Siena, Italy

14 Day Tuscany Itineraries & Tour Packages

Ratings of Zicasso's Service
<p>Fourteen-day Tuscany itineraries immerse you in the splendor of rolling emerald hills, terraced vineyards, and the quintessential medieval towns that construct the picture-perfect ambiance of Italy. Whether exploring the grand visions of the Medici in Florence or sipping wine in Montalcino accompanied by a panoramic view, visiting the home of Leonardo da Vinci or discovering a charming coastal village, the wonders of history and passion for daily life will emerge in every moment. Zicasso Italy travel specialists have planned thousands of personalized trips and can design your dream Italian vacation with local expertise and recommendations.</p>

Fourteen-day Tuscany itineraries immerse you in the splendor of rolling emerald...

Fourteen-day Tuscany itineraries immerse you in the splendor of rolling emerald hills, terraced vineyards, and the quintessential medieval towns that construct the picture-perfect ambiance of Italy. Whether exploring the grand visions of the Medici in Florence or sipping wine in Montalcino accompanied by a panoramic view, visiting the home of Leonardo da Vinci or discovering a charming coastal village, the wonders of history and passion for daily life will emerge in every moment. Zicasso Italy travel specialists have planned thousands of personalized trips and can design your dream Italian vacation with local expertise and recommendations.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
Sunest view of Florence from the Giardino delle Rose

A Perfect Private Tour of Tuscany in 2 Weeks

Places Visited: Florence, Siena +14 more
Places Visited: Florence, Siena, Pisa, Lucca, San Galgano +11 more

14 Day Custom Tour

From $13,700

View of Capri Island from Mount Solaro in Italy

Iconic Italy: Fast-Paced Exploration from Venice to Sicily

Places Visited: Venice, Milan +7 more
Places Visited: Venice, Milan, Sorrento, Chianti, Amalfi Coast +4 more

14 Day Custom Tour

From $6,200

The village of Montefioralle is one of the most beautiful in the Chianti Valley, Tuscany

All Star Italy Luxury Tour: Milan, Como, Tuscany & Amalfi

Places Visited: Milan, Lake Como +3 more
Places Visited: Milan, Lake Como, Amalfi Coast, Florence, Siena 

14 Day Custom Tour

From $13,700

Vernazza, one of the five centuries-old landmarks where car traffic is prohibited, Cinque Terre National Park, Italy

Tuscany & Cinque Terre Tour

Places Visited: Tuscany, Cinque Terre 
Places Visited: Tuscany, Cinque Terre 

13 Day Custom Tour

From $5,900

Positano on Italy's Amalfi Coast

Treasures of Italy Tour: Venice, Florence, Rome & Positano

Places Visited: Venice, Florence +2 more
Places Visited: Venice, Florence, Rome, Amalfi Coast 

13 Day Custom Tour

From $5,900

Trod the paths that were once walked by Cicero and Caesar during a visit to the Roman Forum

Best of Italy in Autumn: 14-Day Romantic Tour

Places Visited: Turin, Florence +3 more
Places Visited: Turin, Florence, Rome, Stresa, Vatican City 

14 Day Custom Tour

From $6,300

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Benefits of Using Zicasso

Plan Your Trip with
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Travel with a personalized itinerary and experiences designed for you.
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24/7 support and local assistance for every moment of your vacation.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Reviews of Zicasso's Referral Service

4.9 stars based on 5944 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.