Italy 'Classico' Tour - Revised Route

Description

An 'Classic' Italian Adventure 

Tour Summary

You’ll be exploring 800 miles and ascending 50,000ft on this incredible Italian 'Classico' tour. We start in the ancient city of Pisa in Tuscany.

Through Tuscany you will find roads lined with iconic evergreen cypress, rolling hills of wheat and hectares of vines. Medieval hilltop villages, like San Gimignano below, invite you up to enjoy the stunning views. Before browsing cobbled streets where trattorias vie with gelaterias to satisfy your appetite and shops sell Tuscan olive oil, truffles, Cantuccini biscotti and lots of wine.

We continue east into Umbria and the stunning Apennnine Mountains through Marche you'll experience the different types of terrain, from challenging climbs to rolling hills and flat river roads as we head towards the impressive Adriatic coast. 

However quiet inland roads provide a safe environment for you to immerse in the diversity of the history, culture and traditions Italy has to offer incuding the incredible UNESCO world heritage site of Matera shown below.

Throughout the tour be it a Pedal Europe picnic lunch or handpicked trattoria for the evening you'll be able to experience the very best Italy has to offer for food and drink escpecially as we explore wine regions such as Chianti. 

Finally we arrive in Puglia, where via Lecce we meander on stunning coastal roads to our end point the very heel of Italy in Santa Maria di Leuca. Here you can reflect on having dined and slept in some charming local hotels and having experienced the very best of this part of the country has to offer.

 Overview of Route

Itinerary

Arrival Day: Tuesday > Pisa

When you arrive in Pisa, make sure you have time to take a stroll around in this famous city of art. Do not miss the Piazza dei Miracoli where you'll admire the well-known leaning Tower and all the other monuments. Get pleasantly lost in the ancient and lively streets of the city centre, just to have a first experience of the Italian's life style.

We'll overnight in a hotel in Pisa.

We ask that people try to arrive at the Hotel by 6pm latest on Arrival day. This is because at 6.30pm we normally have a tour briefing session at which important information relating to safety and general advice on how to survive 13 days in the saddle is provided.

After this we have a group evening meal at 7.30pm so you can socialize and meet your fellow riders.

Day 1: Peccioli to Siena

54 miles | 87km | 4456 ft | 1358 m

We start in Peccioli an ancient hill top village with stunning views of the quintessential Tuscan landscape. Click the picture to get a sense of our start point.

Ride on smooth country roads through rolling hills, vineyards, olive groves and cypress-lined lanes, with postcard views at every turn. 

Pause in San Gimignano—the famed “medieval Manhattan”—to wander its atmospheric streets and raise a glass of Vernaccia di San Gimignano before continuing to storybook Monteriggioni, a perfectly preserved fortress village encircled by walls and towers.

The day finishes in world-famous Siena, rolling into the historic centre for an evening of Tuscan cooking—think hearty local plates like pici—and a well-earned aperitivo in one of Italy’s great medieval cities. 

Day 2: Siena to Chianciano Terme 

50 miles | 80km | 4743 ft | 1446 m

Today’s ride dives deeper into Tuscany’s most cinematic terrain: the Crete Senesi—the iconic Sienese “badlands” of pale clay hills, sweeping ridgelines and big, open skies. Expect a beautifully rhythmic road day with rolling terrain and a few testing climbs, rewarded by huge views and that unmistakable “white roads” atmosphere that has made this region legendary in cycling.

You’ll thread through postcard-perfect Castelmuzio, a tiny hilltop village tucked between the Val d’Orcia and Crete Senesi landscapes.

Before continuing to Pienza, the elegant Renaissance jewel of the Val d’Orcia—an ideal place to pause for an espresso, soak up the views, and sample local flavours (this area is famously associated with pecorino).

The day finishes in Chianciano Terme, one of Tuscany’s classic spa towns—perfect for unwinding after the ride with a relaxed evening.

Day 3: Chianciano Terme to Assisi 

56 miles | 90km | 3433 ft | 1046 m

A beautiful transition day as you roll out from Chianciano and leave Tuscany behind on quiet roads that still feel unmistakably Italian.The air shifts as you ride: olive groves and tall, dark cypress scent the breeze, and the horizon gradually changes from Tuscan tones to Umbria’s softer greens.

En route, you pass through Tavernelle and into the vineyards around Torgiano, one of Umbria’s most respected wine corners—famous for Torgiano Rosso Riserva DOCG.

The finale is unforgettable: you arrive in Assisi, the hilltop city of Saint Francis, where the atmosphere becomes palpably calmer—stone lanes, sweeping views, and the profound artistic and spiritual heritage that made it a UNESCO World Heritage Site. If you choose, visit the Basilica of Saint Francis of Assisi, celebrated for its extraordinary fresco cycles associated with artists including Giotto and the great late-medieval schools.

Day 4: Assisi to Polverina 

45 miles | 71km | 4134 ft | 1260 m

A mountain-to-lake stage that trades Assisi’s hilltop beauty for big Umbrian horizons. Roll easily through the valley past Capitan Loreto and San Giovanni Profiamma (an olive-growing hamlet near Foligno), before the road tilts upward into quiet forests and onto the high plains around Colfiorito—a broad plateau system sitting roughly 750–800m above sea level with huge skies and a real sense of space.

From there you descend into the Apennines via Serravalle di Chienti, where stone villages and mountain scenery frame the route, then finish beautifully beside Lake Polverina—a tranquil lake setting at the gateway to the Sibillini area and a wonderfully calm place to end the day. 

Day 5: Polverina to Ascoli Picerno

57 miles | 92km | 4762 ft | 1451m

A gorgeous Marche stage that rides the edge of the Monti Sibillini—smooth ribbons of road through rolling green hills, forested folds and wide-open Apennine views, with medieval villages appearing like lookout points over the valleys.

You’ll pass through Sarnano, a beautifully preserved hill town at the foot of the mountains, then continue via Amandola, often described as a natural gateway to the Sibillini, before finishing in Ascoli Piceno, the elegant “travertine city,” where the day ends perfectly with an aperitivo in Piazza del Popolo—famously nicknamed the city’s “living room.” 

Day 6: Ascoli Piceno to Pescara 

64 miles | 103km | 4628 ft | 1411m

Today you leave the foothills behind and glide onto the Adriatic, linking bike paths and quiet minor roads for an easy, fast day with salt air, wide skies, and long sea views.

In the off-season the coast feels wonderfully authentic—locals reclaim the promenades, cafés set out chairs, and the shoreline shifts into its relaxed, between-the-crowds rhythm as you roll through classic resort towns like Alba Adriatica and Roseto degli Abruzzi, before finishing on Pescara’s seafront and spin across the elegant Ponte del Mare, one of the city’s signature cycle-pedestrian landmarks.

Day 7: Pescara to Termoli 

75 miles | 121km | 3738 ft | 1139m

A pure-Adriatic day that strings together bike path and quiet seaside lanes, building toward one of Italy’s most iconic coastal rides: the Via Verde / Ciclabile dei Trabocchi, a “greenway” laid along the shoreline with constant sea views.

You’ll roll into San Vito Chietino, perched above the water on the heart of the Trabocchi Coast, then continue south with the trabocchi—the region’s wooden fishing platforms—appearing out over the waves. Once working tools of the fishermen, many are now atmospheric, high-demand seafood spots literally on the water, and they make this stretch feel completely unique to Abruzzo. 

From there the route carries you through the coastal elegance of Vasto—a hilltop historic town overlooking the Adriatic—before finishing in Termoli, where the Borgo Antico sits on a promontory above the sea, 

Day 8: Termoli to Lucera

66 miles | 106km | 4070 ft | 1241m

A true “crossing-the-map” stage: you leave the Adriatic behind at Termoli and drift inland on quiet, winding roads that trade sea breezes for wide-open farmland—golden grain fields and olive groves rolling toward the horizon as you transition from Molise into Puglia for the final chapter of the tour.

Then Lucera rises ahead—sun-warmed stone, a proud hilltop skyline, and an arrival that feels cinematic. You enter a city shaped by layered civilizations: the commanding Lucera Castle (Swabian-Angevin fortress tied to Frederick II and Lucera’s Saracen history), the monumental Roman legacy of the amphitheatre, and the elegance of the Lucera Cathedral—all wrapped into an atmosphere that’s quietly grand, authentic, and beautifully off the beaten path.

Day 9: Lucera to Canosa di Puglia 

77 miles | 124km | 3114 ft | 949m

A quieter, more elemental ride—empty horizons, scattered cereal fields, and long straight roads that make the miles feel meditative as you roll deeper into Puglia’s interior. Then Canosa arrives like a revelation: a place that doesn’t “have history” so much as sits on it, layer upon layer, with ancient time still present in the streets.

Here, Roman Canusium is more than a name: you’re in one of Apulia’s major archaeological centres, where the landscape and the city feel inseparable, and ruins appear as naturally as olive trees. 

Day 10: Canosa di Puglia to Matera 

69 miles | 111km | 3896 ft | 1188m

A showstopper stage as you roll into southern Italy’s most dramatic terrain: deep ravines and limestone cliffs that open and close around you, with the Gravina carving a wild gorge through the landscape—perfect for a photo stop at Gravina’s extraordinary Ponte Acquedotto suspended above the canyon. 

Then it’s on to Matera, where the finish is nothing short of iconic: the Sassi and the Park of the Rupestrian Churches of Matera—a UNESCO World Heritage Site—unfold as a labyrinth of rock-cut streets and ancient cave dwellings, best explored slowly as the light turns the stone honey-gold.

Day 11: Matera to Alberobello

46 miles | 74km | 1801ft | 548m

Start cycling and enjoy this ride through olive groves and vineyards on the way to the “Valle d’Itria” which is the heart of Puglia’s trulli region. Trulli are conical shaped dwellings unique to this part of Italy. Originally used as storage sheds for farmers, they quickly became popular as temporary shelters.

Immerse yourself in the rich cultural heritage of Gioia del Colle, with its medieval castle standing sentinel over the surrounding countryside. Continue pedaling onwards towards Alberobello, a Unesco city since 1996, where whitewashed buildings and narrow cobblestone streets transport you to another era. Lose yourself in the labyrinthine alleys of its historic centre, where Baroque architecture and ancient traditions produce an interesting mixture.

Day 12: Alberobello to Lecce 

73 miles | 116km | 2039ft | 621m

Follow the winding roads that lead through the rugged terrain of southern Italy, where each bend reveals a new panorama of breathtaking splendor before reaching our final destination, arguably Puglia’s most beautiful city – Lecce. Also known as the baroque Florence of Southern Italy, Lecce’s pink sandstone buildings and pedestrian city centre make for an inviting afternoon of exploration. 

Day 13: Lecce to Santa Maria di Leuca

60 miles | 96km | 2847ft | 891m

Our route will take us from the inland to the coast and then going through a nature reserve. We'll continue south to Otranto, historically one of the most important trading cities in Puglia and from here it is along the jagged coast, dotted with karstic caves and ancient defense towers or castles. Before arriving in the small town of Leuca, you can stop by the land’s end and the sanctuary Santa Maria di Leuca. Enjoy the seafront promenade as a reward for accomplishing this Coast to Coast Adventure across Italy.

On the final day we finish cycling on Monday around 3pm. After toasting your successful traversing of Italy we'll head to our nearby Hotel where you can relax before we will have a final celebratory meal in the evening. 

Transfer to Bari: Monday 

After a swift celebratory drink in the bar situated at the end, a coach will transfer you from Santa Mari di Leuca the 2hr 30min to our Hotel in Bari. 

Departure Day: Tuesday

You will need to arrange your own transport from our Hotel, obviously we'll help you get this organised. The airport is just 15-20 mins away by Taxi or there is a regular train service direct to the airport. 

Obviously you are welcome to stay on in Italy and make your own way back to the UK whichever way you wanted. We'll establish your plans nearer the time.

What's included

   14 Nights Bed & Breakfast Accommodation

We stay in good quality Hotels some of which will have swimming pools. Where ever it is possible we all stay together in the same accommodation as a group. No need to check in Pedal Britain team will have done that for you, just collect your key and relax. Bikes are either locked in a secure area of the hotel or in your room. Breakfasts are all included.

 Fully Supported Tour 

The Pedal Britain support vans are never far away to provide any assistance you need, be it access to your day bag, resolve a mechanical issue, report a first aid problem or just have a morale boosting chat. Just phone the driver or tap helmet as we pass if you need anything and we'll stop for you.  

Daily Luggage Transfer

The support vehicle moves all of your luggage between each nights accommodation. Also we recommend leaving a day bag in the support van to further reduce what you need to carry on the bike.

Includes Lunch and Brew Stop Refreshments 

Lunches will be mainly in local cafe/restaurants however there may be a few picnics too. The famous Pedal Britain pop up café delivers welcome brew stops at strategic points along the route to keep energy levels up providing you with water, tea, coffee, fruit, biscuits, cake etc.. and anything else you specifically request.

Expert Cycling and Tour Guides

Pedal Britain prides itself on having staff with a 'can-do' attitude, their entire focus is on ensuring they attend to your every need, to ensure that you have the best experience possible. They have detailed knowledge of the route, are first aid qualified and decent mechanics - but most importantly they care about you. When asked 'What makes Pedal Britain better than others?' quite simply it is our amazing staff - the one thing our competition cannot copy.

Pedal Britain Tour App & Detailed Route Notes

From here you can download the relevant file format for the daily route maps - GPX, TCX etc.. These can then easily be transferred to whatever GPS unit you are using such as a Garmin or Wahoo.

Don't have a GPS unit? No problem, just download our APP and it turns your Smart Phone into a GPS unit with turn by turn route navigation.

Live Tracking App

Pedal Britain Live Tracker app allows family and friends to see how well your progressing. The same tracker also helps us keep you safe and also ensure your following the route!!

WhatsApp Tour Groups

We will invite you to join a closed WhatsApp group for your specific tour. This enables you to get to know people before the holiday and provides a platform to share training experiences or any questions, concerns you may have before the tour.

Not Included

Evening Meals - although group bookings will be made at local restaurants attendance is optional.

Travel Insurance - We highly recommend you take out insurance 

Transport to Start at Pisa or home from the End in Bari 

Easy Bike Transfer (Available for a Fee or Free if dropping & collecting)

Single Room Option (Limited number available)

Travel logistics

Getting to the Start - Pisa

Air

London airports with direct flights to Pisa include Stansted, Heathrow and Gatwick airports. Manchester also offers a direct flight option.

Once you arrive at airport the best option of getting into the City to our Hotel is: 

1. The People Mover - this automated system connects the airport with the City Centre in just 5mins. From there you can continue on foot or 

Obviously with the tour starting on Tuesday there is the option to arrive a few days earlier and explore everything Pisa has to offer, perhaps combining a trip to explore the nearby Florence. 

Getting Home from San Maria di Leuca via Bari 

Air 

Transfer to Bari: Monday 

After a swift celebratory drink in the bar situated at the end, a coach will transfer you from Santa Mari di Leuca the 2hr 30min to our Hotel in Bari. 

Departure Day: Tuesday

You will need to arrange your own transport from our Hotel, obviously we'll help you get this organised. The airport is just 15-20 mins away by Taxi or there is a regular train service direct to the airport which takes around 20 mins. 

Bike transfer

Getting Your Bike to Pisa & from Santa Maria di Leuca

Procedures for taking our vans full of equipment and bikes into the EU changed from 1st January 2022. There are now many extra pieces of paperwork that we need to complete, but the one that affects customers joining our European tours is called an ATA carnet.

This document details every item and piece of equipment that we take into the EU, for customs this has to be the same when we return to the UK and has to be completed for every van that we take to/from the EU.

Good News

We can still take bicycles, helmets and saddle bags over into the EU.

Bad News

I'm afraid that we can no longer take your personal luggage.

A further restriction is what we take out has to be exactly the same as what we bring back, so there is no flexibility to offer one way transport for your bike. If that did happen then we would be subject to a 20% charge of the value of the bike.

Each ATA carnet is subject to a fee and also a security bond payment which is dependent on the value of the bikes that we are carrying over in each van. You will be requested 8 weeks prior to the trip to complete a customs declaration form that we use on the ATA Carnet. 

It is for this reason that sadly we can no longer take bikes to/from the EU for free and will have to charge £50 per bike to cover the additional charges (covers both ways) which is in addition to any charges listed below for bike transfers and will be added to your balance invoice. 

Option 1: Customer Drop Off / Collection

FREE of Charge

If you can bring your bike to our offices in Northamptonshire then we will take your bike Free of Charge. No need to dismantle we'll take it fully assembled and safely secure it in the support vehicle for transporting to Porto and Pedal Britain will bring your bike back from Tavira.

Option 2: Bike Collection or Delivery - Pedal Britain Support Van

Cost for this service is £75.00 per bike - One Way to Start or From the End

On the Tuesday and Wednesday before a tour starts and in the week after a tour end, based on geographical location of clients that have signed up for this service, Pedal Britain's support van will come to an address of your choosing, which could be work, home or cycle shop to collect / deliver your bike. This means our van will transport your bike to Porto for the start, and will bring your bike back from Tavira then deliver to you in week after.

No need for dismantling we'll take it fully assembled and safely secure in the support vehicle for transporting. 

Option 3: Bike Collection or Delivery - Transport Partner

Cost for this service is £75.00 per bike - One Way to Start or From the End

If you happen to fall outside the geographical area being covered by the support van prior to the tour then do not despair we have an alternative solution.

On the Monday before a tour starts we'll arrange for our trusted transport partner to collect your bike from an address of your choosing, which could be work, home or cycle shop and deliver your bike to Pedal Britain.

Clients will need to securely package up their own bike in a Medium size (150 x 22 x 90 cm) cardboard bike box. A local bike shop will for free or small fee provide a suitable box and much of the packing material you will need for this. Pedal Britain will bring your bike back from Nice and return your bike to you the same way in the week after a tour ends.

We cannot via this service accept helmets or any day bags packed inside the boxes.

Bike Transfer Service: Both Ways

Total Cost is £150.00 per bike 

Terms & Conditions of Bike Transfer Service

• Pedal Britain cannot be held responsible for any damage that occurs in transit - although we will obviously take great care of bikes in transit
• Where a third party is being used Pedal Britain cannot be held responsible for any damage in transit
• We recommend that you have insurance in place to cover you for any accidental damage or theft during transit