Beautiful view of Medieval town of Monteriggioni in Tuscany, Italy

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

Ratings of Zicasso's Service
Customizable Itinerary

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

Countries Visited

Italy

Places Visited

Rome, Spoleto, Assisi, Montefalco...

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Suggested Duration

10 Days

Your 10-day romantic adventure of Tuscany and Umbria will keep your love at the forefront on your personalized Italy tour. Enjoy a passionate embrace on a vineyard, drift down the Tiber River dining on delectable dishes, and climb to the top of a medieval tower for unrivaled views. Take the chance to sneak a kiss around every corner, and fall in love anew amidst the beauty of Italy.

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
  • Deilght in 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

Starting Price

$4,500 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.

Reviews of Zicasso's Referral Service

4.9 stars based on 5972 reviews.

Italy Trip Review: Rome, Amalfi, Positano, 12 Days

The trip Zicasso's travel specialist arranged for us exceeded all our expectations. It was absolutely wonderful; not a single detail was overlooked. The hotels were excellent, the tours were great, and the drivers were always on time. I totally recommend Zicasso and the agency, and will undoubtedly use them for future travel plans.

Reviewed By Philip S.

Italy Travel Review: Lake Como, Ostuni, Private Boat Tour,...

Zicasso's travel designer did a terrific job. We had the initial phone consult, after which she delivered a first draft of the itinerary. From there, she helped guide us through a few revisions until we got the details smoothed out. We are experienced travelers and can appreciate a well-constructed trip, and that's what our experience with our agent reflected.

One crucial thing is that all the drivers who are engaged to move you around are prompt. Every one of them was right on time and friendly and helpful to boot. It was much appreciated.

To sum up our experience, I would do it all again with Zicasso and the agency and our agent. Our trip to Italy in the late summer of 2025 was something we will not soon forget!

Reviewed By tony B.

Italy Tour Review: Calabria, 11 Nights

Zicasso's travel partner is very thorough and makes sure the trip is tailored to your vision. They are flexible and very responsive. We would recommend them to anyone traveling.

Reviewed By Evan C.

Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii,...

Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

Reviewed By Kevin S.

Italy Travel Review: Dolomites, 2 Weeks

Zicasso's travel designer made the whole trip run very smoothly. It was a pleasure working with her.

Reviewed By Joseph B.

Italy Vacation Review: E-bike Tour, Kayaking, 10-Night Trip...

This was the best trip ever!!! I am so grateful Zicasso introduced us to our tour operator. This team was amazing! They set up a call to learn more about us and jumped into action. Within a short time, they came back to us with a presentation on ideas, with recommendations. There is no chance our trip would have been half as good without them. They even had a text group on standby while we were here in case we needed anything.

Reviewed By Linda C.

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