The Italian sweet spot: A Month-by-Month Guide to Cycling in Italy in 2027

When is the best time to head to Italy with your bike? 

TLDR; It depends on where you want to ride. Start in the south and the hills in April and May: Puglia (new!), Tuscany and the Prosecco Hills. Go high from June to September, when the Dolomites passes, the Stelvio and the high passes of Piedmont are open and at their best. Finish among the vineyards in late September and October, in Piedmont, Tuscany and the Prosecco Hills. Avoid Puglia and Tuscany in high summer, and the high passes before June.

That's the short answer. It's usually the first question riders have. Below is the longer one, month by month, with key event dates worth planning your 2027 around.

A bit of background: I grew up in Treviso, not far from the Prosecco Hills and the majestic Dolomites. Although these two areas are only about 1 hr driving time from each other, the best time to visit them varies significantly.  This applies to many other popular cycling areas in Italy: April is a great time to visit the Langhe in Piedmont, but go a bit further West and you will encounter closed alpine roads and abandoned villages.

The first thing Bob & I consider when we are planning our tour calendar for the next year is timing: being in the right place in the right week. Your dates and your region should be your first two decisions, and the ones that shape all the others.

One thing to keep in mind: mountains make their own rules. Snow flurries on the Stelvio in August are not unheard of. That’s another reason to have a supported trip, you can ride in the van back down if the weather is less than ideal!

April: the hills wake up

Where to ride: the Prosecco Hills, Tuscany and Puglia. The vineyards are turning green, the white roads are firm, and in Puglia the fields fill with poppies. The high passes are still under snow, so leave them for later.

Weather and crowds: mild days, cool mornings and the odd spring shower, so pack a light jacket and arm warmers. Roads are quiet, and hotels are just opening for the season.

Worth planning around: Nova Eroica Buonconvento, April 11, a modern gravel event on the white roads south of Siena.

May: the best month below 1,500 metres (4,920 feet)

Where to ride: almost anywhere except the highest passes. Lake Garda, the Prosecco Hills, Tuscany, Piedmont and Puglia are all at their best. Bormio's big climbs usually start to open late in the month: in 2026 the Stelvio opened on May 22 and the Gavia on May 27.

Weather and crowds: warm and longer days, with some rain to plan around. It's a busy month for events, but the roads stay calm on weekdays.

Worth planning around: the Bike Festival at Riva del Garda (around May 1), Nova Eroica Prosecco Hills (May 2), Nove Colli in Romagna (May 23) and Eroica Montalcino (May 30). The Giro d'Italia runs from May 8 to May 30, starting in Trieste for 2027.

June: the mountains open

Where to ride: the Dolomites, plus anywhere still fresh lower down, such as Piedmont, Garda and the Prosecco Hills. The Stelvio and the Gavia are normally open by now, though you can still ride between walls of snow near the top. Friuli and Slovenia come into their own this month.

Weather and crowds: this is our favourite way to see the Dolomites: green valleys, long days and little traffic before the summer holidays. Carry a proper layer for every descent, because the top of a pass can be 15°C (59°F)  colder than the valley.

Worth planning around: June is the richest month of the year.

• June 5: Sellaronda Bike Day. Gardena, Sella, Pordoi and Campolongo are closed to cars from 9:00 to 16:00. It's free, and there's no timing.
• June 19: Dolomites Bike Day. Campolongo, Falzarego and Valparola are closed to cars.
• June 20: Sportful Dolomiti Race from Feltre, up to 204 km (127 mi) and 4,900 m (16,080 ft) of climbing.
• June 27: Granfondo La Fausto Coppi from Cuneo, up to 172 km (107 mi) over the Cottian Alps.

July: Maratona month

Where to ride: go high. The Dolomites and the Stelvio are the coolest places to be, while Tuscany and Puglia are getting too hot for long days in the saddle.

Weather and crowds: warm in the valleys and comfortable up high, but afternoon storms are common in the mountains. Start early and aim to be off the top of the last passes by early afternoon. Traffic builds through the month, and an early start helps with that too.

Worth planning around: the 40th Maratona dles Dolomites on July 4, from La Villa to Corvara, with the longest course at 138 km (86 mi) and 4,230 m (13,880 ft) of climbing. The passes are closed to traffic. Half of the 8,000 places go through a lottery, while a CyclingHero package comes with guaranteed entry.

Your dates may not match any of these tours, and that's fine. Every CyclingHero trip can be customized and built around you.

August: high, early and away from the crowds

Where to ride: the Stelvio, Gavia and Mortirolo, and the Dolomites if you can ride early. Avoid Puglia this month, and ride Tuscany and the Prosecco Hills only with very early starts.

Weather and crowds: the busiest weeks on the passes, especially around Ferragosto on August 15, when much of Italy is on holiday. On the most popular climbs, the first hours of the day are the ones to ride. The second half of the month is often calmer.

Worth planning around: Stelvio Bike Day, August 28. All three sides of the pass are closed to cars for the day.

September: the insiders' month

Where to ride: nearly everywhere. If you can choose any month for a first trip, this is the one we'd suggest. The crowds of the Dolomites are thinning out, Garda and the Prosecco Hills have cooled down, and the harvest is starting in the vineyards of Piedmont.

Weather and crowds: mostly clear days and low, warm light, with fresh mornings. Snow can come early on the highest passes by the end of the month, but it never lasts long. Puglia comes into its own later in the month, and the sea is still warm.

Worth planning around: the second Sellaronda Bike Day, September 11, and Nova Eroica Ivrea in northern Piedmont.

October: wine country

Where to ride: Piedmont, Tuscany, the Prosecco Hills and Puglia. In the Langhe, the Nebbiolo is in full harvest and white truffle season is starting. In Tuscany, the white roads are back to their best after the summer dust & heat. The Dolomites are possible early in the month, with golden larches and cold descents.

Weather and crowds: cool mornings, golden afternoons and shorter days, so shorter routes work better. Rain becomes more likely as the month goes on.

Worth planning around: Prosecco Cycling (October 3) and the 30th edition of L'Eroica in Gaiole in Chianti, traditionally held on the first weekend of the month.

Two new regions we're opening

Puglia extends the season at both ends. It's the best place to ride in April and October, on quiet lanes between olive groves, white towns and two seas. It's built for riders who prefer rolling roads over big mountain passes. Skip July and August.

Friuli Venezia Giulia and Slovenia are for riders who have done the Dolomites and want the same dramatic scenery without the crowds. In one trip you can ride Monte Zoncolan, one of the steepest climbs the Giro has ever used, then the Collio and Brda vineyards across the border, and the Vršič Pass and the Mangart Saddle, Slovenia's highest paved road. June and September are the sweet spots.

Neither region has a set tour yet, so your trip would be built from scratch. Tell us if you'd like to be among the first to ride them with us.

How to choose your month

Start with what matters most to you, then match it to the calendar:

• A bucket-list climb: June to September for Passo Giau and the Stelvio.
• A car-free day or a big event: June, or the Bike Days in late August and September.
• Food, wine and easier riding: April, May, September or October.
• Fewer people: June or September in the mountains, May or October lower down.
• Gravel: Tuscany in spring or autumn.

Already know your month, or still choosing between two? Send us what you have. We'll match it to the right roads, hotels and support, and build your trip around you.

Frequently asked questions

What is the best month to cycle in Italy?

September is the best all-round month, because most regions are good at the same time. June is the best month for the Dolomites, and October is the best month for lovers of wine.

When do the Stelvio and Gavia open?

Usually in late May or early June, once the snow is cleared. In 2026 the Stelvio opened on May 22 and the Gavia on May 27. Dates change every year, so we check the passes for your exact dates before we confirm your route, and we always have a backup plan.

When is the best time to ride the Dolomites?

June, July and September. August is good but busier. Early October is possible, but it can be cold, and some hotels have closed by then.

Do I need an entry for the Sellaronda Bike Day?

No. It's free, open to everyone and not timed. In 2027 it will take place on June 5 and September 11.

Can I ride the Maratona dles Dolomites without winning the lottery?

Yes. Official tour operator packages include a guaranteed place. Our Maratona 2027 packages include entry, and for 2027 the event takes place on July 4.

Is it too hot to cycle in Italy in summer?

In Puglia and Tuscany, usually yes, at least for long days. In July and August, head for the Dolomites and the numerous climbs around Bormio (Stelvio, Gavia, Mortirolo, Cancano), where it stays cool up high.

Can you build a trip around my exact dates?

Yes. Every CyclingHero trip is custom, so the route, the pace and the dates can be adapted to your specific preferences.