Tuscany, Italy
Seven nights of white gravel roads, hill towns and long Tuscan dinners, looping from Siena.
Get first accessSee the daysTuscany in May, before the crowds
Green fields, cypress-lined roads and hill towns. We loop from Siena west to the towers of San Gimignano, through the vineyards of Chianti, and south into the Val d'Orcia for Brunello in Montalcino and Vino Nobile in Montepulciano. Lunches are long, dinners are longer.
- White gravel and cypress roadsThe classic strade bianche and the most photographed roads in Italy, in green May.
- Brunello in MontalcinoA tasting in the town that makes one of Italy's great wines.
- Signature dinner at OsmosiOur big night out, in Montepulciano.
- Three 2-night staysUnpack less and ride loop days straight from the door.
- Val d'Orcia and PienzaRolling hills, hill towns and pecorino country.
The route
A loop through four of Tuscany's best areas: San Gimignano, Chianti, Montalcino and the Val d'Orcia, and Montepulciano. Three of the stays are two nights, so you unpack less and get easy loop days from the door. Expect white gravel roads (strade bianche), short punchy climbs into hill towns, and quiet roads between vineyards. The van carries your bags and can pick you up anytime. Exact route and stats are coming soon.
- Nights
- 7 (three 2-night stays)
- Distance
- Full route coming soon
- Climbing
- Constant rolling hills
- Fly in / out
- Florence or Pisa, then train to Siena
Eight days, at a glance
Breakfast every day. On nights without a group dinner, I'll point you to my favorite spots nearby.
You'll enjoy this if you ride regularly and are comfortable with 30–50 mile days on rolling hills. There are short climbs into the hill towns, but nothing long. You don't need to be fast; you need to be steady.
- Short, punchy climbs into hill towns, every day
- Some sections on smooth white gravel roads
- Daily rides of roughly 30–50 miles
Good to know about the riding
Parts of the route use the white gravel roads Tuscany is famous for. They're smooth and fine on a road bike, but tires 28mm or wider make them more comfortable. The final route is still being drawn, so distances will be added soon.
What a typical day looks like
Breakfast together, then we roll out mid-morning. We stop for coffee and a long lunch along the way, and arrive at the next stay in the afternoon with time to shower, explore or nap. Evenings are for dinner, whether it's a group dinner or one of the places I've picked for you to try on your own.
How the riding works
- I ride with the group every day.
- A support van carries your luggage, follows the ride with snacks and water, and can pick you up anytime.
- You'll get every day's route ahead of time for your GPS or phone.
- Ride at your own pace. We regroup at coffee and lunch stops.
Can the plan change?
Routes, stays, restaurants and daily plans may change. We reserve the right to update the itinerary for weather, road conditions, availability or safety, and if something changes we'll swap in something just as good.
Where we eat, where we sleep
The food
The highlight is a signature dinner at Osmosi in Montepulciano. Around it: pici and ragù, bistecca, pecorino from Pienza, a Brunello tasting in Montalcino, Vino Nobile in Montepulciano, and long lunches in hill towns. The trip closes with a group dinner to remember.
The stays
Small, characterful 3–4 star stays: a hotel in Siena to start, a farm estate between San Gimignano and Chianti, a wine estate near Montalcino, and a hotel near Montepulciano. Three of the stays are two nights. Exact properties are confirmed closer to the trip.
Book it, then just ride and eat
- 7 nights of hand-picked stays
- Breakfast every day
- Group dinners, including the signature dinner at Osmosi
- Wine tasting in Montalcino
- Luggage van between stays, and van support on every ride
- Van back to Siena on the last day
- Snacks and water on rides
- Rider jersey and cap
- Alex riding with you every day
- Pro photos and video of the trip
Not included
- Flights
- Airport and train transfers
- Most lunches
- Dinners on free nights
- Drinks beyond the wine at group dinners
- Bike rental (offered as an add-on)
- Travel insurance (required)
Be first in line
Pricing is announced Nov 16, and each trip has just 8 spots. Leave your name and email and I'll send you pricing and first access before booking opens to everyone on Nov 19.
How booking works
- Deposit
- $1,500, non-refundable
- Balance due
- 120 days before the trip
- Rooms
- Shared, or your own room
- Bike
- Bring your own, or rent one
- Group
- 8 riders max, 5 to run
- Trip confirmed by
- January 8, 2027
Alex Blosil, chef and ride leader
I'm a chef from Utah who cooked in Paris and speaks French fluently. I plan every trip around the best tables in each region, and I ride every mile with the group. More about me
Good to know
How do I get there?
Fly into Florence or Pisa, then take the train or bus to Siena (about 1.5 hours from Florence). We meet at the start hotel on Saturday afternoon for the opening dinner. On the last Saturday the van brings everyone back to Siena after breakfast. Want to arrive early or stay longer? Just ask and I'll help you book extra nights.
Is the gravel hard to ride?
No. The strade bianche are packed and smooth. Wider road tires (28mm or more) help, and rental bikes come set up for them.
How fit do I need to be?
See “Is this trip for me?” above, under Your days. You don't need to be fast. The van can pick you up anytime, so you choose how much you ride.
Can I bring my own bike?
Yes. Or rent a quality bike from us as an add-on, fitted and ready when you arrive.
Can I get an e-bike?
Not on our 2027 trips. The van follows every ride, so if you need a break, you can hop in anytime.
I'm traveling solo. Can I have my own room?
Yes. You can choose your own room, or a shared room if you're booking with a friend or partner.
I have dietary needs. Is that OK?
Of course. Tell us when you book. I'm a chef, and I'll make sure you eat well.
Can a non-riding partner come?
Get in touch and we'll see what we can work out.
When do I pay?
A $1,500 non-refundable deposit holds your spot. The balance is due 120 days before the trip.
Do I need travel insurance?
Yes, it's required. Choose a policy that covers cycling and trip cancellation.
What should I pack?
We'll send a packing list after you book. Plan on cycling kit for each riding day, a rain jacket, warm layers and casual clothes for dinners.
Can I arrive early or stay longer?
Yes. Just ask and I'll help you book extra nights.
How big is the group?
8 riders at most, plus me, our support driver and our filmmaker.
Still have a question? Email alex@chefalextours.com.