Beautiful view of Medieval town of Monteriggioni in Tuscany, Italy

Charm & Romance in Italy’s Countryside: Tuscany and Umbria Tour

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Rome, Spoleto, Assisi, Montefalco...

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Suggested Duration

10 Days

Your romantic adventure together will keep your love at the forefront and be enhanced by the lush landscapes and majestic towns of Umbria and Tuscany on your personalized romantic tour of Italy. Enjoy a passionate embrace in a stunning vineyard before sampling celebrated Brunello di Montalcino, indulge in the uninterrupted company of each other as you drift down the Tiber River dining on a selection of delectable dishes, and then climb to the top of a medieval tower for unrivaled views of Tuscany....

Customizable Itinerary

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Trip Highlights

  • Indulge in the romantic atmosphere and delicious cuisine during a four-course meal on a scenic cruise down the Tiber River in Rome
  • Delight in the flavors during a private wine and olive oil tour through the secluded and stunning countryside of Umbria
  • Climb to the top of Torre Grossa at nearly 175 feet above the cobbled lanes of San Gimignano for an unparalleled view of the Tuscan countryside
  • Relish luxury, charm, and romantic ambiance in unrivaled accommodations across Umbria and Tuscany
  • Bask in the simple yet captivating flavors of Umbrian cuisine with a private couple’s cooking class near Spoleto
  • Immerse yourself into the fairytale setting of the medieval towns that decorate the lush hilltops covered with olive groves, chestnut orchards, and vineyards
  • Marvel at grand design and intimate details of Michelangelo’s David in Florence before listening to the melodic Gregorian chants at a secluded church above the city
  • Visit the Basilica of St. Valentine in Terni, home to the tomb of the patron saint of lovers, St. Valentine, for whom Valentine’s day is named 

Detailed Description

Cypress trees, hilltop towns, historical homes, and idyllic artwork will abound throughout your 10-day Italy tour.  The picturesque beauty of Umbria and Tuscany invite love and romance from the charming fountains to the beautiful churches, the private dining experiences to the delicious wine pairings. The two of you will indulge in the passionate lifestyle at your preferred pace and discover the sculptures of Michelangelo and preserved ruins that date back to the Etruscans for a charismatic journey through Italy. Your journey will begin with your arrival at Rome Fiumicino Airport as your private transfer greets you at customs and escorts you into the heart of the Eternal City. Spend time strolling along the cobbled lanes and watching the gorgeous fountains before boarding your boat on the Tiber River for a fantastic dinner cruise.

Umbria offers a unique perspective of Italy and often overlooked by visitors traveling between Tuscany and Rome. Grandmothers cook pasta framed by their open doors along cobblestone streets as the landscape undulates between rugged mountain tops and hills bedecked with wildflowers and meadows. Explore the towns of Terni and Narni as the past meets the present, and then visit the tomb of St. Valentine and enjoy a view to the remarkable Marmore Falls before reaching Orvieto. Learn the art of making pasta and delectable traditional dishes with a couple’s cooking class on the historical streets of Spoleto, and then sample wine and olive oil as you stroll along the sloping cobbled streets of Assisi, home to the remarkable Basilica of St. Francis.

Begin with a wine tasting tour around Montalcino and sample the “King of Wines,” Brunello di Montalcino, while enjoying each other’s company around sensational Val d’Orcia. Tuscany is popular for its idyllic scenery as historical hilltop towns bring contemporary life into a world of fairytale architecture and remarkable medieval and Renaissance stories. The towns of Siena and San Gimignano offer magnificent vistas and secluded ambiance in which you can revel while Florence offers spectacular museums and a touch of Renaissance flare from the architecture, art, and Gregorian chants at San Miniato Church.  The two of you will have time to take it all in and add to your own romantic story while enjoying it all.

Starting Price

$2,745 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

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