Florence is celebrated around the world for its Renaissance art, magnificent cathedrals, and charming streets that seem frozen in time. Beyond Florence’s famous art and architecture, the surrounding region offers undulating countryside, quaint medieval towns, and glistening coastal views, all ready to be explored. Exploring these areas with the freedom of your vehicle turns each day trip into a relaxed and personalised adventure.
Driving yourself opens up possibilities that tours and public transport cannot always offer. You can stop for a photo when a vineyard catches your eye, wander through quiet villages, or take scenic detours to hidden spots away from the crowds. For those looking to experience Tuscany beyond the usual sights, these self-driven journeys reveal a more intimate and flexible way to travel. Keep reading to discover some of the region’s most captivating day trips that start and end in Florence, with practical tips for making the most of each route.
Trains and buses in Tuscany are reliable, yet schedules and fixed routes limit flexibility. Public transport rarely reaches many of the smallest hilltop villages, vineyards, or scenic viewpoints. A self-driven journey, in contrast, lets you stop for photos or lunch in quiet spots, revisit your favourite view, or take a scenic detour without waiting. This is especially useful if you are travelling with family or friends, or if you have a flexible itinerary, as it allows you to set your own pace, choose your schedule, and decide your route.
About an hour and fifteen minutes from Florence, Siena offers a perfect blend of history and elegance. It is known for its piazza, shaped like a shell, the Piazza del Campo, where the famous Palio horse race still takes place. As you arrive, park outside the historic centre and enter on foot, allowing yourself to immerse in its winding stone streets.
The cathedral (Duomo) is a standout, with its striped marble façade and intricate floors depicting biblical stories. Climb the bell tower for sweeping views, then stroll through medieval alleys to discover local bakeries selling ricciarelli biscuits or panzanella salads. The city has a timeless, peaceful air, making it a rewarding escape from Florence’s bustle even if you only have a few hours.
About seventy minutes from Florence lies San Gimignano, famous for its skyline of medieval towers piercing the Tuscan sky. Often referred to as the “Medieval Manhattan,” it is small enough to explore easily, yet layered with charm. Walk through its cobbled streets and pause in Piazza della Cisterna to enjoy local Vernaccia white wine.
Visit the Duomo to marvel at frescoes that show life in the Middle Ages, then climb Torre Grossa for rolling vine-covered hills in every direction. Budget some gelato time at Gelateria Dondoli, a world-renowned favourite. Because the roads approaching San Gimignano are scenic and narrow, driving yourself allows you to pull over at olive groves or vineyards and soak in the surroundings at your leisure.
Though famous for its leaning tower, Pisa has more to offer once viewed. Around an hour from Florence via motorway, the city welcomes drivers with spacious car parks near the iconic Piazza dei Miracoli. Climb the tower if you wish, but also take time to enjoy the soaring Cathedral and elaborate Baptistery.
The Baptistery often has remarkable acoustics, so listen quietly when someone sings. For a change of pace, follow the Arno river through historic neighbourhoods away from the crowds, or enjoy the joyful energy of local cafés. Pisa blends grand monuments with everyday life, giving you both spectacle and authenticity in one outing.
Approximately eighty minutes from Florence, Lucca surprises visitors with its wide, tree-lined Renaissance walls. You can walk or cycle these elevated pathways, pausing to admire the terracotta rooftops and bell towers below. Inside, the city is navigable and calm, with elegant churches, hidden piazzas, and a relaxed atmosphere.
Climb Guinigi Tower, topped with an unusual rooftop garden, or wander through Piazza dell’Anfiteatro, built on a Roman amphitheatre’s remains. Want to shop local? Explore artisan stores in narrow alleys or sip coffee while watching locals do the same. A day here feels like a gentle breath after museum-rich Florence.
Less than thirty minutes south of Florence lies the famed Chianti wine region, vineyard-draped hills, rustic stone cottages, and serene country roads. Driving through it is a highlight in itself. Follow the SR222 route and pause in towns like Greve, Castellina, or Radda. At each stop, you will find wine producers offering sampling and cellar tours, accompanied by local olive oil and cheese.
Greve’s triangular piazza hosts a market where local meats and produce shine. Throughout the day, let the scenery guide your stops, a vista, a quaint chapel, or a vineyard view for lunch. Chianti rewards spontaneity.
Just an hour away, Arezzo is a calmer alternative to busier sights. Piazza Grande, sloping and historic, hosts an antiques fair on the first weekend of every month. Even outside that weekend, the square’s cafes and architecture make it a beautifully nostalgic place to unwind.
Beyond the piazza, visit the Basilica of San Francesco to behold Piero della Francesca’s frescoes, painted with quiet dignity and emotional depth. Cobblestone streets outside the centre lead to artisan workshops offering handmade leather goods. Arezzo’s laid-back feeling invites you to slow your pace and enjoy art, food, and fewer crowds.
If you crave sea air, drive ninety minutes west to reach the Tuscan coast. Start in Livorno, a port city with canals and seafood restaurants, or continue to Castiglioncello or Rosignano for beach time. In Livorno, hearty fish soups and grilled seafood are best enjoyed by the harbour. Then, feel the spray of the Mediterranean on your drive, with beaches, promenades, and sunset views easily accessed by rental car. This is something difficult if relying on public transport.
If you’re inspired to explore even further, check out our Breathtaking Seven-Day Itinerary From Rome to the Amalfi Coast for more unforgettable Italian road trip ideas. It’s packed with scenic drives, historic towns, and insider tips to make every day of your journey truly memorable.
Maximising a day trip in Tuscany means planning smartly while leaving room for spontaneity. These tips will help you enjoy smooth, stress-free journeys while uncovering unexpected delights along the way.
Renting a car with Final Rentals makes exploring Tuscany simple, convenient, and worry-free. Our services are designed to let you focus on the journey, not the logistics.
For additional tips on driving in Italy and making the most of your rental experience, check out Everything You Need to Know Before Taking the Wheel in Italy for the First Time.
Within a single day, you can combine close destinations. For example, explore Siena’s medieval charm in the morning, then wind through Chianti’s vineyards and end with a sunset wine tasting. Alternatively, start on the coast in Livorno, travel back through Lucca, and stop in Pisa for dinner with a view. A car makes it possible to tailor your trip to the unexpected joys along the way, something a rigid tour cannot provide.
Tuscany is vast, sunlit, and full of surprises waiting just beyond Florence’s walls. Towns of medieval pride, landscapes of quiet beauty, and stretches of coastline lie within easy reach, made all the more accessible when you rent a car in Italy with Final Rentals. Each destination offers its own story.
Siena’s historic fervour, San Gimignano’s timber past, Pisa’s architectural splendour, Lucca’s calm charm, Chianti’s gentle hills, Arezzo’s artistic core, and the coast’s salt-tinged breeze. Embrace the open road, the endless skies, and Tuscany’s timeless beauty. Rent a car, take it slow, and let each mile bring a discovery under the sun!
