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3 Days in Siena – A Tuscan Dream Itinerary

I chose Italy for my honeymoon. There’s nowhere quite like it. Just like my other careful curated guides, this 3 days in Siena itinerary gives you a plethora of choices, letting you carve out your own Tuscan tale. If you are short on time, consider a panoramic balloon ride over the Tuscan countryside, catching the rolling hills and terracotta roofs of Siena from a bird’s eye view.

Ensure you’ve got all the necessary travel documents for Italy, and be prepared for the whimsical Tuscan weather, which can range from sun-kissed to a gentle drizzle.

This journey through Siena involves a fair bit of wandering on cobbled streets, striking a harmonious chord between open-air escapades, majestic lookout points, historical wonders, and gastronomic delights. Depending on the season, you might want to rejig a few recommendations to align the radiant sunsets with my culinary tips.

Getting Around Siena

Navigating through Siena can be both an adventure and a breeze, given its pedestrian-friendly zones and efficient public transportation.

On foot – The historic centre of Siena is a UNESCO World Heritage Site, and much of it is pedestrian-only. Walking is perhaps the best way to absorb the ambiance, admire the architecture, and stumble upon hidden gems. The city’s compact size makes most attractions accessible within a comfortable walk.

Public Buses – Siena’s bus system is efficient and covers the city and its outskirts comprehensively. Tickets can be purchased from kiosks or onboard. Remember to validate your ticket once on the bus!

Bicycle – If you are feeling a bit adventurous and want to explore the city at your own pace, renting a bicycle can be an enjoyable option. The local topography, with its occasional hills, provides both challenge and charm for cyclists.

Car – While having a car is advantageous for day trips outside Siena, it is worth noting that the city centre has limited traffic zones (ZTL) where only residents and authorised vehicles can enter. Parking can also be a bit difficult, so it is often advised to park outside the centre and walk or take public transport in.

Where to Stay in Siena

Siena offers a range of neighbourhoods that cater to mixed traveller tastes. Your experience can greatly vary depending on where you choose to base yourself. Here is a breakdown of the best areas to stay in, according to what you are seeking:

Historic Centre – Perfect for history buffs and first-time visitors, the historic heart of Siena is brimming with iconic landmarks like the Siena Cathedral and Piazza del Campo. Staying here, you will be within walking distance of the major attractions and will feel the city’s pulse.

San Prospero – Located just north of the historic centre, San Prospero is a tranquil region that is ideal for those wanting a quiet retreat, yet still being in proximity to the main attractions.

Santa Maria – A blend of modernity and history, Santa Maria is known for its green spaces and relaxed vibe. It is an excellent choice for families and those looking for a balanced experience.

Fontebranda – A tad more residential, Fontebranda offers a peek into the daily life of Siena residents. With local markets and cafes, it is a charming choice for long-term visitors.

Style of stay

Of course, you may decide to stay in the outskirts of Siena and the idyllic countryside encompassing the mediaeval city. When it comes to accommodation, again abundance characterises your options, which include:

Luxury Villas – For those who cherish privacy, space, and a touch of opulence, luxury villas are a matchless choice. Overlooking picturesque landscapes, these mansions offer a blend of Tuscan aesthetics and traditional architecture with top-notch amenities. Plus, you may even find even more specific types of villas, such as luxurious farmhouses and agriturismo properties for a truly 360-degree Tuscan experience. Some exceptional picks are Villa Campo al Doccio, Podere san Gerolamo, Villa Volterra, Casale la Casa, and Villa Collalto.

Boutique Hotels – Scattered throughout the city, boutique hotels offer a personalised experience. Infused with local culture, they often come with themed rooms and bespoke services. NH Siena Hotel, Grand Hotel Continental Siena, and Four Points by Sheraton Siena are some top ones to consider. 

Bed & Breakfasts – A great way to experience Sienese hospitality, B&Bs are intimate and homey. They are ideal for travellers seeking a cosy ambiance. B&B Il Corso, Il giardino di Pantaneto Residenza D’Epoca, and B&B Governo dei Nove will steal your heart for sure. 

Hostels & Guesthouses – For budget travellers and backpackers, Siena’s hostels and guesthouses provide a sociable stay without breaking the bank. Hostel Ciompi and Il Giardino di Pantaneto are both  fab options. 

3 Days in Siena

Day 1: Heart of the Medieval City

Morning:

Start your day bright and early at Piazza del Campo. Feel the city’s pulse as you stroll through one of Europe’s greatest mediaeval squares. Notably, the twice-a-year horse race, Palio di Siena, takes place here.

Ready for some awe-inspiring views? Hike up the Torre del Mangia. Every step is worth it as you are greeted with panoramic views of the city and the Tuscan countryside.

Take a moment to visit Chiesa di San Cristoforo. This small but significant church holds centuries of history within its walls.

Late morning:

Dive into Siena’s art scene with a visit to Complesso Museale Santa Maria della Scala. Once a hospital, this massive complex is now home to some of the city’s most treasures artworks and historical pieces.

Afternoon:

Amble around the maze-like streets, and you might just find yourself at Via di Citta, a street buzzing with life, local boutiques, and delightful trattorias.

For a touch of spiritual wonder, the Siena Cathedral (Duomo di Siena) beckons. Marvel at its intricate floors, the Piccolomini library, and its stunning facade. Don’t miss the pulpit by Nicola Pisano – a masterpiece of mediaeval sculpture.

Sunset:

For a peaceful transition from day to evening, head to the Orto Botanico. Among its diverse collection of plants and trees, find a spot to relax and reflect on your day as the Tuscan sun bids goodbye.

Dinner:

As dusk settles, it is time for some mouth-watering Tuscan cuisine. Head to Osteria La Piazza and let each bite introduce you to Tuscan’s rich culinary heritage. Pair it with a local Chianti wine for the complete experience.

After sunset:

Conclude your day with a serene stroll through Via Banchi di Sopra. As the city lights sparkle, this street comes alive, making it the perfect endnote for your first day in Siena. Day one done and dusted!

Day 2: Discovering the Hidden Gems of Siena

Breakfast:

Begin your day with a traditional Tuscan breakfast at Pasticceria Nannini and delight in pastries like Ricciarelli, a soft almond cookie, or Cavalluci, spiced cookies with walnuts and candied fruits. Pair it with a rich cappuccino or espresso for that perfect morning kick.

Morning:

Begin with the splendour of the Basilica of San Domenico. Known locally as Basilica Cateriniana, it is dedicated to Saint Catherine of Siena. The simplicity of its exterior contrasts beautifully with its art-rich interior.

Dive deeper into the local history by exploring Siena’s Jewish Quarter. Though smaller than other Jewish quarters in Italy, the remnants of its history provide a fascinating insight into the city’s diverse past.

Late Morning:

Head over to the Palazzo Salimbeni. This Gothic urban palace houses the headquarters of Monte dei Paschi di Siena, one of the oldest banks in the world. The surrounding square is a great spot for some candid photography.

Afternoon:

Time for a serene escape at the Medicean Fortress. With its vast green spaces, it is the ideal location for a picnic lunch. Grab some Pecorino cheese, Tuscan salami, olives, and a bottle of local wine and savour them with the breathtaking views around.

A visit to the Santa Maria del Servi should follow next. This lesser-known church offers a peaceful atmosphere and houses some striking pieces of Renaissance art.

Sunset:

Make your way to Monte del Paschi’s rooftop bar. It is a local secret, offering the best views of Siena’s skyline. As the golden hues of the setting sun kiss the mediaeval towers, sip on a glass of Prosecco and immerse yourself in the moment.

Dinner:

Experience a rustic Tuscan dinner at Trattoria Fonte Giusta. The cosy ambiance and hearty dishes, like Pappa al Pomodoro and Osso Buco, promise an unforgettable meal. Don’t forget to try their Tiramisu for dessert – it is a game changer!

After Dinner:

As night falls, dive into Siena’s vibrant arts scene. Catch a live performance at Teatro dei Rinnovati, housed inside the Palazzo Pubblico. Whether it is opera, drama, or a classical concert, the artistic spirit of Siena is bound to captivate you. And, thus, Day 2 wraps up, Until tomorrow, buona notte!

Day 3: Exploring Beyond the City Walls

Morning Delight:

Antica Pasticceria Bini is where you will want to be. This historic pastry shop has been serving the finest Tuscan treats for generations. Opt for a plate of Cantucci, a local almond biscuit, dipped in Vin Santo, a sweet dessert wine. This combo is a Tuscan morning staple you can’t miss.

Mid-Morning Stroll:

Wander to the picturesque Orto de’ Pecci, a mediaeval garden that provides a tranquil start to your day. The garden’s panoramic views of Siena are worth every step, plus the on-site restaurant serves as an ideal pit-stop for a refreshing drink.

Lunchtime Feast:

Trattoria La Torre beckons for an early lunch. Located near the iconic Torre del Mangia, this eatery serves classic Tuscan dishes. Try the Ribollita, a thick soup made from bread and vegetables, or the Tagliatelle al Tartufo, pasta with truffle – local favourites that embody the soul of Sienese cuisine.

Afternoon Adventure:

Post-lunch, head to Eremo di Santa Caterina, a quiet hermitage nestled on the hills overlooking Siena. The journey here, either on foot or a short taxi or car ride, is filled with picturesque landscapes. Once there, you will be greeted with silence, interrupted only by chirping birds and the rustling leaves.

Sunset Experience:

Venture to Forte di Santa Barbara, an underrated gem. This ancient fort, though partly in ruins, provides an unparalleled view of the sun setting over the terracotta roofs of Siena. As you soak in the atmosphere, it is a moment of pure Tuscan magic.

Dinner in the Countryside:

Take a brief excursion out of the city to Agriturismo Il Caggio, a rustic farmhouse offering authentic farm-to-table Tuscan meals. Surrounded by vineyards and olive groves, indulge in a hearty dining venture. The house-made Pici pasta and Chianina beef steaks are legendary.

Starry Night:

conclude your evening with a trip to the Siena Observatory, located just outside the city. Here, you can gaze at the stars through telescopes, capturing the vastness of the universe while reflecting on your adventures in this mediaeval wonder.

Wrapping Up Your Sienese Sojourn

Three days might seem fleeting, but in a city like Siena, every moment is steeped in rich history, spellbinding landscapes, and a culinary scene that celebrates the soul of Tuscany. You have ambled through mediaeval streets, basked in the golden Tuscan sun, savoured mouth-watering dishes, and connected with a past that still resonated vibrantly in every corner of the city. However, some love affairs, especially those enchanting Tuscan towns, are destined to be rekindled. Until next time, arrivederci!