11 Days/10 Nights, 6-12 travelers per departure – NOW booking 2027 dates!
It’s your time to rediscover the simple pleasures of life, while enjoying a stress-free vacation on our Tuscany Italy tour. Starting and ending in Florence, you’ll spend 3 nights in the city. Enjoy private walking tours in Florence, including priority access to see Michelangelo’s David at the Galleria dell’Accademia.
Then, make yourself at home in a beautiful Tuscan villa hotel for a whole week. From there, take day trips in executive Mercedes vans to explore surrounding Tuscany countryside, including Siena & San Gimignano, the Chianti wine district, Montepulciano, Pienza, Cortona, and many more.
The region of Tuscany is full of amazing and unique historical and cultural sites. And just as rich as its history and culture is the food and wine that’s offered there!
Cooking class & lunch in a 13th-century castle – roll up your sleeves to prepare authentic Tuscan dishes in a historic castle kitchen.
Guided culinary tour in Florence – taste artisanal cheeses, cured meats, olive oils, and sweet treats while discovering the city’s food culture.
Private wine tastings – sample world-renowned Tuscan wines in atmospheric cellars and panoramic vineyards.
Farm-to-table dining – enjoy meals crafted with fresh, seasonal ingredients that reflect Tuscany’s rich culinary traditions.
Regional specialties – from hand-made pasta to rustic breads and olive oils, experience the flavors that define Tuscan cuisine.
Intimate Group Size: Limited to just 6–12 travelers, this tour provides a relaxed pace, deeper access, and personal attention that larger groups simply can’t provide. (Learn why group size makes such a difference.)
Luxury & Ease: Travel in comfort via Mercedes executive vans, enjoy priority access to top sights, and stay in hand-selected boutique hotels.
Authentic Immersion: Go beyond the usual—cook pasta in a centuries-old castle kitchen, sip wine in panoramic piazzas, and connect with Italy through its people, food, and traditions.
White-Glove Service: A full-time English-speaking journey leader, private drivers, and zero-stress logistics let you focus fully on the experience. The tour includes most meals, local tips, taxes, gratuities, and special extras like return-traveler credits.
When you want to experience the absolute best that Italy has to offer, trust no other than Nada’s Italy. Our professional, fully escorted tours through Italy is only limited to 6-12 travelers, allowing us to create an intimate experience you can’t find anywhere else. To learn more about our tours, call us today at 877-959-8365 or inquire for the date you’re interested in to the right!
👉 Have more questions about our tours in general? Check out these Frequently Asked Questions.
Florence
Tuscany
Siena
San Gimignano
Montepulciano
Pienza
Cortona
Welcome to Italia! Tonight you will rest in a beautifully restored palazzo, now a luxury boutique hotel, in the historical heart of Florence and relax after a long trip overseas. You can regain your energies tonight and start the trip of a lifetime in one of the world’s most beautiful cities!
No meals included
Meet in the lobby in the morning and enjoy an orientation tour through the historical streets of Florence, guided by your expert local guide who will show you the main sites, churches, and shopping areas that Florence is known for. Enjoy lunch on your own.
Before we make our way to the Tuscan countryside, we’ll stop on one of the side-hills of Florence from where you can enjoy the most breathtaking view of the Renaissance city. Later, we’ll arrive on the scenic property of a beautiful local Tuscan Villa Hotel (50 min. drive from Florence) surrounded by cypress trees, vineyards, and olive groves. After our arrival, you’ll be able to enjoy some free time to relax, have a glass of vino, water, unpack, walk, take a power nap, explore the grounds, and freshen up. In other words make yourself at home in Tuscany. Benvenuto dinner in the property.
Meals included: breakfast, dinner
You’ll take your first peak into the Italian lifestyle in a small sleepy village in Umbria: Castiglione del Lago by Lake Trasimeno. Visit the various deli’s and specialty gourmet shops, enjoy a typical Italian Sunday morning seeing families come out to greet their neighbors and stretch out with their morning “passeggiata” (stroll). Group lunch in a historical trattoria.
Then to Cortona, the charming Etruscan hilltop village where “Under the Tuscan Sun” was filmed. Its massive 3,000-year-old walls are still standing! Enjoy some free time and have a gelato as you mingle with the locals, explore the intricate alley ways, picturesque views of the countryside, or sit back at a coffee shop.
Group meets in Piazza della Repubblica to return to the Villa. Stop on the way for your group dinner in an oldest family-owned locanda with some traditional Tuscan dishes.
Meals included: breakfast, lunch, dinner
Today is a super-fun day where you’ll have the chance to take part in a special hands-on cooking class by a local Chef, as he shows you how to make some simple Tuscan recipes that we’ll enjoy for lunch. Enjoy a relaxing afternoon on your own at the Villa or a quiet walk in nature (the property offers several panoramic hiking trails). We’ll then have a group dinner at a nearby family-owned Pizzeria for a fun, casual, fresh, piping-hot pizza!!
Meals included: breakfast, lunch, dinner
San Gimignano, our first stop, is an absolutely astonishing example of a walled Medieval hilltop town, also known for its dry white wine, Vernaccia and its colorful local crafts: hand-painted pottery, alabaster, olive wood items, and much more. Enjoy plenty of free time and lunch on your own.
After lunch we will drive to amazing Siena, where a local guide will meet us and give us a true “insider’s tour” of the city: she’ll tell us about the Sienese peculiar lifestyle, taking us through hidden parts of the city and pointing out things most tourists don’t know about! You will also have free time to explore the town and visit its amazing Cathedral. Group dinner in a typical local restaurant. Delizioso!
Meals included: breakfast, dinner
Enjoy a relaxing morning at the villa to spend at your leisure. Enjoy a glass of wine & book under the trees…or relax by the pool and gardens. This is your slice of La Dolce Vita!
In the afternoon, we’ll depart for more wine and cooking again! We will experience another fun group cooking lesson by a local chef (participation is optional). Bring your aprons to the old kitchen and learn to make fresh pasta! Group dinner after the cooking class with a wine tasting.
Meals included: breakfast, dinner
Our first stop is one of Tuscany’s most charming villages, Pienza, the drive alone offers some of the most stunning views of the countryside. Pienza was built as the ideal Renaissance city by Pope Pius II who “remodeled” it according to his taste. Lunch in a small family-owned trattoria, and then enjoy some free time in this fairytale-like community.
Our next stop is the region’s highest hilltop town: Montepulciano, land of the Vino Nobile (“the noblemen’s wine”). Group walk through town, stopping for a visit at an ancient wine cellar. We meet at the Porta al Prato (large brick archway at bottom of hill), our final stop of the day will be for a delicious dinner made with farm-fresh ingredients and wines included. Buon Appetito!
Meals included: breakfast, lunch, dinner
Drive to the nearby Greve in Chianti (only 15 minute drive) where we’ll have some free time to shop and explore. Shortly afterwards, we will have panoramic drive through the heart of the oldest part of the Chianti Classico hills. We’ll make a quick stop in the amazingly small and uniquely charming Montefioralle to walk around and explore. Then we’ll visit an historic wine estate, with a private tour of the beautiful wine cellars, followed by group lunch paired with wines.
Once we return, you’ll have a little free time before our last group dinner, at the Villa. Please reserve some time after dinner to prepare your luggage for morning checkout.
Meals included: breakfast, lunch, dinner
We transfer back to Florence in the morning. At our arrival, a local guide will meet you in the lobby for a private tour of the Galleria dell’Accademia to see Michelangelo’s David up close and personal. And right after that, we will take a nice walking tour through the street of the cradle of the Renaissance! Dinner will be on your own tonight.
Meals included: breakfast
You can shop around Florence or.. take a day trip to Rome or Venice! Enjoy a day of total freedom in one of the world’s most beautiful cities or easily take day trips to other areas by train, as Florence is centrally located. Ask us for recommendations on activities in Florence or other day-trips you can take from here. Tonight will be your last night of the tour so make it special!
Meals included: breakfast
Hopefully, you can stay longer in this gorgeous country and explore other regions. Nada’s Italy wishes to have you back and experience more parts of this colorful culture! Until next time, beautiful ITALIA says Ciao!
Meals included: breakfast
Small group travel: maximum of 12 travelers per group!
Fully escorted day trips with a full-time English-speaking Tour Leader and professional private drivers.
Meals included: all breakfasts, some lunches and dinners (included meals are shown at bottom of each day’s itinerary.)
Beverages included: bottled water, soft drinks, coffee, and 2 glasses of wine per meal (choice of red or white wine).
Private Walking Tours by licensed English-speaking City Guides, including PRIORITY entrance & tickets to attractions.
Private Transportation for day trips and transfers in comfortable air-conditioned Mercedes Executive vans (does not include: transfer from and to the airport, airfare, or any other personal travel expenses).
A+ Rated Customer Service with Nada’s Italy you can rest assured that your travel experience will be completely stress-free. Your personal Journey Coordinator will assist you with any additional services you may need, provide expert packing and travel advice, and answer any questions you may have before your trip.
Return Traveler Program: receive up to $800 credit per person towards any future trips you take with Nada’s Italy!
No bag limit (many tour companies have a 1-bag limit per person).
Taxes & Fees: Local VAT taxes and government fees, City Tax, gas, highway tolls, city access licenses and permits, parking fees.
Book an extra night at the same hotel before or after your tour.
Private luxury vehicle transfer with English-speaking driver.
Add a few extra days prior to or after your tour, tailored to your needs.
We work with a wholesale airfare broker who will search for lower-than-published fares for First, Business, or Premium Economy classes.
We work with a trusted insurance broker who will help protect your trip.
Indulge in the laid-back and luxurious Tuscan lifestyle. The perfect Tuscan villa hotel experience awaits.
"Wow, just returned from the Florence & Tuscany tour and am so enchanted by that region. This tour gave us a solid immersion in the history, culture, significance, foods , and wines of this incredible area. Roberto, our tour guide was full of insider information, customs, etc. He was everything you could ask for is a tour guide, and a great guy to know! The food, oh my ……the food!!!!! So delicious, we had so many dishes we had never even heard of before, as well as the best quality of food I have ever eaten. Great choices in venues. Lastly, the wines…..I am convinced you cannot get a bad wine in Tuscany, each more delicious than the next. If you want to truly experience this important region, do yourself a favor and sign up with a Nada’s Italy tour, you won’t be disappointed. They have set up the perfect way to experience Tuscany. Well worth the time and money."
"I couldn’t possibly say enough amazing things about every single member Nada’s Italy team and everyone associated with our two week, Italian vacation!! From the private drivers to the tour guides to the hotel concierge and the cleaning staff ……..absolutely first rate ..,..five star all the way!! My husband and I could not have ever even imagined the incredible experience that we were going to have! Thank you Nada’s for the trip of a lifetime!!!"
"I'll never travel to Italy without Nada's Italy!!! Wow wow wow! What a great experience. From start to finish, Nada's took care of everything and my entire trip was worry-free. Enzo, our journey director was fabulous!!!! He took care of all details of our dinners, and day excursions, everything went perfectly smooth. I cannot recommend this company enough. Worth every penny!!!!"
