Top 3 Itineraries in Siena

No matter how long you plan to stay, there’s a perfect trip to Siena.

If you only have a few days, Siena weekend getaways are the perfect option. A 3 to 5-day stay in Siena offers just enough time to soak in the highlights

For a balanced mix of sightseeing and relaxation, city breaks in Siena are ideal. With a few extra days, you can dive deeper into Siena’s most iconic landmarks, stroll through charming neighborhoods, and savor local cuisine at a leisurely pace.

For those who crave freedom and discovery, road trips through Siena offer the perfect opportunity to explore beyond the city. With the open road ahead, you’ll uncover Italy's most scenic landscapes, visit charming towns, and discover hidden gems along the way.

Explore all the best trips for every travel style below and make your next trip to Siena truly unforgettable!

If you’re as convinced as we are that Siena belongs on your bucket list, you're in luck. The best trips to Siena are just a quick search away.

Enter your dates below to discover the best travel packages in Siena and start planning your next trip!

Discover the perfect Siena itinerary with our handpicked list. Whether you're in Siena for a short stay or a longer visit, there's an itinerary for you.

With detailed routes, top attractions, and insider tips, these 3 itineraries will help you experience the best of Siena without missing a thing. Dive into our list and learn how to plan the ultimate trip to Siena!

A scenic 10-day road trip through Firenze, Siena, Rimini, Roma, and Bologna is one of the best ways to experience Italy. With the freedom to travel at your own pace, you’ll have plenty of opportunities to make spontaneous stops between the planned activities on your itinerary.

A 10-day itinerary means that Siena can easily be combined with other top destinations in Italy without stress. While it’s possible to travel between Firenze, Siena, Rimini, Roma, and Bologna by public transport, renting a car in Italy opens up a whole new level of freedom!

So, with 10 days to spend, all you need is a rental car, some hotel reservations, and this iconic road trip itinerary:

Day 1: Arrive in Rimini

• Arrival city: Rimini
• Accommodation: 4-star hotel in Rimini, e.g., Yes Hotel Touring
• Sightseeing: Piazza Cavour

Begin your road trip adventure by picking up your rental car at the airport upon arrival in Rimini. Drive to your centrally located hotel, which offers convenient access to local attractions. Spend the day exploring nearby sights, and in the evening, enjoy dinner at a local restaurant, sampling regional flavors and soaking up the atmosphere.

Day 2: Explore Rimini

• Destinations: Rimini
• Driving distance: 184.31 km, approx. 2 hours and 46 minutes
• Accommodation: 3-star hotel in Perugia, e.g., Etruscan Chocohotel
• Sightseeing: Fountain of the four horses, La Ruota Panoramica, Spiaggia libera, Parco Federico Fellini, and Malatestiano Temple
• Recommended tour: Organic cooking class with a sommelier in an Olive and wine farm

Set out on a day of discovery and visit Fountain of the four horses, La Ruota Panoramica, Spiaggia libera, Parco Federico Fellini, and Malatestiano Temple. Take time to enjoy the scenery and local highlights of Rimini, with the freedom to stop at whatever sight catches your interest. By the end of the day, check-in at a new hotel, located in central Perugia.

Day 3: Discover Civitas Vaticana - Città del Vaticano

• Destinations: Civitas Vaticana - Città del Vaticano
• Driving distance: 184.84 km, approx. 3 hours and 53 seconds
• Accommodation: hotel in Rome, e.g., The RomeHello
• Sightseeing: Sistine Chapel, Vatican Museums, St. Peter's Basilica, and Saint Peter's Square
• Recommended tour: Jewish Ghetto and Trastevere Tour in Rome

Spend the day exploring Sistine Chapel, Vatican Museums, St. Peter's Basilica, and Saint Peter's Square. Take scenic drives or walking tours to experience the area’s charm at your own pace. End the day by checking into a new hotel, conveniently located in central Rome.

Day 4: Experience Roma

• Destinations: Roma
• Driving distance: 7.77 km, approx. 59 minutes
• Accommodation: hotel in Rome, e.g., The RomeHello
• Sightseeing: Castel Sant'Angelo, Roman Forum, Campo de' Fiori, Piazza Navona, and Colosseum
• Recommended tour: Skip the Line: Colosseum, Roman Forum & Palatine Hill Guided Tour

Continue your journey through Roma, where you can explore Castel Sant'Angelo, Roman Forum, Campo de' Fiori, Piazza Navona, and Colosseum. Make time for a break at a cozy café or scenic picnic spot.

Day 5: Enjoy Sightseeing in Roma

• Destinations: Roma
• Driving distance: 9.25 km, approx. 1 hour and 8 seconds
• Accommodation: hotel in Rome, e.g., The RomeHello
• Sightseeing: Trevi Fountain, Basilica Papale di Santa Maria Maggiore, Piazza di Spagna, Spanish Steps, and Villa Borghese
• Recommended tour: Vatican Museums, Sistine Chapel, and St Peter’s Basilica Guided Tour from Rome

Drive through Roma, stopping to visit Trevi Fountain, Basilica Papale di Santa Maria Maggiore, Piazza di Spagna, Spanish Steps, and Villa Borghese. Don't forget to embrace the opportunity to explore smaller towns and hidden gems along the way.

Day 6: Embrace the Spirit of Roma

• Destinations: Roma
• Driving distance: 241.82 km, approx. 3 hours and 31 minutes
• Accommodation: hotel in Siena, e.g., Il Giardino di Pantaneto
• Sightseeing: Altar of the Fatherland, Piazza del Popolo, Largo di Torre Argentina, Pantheon, and Circus Maximus
• Recommended tour: Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Spend time discovering Altar of the Fatherland, Piazza del Popolo, Largo di Torre Argentina, Pantheon, and Circus Maximus, with plenty of opportunities to engage in outdoor activities or enjoy local culture. After a day of exploring, check into a hotel in Siena.

Day 7: Spend Time in Siena and Pisa

• Destinations: Siena and Pisa
• Driving distance: 216.1 km, approx. 3 hours and 30 minutes
• Accommodation: 4-star hotel in Florence, e.g., 25hours Hotel Piazza San Paolino
• Sightseeing: Piazza del Campo, Piazza del Duomo, Duomo di Siena, Leaning Tower of Pisa, and Camposanto
• Recommended tour: Walking Tour through Florence: Renaissance and Medici Tales

Explore Piazza del Campo, Piazza del Duomo, Duomo di Siena, Leaning Tower of Pisa, and Camposanto at a relaxed pace. Make spontaneous stops for sightseeing, photography, or lunch at a family-run restaurant. Finish the day by checking into another comfortable hotel in the center of Florence.

Day 8: Explore Firenze

• Destinations: Firenze
• Driving distance: 4.98 km, approx. 1 hour and 10 minutes
• Accommodation: 4-star hotel in Florence, e.g., 25hours Hotel Piazza San Paolino
• Sightseeing: Uffizi Gallery, Basilica of Santa Croce in Florence, Piazza della Signoria, Piazzale Michelangelo, and Ponte Vecchio
• Recommended tour: Best Tour in Florence, Italy: Renaissance & Medici tales with a storyteller

Continue your road trip through Firenze, enjoying the flexibility to explore Uffizi Gallery, Basilica of Santa Croce in Florence, Piazza della Signoria, Piazzale Michelangelo, and Ponte Vecchio and nearby points of interest.

Day 9: Wander Through Firenze and Bologna

• Destinations: Firenze and Bologna
• Driving distance: 224.22 km, approx. 3 hours and 22 minutes
• Accommodation: 4-star hotel in Rimini, e.g., Yes Hotel Touring
• Sightseeing: Cathedral of Santa Maria del Fiore, Two Towers, Central Market, Piazza Maggiore, and David of Michelangelo

Visit Cathedral of Santa Maria del Fiore, Two Towers, Central Market, Piazza Maggiore, and David of Michelangelo as you navigate scenic routes. Take time to enjoy local markets, trails, or viewpoints that catch your eye. At the end of the day, check-in at a comfortable hotel in central Rimini.

Day 10: Bid Farewell to Rimini

• Departure city: Rimini
• Driving distance: 690 metres, approx. 9 minutes
• Sightseeing: Arco di Augusto

Savor an hour or two for souvenir shopping or revisiting a favorite spot before it’s time to say goodbye to Rimini. Drop off your rental car at the airport a couple of hours before departure for a seamless end to your trip.

The estimated cost for a rental car and accommodations for each night along this route is around 1251 EUR, providing a value-for-money way to experience what's beyond Siena.

Looking for something different? Explore more road trips with a stop in Siena for alternative itineraries, routes, and durations.

Enjoy a 3-day city break in Siena with the perfect itinerary, designed to showcase the city’s top sights, local flavors, and hidden corners.

No need to stress over the details – we’ve curated the perfect 3-day itinerary to give you a seamless outline for your trip. Use this itinerary to capture the best of Siena without the hassle of planning.

Day 1: Begin Your Journey in Siena

Arrive in Siena and start your trip with a relaxing walk through town, discovering highlights like Fortezza Medicea.

Take in the local charm as you wander the streets, and as evening approaches, indulge in a delicious dinner at a local restaurant. Enoteca I Terzi is a top-rated recommendation. Say 'cheers' and set the tone for an amazing vacation ahead!

Day 2: Discover Siena's Most Iconic Attractions

Enjoy your first full day in Siena by heading out for some must-see sightseeing. Explore around town and visit popular attractions like the iconic Porta Camollia, Piazza del Campo, Basilica Cateriniana San Domenico, Palazzo Salimbeni, and Duomo di Siena.

One of the best ways to quickly learn how to navigate the city is to join one of the many great city sightseeing tours in Siena. Choose a walking tour to embrace a relaxed exploration. Alternatively, go for a tour by bus or bike to cover a larger part of Siena in the same amount of time.

In the evening, head out for another lovely dinner and raise a glass to a fantastic day of exploring!

Day 3: Savor Your Final Moments in Siena

Spend your last few hours in Siena soaking up the charm of the city at your own pace. Stroll through favorite spots or revisit local markets before bidding farewell to the city.

We recommend booking your transfers from Siena in advance.

For more inspiration, explore the complete selection of city breaks in Siena, all including pre-planned itineraries you can customize to suit your style. Start with a ready-to-go Siena travel plan and make it your own by selecting tours, accommodations, and more.

A 3-day weekend getaway in Siena offers the perfect break from the hustle of daily life.

However, with a well-planned Siena itinerary, you can effortlessly experience the best of the city in just a few days. Picture yourself exploring iconic landmarks, savoring local cuisine, and wandering charming neighborhoods—it's all within reach as long as you know how to plan your trip properly.

With 3 days to spend, this is the perfect Siena weekend itinerary for your trip:

Day 1 - Arrive in Siena

Arrive in Siena around noon and head to your hotel for an early check-in.

• Morning: Take some time to relax and refresh after your journey, or get a head start by visiting a nearby landmark.
• Afternoon: Ease into your trip with some sightseeing, for example, visiting Fortezza Medicea, and soak in the surroundings.
• Evening: Dine at a popular restaurant and celebrate the start of the vacation with some drinks.

Day 2 - Discover Siena’s Famous Sights

Maximize your first full day in Siena with sightseeing, food, and drinks.

• Morning: Visit Porta Camollia early to avoid crowds and enjoy the views.
• Afternoon: Continue to Basilica Cateriniana San Domenico, stopping by Piazza del Campo for a break and some photos.
• Evening: Dine at a popular restaurant and cap off the day at a local bar.
• Tip: Use part of the morning to join one of the many city sightseeing tours in Siena and get a guided journey through the top attractions in the city.

Day 3 - Depart from Siena

Make the most of your last few hours in Siena before your departure.

• Morning: Grab a light breakfast at a local bakery or café and take a final stroll nearby.
• Afternoon: If you have time, do some last-minute sightseeing.

For more ideas, explore our complete selection of weekend trips to Siena. Whether you’re looking for a quick getaway or want to extend the weekend, these trips all come with pre-planned but customizable Siena itineraries, ensuring an effortless travel experience.

As you explore Siena, you’ll find countless layers of history, art, and local charm waiting to be uncovered.

Finding the right place to stay is essential for a comfortable trip. This is why we've also gathered our top recommendations for the best places to stay in Siena for you.

Wherever your journey takes you, we’re here to make every step memorable. From expert tips to local insights, count on us to help you experience Siena in a way that feels truly unforgettable!