaces and wine cellars carved into the cliffs.
⏱️ Full day
💡 Tip: Highlights: Piazza Grande, Wine tasting in cantinas like Cantina Contucci, Tempio di San Biagio (church below town), Views over the Val di Chiana.
Day 7: Terzo di San Martino & Hidden Gems
Spend your last day away from the main sights: slow down in Terzo di San Martino and seek out a few places most visitors to Siena never find.
1
Terzo di San Martino
A quieter, more residential area stretching south from the Campo. Characterized by steep, narrow streets, local markets, and a strong connection to Saint Catherine, Siena's patron saint.
⏱️ Half day
💡 Tip: Don't miss: Basilica of San Domenico (housing St. Catherine's head), Santuario e Casa di Santa Caterina, Fontebranda medieval fountain.
2
Bottini di Siena
The city's ancient, 25km-long network of underground aqueducts dating from the 12th century.
⏱️ 1-2 hours
💡 Tip: Guided tours (bookable through the museum Santa Maria della Scala) offer a unique, subterranean perspective on the medieval engineering that sustained the city.
3
Chiesa di San Pietro alla Magione
A small, austere Romanesque church on the Via Francigena pilgrimage route, now a Knights Templar site.
⏱️ 1-2 hours
💡 Tip: It's one of Siena's oldest buildings, with a stark, powerful atmosphere and fascinating history, yet often overlooked by visitors.
Top tours and experiences in Siena
The tours and tickets travellers book most, with ratings and reviews from Viator.
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
4.8365 reviews4h
from €130
Check availabilityAll things to do in Siena →
Tours and prices from Viator, a Tripadvisor company. Prices change with your dates. We may earn a commission if you book, at no extra cost to you.
Why Visit Siena
Experience the Palio's Raw Passion: Witness the Palio horse race on July 2nd or August 16th, where the city's 17 *contrade* compete in a bareback, no-rules sprint around the Campo. The real drama unfolds in the days prior with flag-waving parades, historic rivalries, and intense neighborhood pride.
Marvel at Gothic Architectural Mastery: Explore the Siena Cathedral (Duomo), a stunning symphony of black and white marble. Don't miss the Piccolomini Library's vibrant frescoes, the intricate marble mosaic floor, and the panoramic views from the 'Facciatone' of the unfinished 'Duomo Nuovo'.
Get Lost in a Perfectly Preserved Medieval Labyrinth: Wander the 'Terzo di Città', 'Terzo di San Martino', and 'Terzo di Camollia' districts. Each has its own character, from the artisan shops near Via di Città to the quieter, residential feel of the Fontebranda area near Saint Catherine's house.
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How much do 7 days in Siena cost?
Plan on roughly €490 on a budget, €1,169 mid-range or €2,170 for a comfortable trip, per person and excluding travel to Siena.
| Budget | Mid-range | Comfort | |
|---|---|---|---|
| Accommodation (per night) | €45 | €110 | €190 |
| Food and drinks (per day) | €17 | €35 | €70 |
| Sightseeing and activities (per day) | €8 | €22 | €50 |
| Total per day | €70 | €167 | €310 |
| Total for 7 days | €490 | €1,169 | €2,170 |
Estimates exclude flights and long-distance transport. Compare daily costs across cities
Where to stay in Siena
Hotels close to the centre of Siena, from budget to luxury. Prices are typical nightly rates at our last check.
Budget
Mid-range
UpscaleHotel prices come from Traveloka, last checked on February 4, 2026, and change with your dates. We may earn a commission if you book through our links, at no extra cost to you.
Travel Tips
- 1Book accommodation in the city center for easy access to attractions. Siena is best explored by combining walking with public transport.
- 2The best time to visit Siena is April to June, September to October. Shoulder seasons offer fewer crowds and pleasant weather.
- 3The local currency is Euro (€). Cards are widely accepted.
- 4A few words in Italian go a long way with locals. Even "please" and "thank you" will earn smiles.
- 5Download offline maps and translation apps before your trip. WiFi can be spotty in historic areas.
- 6With 7 days, consider a day trip outside Siena to experience more of Italy.
Must-Try Food in Siena
Pici all'aglione (hand-rolled pasta with tomato-garlic sauce)
Ribollita (Tuscan bread & vegetable soup)
Cinta Senese (heritage breed pork, often as chops or salami)
Panforte (dense fruit and nut spice cake)
💡 Dine where the locals do: avoid restaurants with menus pictorially displayed on the Campo. Head a few streets away to places like Osteria Le Logge or Trattoria La Torre for better quality and value.
Neighborhoods to Explore in Siena
Terzo di Camollia
The northern commercial district, historically the gateway for pilgrims on the Via Francigena.
Contrada dell'Oca (The Goose District)
Not an official administrative area, but experiencing Siena through its *contrade* is key.
Day Trip Ideas
With 7 days in Siena, you have time for a memorable day trip. Here are some great options nearby:
Crete Senesi & Abbey of Monte Oliveto Maggiore
45 min by car
Journey into the surreal, clay-colored 'Sienese Crete' hills, a landscape of rolling biancane formations, cypress trees, and isolated farmhouses, culminating at a stunning Benedictine abbey.
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