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Bicycle Tours — Italy

Self-guided Bike Tour of Puglia - Southern Italy & the Heel of the Boot

On the Adriatic Coast, Puglia occupies the "heel" of Italy's boot. Here, ancient Greek and Italian culture mingle in hillside vineyards, olive groves, and whitewashed villages nestled against the blue of the Mediterranean. Pedal through a landscape filled with unique conical shaped dwellings known as trulli, and enjoy meals prepared with Italian, Greek, and Middle Eastern influences. Discover the warmth and hospitality of Southern Italy's friendliest people as you ride as far southeast as possible on Italy's mainland.

For more information download the Tour Factsheet

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  • Day 1

    Arrive in Monopoli and test ride to ruins of Egnazia

    Highlights: Byzantine and Norman towns; Castle of Charles V; Egnazia Roman ruins

    Arrive in Monopoli this afternoon at our Masseria, a typical Apulian farm with lodging just outside town. Your host meets you to fit your bikes and to discuss your tour. They'll suggest an orientation ride along the Adriatic coast to Egnazia, with some of the best Roman ruins in the region. Enjoy Monopoli with its charming mix of Norman, Venetian-Byzantine and Arabic architecture. Dinner is included tonight. Daily mileage: optional 35 km (22 miles).

  • Day 2

    Cycle to Conversano

    Highlights: Charming coastal town of Polignano, including dry gorges and beaches (the Lama, Grotta Palazzese and Rondinelle); the town of Conversano

    Before you leave Monopoli be sure to visit the main food market with its fresh fish, fruit and vegetables. You bike north-west following the coast towards Polignano this morning, a small and vibrant fishing village surrounded by clear blue waters. This is a good stop for lunch or for ice cream. The small little hamlet of San Vito is another great stop along the sea with plenty of great picture opportunities. Your destination tonight is inland in the small town of Conversano, where you'll enjoy your resort hotel. We'll provide a list of several restaurants in town. Daily mileage: 29 km (18 miles)

  • Day 3

    Ride to Alberobello the city of trulli

    Highlights: Small villages, beautiful riding, and a final view on the trulli (limestone conical houses)

    This morning you bicycle to beautiful Alberobello and its unique trulli. These are cone-shaped dwellings made of dry limestone, traditionally stacked without mortar. Trulli are the most widely recognized symbol of Puglia and are unique to a small area around Alberobello. This ride is one of the most spectacular of the trip. You pedal through small villages, past fairy-tale landscapes with finely trimmed vineyards and conical trulli. Stop anywhere in this enchanting landscape for a picnic. Your destination Alberobello, the heart of the trulli region! Daily mileage: 38 km (24 miles)

  • Day 4

    Loop ride around Alberobello to Locorotondo

    Highlights: Wine village of Locorotondo, Trulli landscape, Medieval town of Martina Franca

    Sleep in today or get up early for a long ride as you'll be back in your same lodging tonight. Our routes follow winding roads among almond and olive trees. Your first stop is the village of Locorotondo perched as if a natural balcony overlooking the Itria Valley with its trulli and carefully kept vineyards. Locorotondo is like a typical town in the Greek Islands with its whitewashed houses, cul-de-sacs and small squares. Your next stop is the rich, 16th century baroque town of Martina Franca, also overlooking the Itria Valley. We suggest lunch in Martina Franca. You are back in Alberobello tonight. Daily mileage: 49 km (31 miles)

  • Day 5

    From Alberobello to Pezze di Greco

    Highlights: Stone lined country roads, olive oil tasting and olive grove stroll, eat and sleep in a traditional farmhouse

    Country lanes lined by weathered stone walls take you off the Murgia plateau you've been on for three days. Coast downhill while enjoying the breathtaking view of the surrounding countryside. This incredible descent will bring you down to Capitolo and south along an ancient farming road, finishing through a patchwork of almond orchards, olive groves, vineyards and gloriously coloured fields of fresh tomatoes and peppers. Your destination is a Masseria which still harvests olives and produces its own olive oil. Enjoy a walk through centuries old olive groves. Dinner is included tonight. Daily mileage: 43 km (27 miles)

  • Day 6

    Loop ride to Ostuni

    Highlights: Cisternino and Ostuni, the "white town"

    If it's not too early or late in the season relax and enjoy the pool this day if you are not up for a loop ride! Today's ride takes you back to the Murgia on a slow ascent before taking you into the village of Cisternino. This is a good lunch spot as you can stroll along the promenade with superb views of the valley and glimpses of the Adriatic coast. Your route from here continues along a beautiful ridge road to Ostuni, an impressive "white city" spanning three hilltops. Take a stroll in the center to admire the cobblestone streets and picture-perfect whitewashed houses before heading back to your hotel. Daily mileage: 65 km (40 miles).

  • Day 7

    Train and bike the heel of Italy

    Highlights: Train ride with your bike, bicycle along the coast, the gem town of Otranto

    You'll have a late start this morning with a one-hour train ride with your bike to avoid the traffic surrounding the port-city of Brindisi. Get off the train and you're now in the Salentine peninsula, the so-called "heel" of Italy. Start your ride through the interior before emerging onto the coastal roads, where white sandy beaches call you into the waters for a leisurely swim. Along the way you can have a lovely local lunch in the Castle town of Acaya. Stop along any of these beaches for a picnic before pedaling into the gem of the peninsula: the city of Otranto. Here you will lodge in the gorgeous Relais Valle dell'Idro and enjoy lovely evening walks along the giant piazza and the pristine beach. Thanks to its peculiar location, you have a panoramic view of all of Otranto, from the sea to the old town centre. Visit the architectural beauties of the Otranto martyrs' Cathedral, the Byzantine Church of Saint Peter, the old city centre, and much more. There are numerous lovely suggestions for dinner as well as one of the best pizza places in Puglia is right in the main Piazza. Welcome to Otranto! Daily mileage: 68 km (42 miles).

  • Day 8

    Bike to the southern-most point of the heel

    Highlights: Reach the tip of Italy's heel, visit the winery Castel di Salve winery thermal waters of Santa Cesarea Terme, karstic cave in Zinzulusa

    We have saved the best ride for last! Pedal along the coast south and west of Otranto where you will see the easternmost and southernmost points of Puglia both on the same day. You'll also visit the winery Castel di Salve winery on your way to Santa Maria di Leuca, a city noted for gleaming white as you arrive from the sea and its position as De Finibus Terrae, the end of the earth). You can make today as challenging as you like, as your route notes will provide cycling options up to 110km, but will also make it easy for you to pick a point to turn around and head back at any time. And, of course, whatever route(s) you choose to take, it will be easy to find places to stop for food and sightseeing along the way! Daily mileage: 55 - 110 km (34 - 68 miles).

  • Day 9

    Cycle Otranto to Lecce

    Highlights: Flat ride, olive tree orchards, Baroque architecture of Lecce

    Today, you will head to the wonderful town of Lecce, cycling the last 38km. You will find the terrain mostly flat and in between endless olive orchards. Your ride will lead you through the small enchanting villages of Borgagne, Melendugno, Castri' di Lecce e Lizzanello.... all villages in which time seems to have stopped, so be sure to stop and smell the olives. After arrival in Lecce, we will provide you a walking map to reach your final hotel destination, the Palazzo Rollo. This Palace is a charming bed and breakfast located in a 17th century palace in the heart of the historical centre of Lecce. The beautiful structure offers the opportunity to appreciate Lecce's baroque masterpieces in just a few steps. No matter how you choose to spend the day, be sure to stop for a coffee and the amazing local pastry known as Pasticciotto Leccese (filled with yummy custard cream). Take in all that Lecce has to offer on this last day of your Italian Holiday! Daily mileage: 37 km (23 miles).

  • Day 10

    End of your Bike Tour in Puglia

    Highlights: Explore Lecce, Continue traveling or return home

    Your bike tour of Puglia finishes today. You can spend more time in Southern Italy, or take the train to Bari or Brindisi for your homebound flight. Buon viaggio!

Includes 10 days, 9 nights in 3-4 star hotels, all breakfasts, 2 dinners, use of a quality 24-27 speed racing or hybrid bicycle; bike fitting and briefing; roadbook and map; GPS tracks; luggage transfers;
Countries Italy
Begin/End Monopoli / Lecce
Arrive/Depart Bari Airport (BRI) or Brindisi Airport (BDS)
Total Distance 411 - 612 km (255.5 - 380.5 miles)
Daily Distance 30 - 100 km (19 - 62 miles)
Rating 301
Notes Optional activities include: guided walk of Alberobello. Optional Shuttles to/from Bari or Brindisi Airport(s). You can make this a 9 days tour. Ask for details.
Tour Factsheet
Terms Terms & Conditions
Dates Prices Single Supplement
Dates Tour begins any day except Sundays in March, April, May, June, September, October and November.
City taxes not included.
Prices €1620 Single Supplement €550
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  • The hotels were fine and met my expectations. Masseria was great and the hosts wonderful. My favorite experience on this trip? Riding among the ancient olive trees and along the spectacularly beautiful coast of Puglia.

    October 2014

  • We felt really spoiled with the hotels. They were great. Our favorite ride was the trip up from Leuca to Otranto. The weather was fantastic and the view spectacular. We also enjoyed many of the cities we visited.

    Karl P.
    CA, USA
    October 2015

  • Our favorite experience on this trip was staying in the trulli. It was especially nice to be have our own ''house'' which enable us to share a home cooked meal using local produce. We were impressed with the on-tour transfers. The drivers were punctual and friendly. Thank you.

    Janet N.
    New Zealand
    July 2016

  • The route notes provided were excellent, easy to follow. The hotels were excellent. They had "character".

    Alan H.
    March 2013

  • Oh the hotels and staff made the trip what it was! The best!

    Jennifer B.
    June 2014