Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
4.91,049 reviews9h
from €190
Check availabilityBudget · 5 Days
€350
Mid-range · 5 Days
€835
Best months
April to June
Hotel per night (mid-range)
€110
With 5 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: Day Trip to Crete Senesi & Abbey of Monte Oliveto Maggiore
Leave Siena behind for a day and head to Crete Senesi & Abbey of Monte Oliveto Maggiore (45 min by car).
1
Crete Senesi & Abbey of Monte Oliveto Maggiore
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.
⏱️ Full day
💡 Tip: Highlights: Photograph the iconic 'crete' landscape near Asciano, Visit the Abbey of Monte Oliveto Maggiore's frescoed cloisters, Taste pecorino cheese from local farms, Stop at the medieval village of Buonconvento.
Day 5: Terzo di Camollia & Hidden Gems
Spend your last day away from the main sights: slow down in Terzo di Camollia and seek out a few places most visitors to Siena never find.
1
Terzo di Camollia
The northern commercial district, historically the gateway for pilgrims on the Via Francigena. It's less polished, with vibrant street life, eclectic shops, and a more modern, lived-in feel.
⏱️ Half day
💡 Tip: Don't miss: Porta Camollia (northern city gate), Fortezza Medicea (public park with wine bar), Bargello Museum of Medieval Arms.
2
Museo delle Tavolette di Biccherna
A tiny museum in the State Archives displaying painted wooden book covers from the city's medieval tax office.
⏱️ 1-2 hours
💡 Tip: These exquisite miniature artworks offer a vivid, colorful snapshot of Sienese life, politics, and history across centuries, seen by very few tourists.
3
Fonte del Pescaia
A picturesque, 13th-century Gothic fountain located in a quiet park just outside the Porta Pispini gate.
⏱️ 1-2 hours
💡 Tip: It's a beautifully preserved example of a medieval public fountain, set in a tranquil spot perfect for a picnic, away from all crowds.
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
4.8366 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
Discover World-Class Art Beyond the Crowds: The Pinacoteca Nazionale houses the definitive collection of Sienese School paintings by masters like Duccio, Simone Martini, and the Lorenzetti brothers, offering a serene alternative to Florence's crowded Uffizi.
Stand Atop the Torre del Mangia: Climb the 400 steps of the 102-meter-tall Torre del Mangia in the Palazzo Pubblico for a breathtaking, 360-degree view over the terracotta rooftops and the rolling Tuscan countryside beyond the city walls.
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.
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How much do 5 days in Siena cost?
Plan on roughly €350 on a budget, €835 mid-range or €1,550 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 5 days | €350 | €835 | €1,550 |
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.
- 65 days gives you time to see the highlights and discover some hidden gems.
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 Città
The historic civic and religious center, home to the Piazza del Campo and the Duomo.
Terzo di San Martino
A quieter, more residential area stretching south from the Campo.
Contrada dell'Oca (The Goose District)
Not an official administrative area, but experiencing Siena through its *contrade* is key.
Day Trip Ideas
With 5 days in Siena, you have time for a memorable day trip. Here are some great options nearby:
San Gimignano
40 min by bus or car
The 'Medieval Manhattan' famous for its 14 surviving stone tower houses.
Montepulciano
1 hour by bus or car
A majestic Renaissance hill town renowned for its noble Vino Nobile red wine.
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