Day Trips from Rome to Siena

If you’re short on time but want to make the most of your visit to Italy, experience the famous Tuscan countryside with this full-day tour from Rome. Travel by air-conditioned minivan to a landscape of rolling hills, olive groves and vineyards, stopping to stroll through the UNESCO-listed hilltop village of San Gimignano. Visit a winery in the famed Chianti region for a tour and tasting with appetizers, and explore the well-preserved medieval city of Siena, home to the popular Il Palio horse race.

Escape the bustle of Rome for the day with this private driving tour through Tuscany. Take in Chianti’s rolling vineyards during the drive and visit the medieval towns of Siena and San Gimignano. Enjoy free time to admire Siena’s Piazza del Campo and Duomo before continuing on to a winery to taste some local wine and have lunch (included in the price). End your day with a stroll through the UNESCO-listed old town of San Gimignano.

Get medieval on this action-packed semi-private day trip from Rome to the gorgeous Tuscan towns of Siena and San Gimignano, strolling the streets of the two UNESCO world heritage-listed towns, sipping local wine and learning all about the history of the places.

Take advantage of your travel time between Rome and Florence to explore the Tuscan countryside with this combined private transfer and tour. Set off with your dedicated driver on a customized itinerary that can include stops to visit San Gimignano or Siena, a tasting lunch in a Chianti winery, or a scenic drive through the most picturesque corner of the rolling countryside.

Explore the culture and cuisine of Tuscany without the hassle of coordinating public transportation or renting a car with this all-inclusive day trip from Rome. Set off directly from your Rome hotel and take in the Tuscan scenery and you head to Monteriggioni, where you have free time for a stroll in the walled town. Visit a local winery for a tasting and lunch, then stop to visit San Gimignano before returning to Rome.

Spend an unforgettable day exploring the highlights of Chianti on this full-day private tour of Siena and San Gimignano from Rome. Walk the medieval cobblestone streets in the historic centers of both cities. Visit a local winery to taste different types of wine and oil, and enjoy lunch in the restaurant on the estate.

Visit two of Tuscany’s most celebrated towns during this private full-day excursion from Rome. Explore the historical center of medieval-era Siena, including its distinctive striped cathedral. Then, head to picturesque San Gimignano—nicknamed the “Medieval Manhattan”—to taste its local wine and enjoy panoramic views from the top of its bell tower. Door-to-door transportation in a private vehicle is included.

Experience the allure of Tuscany without the hassle of tricky logistics with this all-inclusive day trip from Rome. Save time with a high-speed train to Florence, where you’ll hop on a minibus with your tour leader and small group to visit Monteriggioni, Siena, and San Gimignano. End your Tuscan adventure with a wine and olive oil tasting in Chianti before heading back to Florence for the return train to Rome.

Embark on an unforgettable full-day adventure, exploring the rolling hills of Tuscany. Indulge in a private chauffeured journey from Rome, beginning your day with panoramic views of San Gimignano as you wander its ancient narrow streets and unique shops. Discover Siena’s captivating gothic architecture—a true testament to medieval grandeur. Enjoy this exclusive tour to two remarkable cities that will leave you feeling inspired by their breathtaking beauty.

Explore two top cities in Tuscany without the hassle of driving and parking with a private driver from Rome. Enjoy hotel pickup and head to Florence, where you’ll meet your guide for a walking tour of the Renaissance capital’s highlights followed by free time to dine and shop. Then move on to Siena for a guided stroll and a stop to marvel at the city’s cathedral before the drive back to Rome.

Explore the Tuscan countryside on this fun and hassle-free all-day tour from Rome. After a convenient hotel pickup, travel by private minivan with an English-speaking driver. See the walled, medieval villages of Monteriggioni and UNESCO-recognized San Gimignano, and hill town of Castellina in Chianti. Upgrade to be accompanied by a professional guide and customize your itinerary. Enjoy a wine tasting included in the tour price.

Enjoy a day exploring the landscapes and artistic small towns that Tuscany can offer: • Monteriggioni • San Gimignano • Castellina in Chianti Lunch and WineTasting Included. Pick up and drop off will be at your accommodation in Rome. Upgradable with licensed local guide in Private option. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides (when booked) • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

Without doubt, Siena is one of Italy’s most enchanting cities, built on three steep hills and unchanged since medieval times, it’s a must-see attraction of Tuscany. You will have the chance to see all the major locations like the gothic cathedral (Duomo) and the taut needle of the Torre Del Mangia. The Duomo of Siena is one of the most spectacular in Italy, and one of the few to have been built south of the Alps in full gothic style From Siena, your driver will whisk you away through the hills, vineyards and Olive groves directly to San Gimignano, another charming little village in Tuscany. At the end of this interesting and relaxing day you will enjoy a pleasant journey back to Rome.

San Gimignano and Siena are two of Tuscany’s most picturesque towns, but visiting from Rome by train can be tedious. Save hours with this driving tour that includes convenient hotel pickup, leaving enough time for stops in both hilltop villages. Stroll through San Gimignano to admire its medieval towers and enjoy a food and wine tasting. Afterwards, continue to Siena to visit the Piazza del Campo and relax with a coffee and pastry.

Embark on a captivating full-day private excursion from Rome to the medieval treasures of Siena and Orvieto, beginning with the convenience of hotel pick-up. Discover the enchanting beauty of Siena, famed for its stunning Gothic architecture and the historic Palio horse race. Traverse the city's picturesque streets and immerse yourself in the vibrant atmosphere of the Piazza del Campo. Continue your journey to Orvieto, perched atop a volcanic plateau, where you'll explore its remarkable cathedral and delve into its fascinating underground network. With personalized attention and the comfort of hotel pick-up, this exclusive excursion ensures an immersive and enriching experience, leaving you captivated by the medieval allure of Siena and Orvieto.

Siena is a hilly, with the most beautiful square in Italy (Piazza del Campo), the 2nd highest tower in Italy (Torre del Mangia), and the most impressive Duomo (cathedral). The interior of the cathedral is absolutely jaw dropping. It is a city full of churches, museums, and great views over the surrounding countryside. The Piazza del Campo is famous for the Palio, which is a no-holds-barred race run here twice a year. These races pit the 17 different neighborhoods of Siena against each other. A beautiful bronze dome, a sculpture of St. Peter by Michelangelo. The whole cathedral was painted, sculpted, and decorated by the most celebrated Italian artists of that time.

You'll enjoy the beauty of Tuscany through this tour. You'll spend a day exploring some of the most beautiful medieval villages in Tuscany and tasting the wine produced in this area, surrounded by the wonderful landscape of Sienese's Hills. Our English speaking chauffeurs will drive you with courtesy and comfort; our vehicles are meticulously maintained and equipped with air-conditioning and free Wi-fi service. It is possible to upgrade your experience booking this tour with an English speaking assistant that will take care of you during the journey

A wonderful day full of important events for the history and culture of two medieval cities. A journey into the heart of Tuscany immersed in the fantastic and verdant hills, which offer fascinating landscapes and undulating paths, colored by its vegetation. Siena is one of the best preserved historical cities of Tuscany, it is a medieval jewel made of bricks and stones, with dozens of Gothic palaces, churches and squares of enchanting beauty. Admirable the Gothic cathedral "Il Duomo di Siena", for the famous Palio of Siena (horse race) and for other monuments of great historical value. After we will go to San Gimignano, a marvelous medieval hilltop village, surrounded by walls and famous for the 14 tower houses that dominate the panorama, it is nicknamed the Manhattan of the Middle Ages, we will visit its cathedral, a 12th century church and Piazza della Cisterna ( of triangular shape). Here it produces Vernaccia, one of the best white wines and saffron cultivation.

Embark on an enchanting journey back in time with our "Medieval Marvels" private day tour from Rome to Siena and San Gimignano, starting with the ease of hotel pick-up. Experience the allure of Siena, a medieval gem renowned for its splendid Gothic architecture and the historic Palio horse race. Wander through its charming streets and marvel at the magnificent Piazza del Campo, the heart of the city. Continue your adventure to San Gimignano, a UNESCO World Heritage site famous for its well-preserved medieval towers. Explore its captivating streets, soak in the panoramic views, and savor the town's timeless atmosphere. With our personalized tour, enjoy the comfort and flexibility of private transportation as you immerse yourself in the rich history and culture of these medieval treasures, creating cherished memories of your day in Siena and San Gimignano.

San Gimignano and Siena are two of the most delightful towns in Tuscany, but visiting both in one day from Rome can be tricky. With this private minivan tour, skip the hassle of public transportation and relax during the drive. Explore the medieval center of San Gimignano on your own and enjoy lunch at a nearby winery (own expense) before continuing on to picturesque Siena.

Taste wines from Chianti at the source with this full-day tour from Rome. Drive along narrow roads past olive groves and vineyards without the hassle of a rental car. Visit an organic winery and taste several different types of Chianti Classico along with local olive oil, balsamic vinegar, and traditional Tuscan snacks. The itinerary also includes a stop in the quaint Etruscan city of Castellina in Chianti.

Enjoy a day exploring the landscapes and artistic small towns that Tuscany can offer: • Monteriggioni • San Gimignano • Castellina in Chianti Lunch and WineTasting Included. Pick up and drop off will be at your accommodation in Rome. Upgradable with licensed local guide in Private option. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides (when booked) • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • San Gimignano • Monteriggioni • Siena Wine and Light Lunch in the Tuscany countryside included! Upgradable with licensed local guide in Private option. Pickup and dropoff will be at your accommodation. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles