Cycle Tuscany & Chianti

(20 reviews)

From:

CAD $3675

8 Days

Best Rate: Guarantee

Trip Type: Small Group

Activity Level: Average

Explore the rolling hills and olive groves of Tuscany on this eight-day cycling adventure from Florence to Pisa. Cycle through small, traditional villages backdropped by mountain views in Barga, then ride the pulsing streets of Pisa to the famed lopsided tower.

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Price based on per person in Double Room for departure 24 Apr 2027

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Experience Overview

Explore the rolling hills and olive groves of Tuscany and Chianti on this eight-day cycling adventure from Florence to Pisa. Cycle through small, medieval villages backdropped by mountain views in Chianti and the Crete Senesi region, then ride the pulsing streets of Pisa to the famed lopsided tower. Trace the ancient Via Lauretana, ride along part of an ancient pilgrimage route on Via Francigena and wind through the white roads and clay dunes of the Strade Bianche. With stops in stunning Siena, UNESCO World Heritage-listed San Gimignano and Lucca, you’ll have ample time for bowls of pasta and glasses of Chianti to wind down after rewarding days on the saddle.

Highlights

Ride the Strade Bianche, Tuscany’s famous white gravel roads that are the namesake of the annual cycling race. On the way, pass through the famous white clay dunes known as ‘biancane’.
Cycle in the footsteps of pilgrims along the historic Via Francigena – part of the ancient route from Canterbury to Rome – taking in vistas of vineyards and oak forests along the way.
See the contrasting landscapes of the famous Chianti wine region and the broader Tuscan countryside from your unique vantage point on two wheels. Plus, do some exploring on foot – weave through Florence’s bustling streets and wander the quiet cobblestone lanes of San Gimignano by night.
Spend two nights in stunning Siena – the medieval hilltop town with a historic rivalry with Florence – and venture into the striking landscapes of the Crete Senesi, full of shifting colours and dramatic hills.
Follow the Serchio River by bike from Lucca to the world-famous Leaning Tower of Pisa. Snap a classic photo in front of the tower or settle in at the best local cafe for some people-watching.

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Trip Details

Product Code: 3279

Tour Type: Small Group

Accommodation: Moderate

Transport: Bicycle (e-bike option available, subject to availability), Support vehicle, Local bus

Guide Language: English

Travel Styles: Cycling, Budget

Tour Operator: Intrepid Travel

Supplier Code: ZMXT

Starts: Florence, Italy

Finishes: Pisa, Italy

Duration: 8 days

Departures: Not Guaranteed

Physical Rating: Average

Includes

Meals: Breakfasts (7),
Accommodation: Hotel (5 nights), Pension/B&B (2 nights)

Price

Price per person: (Double Occupancy) CAD $3675 ($459 /day)

Itinerary

Day 1: Florence

Buongiorno! Welcome to Italy. Your adventure begins in Florence with a welcome meeting at 6 pm. The trip spends very little time in Florence, so it’s strongly recommended that you arrive a few days early if you want to experience all that this amazing city has to offer. If you do arrive early, maybe take a stroll around the historic Florence Cathedral or visit the Uffizi Gallery, Ponte Vecchio and the Piazzale Michelangelo. After your meeting tonight, consider heading out with your new group and local leader and hunt down some excellent pizza, your favourite Italian wine or a plate of bistecca alla Fiorentina (grilled steak cooked on the bone).

Included Activities:

Bicycle hire included

Optional Activities:

Florence - Uffizi Gallery (29 EUR)
Florence - Accademia (20 EUR)
Florence - Medici Chapels (15 EUR)
Florence - Bargello Museum (13 EUR)
Florence - Ghiberti 3 days pass - Baptistry, Museo Opera del Duomo and Santa Reparata (15 EUR)
Florence - Giotto 3 days pass - Giotto Bell Tower, Baptistry, Museo Opera del Duomo, and Santa Reparata (20 EUR)
Florence - Foodies Walk Urban Adventure (89 EUR)
Florence - Pitti Palace, Gallery of Modern Art & Palatine Gallery (19 EUR)
Florence - Palazzo Vecchio (18 EUR)
Florence - Brunelleschi 3 Days Pass - Baptistry, Museo Opera del Duomo, Giotto Bell Tower and Brunelleschi Dome (30 EUR)

Accommodation:

Hotel (Number of Nights: 1)

Day 2: Siena

After breakfast this morning, take a private transfer to Radda in Chianti, where your cycling adventure officially begins. Relax with a coffee, then you’ll have a bike fitting. After, it’s time to take to the regional roads and wind your way through the countryside of the acclaimed Chianti wine region. Stop for lunch in Gaiole, then continue to the 12th-century Castello di Brolio. Next, visit the Casa Eroica – a multimedia museum focussed on L'Eroica, a cycling movement dedicated to riding vintage bikes on gravel roads. After, jump back on your bike and cycle through the green hills that lead to the medieval city of Siena. Built across three hills, the city’s three major streets connect in a valley at the sloping Piazza del Campo. According to Roman mythology, Siena was founded by Senio and Ascanio, the twin sons of Remus. Tonight, why not seek out some local specialties for dinner – pici is a popular Sienese pasta shape (similar to spaghetti, but thicker) and is typically served with either wild boar ragu or a simple tomato sauce.

Included Activities:

Gaiole in Chianti - Visit to Casa Eroica
Radda in Chianti to Siena Guided Cycling

Accommodation:

Hotel (Number of Nights: 1)

Day 3: Siena

Cycle through the rolling Tuscan countryside as you head out of Siena towards Taverne d'Arbia. Take in views of the striking Crete Senesi region as you ride – from the saddle, you have a unique viewpoint from which you can see the spectacular colours transforming from green to orange, grey and brown. Follow the ancient Via Lauretana towards Asciano, winding through the white clay dunes (known as ‘biancane’), cypress trees and farmland. You’ll also traverse part of the Strade Bianche – the white gravel roads that form the cycling race of the same name. Arrive in the medieval town of Asciano in time for lunch. Explore the winding streets of this walled town on an orientation walk with your leader, then hop back on your bike to cycle back to Siena. The afternoon is free for you to explore Siena at your own pace. Maybe visit the Duomo di Siena, people-watch with a drink in hand in the Piazza del Campo or climb the 400 steps that lead to the top of the Torre del Mangia for panoramic views of the city.

Included Activities:

Asciano - Orientation walk
Siena to Asciano (Strade Bianche) Guided Cycling

Optional Activities:

Palazzo Comunale - Free
Siena - Torre del Mangia Climb (10 EUR)
Siena - Duomo di Siena (15 EUR)

Accommodation:

Hotel (Number of Nights: 1)

Day 4: San Gimignano

Say farewell to Siena and cycle north through the rolling countryside towards the medieval walled town of Monteriggioni. Built in the 13th century as a fortress to defend Siena against the city’s historic rival, Florence, this is one of Italy’s best-preserved medieval towns. Hop off your bike, have a coffee and explore the town on foot, then continue your ride to the Parco Fluviale Alta Val D’Elsa, home to the charming streams and waterfalls of the Elsa River. After wandering some of the nature trails and maybe spotting some of the local fish or birdlife, get back on the saddle and head to the clifftop town of Colle Val D'Elsa, AKA the ‘Bohemia of Italy’. This small town is a global centre of handmade crystal glassware, producing almost all of the handmade crystal in Italy and 15 per cent of the crystal in the world. Ride on to your final stop for the day – San Gimignano. This UNESCO World Heritage-listed medieval walled town is home to 14 tower houses that were built by wealthy patrician families and offer excellent views over the town. The afternoon is free for you to explore. Kick back at a cafe or try some of the world championship-winning gelato at Gelateria Dondoli.

Included Activities:

Monteriggioni - Coffee and orientation walk
Colle Val D'Elsa - Parco Fluviale Alta Val D-Elsa visit
Siena to San Gimignano Guided Cycling

Optional Activities:

San Gimignano - Gelateria visit (5 EUR)
San Gimignano Civic Museum Combo Tickets (6 EUR)
San Gimignano - Wine Museum (6 EUR)

Accommodation:

Hotel (Number of Nights: 1)

Day 5: Lucca

Gear up for a rewarding day on the saddle. Leave San Gimignano early this morning and ride through the undulating Elsa Valley, passing vineyards and dense oak woods and following in the footsteps of pilgrims as you cycle along the white gravel roads of the Via Francigena – the ancient pilgrimage route from Canterbury to Rome. Stop for a coffee break in the small village of Gambassi Terme. Continue on to the hilltop hamlet of San Miniato, where your cycling ends for the day. Have some lunch and join your leader on an orientation walk through town, where you’ll see buildings dating back to the 13th century. Take in panoramic views over the lower Arno Valley from town, then board a private vehicle for the drive to Lucca. The rest of your afternoon and evening are free. Ask your leader for recommendations on where to start exploring or simply relax – you have a full free day to explore laid back Lucca tomorrow.

Included Activities:

San Miniato - Orientation walk
Ride a section of the Via Francigena
San Gimignano to San Miniato Guided Cycling

Accommodation:

Pension/BB (Number of Nights: 1)

Day 6: Lucca

Today is a free day off the bike in Lucca. Take the opportunity to see all the sights this city has to offer – maybe wander the former Roman amphitheatre off Via Fillungo and visit the medieval houses now standing in its place. Grab a seat at one of the Piazza dell'Anfiteatro's many outdoor cafes and watch the world go by with a coffee or glass of wine or stop by Foro Square and see the San Michele Church, which was built over the top of an ancient Roman forum. If you’re looking for the best spots to eat, your local leader will always have the best recommendations!

Optional Activities:

Lucca - Cathedral of San Martino & Ilaria del Carretto Tomb (3 EUR)
Lucca - Palazzo Pfanner House & Gardens (7 EUR)
Lucca - Puccini concert (20 EUR)
Lucca - Guinigi Tower Climb (8 EUR)
Lucca - Torre delle Ore Climb (8 EUR)
Lucca - National Gallery Villa Guinigi (5 EUR)
Lucca - Cathedral Museum (4 EUR)

Accommodation:

Pension/BB (Number of Nights: 1)

Day 7: Pisa

Leave Lucca by on your final bike ride this morning and follow the flat leafy bike paths downstream along the banks of the Serchio River to Pisa – home to the legendary leaning tower. After cycling through Pisa's bustling streets and taking your classic Pisa photo, maybe take some time to wander the shopping streets here or sip on an aperitif at one of Pisa’s many cafes and bars. Later, maybe head out for a final dinner with your group and indulge in a well-earned Italian feast one last time.

Included Activities:

Lucca to Pisa Guided Cycling

Optional Activities:

Pisa - Leaning Tower of Pisa (27 EUR)

Accommodation:

Hotel (Number of Nights: 1)

Day 8: Pisa

As there are no further activities planned today, your adventure comes to an end after breakfast. If you'd like to extend your stay, and it’s highly recommended you do, just speak to your booking agent ahead of time to organise additional accommodation.

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Reviews

Dennis - Traveled, October 2023

Great ride great guides great food great trip??

Source: Tour operator Submitted: 10/14/2023

Chloe - Traveled, September 2023

Overall a great trip, due in large part to the leader (Andrea) and support driver (Dav). There are some parts of the route that I would strongly recommend Intrepid change to ensure a higher level of safety - I was very grateful for the efforts of the guide and driver to ensure our safety during these instances (the route is out of their hands). Some of the hotel options could be improved as well. Overall, biking through such a beautiful part of Italy and visiting the small countryside towns was an unforgettable experience. Thanks Andrea and Dav!

Source: Tour operator Submitted: 09/23/2023

Patricia - Traveled, September 2023

I’m not a great blogger so there’d be others who’d do a better job than me.

Source: Tour operator Submitted: 10/15/2023

Cameron - Traveled, September 2023

Excellent trip through Tuscany experiencing the mountains, villages & sea. Surrounded by olive trees and vineyards. Great way to see Italy in a different way with great people and a great support crew including Andrea our guide.

Source: Tour operator Submitted: 09/23/2023

Zachary - Traveled, September 2023

Cycle Tuscany was everything I expected from Intrepid. Walter and Alice were terrific trip leaders, the itinerary was interesting and the group was fun. I've already booked my next trip in 2024.

Source: Tour operator Submitted: 09/13/2023

Tiffany - Traveled, August 2023

This trip exceeded my expectations. I had not expected to enjoy it so much because the weather that week was ridiculously hot. But Intrepid made an adjustment to the itinerary to take us to the beach for one night, and Walter (our driver) was always available to fill up our water bottles, pour water on our necks, and provide encouragement. Too, our group gelled quite well and we managed to make our own fun on the rides. If you are considering the trip, just book it and go. You will have a wonderful time!

Source: Tour operator Submitted: 09/04/2023

David - Traveled, September 2023

The Cycle Tuscany trip was awesome and Ali was the best guide I could imagine. We have a small group so could be very flexible and easily get into restaurants and other touristy places. A great mix of exercise, eating, socializing and seeing some amazing places. Well organized and a lot of fun. My first group tour with Intrepid, but definitely not my last!

Source: Tour operator Submitted: 10/09/2023

Charles - Traveled, September 2022

Cycle Tuscany was a wonderful experience for us. The tour leader and driver were personable and took great care to see that we enjoyed a safe and interesting trip. It as challenging but reasonable for us (ages 74 and 72). We especially enjoyed the comaraderie of the other cyclists.

Source: Tour operator Submitted: 10/17/2022

Charles - Traveled, September 2022

Our Cycle Tuscany tour with Intrepid was excellent in every way. It was described accurately. The tour leader and driver were personable, attentive and quite competent. Equipment and accommodations were excellent. And we really enjoyed meeting and riding with others on the tour.

Source: Tour operator Submitted: 10/02/2022

Ronn - Traveled, September 2022

Intrepid's Tuscany Cycling Trip is an incredible adventure, full of daily surprises, wonderful meals and scenic cycling. Highly recommended.

Source: Tour operator Submitted: 09/21/2022

Fiona - Traveled, September 2022

My cycling trip in a Tuscany was brilliant. Was lucky to strike an amazing group of people, a fantastic tor leader Walter and our driver Davor. Together they made our trip fun, safe and authentic. Would recommend to anyone.

Source: Tour operator Submitted: 09/12/2022

Katherine - Traveled, September 2022

If you’re someone who is interested in travel but may not have time (or friends who are interested in traveling) this is the company for you. You will cram in as much as possible, feel so welcome and meet some new friends, and feel safe. Traveling with Intrepid is fun, not stressful. Intrepid covers all age groups. I met likeminded people and felt I could just be myself and laugh.

Source: Tour operator Submitted: 09/12/2022

Paola - Traveled, September 2022

Traveling with Intrepid has been an amazing experience. I will recommend booking any trip with this company. The Tuscan cycling tour was overall one of the best trips I´ve had in my whole life.

Source: Tour operator Submitted: 09/12/2022

Cynthia - Traveled, July 2023

This is a fabulous cycling vacation for those who want to experience small towns and wonderful cities in Tuscany. Florence, Pisa and Lucca are great. The small towns such as Vinci and Barga really stood out. They had a lot of local flavor with not many tourists. The bike riding is easy, which keeps the group together. There is plenty of time to enjoy the towns and wine as well. Very well organized, good bikes and van transport. The leaders Ali and Walter were the best! I highly recommend this tour.

Source: Tour operator Submitted: 08/11/2023

Barry - Traveled, June 2023

As a returning customer of intrepid travel my expectations were higher. While the itinerary and equipment was good. Leadership was somewhat robotic and insincere. Although the support person was communicative enthusiastic and very hard working. Accommodation was average to poor. Paid single supplement had to share on the last night. Found my own accommodation at my expense. Breakfasts were mostly inadequate and embarrassing. Was really looking forward to this trip as my past experiences with intrepid have been excellent and memorable. I sense that this is not the norm with intrepid. As I have recommended intrepid travel to many of my friends and acquaintances who has had positive experiences. Some friends are currently booked upcoming intrepid travel tours. I am confident that their experience will be a memorable one like I have had in previous years.

Source: Tour operator Submitted: 06/30/2023

Rachele - Traveled, June 2023

What a trip! If your on the fence do it! The itinerary gives you a flavour of what’s to come but it doesn’t give away all of the gems and hidden treasures. Ali and Walter brought Tuscany to life and there’s no one else I would have wanted to explore Tuscany with

Source: Tour operator Submitted: 06/16/2023

Andrea Dawn - Traveled, May 2023

Highly recommend Intrepid cycle trip of Tuscany. Excellent equipment provided and our driver, Davor and our guide,Saf were awesome. An excellent adventure!

Source: Tour operator Submitted: 06/04/2023

Dan - Traveled, May 2023

Cycling the hills of Tuscany with wildflowers lining the roads, breaking for capuccino or gelato, accompained by delightful people and charming guides, what could be better?

Source: Tour operator Submitted: 05/19/2023

Gloria - Traveled, September 2022

The Cycle Tuscany tour was an epic experience with fantastic tour leaders in Walter and Davor yielding us an amazing cycle journey. They worked well together to make sure we enjoyed the riding, classic cuisine, wines and experiences so authentic to Tuscany!!! Don’t miss this ride!!!

Source: Tour operator Submitted: 09/15/2022

David - Traveled, September 2022

We loved this trip and made lots of new friends amongst our fellow travellers. The itinerary was very good with the variety of beautiful scenery and terrain. The equipment was a good standard, and our tour leader and support driver were absolutely superb - great company and always looking after us along the way. We would definitely recommend this trip.

Source: Tour operator Submitted: 09/21/2022