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 4-day road trip through Firenze, Siena, and Roma 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 4-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, and Roma by public transport, renting a car in Italy opens up a whole new level of freedom!

So, with 4 days to spend, all you need is a rental car, some hotel reservations, and this iconic road trip itinerary:

Day 1: Arrive in Rome

• Arrival city: Roma
• Accommodation: hotel in Rome, e.g., The RomeHello
• Sightseeing: Trevi Fountain

Begin your road trip adventure by picking up your rental car at the airport upon arrival in Rome. 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 Firenze and Roma

• Destinations: Firenze and Roma
• Driving distance: 281.19 km, approx. 3 hours and 59 minutes
• Accommodation: 4-star hotel in Florence, e.g., 25hours Hotel Piazza San Paolino
• Sightseeing: Roman Forum, Obelisco del Pantheon, Accademia Gallery, Piazza della Signoria, and Colosseum
• Recommended tour: Best Tour in Florence, Italy: Renaissance & Medici tales with a storyteller

Set out on a day of discovery and visit Roman Forum, Obelisco del Pantheon, Accademia Gallery, Piazza della Signoria, and Colosseum. Take time to enjoy the scenery and local highlights of Firenze and Roma, 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 Florence.

Day 3: Discover Firenze and Siena

• Destinations: Firenze and Siena
• Driving distance: 320.69 km, approx. 4 hours and 15 minutes
• Accommodation: hotel in Rome, e.g., The RomeHello
• Sightseeing: Piazza del Campo, Pubblico Palace, Basilica of Santa Croce in Florence, Duomo di Siena, and Ponte Vecchio
• Recommended tour: Skip the Line: Colosseum, Roman Forum & Palatine Hill Guided Tour

Spend the day exploring Piazza del Campo, Pubblico Palace, Basilica of Santa Croce in Florence, Duomo di Siena, and Ponte Vecchio. 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: Bid Farewell to Rome

• Departure city: Roma
• Driving distance: 12.13 km, approx. 33 minutes
• Sightseeing: Spanish Steps

Savor an hour or two for souvenir shopping or revisiting a favorite spot before it’s time to say goodbye to Rome. 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 342 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 5-day city break in Siena with the perfect itinerary, designed to showcase the city’s top sights, local flavors, and hidden corners.

With a long list of top-rated attractions in Siena and Siena's widest selection of tours and activities at your fingertips, it's easy to plan a travel itinerary filled with unforgettable moments and discoveries.

No need to stress over the details – we’ve curated the perfect 5-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 Porta Romana.

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 Piazza del Campo, Basilica Cateriniana San Domenico, Pubblico Palace, Tower of Mangia, 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 4: Explore the Local Flavors of Siena

Start the day with breakfast at a local cafe before you head out to explore. Musei dell’Accademia dei Fisiocritici and Porta Tufi are attractions you could discover today.

Afterward, enjoy lunch or visit a local market. Spend the afternoon shopping for unique souvenirs to memorialize your city break in Siena.

For a fun and interesting evening, check out the food and drink tours in Siena. Take the opportunity to sample local specialties and learn more about the food culture of Italy!

Day 5: 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 Piazza del Campo early to avoid crowds and enjoy the views.
• Afternoon: Continue to Pubblico Palace, stopping by Basilica Cateriniana San Domenico 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!