Classic Tuscany Tour

Choose your dates

Discover Tuscany

Indulge in the ultimate Tuscan experience!

Our “Classic Tuscany” tour is an exceptional combination of activities, food, wine, and excursions that will give you an in-depth exposure to the culture of the Tuscany region.

On your private tour, there will be plenty of sightseeing and experiences: you’ll eat like the locals, learn all about the art & history with our expert local guides, and experience the simple pleasures of exploring the Tuscany region with its incredible scenery and history.

Discover the hilltop towns, the regional cuisine and boutique wineries, get to know local artisans, and experience the Italian lifestyle.

Classic Tuscany Tour
Classic Tuscany Tour

This tour has all of your accommodations, excursions & tours, transportation and most of your meals completely arranged and included.

However, we’ve left you some flexibility for free time to just read a book, take a swim, meander the small villages we will be visiting, or do some shopping.

There will be plenty of food, wine, and opportunities to enjoy some memorable experiences!



David D

Trip was well organized. My wife and I really enjoyed all of our daily excursions. Food and wine were incredible. Our hotel villa was topnotch with a great view. Catherine thought of everything and even had activities planned for our boys (ages 6 & 8).

David D

Elisa Y

Enjoyable, pre-organized trip with a pleasant, experienced, knowledgable tour guide throughout Italy. Excellent choices of hôtels, restaurants, vine yards, organic farms, and attractions. Best Birthday Ever! Highly recommended if you want a carefree vacation.

Eliza Y

Kati H

WOW – this was amazing! Thank you so much for all of the suggestions for our itinerary. Your tips on places to eat are PRICELESS…as we plan on eating our way through Italy. Thank you so much for pulling our trip together for us. Thanks again…this is all priceless!

Kati H

F. Faugno

My husband and I just returned from the Chianti Tour, our third trip with Vitalia! Needless to say, we are more than pleased. We have so many new memories, from the lovely towns we visited, the places we stayed, the food, wine, cheese tastings, olive oil tastings, winery tour, cooking classes and our accommodations. I could go on and on but you need to see for yourself. Can’t wait for next year to see what Vitalia has in store. Thank you Catherine for all you do!

F. Faugno
Classic Tuscany Tour

Tour Highlights

  • ​8 Days/7 Nights
  • ​​7 nights stay in a Tuscan villa farmhouse
  • ​Discover the hidden gems of Florence
  • ​Indulge in several winery tour & tastings
  • ​Visit an ancient olive oil mill with tasting & lunch
  • ​Taste delicious Pecorino cheese with farm tour and tasting
  • ​Shop the vibrant local markets
  • ​Watch local artisan demonstrations​​
  • ​Sip delicious wines while taking in the views
  • ​It's poppy season!

Pricing starts at:
$3,595.00 USD per person/double occupancy

Day 1 - Arrival Day/ Benvenuto!

Welcome to Italy!

Upon arrival to Rome airport, meet your private driver for your transfer to your accommodations in Tuscany. 

On the way, you'll stop in Orvieto – a town set atop a tufa plateau in Umbria, for “free time” & lunch. Continue on to the Tuscan countryside.

Check into your accommodations, a farm villa set in the heart of Tuscany.

Dinner at your agriturismo (D)

Day 2 - Val d'Orcia & Pecorino Cheese

Today after  breakfast, you will depart for two of Tuscany’s most famous towns: Montepulciano & Pienza, set in the Val d’Orcia – what many view as the “quintessential” Tuscany.

Along the way, you'll see rolling hills dotted with small villages, cypress lined roads and miles and miles of vineyards. Depending on the time of year, you might see fields of sunflowers or red poppies. 

Your first stop will be in Pienza, famous for its Pecorino cheese. Here you'll enjoy a tasting of this famous regional cheese. 

After lunch, it's off to the hill town of Montepulciano where you can wander the streets, stop at shops, churches and town squares. As well, there are many enoteche where you can visit the ancient cellars and have a wine tasting.

Head back to the villa and perhaps relax by the pool before dinner. (B, L, D)

Day 3 - Arezzo: Where Life is Beautiful

Visit an elegant local villa set in the countryside. Enjoy a tour, learning all about its interesting history and secrets, followed by a wine tasting.

Then head on to Arezzo, a beautiful medieval town, which has its origins in Etruscan history and later, the Romans. 

The town was also made famous in the movie ‘Life is Beautiful’ by Roberto Benigni.

Parts of the city were destroyed during WW2, but many historical buildings remain including the Piazza Grande, a Roman Amphitheater, and the remains of a fortress.

Dinner with local wine. (B, D)

Day 4 - Florence & The Renaissance

Full day in Florence. Upon arrival, you will meet up with your English speaking local guide and enjoy a walking tour of Florence.

During the tour our guide will point out famous sites such as the Duomo, Ponte Vecchio, the Uffizi Gallery, Piazza della Signori, Piazza della Repubblica, and more.

You'll learn all about the dark secrets of Florence's famous noble families and artists with this behind the scenes & highlights tour. Enjoy time for lunch on your own.

The afternoon is free for you to shop, visit one of its famous museums such as the Uffizi (Botticelli) or the Accademia (The David), or just soak in the vibrant life of one of the many piazze while having a caffè or spritz. Perhaps visit the colorful markets where you can find anything from a tripe sandwich to a silk scarf!

Dinner back at your villa with local wine. (B, D)

Day 5 - Chianti: Farm Lunch & Wine

After breakfast, you'll depart to the Chianti region – an area of Tuscany made famous by the red wine of the same name.

This is a beautiful region of terra-cotta-roofed towns and winding roads, leading through groves of olive trees, with cypress and endless vineyards stitching sun-dappled rolling hillsides – this is wine country.

You'll visit some quaint villages, have lunch on a local farm and sample some wine. What else would you do in Chianti?

And since you are in Italy, stop for some famous gelato!

Dinner at your villa with local wines. (B, L, D)

Day 6 - Cortona: ‘Under the Tuscan Sun’

Today, depart for Cortona, made famous by Frances Mayes’ book & movie “Under the Tuscan Sun”.

Cortona which also has its roots in Etruscan history, is a quiet and romantic town nestled in the beautiful hills.

It is surrounded by a countryside, in which lavish villas are surrounded by large gardens and hosts many monasteries, churches and monuments.

Enjoy a guided tour and then free time on your own to explore further and have some lunch. There are plenty of options highlighting the traditional cuisine.

Back to the villa in the afternoon for some time to relax before dinner. 

Dinner with at your villa local wine. (B, D)

Day 7 - Local History and Daily Life in Tuscany

Today will be a full day of experiencing the local countryside life.

First you will visit one of the most famous sanctuaries of St. Francis of Assisi. Enjoy a tour with an opportunity to visit the gift shop with items made by the Franciscan monks such as honeys, chocolates, soap, & liqueurs.

After, visit an ancient olive oil mill operating since the 1400’s with a tour, tasting & lunch with the owner’s family.

Finally you'll stop in a quaint village that hasn't changed since the medieval ages.

Back to the villa in the evening for your final dinner. (B, L, D)

Day 8 - Departure Day

Breakfast at your villa. Then meet your private driver for your transfer to the train station or airport.

Bid Arrivederci to Italy! (B)

**If you would like to continue your journey through Italy, we can add optional tours to Rome, Venice, or Florence
Key: B = Breakfast / L = Lunch / D = Dinner​,  included
*Itineraries are subject to change. Vitalia Tours and its partners will strive to provide you with the best possible tour and experience. It is our intention to adhere to the outlined itinerary as published. However, please be advised that it may be occasionally necessary to substitute an activity due to events that cannot be predicted. Therefore, Vitalia Tours reserves the right to make changes in accommodations, tours or excursions, meals, and itineraries at any time should it become necessary or desirable.

This Tour Includes:

  • Private tour
  • 8 days/7 nights
  • Accommodations in a countryside villa set in Tuscany w/pool
  • Private transfers from/to Rome airport or train station
  • All breakfasts - Buffet style
  • 3 Lunches
  • 7 Dinners with local wine
  • Private driver/van for all excursions
  • All excursions and tours per itinerary
  • All private wine and food tastings
  • All entrance fees per itinerary
  • Private guided walking tour of Florence
  • Private guided walking tour of Arezzo
  • Private guided walking tour of Cortona
  • Pre-trip information packet
  • All VAT taxes and government fees, gas, tolls, city access licenses & permits, parking and guide fees.

Not Included:

  • Airfare
  • Any Taxi/Cab fare
  • Travel insurance*
  • Any Covid related expenses including testing, medical expenses or quarantine/isolation costs
  • Travel documents & fees: i.e. passport and visas (if required)
  • Any telephone, cell, data & internet usage (most hotels have free wifi)**
  • Items of a personal nature​
  • Travel-related expenses outside of the tour itinerary
  • Any food or beverage ordered by traveler that is not included in the above itinerary
  • Any taxes on personal items purchased
  • Optional tips to guides, staff or drivers

* We highly recommend purchasing trip insurance to protect your investment. This is to ensure that you are covered in the event of loss of deposit and cancellation fees, medical emergency or health expenses, personal accident, flight cancellation or delays and to protect your luggage against any loss or damage.​ ​​​​​​ ​

** There is free wifi at our accommodations


Dates: Choose your dates
8 Days/7 Nights

Where: Florence & Tuscan Countryside
Group size: No Maximum

Tour Cost: Starting at $3,595.00 USD per person/double occupancy

Tour can be modified.

Deposit: $1000.00 at time of booking to reserve your spot

Balance due: 60 Days Prior to Travel

Ask us about a payment plan

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