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Private & Small Group Cycling in Tuscany

Private · Italy

Cycling from Florence through Chianti to the Tuscan Coast

8 Days Tuscany

The Overview

Overview

Cycling holiday in Tuscany

We make your vacation easy and your experience active!

 

A Tuscan cycling vacation is what dreams are made of with the rolling hills and breath-taking views unforgettable little towns with some of the best food in Italy. On this tour you will see the best of both worlds we will take you to from the Tuscan hills to the Mediterranean sea .

 

The quiet, hilly roads of the Tuscan countryside offer beautiful terrain that will be enjoyed by both professional cyclists and beginners. Taste some of the best wines in the world. Explore the stunning scenery of this Italian region and enjoy the amazing photo opportunities that only a bike tour can provide. The fascinating, laid-back pace of Italy is how you can recenter and find complete euphoria on our Tuscany bike tour - a experience  you'll never forget.

Duration

8 days

7 nights

Pricing

On request

Tailored to your dates and group.

A Tuscan cycling vacation is what dreams are made of with the rolling hills and breath-taking views unforgettable little towns with some of the best food in Italy. On this tour you will see the best of both worlds we will take you to from the Tuscan hills to the Mediterranean sea .

Regions
Tuscany
Tour Style
Private
Departs From
Italy
Meeting Point
Florence
Included Meals
6 breakfasts · 3 dinners · 1 wine tasting
Day by day

Itinerary

Follow the route as you read. The map traces each day of the journey, moving with you from place to place.

Tuscany

Chapter 1 · Days 1–8

Welcome to Tuscany

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others. Food is prepared with seasonal…

Explore Tuscany
Day 1

Tuscany, Florence

Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner

  • Dinner
Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner — photo 1 Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner — photo 2 Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner — photo 3 Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner — photo 4 Arrival in Florence - Private Transfer to Hotel in Central Florence - Welcome Dinner — photo 5


Arrive in Florence, one of our English speaking drivers will greet you at the airport. A complimentary luxury car service will take you to your centrally located hotel. From here, you are perfectly positioned to explore the charming city of Florence at your leisure.

Where we meet Florence
Day 2

Tuscany, Florence

Private Walking Tour of Florence

Private Walking Tour of Florence — photo 1 Private Walking Tour of Florence — photo 2 Private Walking Tour of Florence — photo 3 Private Walking Tour of Florence — photo 4 Private Walking Tour of Florence — photo 5

Be sure to wear comfortable footwear today, for we will be doing a unique walking tour of Florence, following a delectable buffet breakfast at your hotel.

Our guide will meet this morning to take you to the Pitti Palace, the entrace to the Boboli Gardens, which are some of the most beautiful gardens in Europe and offer spectacular views over the entire city,  You won't want to miss a visit here and before setting out to ride the next day, through Tuscany, this will be a good opportunity to enjoy some of the most beautiful corners of Florence by foot! 

Following our visit of the Boboli gardens, you will have time to visit the Pitti Palace (home of the Medici family) as well as many of the major squares in Florence.  

Our guide will offer many top restaurant selections for lunch ( on your own ) and then,  in the later afternoon you will have time for shopping and exploring Florence on your own.

Dinner is on your own this evening, though we have many to restaurants in Florence, which we will be happy to share with you.  We always recommend reserving our top choices in advance, since dining options in Florence are ilmited and book up fast!

Overnight at your hotel in Florence. 

Day 3

Tuscany, Florence Tuscany, Chianti, Panzano in Chianti

Cycling Florence to Chianti 40 Km

  • Breakfast
Cycling Florence to Chianti 40 Km — photo 1 Cycling Florence to Chianti 40 Km — photo 2 Cycling Florence to Chianti 40 Km — photo 3

After an included breakfast this morning, we officially start our cycling adventure in Tuscany were you will meet your trip guide and have a safety and bike-fitting session.

 

At around 10: 00 we start our ride to our next hotel through the rolling hills of Tuscany we will be riding through the Chianti region, one of the most famous wine regions in the world. Throughout this ride you will be surrounded by vineyards and olive groves and enjoy stunning views of the Tuscan countryside.

 

Panzano in Chianti is the perfect stop for lunch on your own in a charming hill top town where you can find good restaurants, panoramic views and local artisans.

 

After Lunch we will head to our hotel in the quiet hills of Tuscany for a relaxing afternoon and a welcome drink before dinner at the hotel. 

Day 4

Tuscany, Chianti, Panzano in Chianti Tuscany, Siena

Chianti ride to Siena 51 km

  • Breakfast
Chianti ride to Siena 51 km — photo 1 Chianti ride to Siena 51 km — photo 2 Chianti ride to Siena 51 km — photo 3 Chianti ride to Siena 51 km — photo 4 Chianti ride to Siena 51 km — photo 5

After an included breakfast, our ride today takes us on a spectacular roads lined with vineyards, rolling hills, and beautiful landscapes that will satisfy all your efforts, with delicious stops on the way, where you can let yourself be captivated by typical products of this region of Tuscany.

 

After lunch on your own in the Chianti Senese region we will make our way toward Siena.

Siena is a hidden gem in the hills of Tuscany and is one of the most magical places in Tuscany. Siena is known for its fine wines, stunning architecture, and delicious cuisine. It is smaller than all the "big cities" in Italy, but has its own charm. 

 

Get to your centrally located hotel  and enjoy the afternoon exploring Siena. This evening you have the chance to have dinner on your own in one of the many fantastic local restaurants in town.

Day 5

Tuscany, Siena Tuscany, San Gimignano

Siena to San Gimignano

  • Breakfast
  • Dinner
  • Wine Tasting
Siena to San Gimignano — photo 1 Siena to San Gimignano — photo 2 Siena to San Gimignano — photo 3 Siena to San Gimignano — photo 4 Siena to San Gimignano — photo 5

Today, our ride starts leaving Siena and heading towards San Gimignano with an amazing rolling downhill. We will be cycling along some of the most beautiful quiet roads in Tuscany. 

We start with the famous "Via Francigena", which was used by medieval pilgrims on their way to Rome to receive the Pope's blessing.

You will cycle on roads with so much history and be able to marvel at the same unspoiled landscapes with views of vineyards and sunflower fields along the way.

.

 

After lunch on your own, in a amazing local restaurant that your guide will suggest to you. This afternoon we arrive in the town of San Gimignano. This medieval walled village is known as the city of a thousand towers.

San Gimignano has been declared a World Heritage Site by UNESCO. In the old times, there were over 58 towers that were built all over the city, each warranted by San Gimignano’s richest families, each trying to assert their power and wealth. This area was considered the vogue place of its period.

You will have many things see and do in this cute town.

This evening enjoy a luxury transfer to one of the most important wineries in this area. You will have a chance to enjoy a wine tasting surrounded by vineyards with amazing energy and a full-course Italian meal in pure bliss. 

Day 6

Tuscany, San Gimignano Tuscany, Volterra

San Gimigano to Volterra

  • Breakfast
San Gimigano to Volterra — photo 1 San Gimigano to Volterra — photo 2 San Gimigano to Volterra — photo 3 San Gimigano to Volterra — photo 4 San Gimigano to Volterra — photo 5

Today, we say goodbye to San Gimignano and start our ride to the ancient Etruscan city of Volterra. We will ride through an amazing work of art of wheat fields, olive trees, and sunflower fields.

We will reach the base of the majestic hill on which this amazing town is set. This climb will feel like the last stage of the Tour de France, and entering the gates of the old city center will feel like winning.

Volterra has so much to offer and is such an amazing picturesque town. Even before the Twilight TV series put this town on the map,this town feels like a leap into the past with as you will see by a stroll through the narrow, cobbled alleyways studded with Roman, Etruscan, and medieval buildings.

This town is a particularly rewarding destination for anyone looking to stock up on Tuscan art and handicrafts because of its legacy as an artisanal center, particularly for the cutting of alabaster.

Spend the afternoon exploring this picturesque hilltop town, which features many shops, restaurants, and alabaster boutiques.

Day 7

Tuscany, Volterra Tuscany, Livorno, Donoratico

Volterra to Bolgheri and Marina di Castagneto Carducci

  • Breakfast
  • Dinner

We will leave the majestic city of Volterra and travel along one of the most beautiful panoramic roads in Tuscany to the Tuscan coast of Costa degli Etruschi.Then we will cycle through the village of Casale Marittimo, with a beautiful view of the Tyrrhenian coast, after a long descent through typical Tuscan countryside.

Following, we'll bike into Bolgheri, which is renowned for its Viale dei Cipressi, a street lined with cypress trees that Giosuè Carducci immortalized in his poem "San Guido." A pause in Bolgheri is ideal for a stroll through the typical stores and restaurants in this tiny medieval village. You can sample the "Super Tuscans," a range of red wines that transformed the Italian winemaking business, in addition to the Bolgheri DOC wine.


After lunch we pedal down the lovely Strada del Vino, which is bordered by vineyards and cork trees. Out of all Italy's most renowned wine regions, this is its number one location.

The arrival location will be an amazing 5-star Tombolo Talasso hotel owned by the Antinori family right on the Mediterranean Sea. This hotel is well-known for its amazing spa and thalassotherapy treatments. You will have time this afternoon to swim in the sea and explore this breathtaking sea side area.  

With a fun farewell dinner in one of our beachfront restaurants, we will celebrate and reminisce all of our adventures together.

Day 8

Tuscany, Livorno, Marina di Castagneto Carducci Lazio, Rome

Transfer from Hotel to Rail Station - Option to Continue Tour

  • Breakfast
Transfer from Hotel to Rail Station - Option to Continue Tour — photo 1 Transfer from Hotel to Rail Station - Option to Continue Tour — photo 2 Transfer from Hotel to Rail Station - Option to Continue Tour — photo 3 Transfer from Hotel to Rail Station - Option to Continue Tour — photo 4 Transfer from Hotel to Rail Station - Option to Continue Tour — photo 5

 After breakfast at the hotel, it's time to say goodbye with memories and stories that will remain with you forever. From here, you can get a transfer to the airport or continue your journey with us in Italy.  

The details

Inclusions & Exclusions

What's Included

  • Fully customizable bike-tour
  • Hybrid E-BIKE (POWER-ASSISTED)
  • Road E-BIKE (POWER-ASSISTED)
  • Luggage Transportation
  • Ride with GPS and Daily Route Notes
  • Welcome Reception
  • Custom Bike and Helmet

What's Not Included

  • Food and beverages not mentioned in the program
  • Gratuities of any type
  • Italy hotel tourist tax (must be paid locally at hotel)
  • Personal Expenses or Extras at hotels
In their words

Traveler Reviews

Emily and David Davison Travelled with us

My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She planned the perfect trip with excellent private guides at all of our sites, professional drivers and lovely hotels. We arrived in Italy with all of our train and ferry reservations made by Ele, with tickets in hand. She was in touch with us daily throughout our trip to make sure that things were going smoothly. She was able to make a few changes to our itinerary as needed. We look forward to working with Ele again on our next trip and have put her in touch with another family member to help plan their trip as well.

Ron and Deb Crosby Travelled with us

Dear Guiseppe and Jesse,

We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future.

Hotels

1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were part of their family. I would recommend it to anyone and would specifically ask for it if we were to make a return visit.

2. Hotel La Baia in Monterosso was nice and it's location was very good especially for us older folks humping luggage from/to the train station.

3. Hotel Lucchesi in Florence- what can I say expect FANTASTIC. The rooftop view at sunset is well worth it. Again very friendly and helpful staff. Would recommend it to everyone.

Wine Tour

Money well spent. We had a great time overall. The driver Mario was OUTSTANDING. He had lots of local knowledge as well as about winemaking. USE HIM AGAIN!!!

The various wineries we visited on tour:

Altesino- fantastic and they were not cheap on their pouring. Great experience.

Azienda Agricola Patrizia Cencion Sloaria- Again a great tour by one of the owner's daughters. We felt like we were the only thing on their mind although there were other customers there. A great way to complete the day.

Again we had a fantastic time and are very appreciative of everything you booked for us. We wish you continued success and if our travels should bring us back to Italy, we know who to call.

Leon and Michele Travelled with us

The trip was great we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.

Bob & Sandy Travelled with us

Jesse & Giuseppe,

Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.

Where you are

Location

Italy Italy

Italy and beyond

8 days through Italy, with every stop chosen by the people who live here.

Where we meet

Florence

Where it starts

Italy

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Good to know

Frequently Asked Questions

Is this a private tour, or will we join a group?

Private. You travel with your own guide and driver, and the only people on the itinerary are the ones you bring with you. Nothing is shared with strangers, and the pace of each day is yours to set.

Can the itinerary be changed to suit us?

Yes. What you see here is a starting point, not a fixed departure. Tell us how long you have, what you love and what you would rather skip, and we will reshape it around you. A slower morning, an extra night somewhere you fell for, a different region entirely.

How do we start planning?

Send us a note using the form on this page, or call us on 1-866-779-2565. A travel specialist replies within one business day, usually with a few questions of their own. There is no cost and no obligation in asking.

When should we book?

The earlier the better, particularly for travel between May and September, when the best small hotels and the guides worth having are taken first. That said, we have put together beautiful trips at short notice, so ask and we will tell you honestly what is still possible for your dates.

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8 days · Pricing on request

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