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Puglia cycling holiday

Puglia Cycling Holidays: 8 Days From Matera to Otranto

8 days | Moderate | 5.00
From $4,272 ()
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Puglia is ridiculously good for cycling. Quiet backroads, endless olive groves, whitewashed towns, and the Adriatic popping up just when you need a swim or a seafood lunch. On this 8-day cycling holiday, I ride with you from Matera’s surreal cave city all the way to coastal Otranto, crossing the best of southern Italy along the way. We spin through trulli (stone houses with cone-shaped roofs) villages, vineyard country, and sun-baked countryside, stopping often for what Puglia does best: incredible food, great wine, and long evenings in beautiful countryside masserias.

Adventure Highlights

  • Ride across Puglia: Pedal from Matera all the way to Otranto, linking cave dwellings, trulli villages, and iconic towns like Alberobello, Ostuni, and Gallipoli
  • Big rides, soft landings: Wind down in boutique hotels, countryside masserias, and wine resorts
  • Cycling made delicious: Taste the region: from Altamura bread to olive oil tastings and Primitivo wine in Manduria
Duration
8 days
Season
May through June, September through October
Group size
Up to 12 people
Accommodation
Luxury: 4-star boutique hotels, countryside masserias, and wine resorts
Difficulty
Moderate: Good fitness required, cycling up to 72 km (45 mi) & 4–5 hours per day, with up to 530 m (1,739 ft) of elevation gain
What's included
Guide, lodging, road bike rental, all dinners, luggage transfers, and more

The adventure, day by day

This 8-day cycling journey through Puglia is a slow ride through one of southern Italy’s most delicious regions. Starting in Matera’s surreal cave city, we pedal quiet backroads through olive groves, vineyards, and whitewashed villages as we cross the Valle d’Itria and the Salento peninsula. Along the way, trulli houses, hill towns, and endless countryside set the scene, while stops for olive oil, local wine, and long Italian lunches keep the energy high. We finish on the Adriatic in Otranto, with a week of scenic riding, incredible food, and beautiful masserias behind us.

Day 1: Arrive in Matera
Matera view of the city from a cave

We arrive in Bari and transfer to Matera, one of southern Italy’s most fascinating historic cities. After settling into our boutique hotel in the old town, we head out on a guided walk through the UNESCO-listed Sassi districts, where cave dwellings carved into limestone create one of Italy’s most unique landscapes. In the evening, we gather for a welcome dinner and our first taste of Lucanian cuisine.

Accommodation: Boutique hotel in Matera
Meals: Dinner

Day 2: Ride the Murgia plateau
Altamura biking in Italy

After a bike fitting and technical briefing, we roll out for our first ride across the Murgia plateau. Quiet countryside roads lead us toward the historic town of Altamura, famous for its traditional bread. Later in the day, we dive deeper into local flavors with either a bread-making workshop dedicated to Altamura bread or a guided wine tasting with a local sommelier.

Accommodation: Boutique hotel in Matera
Meals: Dinner
Cycling: 58 km (36 mi), rolling terrain
Elevation gain: 450 m (1,476 ft)

Day 3: Matera to Alberobello
Two bikers in Italy

Today we leave Basilicata and ride into Puglia along quiet rural roads surrounded by farmland and olive groves. As we enter the Valle d’Itria, the scenery shifts and the iconic trulli houses begin to appear along the route. Our destination is Alberobello, the UNESCO-listed town famous for its cone-roofed stone houses, where we spend the night in a traditional trullo-style property or countryside masseria.

Accommodation: Trullo-style hotel or countryside masseria in Alberobello / Valle d’Itria
Meals: Dinner
Cycling: 69 km (43 mi), rolling terrain
Elevation gain: 520 m (1,706 ft)

Day 4: Valle d’Itria ride
Countryside biking in Italy

Today’s ride explores the heart of the Valle d’Itria, a region known for its vineyards, olive groves, and dry-stone walls dividing the countryside. Quiet backroads take us through small villages and rolling landscapes before we approach Ostuni, the famous White City overlooking the Adriatic coast. Along the way, we stop for an olive oil tasting before returning to our countryside masseria.

Accommodation: Countryside masseria in Valle d’Itria
Meals: Dinner
Cycling: 50 km (31 mi), gentle rolling terrain with short climbs
Elevation gain: 530 m (1,739 ft)

Day 5: Ride to Manduria
Primitivo grapes italy

We continue south toward the Salento region, cycling through quiet countryside and small villages as the terrain becomes flatter. Our destination is Manduria, one of the historic homes of Primitivo wine. After settling into a beautiful wine resort, we enjoy a tasting of local wines before dinner.

Accommodation: Vinilia Wine Resort, Manduria
Meals: Dinner
Cycling: 60 km (37 mi), mostly flat terrain
Elevation gain: 300 m (984 ft)

Day 6: Gallipoli and the Ionian Coast
Coastal ride in Italy

Today we follow the Ionian coast toward Gallipoli, passing through the protected landscapes of Porto Selvaggio along the way. The ride is relaxed and scenic, with the sea never too far away. We stop for a picnic on a sandy beach and, if the weather cooperates, take a refreshing swim before continuing to Gallipoli. Dinner and an overnight stay await in this charming coastal town.

Accommodation: Relais Corte Palmieri
Meals: Dinner
Cycling: 55 km (34 mi), flat terrain
Elevation gain: 180 m (591 ft)

Day 7: Ride to Otranto
Posing by the sea in italy

Today we cross the Salento peninsula, linking the Ionian and Adriatic coasts. Quiet inland roads lead us through villages and Mediterranean landscapes before we reach Otranto, one of Puglia’s most beautiful seaside towns. After exploring the town and visiting the cathedral, we celebrate the journey together with a farewell dinner.

Accommodation: Masseria dei Monaci, Otranto
Meals: Dinner
Cycling: 72 km (45 mi), rolling terrain
Elevation gain: 490 m (1,607 ft)

Day 8: Departure
Wine bottles in Italy

After breakfast, the trip concludes. Transfers are available to Bari or Brindisi airports.

Meals: Breakfast

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Lodging & food

Adventure, packed to go

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What others say about this adventure

5.00 (3 reviews)
A
Ameriga Fanigliulo

Experienced incoming tour operator with deeply rooted knowledge of Matera specifically, and beyond (rest of Basilicata region as well as Puglia). Great professionalism, flexibility and creativity of the owner and founder Dora – fluent in so many languages that I cannot name them all… Thanks Dora for having us discover the hidden treasures of Matera: memorable experience for our multi-national group from München!

P
Paulo Maragliulo

Simply the best travel organizer you can find in Basilicata and possibly in Southern Italy! They are focused on outdoor adventures especially hiking and cycling, but run also walking cultural tours!
You can book from them from the equipment you need (including all sorts of bikes and e-bikes) to a trip fully organised.

C
Carlo Magni

Always very nice experiences with the team of Ferula Viaggi cycling in Basilicata and Puglia. It is a pleasure to discover with them new and amazing places.

5.00(3 reviews)
A
Ameriga Fanigliulo

Experienced incoming tour operator with deeply rooted knowledge of Matera specifically, and beyond (rest of Basilicata region as well as Puglia). Great professionalism, flexibility and creativity of the owner and founder Dora – fluent in so many languages that I cannot name them all… Thanks Dora for having us discover the hidden treasures of Matera: memorable experience for our multi-national group from München!

P
Paulo Maragliulo

Simply the best travel organizer you can find in Basilicata and possibly in Southern Italy! They are focused on outdoor adventures especially hiking and cycling, but run also walking cultural tours!
You can book from them from the equipment you need (including all sorts of bikes and e-bikes) to a trip fully organised.

C
Carlo Magni

Always very nice experiences with the team of Ferula Viaggi cycling in Basilicata and Puglia. It is a pleasure to discover with them new and amazing places.

Things to know

  • Included:

      • An experienced, local cycling guide with extensive knowledge of the area
      • 8-day Puglia cycling holiday
      • Accommodation for 7 nights in boutique hotels and wine resorts (double occupancy)
      • 6 dinners and 1 breakfast
      • Bread-making workshop (Altamura bread) or a guided wine tasting on Day 2
      • Olive oil tasting on Day 4
      • Wine tasting at Vinilia Wine Resort in Manduria on Day 5
      • Road bike rental
      • Support vehicle and luggage transfers
      • Bike fitting and technical briefing
      • Mechanical assistance during rides

    Add-ons:

      • Single occupancy room — can be arranged at an additional fee
      • Extra nights in Matera or Lecce — can be arranged at an additional fee
      • Private transfers on request (arrival or departure, with a minimum of 6 participants) — can be arranged at an additional fee

    Not included:

      • Flights
      • Lunches
      • Personal expenses
      • City taxes
      • Anything not mentioned in the “Included” section above
      • Insurance — recommended, available to add at checkout
      • Guide gratuities — optional
  • To join this Puglia cycling holiday, good fitness is recommended. Expect cycling up to 72 km (45 mi) & around 4–5 hours per day, with up to 530 m (1,739 ft) of elevation gain. The terrain is mostly rolling with some flatter coastal sections, and rides take place on quiet countryside roads.

    Want to see what else is there in the area? Discover more Italy bike tours here!

  • Here’s a list of the equipment you need to bring:

      • A small day bag pack for rides
      • Bike helmet
      • Cycling shoes
      • Cycling trousers
      • Eye protection (riding goggles/sunglasses)
      • Water bottle or hydration bladder (2L capacity)
      • Light jacket for riding
      • Insulation layers for cooler conditions (puffy jacket, long-sleeve base layers)
      • Personal toiletries
      • Sunscreen
      • Sunglasses
      • Camera — optional (but recommended)

    Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.

    Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!

  • Group sizes and pricing

      • For this Puglia cycling holiday, the usual client-to-guide ratio is 12:1. 
      • It takes a minimum of 6 people for this tour to operate. The maximum group size is set at 12 participants.

    A Puglia cycling holiday can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors younger than 18 may be permitted to join the Puglia cycling holiday on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has participants under the age of 18, contact us prior to booking to make arrangements.

  • The price for this Puglia cycling holiday is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can leave us a note at checkout if interested.

  • The starting point of your Puglia cycling holiday is Matera. To get there, most people fly into Bari Airport (BRI). From there, you can take a shuttle service, public transport, taxi, or rent a car to reach Matera.

    You will meet your guide on Day 1 at your hotel in Matera.

  • We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.

    Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.

  • Deposits

    Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.

    Cancellations

    Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.

    Basic

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 60 or more days before departure, a 70% refund of the total trip price will be issued.
      • If cancelled within 59 days of departure, no refund will be issued.

    Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 60 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled 30-59 days before departure, a 50% refund of the total trip price will be issued.
      • If cancelled within 29 days of departure, no refund will be issued.

    Super Flexible

      • If cancelled within 48 hours of booking, a full refund will be issued.
      • If cancelled 30 or more days before departure, a full refund of the total trip price will be issued.
      • If cancelled within 29 days of departure, a 50% refund of the total trip price will be issued.
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