Planning Your Cycling House Trip to Tuscany by Owen Gue

I love cycling in Tuscany and I’ve learned a few things from running our cycling trips in Italy over the past six years. I’ve compiled a few pointers, insight, and things to consider when planning your first cycling trip to Tuscany with us.

Two of the most common questions we get regarding our cycling trip to Tuscany are:

1) How should I plan my travel before and after the trip?

2) What does the itinerary look like or what will we be doing each day?

These are great questions and below are my answers to those two big questions and some more helpful information to consider. Over the years we’ve made some tweaks to this trip to make it the best it can be, and I travel to Tuscany every year because I love this particular trip so much.

Travel to Tuscany

How long should I plan on being gone if I book a Cycling House bike vacation to Tuscany?

You’re probably busy and your time is limited. I get it. If you’re trying to minimize your time away from home but still want to get the most out of this cycling vacation, plan on being gone for about nine days. Here’s why:

You may be cutting it a little too close if you try to do this trip without allowing for some buffer time. An overview of your travel would look like this: one day for traveling to Italy; we highly suggest arriving one day before your cycling vacation with us starts. We’ll pick you up on the first day of our scheduled trip (which is hopefully the day after you arrive in Italy). Then you’ll be with us for seven days. We’ll drop you off on our last day of the trip; most riders stay in Italy that night and fly out the next morning (or start the next chapter of their trip!).

Here is a breakdown of what this looks like:

Day 1 – Fly to Europe, arrive in Italy, stay the night in Florence. You’ll need to book these accommodations. (You’ll usually loose a day when traveling to Europe from N. America)

Days 2 – 8  The Cycling House Tuscany Trip. The itinerary is below.

Day 9 – Fly back to North America (usually you won’t loose a day when you travel back).

Still have questions regarding travel? Drop us a line if you have questions regarding your travel to Italy and the above timeline doesn’t work.

Planning your arrival in Tuscany

I suggest landing or arriving in Florence (FLR) at a minimum of one day before your trip starts. This means you’ll probably need to depart two days before the trip start date because you lose a day flying over to Europe. For instance, if you’re on a roster that starts on September 8th, 2019, I suggest you depart the USA on September 6th and arrive in Florence (FLR) mid-day on the 7th. This will allow you to relax a bit after your travels, explore Florence in the evening, and be ready for pickup mid morning on September 8th. Or course, a couple more days would be amazing – but if you’re minimizing your time away from home, this schedule is ideal.

The family that we stay with in Tuscany. 

Other Italy travel options:

  • Fly into Rome or another big city and take the speed train to Florence for pickup on arrival day.
  • Catch a train to Siena and we’ll pick you up at the Siena Train station on arrival day (exact time TBD).
  • Rent a car and drive to the B&B.
  • Shuttle pickup notes: We only do transfer for the start of the trip from the Florence Airport (FLR) and the Siena Train Station.

Where should I stay in Florence before my Cycling House trip?

There are many places to stay in Florence and we encourage you to do some of your own research to find a place that fits your budget and needs. That said, below are a few suggestions of places our guests have stayed in the past and gave us good feedback on them.

Hotels in or near the city of Florence:

  • Palazzo Belfiore. $$ In the heart of Florence. Just near the Ponte Veccio – The iconic medieval stone bridge that spans the Arno River.
  • Hotel Lungarno. $$$$. In the heart ofFlorence. Also close to the Ponte Veccio. The Belfiore and Lungarno are very close to each other.
  • Hotel Torre di Bellosguardo $$$$. Stunning accommodations; located on a hill just outside of Florence overlooking the city. It’s about 3k to Florence from this hotel so it’s not in the city centre but it is an amazing place.

Hotels near the Florence Airport:
If you’re flying in late and just want somewhere easy to get into, a simple google search of “Hotels near Florence Airport” will get you a multitude of results. For ease and convenience, many of our guests who have stayed near the airport will book a room at the Hilton Inn Florence Novoli or the Ibis Florence Airport Hotel.

*Please note that we do not have any partnership or connection with the hotels listed above.
*Remember that you’ll need to catch a taxi or airport shuttle back to the FLR airport for The Cycling House pickup transfer on the cycling trip arrival day.

The Cycling House Tuscany Trip Itinerary

Here are our riding routes and daily itinerary in Tuscany. We have lined up our favorite pedaling routes that cover a variety of areas within Tuscany. Each ride has a fast or slower option and a long or shorter option, to meet everyone’s riding needs.  There are 2-3 guides riding on the road everyday, and each ride (with the exception of the arrival day spin) will have a support van with water, food, and extra gear.

Day 1 – Arrival Day 

Our vans will pick riders up at the Florence Airport

Shuttle Pickup at the Florence Airport – We’ll do a pickup at 10 a.m. at the Florence Airport. We meet everybody at the Cafe Baccanale. This is the only major cafe in the airport and it’s very easy to find. The Cafe Baccanale is located outside the baggage claim doors on the east side of the airport terminal. Once we gather everybody for the shuttle, we’ll jump in our vans and drive one hour to the B&B. If you’d like to see our driving route from FLR to our homebase, take a look at this map.

Cafe Baccanale is where we’ll meet for the arrival day pickup.

Arrival at the B&B

  • Once we arrive at the B&B we’ll get luggage into rooms and riders can get settled in.
  • Our mechanics will get to work on the bikes that need to be built up or rental bikes fitted to riders.
  • Noon – We’ll enjoy lunch at the B&B. If it’s sunny and warm we’ll enjoy this meal in the garden.
  • Ride – In the afternoon we’ll do our arrival day spin. This is about a 2 hour ride and 25 miles. View the arrival day ride route:
  • 6 p.m. – We’ll enjoy some wine and appetizers and the staff will organize the camp briefing. This is when we’ll dive into the details of the trip.
  • Dinner is in enjoyed at the B&B following the camp briefing.
Lunch in the garden.

Day 2 – Tour of the Val d’Merse

7-8:30 a.m. – Leisurely breakfast at the B&B.

Ride – We start and finish this ride from the B&B.

  • Main ride route is 40 miles and 3000′ of climbing.
  • Route:
  • This is a great loop highlighting the Val de Merse area of Tuscany. Not many tourists visit this area and is off the beaten path.
  • We’ll stop for a café in Chiusdino and we also visit the Abbey of San Galgano.
  • There are options to shorten or lengthen this ride route
The Abbey of San Galgano, which we’ll visit on our ride.
  • Lunch – Enjoy lunch at the B&B at the finish of the ride.
  • 4:30 p.m. – Afternoon wine tasting at the winery Tenuta di Trecciano (15 minute shuttle). We’ve gotten to know this place well and Barbara is our host here. Our group will enjoy a walking tour of the winery, followed by  a wine tasting of the winery’s various wines.
  • 7:30 p.m. – We do dinner out in the tiny village of Orgia near the B&B. This is a neat family-run restaurant called Cateni a Orgia.

Day 3 – Val d’Orcia Tour

7-8:30 a.m. – Leisurely breakfast at the B&B.

Ride – Today’s ride will be a point to point tour from the B&B to a small Agritourism property near Asciano. Riders sweep through the heart of the Val D’orcia region.

  • Route : Lunch.
  • Lunch – Picnic lunch at the Il Molinello Agritourismo.
  • After Ride Activity: Shuttle to Montalcino for a 1-2 hour visit. This is where Brunello wine is produced.
  • Dinner will be enjoyed at the B&B.
Picnic lunch at the Agriturimso Il Molinello.


Riding a section of gravel road on our way to the Val d’Orcia region of Tuscany.

Day 4 – Pievescola Loop / Siena Tour

7-8:30 a.m. – Leisurely breakfast at the B&B

Ride – There are two options on this day:

  • Recovery ride = 1 hour tour nearby with a gelato and cafe stop . -Or-
  • Ride the Pievescola loop (~4 hours) .      Route:
  • Lunch enjoyed at the B&B.
  • 5 p.m. – Shuttle to Siena for walking tour of this beautiful city.
  • 7:15 p.m. – Dinner out in Siena – Osteria Boccon Del Prete (in the heart of the village).
  • Shuttle back to B&B after dinner.

Dinner out in Siena.

Leaving Siena after our walking tour and dinner out.

Day 5 – Chianti Tour

Taking in the views in Chianti.

7-8:30 a.m. – Leisurely breakfast at the B&B

Shuttle in vans to ride start of the ride.

Ride in Chianti! This is a wonderful point to point route in the heart of Chianti. There is also a coffee stop at the village of Gaiole in Chianti.  This is where the Eroica Gran Fondo ride starts and finishes. There are some hip bike shops to check out and possibly get a gift or two.

  • Route here:
  • Lunch out in the small village of San Gusme, Chianti Region.
  • 4 p.m. – Cooking class starts at the B&B.
  • Dinner will be enjoyed after the cooking class.
La Botegga is one of our favorite places to get a gift for a cyclist in your life. We stop in Gaiole mid-ride after a cafe stop.  They have a lot of gear from L’eroica and White roads.

Day 6 – San Gimingnano

7-8:30 a.m. – Leisurely breakfast at the B&B.

9 a.m. – Shuttle in vans to ride start in d’Elsa and ride to San Gimignano.

  • Route here:
  • Café break in San Gimignano – A Unesco World Heritage Site.
  • Riders who want extra mileage can ride home to B&.B.
  • Lunch – Enjoyed at the B&B upon finishing the ride
  • Afternoon – Relax at B&B.
  • 7 p.m. –  Pizza party for final dinner!

Finishing our tour with home made pizza!

Day 7 – Departure Day

We’ll be running transfers to:

  • Florence Airport
  • Siena – Train Station

See available Tuscany trip dates here. 

Our Home Base. The B&B Pallazo a Merse

Cycling in Tuscany, Italy is what dreams are made of – the perfect ribbons of road, weaving through the countryside, endlessly linking village after village. Some of the best wine in the world comes from Tuscany, and paired with the region’s incredible food, you have the ingredients for a great cycling vacation.

Our Tuscany trip is truly special because it’s based out of a bed-and-breakfast south of Siena, away from the hustle and bustle. The B&B is run by a family who have become an integral part of our Tuscany experience.

The family prepares the meals we enjoy at the B&B and source many of the ingredients from local farms. They cook over an open fire and make pizza and fresh bread in a 500-year-old wood-fired oven. We’ve found a nice balance between dining in and going out to enjoy the local cuisine.

Each ride is challenging, but always has a few café stops along the way. Wine tasting, soaking in a natural hot spring, taking a cooking class, and touring Siena (a UNESCO World Heritage site) are all on the itinerary. There is a little recovery time built in too, for riders to relax and do some exploring of their own.

Meals in Tuscany

Our food in Tuscany is prepared fresh by the family who runs the bed-and-breakfast. Many of the meats are sourced from a farm a few kilometers down the road. The veggies are grown either in the field behind the B&B or by the neighbors across the street.

While we enjoy many of our breakfasts, lunches, and dinners at the B&B, we’ll also eat out to experience a few of our favorite local restaurants.

And the wine! Don’t forget the wine! Chianti and Brunello wines are everywhere, and a glass with these meals will only elevate the experience. All meals will be included in your rate.

Rental Bikes

We suggest renting a bike that we source in Italy; however, traveling with your own bike is fine too. Renting will make your travel much easier and less stressful. You can expect full carbon road bikes complete with Shimano Ultegra and disc brakes. The geometry on these bikes is called an endurance geometry, but is still considered a “racing bike.” The bike gearing on these bikes is a 52-36 front rings and 11-32 in the rear. The climbing gear will be a 36×32. The rental bikes cost $300 for the week. Bring shoes, pedals and helmet. Your saddle is suggested but optional.

Our rental bikes in Tuscany. Focus road bikes, carbon frames and Shimano Ultegra.

Other things to consider when planning your trip

Climbing! – Riding in Tuscany is challenging. There are not many flat roads so be ready for plenty of up and down when riding in Tuscany. As a general rule, we usually climb 1000′ for every 10 miles ridden.

Passport – Make sure your passport is not going to expire within 6 months of your trip. They will not let you check-in for your flight if you’re within this window.

Cash – I’ve found the best way to get Euros while traveling in Europe is to use an ATM debit card.

View the packing list on this page. It’s very helpful!

Haven’t booked your Tuscany cycling vacation? Check out our Tuscany cycling trip page to see our available dates. We’d love to have you along for the ride!

Thanks for reading. I love sharing this amazing place with our guests. Feel free to contact me anytime regarding our Tuscany trip details.


Owen Gue, President