Multi-Generational Italy Tour: Best of Tuscany and Rome

The Roman Colosseum in Italy

What to expect on this itinerary

Discover Renaissance splendor and picturesque Tuscan countryside, then uncover the secrets of ancient Rome on your eight-day multi-generational Italy itinerary. Walk over Florence's bridges and through its vibrant market, take in the charm of medieval Siena, and relive the glory of gladiators and Papal significance when touring Rome and the Vatican City. A diverse itinerary created for the entire family, highlighting key destinations in central Italy.

Countries Visited

Italy

Places Visited

Florence, Chianti, Siena, Rome

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Florence - Arrive in the Captivating Tuscan Capital

Flanking the River Arno, the Renaissance city of Florence depicts a world of architectural wonder and Italian flare. From the moment you arrive, you will be in awe of how modern buildings blend in with historic sites, beautiful bridges, and famous, must-sees creations. Settle into your hotel before embarking on a half-day guided tour of the city. Take in charming side streets and sidewalks, then step inside the Accademia museum to view a true masterpiece, Michelangelo’s “David”. Take your time as you walk around this iconic and intricate marble creation, observing the crevices and curves of the statue’s inwardly-posed hands, while letting your eyes follow those of the subject’s as you ponder what it is he may be looking at.

What's Included:

Transfer
Accommodation
Tour
Day 2

Florence - Discover Countryside Charm in Chianti and Siena

Day 3

Florence - Soar Above the Tuscan Countryside

Day 4

Florence - Select, Create, and Taste Tuscan Cuisine

Day 5

Rome - Train Travel to Rome and Classic Street Food Tour

Day 6

Rome - A Roman Empire Experience

Day 7

Rome - Visit Iconic Churches and Chapels of Ancient Rome

Day 8

Rome - Transfer for Your Journey Home

Trip Highlights

  • Wander over bridges and through markets in Renaissance Florence
  • Delve into delicious Chianti cuisine and wines
  • Pick local produce at the Piazza Mercato Centrale and participate in a classic Tuscan cooking class
  • Stroll through medieval squares and through alleyways of charming towns in the Tuscan countryside
  • View the rolling hills of Tuscany from clear skies in a hot-air balloon
  • Get your taste buds going on a classic Rome street-food walking tour
  • Marvel at the grandeur of the Colosseum, visit Palatine Hill, and step back in time to experience the great Roman Empire at the Roman and Imperial Forum
  • Admire the artwork, culture, and religious significance at the Vatican City’s museums, including the Sistine Chapel and St Peter’s Basilica

Starting Price

$4,000 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 for two adults staying in standard double rooms, 4-star hotels with breakfast included, and inclusions as per your itinerary for Day 1-9 are $4,999.00 per person. The optional Mallorca trip extension is not included in this starting price
  • 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 414 reviews

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 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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Italy Vacation Review: Florence, Venice, Tuscany, Siena, Cooking Class, Tasting Tour, 9-Day Trip

From the moment we began working with Zicasso's trip planner, our every need was met. He listened and planned an epic trip based on our conversations. Then, for our trip, we worked with another trip planner who was extremely responsive and professional, especially when we were in Italy. Any questions we had were promptly answered. Everything they planned was pure luxury and fantastic. The private pick-ups, drivers, and tour guides were absolutely prompt and fantastic. Every tour was super-fun and informative. Highlights included the wonderful hotels, food tour in Florence, tour in Venice, cooking class, and tasting track in Tuscany. I would highly highly recommend. It was a five-star, wonderful trip!

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Italy Tour Review: Venice, Tuscany, Rome, Amalfi Coast, Capri, Cooking Class, Ferrari Experience, 2-Week Vacation

We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.

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Italy Trip Review: Rome, Florence, Tuscany, Amalfi Coast, Pope Francis’ Funeral, Wine, Cuisine, Culture, Museums, Relaxation, 10 Nights

Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!

We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.

Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us. 

Talk with our tour operator; you will be glad you did!

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Italy Vacation Review: Venice, Florence, Rome, Walking Tours, Cooking Class, 10 Nights

Planning a trip for four generations of family can be daunting. Zicasso’s tour operator was the perfect partner to meet the needs of our group, which ranged in age from 88 to 10 months. The transfers (boat, vans, coaches) were flawless. The guides were engaging, knowledgeable, and so attentive to the children. Restaurant recommendations and the cooking school were sensational. Each hotel in Venice, Florence, and Rome was well prepared for a seamless and efficient arrival and departure. Highly recommended.

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Customizable Itinerary

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

30,000+ Verified Traveler Reviews