Private tour in Florence Massimo C

Highlights of Montalcino, Pienza and Montepulciano

5.0

(7) reviews

-
Hours icon 9 hours
Private transportation
Private tour for 1-5 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 9 hours
Private transportation
Private tour for 1-5 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later

Massimo C.

4.9

Guide rating

307

Reviews

Tours delivered

16 hrs

Avg. response time

Hello, I'm Massimo, your friendly neighborhood driver-guide based in the stunning city of Florence. I specialize in custom escorted travels across Tuscany and Italy for very small groups, chauffeuring you around in my comfy, air-conditioned Mercedes-Benz. Think of me as your personal Italian superhero, minus the cape! I organize private shore excursions from the ports of Livorno or La Spezia, and day tours from the main Tuscan cities. We’re talking wine tours, cooking classes, outlet shopping sprees—pretty much any kind of customized tour you can imagine. Because I work with smaller groups, I can give you the VIP treatment that makes your Tuscan adventure unforgettable. Just a heads-up, though: I don't do full walking tours or guided museum visits. My superpowers have limits! As your chauffeur, interpreter, and travel consultant, I'll help you pick the best sights, optimize your time, and tweak plans on the fly to match your whims. I’ll also point you to the best restaurants and shopping spots, ensuring you get exactly what you're looking for from your trip—whether it's fun, culture, landscapes, shopping, or delicious food. I’m basically your all-in-one travel genie, minus the lamp. In my secret identity as a travel agent, I can book your accommodations and arrange smooth transfers from any Italian location to Tuscany and back. I also offer pre- and post-cruise packages, all-inclusive tours of Italy, and private transfers to France, Austria, Switzerland, and beyond. I’m like the Swiss Army knife of travel! I'll be there to attend to your needs at all times, not only navigating and handling logistics but also introducing you to friendly locals and hidden gems. This is a unique and genuine travel experience that group tours just can't offer. With such tranquility and charm, it's no surprise that so many famous artists, poets, and musicians have been drawn to Tuscany and Italy. Can't wait to share an amazing journey with you. Arrivederci and ciao for now! - Licensed professional driver (Ncc) - Tourist guide ("Accompagnatore turistico", Certificate issued by Provincia di Firenze in 2001) - From 1992 to 2000, Tour manager for an Italian Tour Operator in many countries around the world. - Licensed Travel Agent since 2001 I am a driver-guide only, and I will not be able to accompany you on some portions of the tour which require long walking. The parts of the itinerary denoted by * will be un-guided, so after my introduction you will be able to explore the area on your own

Have a question or want to customize this tour? Message Massimo C.

Overview of your Florence tour

I love this area so I'm the right person for take you there! Leave in the morning and after about 1 hour transfer we reach the characteristic town of Montepulciano. Built in 1500 along a narrow ridge of limestone, well known all over the world for its imposing Renaissance palaces and mostly for the Vino Nobile, one of the most appreciated Tuscan wines all over the world. After my main explanations enjoy some free time on your own. Next stop: Pienza. This is one of the most beautiful Tuscan towns, rare example of Renaissance architecture brought to completion. Enjoy my explanations and after have some free time for lunch and relax. In early afternoon we'll continue through enchanting landscapes to reach Montalcino, famous throughout the world especially for the origin of one of the finest wines in the world: Brunello di Montalcino. Perched on a hill on which the mighty fourteenth century fortress rises still today. Free time for visits, after we'll go to a top winery to taste the famous Brunello wine.

Recent Reviews

Ricardo R.United States
April 2025

A wonderful time visiting this lovely region of Tuscany. Massimo was a perfect guide with an excellent combination of knowledge about the region and Italy. Great sense of humor. Provided us the flexibility we wanted. Highly recommended.

Ashley L.United States
June 2024

Did a Tuscany day tour from Florence. Massimo was super friendly, provided lots of educational information and was very flexible with the schedule for the day and has great recommendations. Great to talk to during the long drive from Florence to Montalcino. Made the day stress free and fun! The winery we visited was beautiful. We visited it first so was less busy. Would definitely use him again for a future tour.

Barbara M.Canada
April 2024

Our second day with Massimo didn't disappoint! Massimo was an excellent driver, extremely personably and very knowledgeable. Always made sure to answer any questions, stopped when we wanted pictures and made sure that everyone was engaged. Highly recommend!

Jerry G.United States
April 2024

Massimo was excellent. He made all people in our party happy (not easy to do). I would definitely recommend him.

Kathleen F.United States
October 2018

Massimo was extremely personable and knowledgeable. Great tour!

Bill C.United States
July 2018

Massimo and this tour was a true highlight of the trip. Our kids loved him and he tweaked the trip real time to give them and is an amazing experience. Definitely did not feel "standard"...was unique and fun.

Your Florence tour itinerary

• Val D' Orcia area (declared Unesco World Heritage Site). • Montepulciano, beautiful Renaissance hilltown, which still adheres to its medieval plan, is embedded in a picture-postcard landscape. • Pienza, a fifteenth-century town built around 1459, surrounded by vineyards and rolling hills. Called the 'ideal city' because shaped by an ambitious man: Pope Pius II whose aim was to transform his birthplace into the ideal Renaissance town. • Montalcino, a medieval small town completely encircled by fortified walls. Renowned for its world-famous wine Brunello di Montalcino, is really a must when in Val D'Orcia. If you have any special interests or wishes, I will be happy to customize this tour for you!

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Private Transportation / Category: Minivan

Mercedes-Benz class V

What's included
Private Guide
Private Transportation
What's not included
Other: The price is for up to 5 people. There is a surcharge for groups larger than five. Please ask
Food Drinks Snacks
Tickets
Meeting location

Florence, Tuscany, Italy

At your accommodation in Florence

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Architecture
History
Layover
Food And Drink
Tour reference number
4652
Languages
Italian
English
Activity level
Light
Accessibility
Kid Friendly

Traveller reviews

5.0

FAQs

Who is this private tour in Florence best suited for?

This private tour is perfect for travellers who want to explore the beautiful Tuscan towns of Montalcino, Pienza, and Montepulciano with a knowledgeable local guide. It's ideal for those interested in Renaissance architecture, world-famous wines like Brunello di Montalcino and Vino Nobile, and picturesque landscapes. The tour is also kid-friendly, making it suitable for families.

Can this private tour in Florence be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What languages is this tour offered in?

What's included in this private tour, and what should I budget for separately?

Is this a private tour? What is the maximum group size and the starting price?

AI-generated. Please confirm details with your guide

-
Hours icon 9 hours
Private transportation
Private tour for 1-5 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 9 hours
Private transportation
Private tour for 1-5 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
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