Exploring the southern jewels of Italy. Starting in the vibrant Adriatic city of Bari, we ride into the heart of Puglia, through olive groves, vineyards, and timeless countryside to the famous trulli of Alberobello. From there, our journey takes us to extraordinary Matera, one of the oldest continuously inhabited cities in the world, renowned for its ancient cave dwellings and spectacular UNESCO-listed historic center. Leaving Matera behind, we turn west toward the Mediterranean and the unspoiled beauty of the Cilento Coast — quiet country roads winding through rolling hills, traditional villages, and magnificent coastal landscapes. And then comes the grand finale: the legendary Amalfi Coast, riding beneath dramatic cliffs, through colorful villages perched above the sea.
Designed for cyclists who want much more than simply putting miles on the bike, this tour brings together great riding, extraordinary scenery, centuries of history, regional cuisine, and genuine Italian hospitality.
The tour also celebrates one of the greatest pleasures of traveling through Italy: its extraordinary food and wine. After each day's ride, we slow down and enjoy the flavors of the regions we've traveled through — local wine tastings, traditional specialties, regional cuisine, and authentic Italian hospitality. It's the perfect combination of cycling, culture, cuisine, and friendship — discovering not only some of Italy's most beautiful roads, but also the true meaning of la dolce vita.
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Day by Day Itinerary
Sunday, May 9, 2027 · Arrival in Bari — Let the Adventure Begin
Welcome to Bari! Upon arrival at the airport, we'll transfer to our hotel in the Bari/Polignano a Mare area, where you'll meet your guide, Raffaele, and your premium Hersh ORO bike, fitted to your specifications and ready to ride. After settling in, enjoy an optional short test ride to stretch the legs, fine-tune the bike, and shake off the jet lag. Then it's time for our first dinner together — a chance to relax, enjoy great Puglian food and wine, and toast to the beginning of an unforgettable Southern Italy cycling adventure.
Monday, May 10, 2027 · Polignano a Mare to Ostuni — Olive Groves & the White City
Experience the authentic beauty of Puglia on a spectacular ride from the dramatic seaside cliffs of Polignano a Mare to the dazzling hilltop "White City" of Ostuni. We follow quiet country roads through centuries-old olive groves, traditional stone walls, and small villages, stopping at a traditional masseria to discover how Puglia's famous extra virgin olive oil is produced — with a tasting, of course. Our ride finishes in beautiful Ostuni, rising above the olive groves and recognizable for miles by its maze of brilliant whitewashed buildings.
Tuesday, May 11, 2027 · Alberobello, Wine Country & the Road to Matera
Our first highlight is Alberobello, home to the world-famous trulli — the whitewashed stone houses that earned the town its UNESCO World Heritage status. We continue toward Gioia del Colle, riding through the heart of Puglia's wine country, with a stop at a local winery for a guided tasting of the region's celebrated wines. A final stretch takes us to one of the great treasures of Southern Italy: Matera, famous for its ancient Sassi, cave dwellings carved into the rock, and extraordinary architecture.
Wednesday, May 12, 2027 · Matera to Craco — Into the Heart of Basilicata
From Matera, our route follows peaceful country roads through rolling hills, open farmland, small villages, and dramatic landscapes, far from the crowds of Italy's better-known destinations. Our destination is the hauntingly beautiful Craco, one of Italy's most fascinating ghost towns — abandoned after landslides forced its residents to leave, the medieval village still stands dramatically on its hilltop.
Thursday, May 13, 2027 · Crossing to the Cilento — From Coast to Coast
Today we cross Southern Italy from one coast to the other, leaving Basilicata behind and heading toward the beautiful Cilento Coast and the blue waters of the Tyrrhenian Sea. No visit to Campania would be complete without tasting one of its greatest treasures: authentic Mozzarella di Bufala Campana — we'll stop to see how it's traditionally produced, and taste it at its freshest.
Friday, May 14, 2027 · Castellabate to the Amalfi Coast — Two Faces of Southern Italy
Our day begins in Castellabate, a charming hilltop village overlooking the Mediterranean, surrounded by the unspoiled landscapes of the Cilento. We enjoy a relaxed ride along quiet roads with beautiful views of the countryside and sea. After the ride, we continue by van and boat to the breathtaking Amalfi Coast — dramatic cliffs rising from the Mediterranean, colorful villages clinging to the mountainsides, spectacular views around every corner. A shorter day on the bike, giving more time to explore and enjoy la dolce vita ahead of the grand finale.
Saturday, May 15, 2027 · Until Our Next Adventure! — Arrivederci
After breakfast, we transfer to Naples Airport for our flights home. It's time to say arrivederci after an unforgettable journey across Southern Italy — from the Adriatic shores of Puglia, through Basilicata and Matera, to the Cilento and the spectacular Amalfi Coast. Airport transfer: approx. 58 minutes driving.
Pricing
| Standard price | $6,250 per person (double room) |
| Early Bird | $4,990 per person — book by November 30, 2026 |
| Single supplement | +$500 (single room, 6 nights) |
| E-bike upgrade | Available at supplemental cost — ask on booking |
| Deposit | $550 to confirm your place |
| Balance due | January 31, 2027 |
Included
- 7 days / 6 nights double hotel accommodation
- Daily breakfast + 6 dinners (half board)
- All carbon road bikes Hersh ORO (e-bikes at supplement)
- All airport transfers within Italy
- Luggage transportation throughout the trip
- Private support vehicle on all rides
- Expert guides
- Free commemorative Hersh Bike Jersey
- Ferry tickets (last stop to hotel)
- Museum entrance
- Farewell dinner at a surprise location
- Daily safety meetings before each ride
- Water & electrolytes on rides
- Mechanical assistance
Not included
- International flights and personal travel insurance
- Lunches
- Mini-bar and personal hotel expenses
- Gratuities for guides
- Optional photographer
- Extra rentals
- Tourist tax
- Drinks and alcoholic beverages
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Ready to ride?
This tour is booked through our partner Bravo Bike Tours — 7 days · 6 nights.
Places available, early bird pricing active.
$4,990 per person — book by November 30, 2026 Early Bird price
Book with Bravo Bike ToursPayment via email, PayPal or Zelle — arranged directly with Bravo Bike Tours, our confirmed booking partner for this tour. Questions about the itinerary? Email Hersh.
Frequently Asked Questions
Are flights included?
No — international flights and personal travel insurance are not included. Airport transfers within Italy on arrival and departure days are covered.
Is a single room available?
Yes — a single supplement of +$500 covers a single room for all 6 nights.
Can I upgrade to an e-bike?
Yes, an e-bike upgrade is available at a supplemental cost — just ask when booking.
How do I secure my place?
A $550 deposit confirms your booking. The balance is due by January 31, 2027.
What fitness level do I need?
This is an active road cycling holiday with daily rides up to 60 miles and climbs up to 3,300 ft of elevation gain (Alberobello to Matera) — see the day-by-day itinerary above for each day's distance and elevation. A good baseline road cycling fitness is recommended.