Price
£2,995.00 based on 2 people sharing a Twin/Double Room
($3,743.75 USD or $5,361.05 AUD)
£500.00 deposit
£750.00 single room supplement
Dates
There are currently no scheduled dates for this tour, but please contact us if you want to schedule a private tour for six or more people.
Tour information coming soon!
Joining the tour
Start: Pisa
Our first night 'arrival day' Tuesday will be spent in Pisa.
For more detailed information please click the "Itinerary" tab below:
Cycling level
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, cycling south along the west coast with its amazing beaches into the Lazio region.
Through Tuscany you will find roads lined with iconic evergreen cypress, rolling hills of wheat and hectares of vines. Medieval hilltop villages, like Bolgheri, 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 then enter Campania and continue east across the stunning Apennnine Mountains through Basilicata you'll experience the different types of terrain, from challenging climbs to rolling hills and flat river roads. 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.
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: Pecioli to Siena
48 miles | 77km | 3630 ft | 1106 m
We start in Pecioli with stunning views of the quintessential Tuscan landscape. 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
48 miles | 77km | 3630 ft | 1106 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
48 miles | 77km | 3630 ft | 1106 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
48 miles | 77km | 3630 ft | 1106 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 Piceno
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
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
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 Peschici
Leaving the Adriatic behind for a moment, you roll inland through the low foothills on the Molise–Puglia border before dropping back toward the sea and arriving on the Gargano, Italy’s “spur”—a limestone promontory shaped by caves and karst landscapes, softened by coastal forests and a patchwork of almond, citrus, and olive groves.
As the day unfolds, the coastline transforms from gentle sand to high white cliffs that break into hidden coves and fine beaches, while inland the Foresta Umbra wraps the headland in deep green—beech, oak and pine—forming the wild heart of the Gargano National Park.
Your finish in Peschici feels like a reward: a cliff-top town of whitewashed houses and winding lanes, poised above the Adriatic and perfectly placed for a golden-hour stroll and a relaxed seaside evening.
Day 9: Peschici to Manfredonia
A coastal classic across the Gargano: roll south from cliff-top Peschici toward Vieste, with the Adriatic pinned to your side and the peninsula’s signature white limestone cliffs, coves and sea caves delivering nonstop views.
From the coast you climb into the airy hill town of Monte Sant’Angelo, home to the UNESCO-listed Sanctuary of San Michele Arcangelo, before a thrilling, fast descent drops you into Manfredonia—a relaxed fortified seaside town with its historic castle and an easy beach finish.
Day 10: Manfredonia to Canosa di Puglia
Day 11: Canosa di Puglia to Matera
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. Source
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 12: 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 13: 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 14: 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.
Departure Day: Tuesday > Bari
A subsidised coach will after breakfast on Departure Day transfer you from our Hotel to Bari airport for €50pp* (may vary as based on 24 seater coach)
Alternatively 8 seater private taxis to the airport will be around €60-€70pp (Based on 8 people sharing)
Bari (2hr 30min transfer) - Has direct flights to Stansted or London Gatwick along with multiple options via hubs in Europe to other UK airports such as Manchester
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.