Tuscany in the Fall 2025

1/11

Tuscany in the Fall 2025

8 Days, Florence, San Gimignano, Certaldo Alto, Volterra, Siena

Oct 1 - Oct 8, 2025

Italy

About this Trip

In Tuscany, you'll experience enchanting landscapes, from rolling vineyards to picturesque hillsides. Immerse yourself in the region's storied history as you explore medieval towns and Renaissance art. Indulge as you visit 5 surrounding cities and delight in the world-renowned Tuscan cuisine, where fresh, local ingredients transform into culinary masterpieces.

Upon returning home, you'll carry a sense of tranquility and rejuvenation from your time in Tuscany. The memories of captivating landscapes, cultural immersion, and culinary delights will linger, offering a lasting source of inspiration and relaxation.

From the Trip Host

My name is Valerie and I am a Tour Operator in Tuscany, Italy where I have been living & working part-time for the past 12 years. The Tuscan Lifestyle & Culture are incredible and it's my passion to deliver it to you through our tour. Hosting from our Chianti Villa & sharing the famous historic locations will be an experience of a lifetime. I can't wait to share it all with you!

Andiamo!!

Valerie

Airport Transfers - Pick up and drop off at Florence Airport (FLR)
Transportation - All transportation included throughout
7 Nights Accomodation - Accomodation details in itinerary
7 breakfasts - Prepared by Private Italian Chef
7 Dinners - Prepared by Private Italian Chef
Cocktail Parties + Prosecco Toasts
Unlimited Wine and Italian Cocktails
Authentic Italian Cooking Class
Tour Highlights - The Duomo of Florence •⁠ ⁠The Ponte Vecchio in Florence •⁠ ⁠Visit to the Uffizi Museum (one of the largest and best-known museums in the world) •⁠ Visit to Andrea Bocelli’s Officine Café and private museum
More Tour Highlights - This Art-Nouveau villa is set on a hill and overlooking the Tuscan countryside surrounded by vineyards and olive groves in the Chianti region.
All Activities Included - Please see detailed itinerary

Trip Itinerary

Arrival

Benvenuto! - Airport Pickup from Florence Airport at 11am or 2pm
Check-in opens at 3pm
Evening Reception
Italian Cocktail Party
Dinner at Villa

Activities

Upon your arrival at Florence Airport, our team will be there to greet you and provide transportation to the Villa. Check-in opens at 3pm, allowing you time to settle in and get acquainted with your surroundings. Later in the evening, join us for a warm welcome reception, and Italian Cocktail Party, followed by a delightful dinner served at the Villa.

Florence Exploration

Breakfast
Day Trip to Florence
Visit Uffizi gallery or Guided tour into iconic Duomo, Cathedral & Baptistery
Dinner at Villa

Activities

Start your morning with a nourishing breakfast at the Villa. We will then embark on a day trip to Florence, where you'll have the opportunity to immerse yourself in the rich cultural heritage of this historic city. Highlights include the choice to explore the renowned Uffizi gallery, showcasing masterpieces of Renaissance art or to enjoy a guided tour into the historic city center buildings of the iconic Duomo, Cathedral & Baptistery. You’ll have some time on your own as well to walk around the historical part of town, shop around and enjoy everything the city has to offer. We'll return to the Villa and meet for a delicious dinner all together.

San Gimignano

Breakfast
Departure for San Gimignano
Return to Villa
Dinner and Cocktails

Activities

Rise early for a wholesome breakfast before setting out on a luxury tour bus to San Gimignano for a group, mini walking tour to learn about the city as well as the options to visit during free time (Medieval Cathedral, art museums, artisan shops & World’s Best Gelato). venture to the medieval hill town of San Gimignano, often referred to as the "Town of Fine Towers." Famous for its 14 preserved tower houses, San Gimignano offers a glimpse into Tuscany’s medieval past. Stroll through the bustling Piazza della Cisterna, visit the Collegiata di San Gimignano to see frescoes, and climb one of the towers for stunning views. Sample the town’s renowned “World’s Best Gelato”. In the evening, gather for an authentic italian dinner.

Certaldo Alto

Breakfast
Departure for Certaldo Alto
Tour of Medieval Town
Return for dinner at Villa

Activities

Awaken and enjoy a nourishing breakfast at the Villa. Today, we head to our local Medieval town called Certaldo Alto, home of Renaissance writer, Boccaccio. Tour the historic buildings with original artifacts to step back in time.

We return to the villa for an authentic italian dinner with wine pairing.

Time at the Villa and Cooking Workshop (Resting Day)

Optional Yoga session
Breakfast
(Optional) Massages
Cooking Class with our Private Chef and Staff
Two different pastas
Desert
Dinner at Villa

Activities

Start your day with an optional morning yoga session. Breakfast will be served promptly after the class. Today is our rest day at the villa. This is a great day for a full body massage at the villa, this will be coordinated with the group. A charcuterie board lunch will be provided followed by a special cooking class lead by our very own private chef and our staff. Together we will cook 2 different pastas with 2 different sauces. We will also prepare dessert. Dinner will be served at the villa.

Cultural Excursion to Volterra

Breakfast
Day Trip to Volterra
Guided Walking Tour
Alabastor Carving Demonstration
Lunch in Volterra
Dinner at Villa

Activities

Begin your day with breakfast Enjoy a leisurely breakfast at the Villa before embarking on a cultural excursion to Volterra, an ancient hilltop town steeped in history. Explore the city with the Volterra Pass, allowing access to its fascinating landmarks and main attractions. Tour the
Etruscan city of Volterra, from the movie, "Twilight". Have a walking tour and learn about their Alabastor history and carving. After free time, we head to the town of Andrea Bocelli. We will have a Prosecco toast in the Bocelli Cafe and then tour his private museum.

We'll return to the Villa for a chef's dinner with wine pairing.

Discover Siena

Optional Yoga Session
Breakfast at the Villa
Visit to Siena
Last Dinner at the Villa

Activities

Begin your day with a revitalizing yoga session followed by breakfast. We will then begin our departure to Siena.

Siena is a historic city in Tuscany, Italy, renowned for its medieval architecture, art, and vibrant cultural heritage. It is famous for its well-preserved city center, the Piazza del Campo, which hosts the annual Palio horse race. Siena's Gothic cathedral, the Duomo, and its narrow, winding streets reflect its rich history, making it a UNESCO World Heritage Site. We will have a guided historic walking tour including the Palio Arena and the Grand Cathedral built in the 1200s.

We will return to the villa for the evening’s farewell dinner.