Tuscany & Umbria Tour
Tours and Vineyards
from €945
9 days - Includes rental car & accommodation
Tuscany & Umbria Tour
Tours and Vineyards
from €945
9 days - Includes rental car & accommodation
Tuscany & Umbria Tour
Tours and Vineyards
from €945
9 days - Includes rental car & accommodation
La Dolce Vita among Tuscan hills and Umbrian charm
How about an unforgettable road trip through the heart of Tuscany and Umbria—two of Italy’s most beautiful regions? Picture this: with your rental car, you set off on your own adventure, weaving through rolling hills and enchanting medieval towns, all while tasting some of Italy’s finest wines.
Start your journey in the lovely town of Lucca, wrapped in impressive Renaissance walls. Then drive on through scenic landscapes to San Gimignano, famous for its medieval towers. Let yourself be wowed by the art and architecture of Florence, the cradle of the Renaissance.
But this Italian road trip goes far beyond the well-trodden tourist trail. You’ll discover hidden gems across Tuscany and experience the authentic soul of Umbria. Wander cobbled streets, indulge in local specialties, and enjoy Italy’s warm hospitality.
This journey offers the perfect blend of culture, history, and nature. From the iconic cypress-lined roads of Tuscany to the spiritual calm of Assisi in Umbria, every day brings new, unforgettable experiences. And with the freedom of a rental car, you get to choose your own pace and path.

Highlights of this tour through Tuscany & Umbria

Lucca
Walk or cycle along the city’s historic walls for sweeping views. Explore the picturesque alleys, marvel at medieval architecture, and climb the famous Guinigi Tower, crowned with oak trees at the top. Lucca is the real deal—authentic Italian charm packed with culture and history.

San Gimignano
This enchanting medieval town, a UNESCO World Heritage site, is famed for its dramatic towers. Stroll through historic streets, try the local delicacies, and take in the stunning views of the Tuscan countryside.

Florence
The vibrant capital of Tuscany and birthplace of the Renaissance, Florence is home to iconic landmarks like the Duomo, Ponte Vecchio, and Palazzo Pitti. See world-renowned masterpieces including Michelangelo’s David and Botticelli’s Birth of Venus at the Galleria dell’Accademia and the Uffizi Gallery.
Program
Per person, from € 945 in low season to € 1279 in high season.
Based on two traveling together sharing a double room and rental car.
What's included?
8 nights in 3* or 4* hotels
Rental car for the entire duration of the tour:
Pick-up and drop-off at the airport
Type: Fiat 500X or similar
Full insurance coverage
Second driver included
Unlimited mileage
Not included
Flights
Travel and cancellation insurance
Meals, activities and entrance fees not mentioned in the programme
Tips and personal expenses
Travel Documents
Belgian citizens (including babies and children) must be in possession of a valid Belgian identity card and be up-to-date with the measures specific to the country of transit and destination. For the most recent updates, we refer you to diplomatie.belgium.be and the websites and apps they bring forward. A valid driver's license (at least 1 year old) and viable credit card in the name of the main traveler and driver of the rental car is also mandatory
Travellers with a non-Belgian nationality and / or persons travelling on a foreign passport are invited to spontaneously report this matter to the Connections travel consultant and shall contact their respective embassy (s) or Consulate (ate) to obtain the latest updates concerning all current travel requirements and documents.
Insurances
Have a safe and carefree trip: travel fully insured with our Protections travel insurance! Our Protections insurance policies offer various formulas in order to offer you the widest possible cover (with even a fly-on-time, natural catastrophes and epidemics) for both single journeys or for the entire year. We guarantee you the best protection at the best price.
Tailored travel
The tours in our brochures are just a few examples of travel itineraries possible. Our trips can be tailored to suit your specific needs. If you want to book a specific destination or combine it with a mini-tour then we will gladly make you a tailor-made offer. For a personalised day-by-day program please contact our destination experts.
Would you like to travel in a group; with your entire family, friends or colleagues? (min. 10 people required). Put our know-how to the test and send us your details and wishes. We will gladly turn the blueprints of your trip into a detailed quote and a lasting memory for you to cherish. Contact our Connections’ Group Service by e-mail at groups@connections.be or by telephone on +32 (0)2 550 01 65. We would love to hear from you.
Health
No mandatory vaccinations. To verify the latest updates on health requirements, please surf to https://www.itg.be
For all latest measures concerning covid we refer you to the website https://diplomatie.belgium.be
Time zones
Belgian time +1 hour
La Dolce Vita between Tuscan Hills and Umbrian Charm
How about an unforgettable road trip through the heart of Tuscany and Umbria, two of Italy’s most beautiful regions? Imagine: with a rental car, explore freely the rolling hills, picturesque medieval towns, and enjoy the world-famous Italian wines.
Start your adventure in charming Lucca, with its impressive city walls. Continue your journey through the scenic landscape to the iconic San Gimignano, known for its medieval towers. Be amazed by the art and architecture of Florence, the cradle of the Renaissance.
But this Italian road trip takes you beyond the well-known attractions. Discover hidden gems in Tuscany and experience the authentic atmosphere of Umbria. Stroll through atmospheric streets, taste local specialties, and enjoy Italian hospitality.
This Italy road trip offers the perfect combination of culture, history, and nature. From the cypress-lined avenues of Tuscany to the spiritual calm of Assisi in Umbria, each day brings new, unforgettable experiences. With the flexibility of a rental car, you set your own route and pace.
Discover the Green Heart of Italy on Your Umbria Road Trip
Umbria is not called the green heart of Italy for nothing. During your journey through this surprising region, you will be surrounded by rolling hills, vast vineyards, and breathtaking views. Unlike popular Tuscany, Umbria still retains its authentic charm and peaceful character. You will find fewer tourists, but just as many historical treasures to discover. From the spiritual atmosphere in Assisi to the medieval splendour of Perugia and Spoleto, each town tells its own story. Enjoy relaxed walks through picturesque towns and feel how time seems to pass more slowly here than in the rest of Italy.
Must-See Sights in Perugia
Perugia, the proud capital of Umbria, is an absolute gem on your road trip. The city sits high on a hill and offers spectacular views of the surrounding landscape. Start your visit at the majestic Palazzo dei Priori, home to the Galleria Nazionale dell’Umbria with masterpieces by Perugino and other Renaissance artists. Then head to the central Piazza IV Novembre with the magnificent Fontana Maggiore, a masterpiece of medieval sculpture. Next, wander through the underground city, the Rocca Paolina, a fascinating labyrinth of medieval streets now below ground. Don’t forget to taste typical Umbrian cuisine in one of the many authentic restaurants.
The Most Beautiful Towns of Tuscany and Umbria
During this road trip, discover some of central Italy’s most charming towns. In Tuscany, be enchanted by San Gimignano, also called “the medieval Manhattan” due to its impressive towers. Nearby Volterra takes you back in time with its Etruscan heritage. In Umbria, Spoleto surprises with its imposing Ponte delle Torri and beautiful cathedral. The smaller San Gemini is also worth a visit with its well-preserved medieval architecture. Nature lovers will enjoy the drive past the spectacular Marmore Falls. Each town has its own character, yet all share the typical Italian hospitality and rich cultural heritage to explore during your journey.
Best Time to Visit Tuscany and Umbria
For your Tuscany and Umbria road trip, spring and autumn are ideal. In May and June, enjoy pleasant temperatures around 25°C, blooming fields, and fewer tourists than in summer. The hilly landscapes are at their greenest and most vibrant. September and October also offer perfect conditions, with mild temperatures and the excitement of the grape harvest. You can then join local wine festivals and taste fresh truffles harvested in autumn in Umbria. The winter months are quieter and cooler but provide an authentic experience of local life without tourist crowds. Summer months, July and August, can be very hot, with temperatures regularly exceeding 30°C.
Culinary Highlights of Umbrian Cuisine
Umbrian cuisine is a feast for the senses and an important part of your road trip. The region is known for its high-quality truffles, found in many local dishes. Be sure to try the strangozzi al tartufo, fresh pasta with truffle sauce, a specialty of Spoleto. The region also produces excellent olive oil, which you can taste during a visit to a local olive grove. Don’t forget to discover the local wines, such as the ruby-red Sagrantino di Montefalco, one of Italy’s most characterful red wines. In Perugia, be sure to try the chocolate, as the city is home to the famous Perugina brand. Meat lovers will enjoy porchetta, roasted pork with herbs, a popular treat at local markets.
A tailor-made quote?
Wish a detailed tailor-made quote? We gladly assist you with your travel plans, thus prepare your ideal tailor-made trip and calculate a detailed price proposal in no time. No hidden costs and entirely to your liking.
Visit our travel shops
Need more info, assistance to tailor your trip or the latest tips by our experienced Travel Designers? Pop in at one of our travel shops or make an appointment now. We will be delighted to set aside time for your travel plans.
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Because we are travellers, just like you. Always looking for exciting experiences, fascinating encounters and new horizons. Because we are 100% Belgian and can assist you in your own language. Because we make it our personal mission to lift your travels beyond your wildest imagination. Because life is more intense when you travel, really travel!
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