Italy, Tuscany – Best of Tuscany
From $5650pp
Please note that prices are indicative only, subject to availability for your travel dates and the exchange rate.-
Duration
8 Days -
Travel Style
Food & Wine Shared Day Tours Small Group Villa Stay -
Product Code
ITCORTAFW2
If you're a first time visitor to Tuscany, and wanting to tick off the main attractions of the region here is the perfect solution.
Stay a week in a typical Tuscan villa and make easy day trips into the countryside to see the ancient hilltop villages and beautiful countryside that you've seen in pictures and on TV! You'll have a driver/guide with you so there's no need to worry about navigating roads or finding your way.
The itinerary ensures you see the best of your surrounds in a relaxed and enjoyable way, with plenty to keep the taste buds happy too.
For no less than 7 nights, you’ll get to experience a Tuscan farmhouse villa complete with your own single, double, or triple bedroom apartment and a luxurious pool that can be enjoyed throughout your stay.
With a first-hand look at some of the most vibrant and traditional locations in Tuscany, from Cortona to Siena, you’ll have the opportunity to indulge in the finest wines, partake of the local cuisine and even stimulate your culinary skills with a 4 course cooking lesson.
Arrival
You will be met on arrival to the Cortona train station and transferred to your accommodation. There’s time to settle in and familiarise yourself with your new surroundings which will be ‘home’ for the next 7 days.
Dinner in Cortona.
Overnight Cortona
Meals D
Cortona
To get the first full day of your stay off to an exciting start, we’ll head into the nearby town of Cortona; where we have plenty of things for you to see and do! Our enthusiastic tour guide will take you on an enjoyable walk of the town, with coffee included.
To integrate you with the Tuscan lifestyle, you’ll experience lunch at a local trattoria. With your stomach full, you’ll have the opportunity to sit and relax to your heart’s content or explore the town in greater detail.
Mid-afternoon you can either return to your apartment, or stay in Cortona. Later this evening everyone with meet up for dinner. What better way to savour the flavours of Cortona than with a traditional aperitivo in the Piazza, followed by dinner!
Overnight Cortona
Meals B, Coffee, L, D
Siena & San Gimignano
San Gimignano is a town so iconic that you have to see it to truly believe it – and this is where we’ll be headed at 9am. Upon arrival we’ll have a brief coffee break and you will be given an overview of the town and its rich history.
Shortly after your introduction, you’ll have free time to explore, meet some locals and partake in activities at your own leisure.
It will then be time to travel to nearby Siena, where you’ll meet your tour guide who will fill you with knowledge, expose you to the traditional lifestyle and offer an understanding of the town first-hand.
Again you’ll have some free time here before enjoying an evening meal at a local restaurant in Siena.
Overnight Cortona
Meals B, D
Lazy Morning & Cooking Class
For fans of cooking, today you’ll be introduced to the art of making Italian cuisine. You’ll have the opportunity to enhance your culinary skills with a Traditional Tuscan Cooking Class where you’ll prepare 4 courses and then enjoy eating with the chef.
The remainder of the day is free.
Overnight Cortona
Meals B, L
Montepulciano & Pienza
Featuring 15th Century architecture, Pienza is today’s first village visit. It’s as stunning as it is traditional. Enjoy a quick break for coffee, before taking some time to explore the town in greater detail. Pienza is undoubtedly one the most romantic destinations in Tuscany, where you’ll find streets with evocative names such as Via del Bacio (Street of the kiss) and Via dell’Amore (Street of Love).
At 12:30pm, you’ll transfer to Montepulciano for a lunch and wine tasting – which takes place in a traditional underground cellar. You’ll then have some free time to enjoy the village. With views as intoxicating as its “noble” red wine, the delightful walled hilltop town is well worth the climb. Especially for its main square (an absolute must for “Twilight” fans) and the elegant Renaissance palaces and churches.
At 5pm, return to your accommodation where you can unwind for a couple of hours before dinner.
Your visit to Tuscany wouldn’t be complete without an authentic pizza, so tonight it’s time for some!
Meals B, Coffee, T (wine), L, D
Chianti
This morning we have an exciting tour of Chianti planned. En-route there will be a stop in Castellina for a coffee following with an opportunity to explore the town and all it has to offer.
Castellina is an ancient town of just under 3,000 people, located in the picture-perfect wine-famous Chianti Hills. The many wonderful sights include the imposing 14th-century Rocca (Fortress), offering spectacular views of the town and surrounding countryside, the 16th-century San Salvatore church and the Via delle Volte medieval arched passageway. Just outside of town are the pre-Roman Etruscan burial tombs of Monte Calvario and the Necropolis of Poggino.
An extended lunch and tasting session is planned at an exquisite organic winery, where there will be the opportunity to meet the winemakers.
Later in the afternoon, return to base.
Overnight Cortona
Meals B, T (wines), L
Tour-Free Day
As your trip slowly comes to an end, we allocate this time for you to choose the types of activities that you’d like to partake in – from exploring the nearby area, to relaxing by the pool.
Whatever you choose to do, we’ll ensure that you’re back in time for a traditional Italian Aperitivo, followed by a farewell dinner to mark your visit.
Overnight Cortona
Meals B, D
Departure
After a leisurely breakfast, we transfer you to the local train station for your departure.
Meals B
Inclusions
-
Seven nights’ in a Tuscan villa (traditional farmhouse complete with modern amenities)
-
Bilingual hosts & tours leaders throughout your stay
-
Breakfast daily – provisions provided
-
Three unique lunches
-
Six dinners at a local Trattoria, wine is included
-
Guided walks in Cortona and Siena
-
Cooking session with fresh, locally sourced ingredients
-
Wine tasting at selected vineyards/establishments
-
All necessary travel to & from your accommodation
-
Transfers to Cortona or train station on tour free days
-
Arrival & departure transfers
Accommodation
-
Located nearby the historical centre of Cortona and set on wonderful grounds which include a swimming pool
-
The apartments within the villa comprise one/two/three bedrooms, living area, kitchen, bathroom and laundry facilities, comprising
-
Air-conditioning and wifi.
-
Your villa provides everything required for a truly memorable Tuscan escape.
-
Located in the valley approximately 10km from the historical centre of Cortona, the accommodations, which are restored Tuscan farmhouses with old world rustic charm, become home base for the duration of the tour, allowing you to settle into your own private apartment and commence your Tuscan experience.
Departure Dates
3 May 2025
24 May 2025
31 May 2025
7 June 2025
14 June 2025
21 June 2025
5 July 2025
12 July 2025
26 July 2025
23 August 2025
30 August 2025
27 September 2025
11 October 2025
If you are looking to travel in 2026, contact us for dates
Please note that prices are indicative only, subject to availability for your travel dates and the exchange rate.Pricing
$5650 per person
based on twin/double share
Add $750
for a single room
Please note that prices are indicative only, subject to availability for your travel dates and the exchange rate.Can’t Find Exactly What You Want?
Not a problem! Think of what you see here as a starting point.
You can change anything you wish about this itinerary, from the duration, to the accommodation and the included activities.
You can even combine two different trips or turn them into a self-drive holiday!
Just click the button below, tell us what you have in mind, and we will design your perfect itinerary.
Personalise This Itinerary