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.

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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

Self-Drive Holiday Tuscany – Explore at Your Own Pace

A self-drive holiday through Tuscany and Umbria is the ideal way to explore these regions. With your rental car, you can easily reach both the famous highlights and the hidden villages off the beaten path. Drive past the iconic cypress trees that line Tuscany’s rolling hills, stop at local wineries to taste renowned Chianti wines, and decide spontaneously when to pause and photograph the stunning landscapes. The well-maintained roads make driving pleasant and allow you to enjoy the many treasures these Italian regions have to offer at your own pace.

Medieval Towns of Tuscany and Umbria

During your journey through Tuscany and Umbria, you’ll pass several enchanting medieval towns, each with its own unique character. Beyond San Gimignano and its iconic towers, a visit to Volterra with its Etruscan heritage is highly recommended. In Umbria, the spiritual town of Assisi invites you to explore the Basilica of Saint Francis, while Orvieto impresses with its majestic cathedral perched on a tuff-stone plateau. Montepulciano—famous for its noble wines—and the picturesque Renaissance town of Pienza are also among the highlights. These historical hilltop towns offer not only cultural richness but also breathtaking views over the Tuscan and Umbrian landscapes.

Tuscan Cuisine & Wine Tastings

This journey through Tuscany and Umbria is a true feast for food lovers. Tuscan cuisine is renowned for its simplicity and pure flavors, with dishes like pappardelle al cinghiale (pasta with wild boar), bistecca alla fiorentina (Florentine T-bone steak) and ribollita (hearty bread soup). As you travel through the wine regions of Chianti, Montepulciano and Montalcino, you can stop at local wineries to taste world-renowned wines such as Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano. Umbria also has a strong culinary identity, offering specialties like truffle dishes and porchetta. Enjoy long, relaxed meals on sunny terraces and experience the true dolce vita.

Art & Culture in Florence and Siena

Art lovers will be delighted during this tour of Tuscany and Umbria, especially in Florence and Siena. In Florence—the birthplace of the Renaissance—you can admire masterpieces such as Michelangelo’s David at the Galleria dell’Accademia and Botticelli’s works at the Uffizi Gallery. The impressive Duomo, with Brunelleschi’s dome, dominates the city skyline. In Siena, you’ll discover the stunning Piazza del Campo—one of Europe’s most beautiful squares—where the famous Palio horse race takes place twice a year. The magnificent striped cathedral of Siena houses artworks by Donatello and Michelangelo. Both cities are steeped in history and culture, with extraordinary frescoes, sculptures and architectural treasures at every turn.

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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Why choose Connections?

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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