Finest Wines of Tuscany & Central Italy Tour

Woman raising a glass of wine, enjoying the view at sunset in Tuscany

What to expect on this itinerary

On this 10-day tour of Tuscany and Central Italy, immerse yourself in the encompassing culture of Italy and enjoy the sumptuous luxuries that the country has to offer. Taste wine from boutique wineries that have mastered the craft over centuries. The authentic Tuscan culture, the appetizing food, and the delectable wine are all within arms reach in this luxury Tuscany vacation.

Countries Visited

Italy

Places Visited

Italy, Tuscany, Rome, Umbria, Pisa, Lucca, Bolgheri, Siena, San Gimignano, Montalcino, Monepulciano, Assisi, Spello, orvieto

Suggested Duration

10 Days

Customizable Itinerary

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Day 1

Rome - The Cradle of the West

Arrive in Rome and be transferred to your fabulous hotel. Settle into the lifestyle with a strong caffe, letting the smooth, earthy coffee revitalize you. Take advantage of your time in Rome. From the Etruscans to the people, the Vatican to Mussolini, Fellini to Berlusconi, you will be able to feel the pulse of the city’s history and beauty from the moment the plane touches down.

Ease into the Italian lifestyle, the pace of life and the food, and the opulent history displayed on almost every corner. If you choose to walk around the city, the smells of fresh pasta and zesty oranges are hard to miss. The city is boisterous with the conversations of the locals as they spend their afternoons in the sun with a glass of white wine and a plate of pasta.

Wander down the Spanish Steps, where the locals spend their nights playing guitar and drinking wine. Located between Piazza Trinità dei Monti at the top and Piazza di Spagna at the bottom, the Spanish Steps are a nice space to sit, relax, and watch the lovers stroll by. If you are in a mood to stroll, the neighborhood at the base of the Spanish Steps has often been referred to as the “Beverly Hills of Rome, ” boasting luxurious shops and restaurants; look through the lavish window displays of the stores before going inside.

What's Included:

Transfer
Accommodation
Day 2

Rome - Open Up to Rome

Day 3

Lucca - Open Up to Italy

Day 4

Lucca - Settling In

Day 5

Siena - Reach Out

Day 6

Siena - Grab Hold

Day 7

Maremma - Pull Italy in Close

Day 8

Umbria - Opening Up to Umbria

Day 9

Umbria - Hold onto Umbria

Day 10

Rome - Open Up and Let Go

Trip Highlights

  • Taste the luscious wines of different communes, like the “Super Tuscans”
  • Experience medieval and ancient architecture in its historical splendor
  • Wander through the quintessential Ancient Rome
  • Get acquainted with the Cathedrals of Assisi and Siena
  • Refine your culinary skills by partaking in a traditional Tuscan cooking class
  • Lean into the Tower of Pisa, and see the famous lean of four-degrees

Detailed Description

Begin your tour in Rome, where the modern roots of Italy and Western Civilization’s wine is entrenched in history. The sights and tastes of the city will urge you through a historical tour of iconic sights such as the Colosseum, the Forum, and the Trevi Fountain. Rome is an open city, inviting everyone and anyone to relish in its history and its modernity. Whether on walking tours or bus tours, your journey through Rome will encompass the food and wine that still make people embrace the city.

Traveling through Tuscany gives you the opportunity to experience the celebrated lush countryside on your way to Lucca, known for its medieval walls and its vicinity to the Vespa museum. Stroll by the Tower of Pisa, notable for its famous tilt. A taste of Bolgheri offers plenty of flavor for your first wine tasting; you will begin to understand the popularity of Italian wines, if you hadn’t already. Moving to Siena gives you more time in the Tuscan hills, the unimaginable experience of seeing Siena’s Duomo and its mosaic floor, as well as the lofty towers of San Gimignano. A day of traveling through Montalcino and Montepulciano shows you medieval architecture and wines that haven’t changed much since the Middle Ages.

Moving to Torgiano in Umbria offers a different view, one of golden Umbrian plains and lush wines, which are just as delicious as the ones you left behind in Tuscany. Touring through Torgiano and Montefalco offers substantial architecture that astounds you with every glance, along with wine that will cause you to pause to enjoy fully its immaculate flavor. Assisi is perched on top of a hill, with inhabitants proud of their history, boasting a connection to Saint Francis. The town of Spello asserts its quaintness in its compact and modest look; the cordial atmosphere welcomes you as you tour the ancient streets. Each city offers a variety of pleasantries, from food to wine and from exuberant storeowners to gaudy cathedrals. If you open your arms to Italy, each moment of this tour will last a luxurious lifetime. 

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.

4.9

Verified Traveler Reviews

Based on 1004 reviews

Italy Family Vacation Review: Venice, Verona, Florence, Tuscany, Siena, Rome, Biking, Cooking, Wine Tasting, Olive Oil Experience, 10 Nights

Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.

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Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.

Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.

Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.

A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.

Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.

When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.

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Italy Tour Review: Tuscany, Florence, Montalcino, Castellina, Chianti, Wine Tasting, Cheese Experience, Local Cuisine, Walking Tour, 9-Day Trip

We loved everything about our trip to Tuscany. We had great, comfortable hotels as bases to explore the beautiful countryside and towns. Our hotels had kind, welcoming staff. Zicasso's travel company provided helpful suggestions and reserved non-touristy restaurants and enjoyable, interesting activities: eating in Florence, wine tasting in Montalcino, and cheese making in Pienza.

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Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii, Tuscany, Venice, Cheese-Making Experience, Cooking Class, 13 Nights

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.

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Switzerland, Italy Solo Vacation Review: Zurich, Lucerne, Interlaken, Zermatt, Lake Como, Venice, Florence, Sorrento, Amalfi, Rome, Skydiving, Gondola Ride, Amalfi Coast Cruise, Scenery, Nature, Local Cuisine, 3 Weeks

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

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Italy Trip Review: Rome, Venice, Florence, Opera, Walking Tours, 10 Nights

We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.

I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.

Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.

As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.

I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews