Overview
In the deep south of Italy, nestled between the Adriatic and Ionian seas, lies the beautiful Puglia region, one of Italy’s best-kept secrets when it comes to cycling. This self guided cycling itinerary explores the unique selection of cultural and natural treasures found here in six cycling days.
From Otranto, crossroads of different cultures, to the whitewashed houses of Ostuni reaching towards the blue sea, from the memorable conical roofs of the “Trulli” in Alberobello to the enchanting white-sand beaches near Gallipoli, enjoy superb rides through sparsely inhabited ancient olive groves, Mediterranean Mache and invigorating coastal roads with views that make you fall in love with the place.
- Lecce, the stunning Baroque city of southern Italy
- Sleep in a real Trullo house in the UNESCO town of Alberobello
- Beautiful sandy beaches, turquoise sea and breath-taking caves
- Friendly people and great traditional Puglian culinary specialities
- Wonderful landscapes with ancient olive groves, vineyards and jagged coastline
- Authentic country towns and villages: Ostuni, Gallipoli, Otranto
Itinerary
Day 1: Arrive in Monopoli
Arrive in the glorious town of Monopoli overlooking the Adriatic Sea. Get lost in the labyrinth of streets amidst whitewashed houses. Visit the main church, known as Basilica concattedrale Maria Santissima della Madia patrona, and the stunning, unique squares. In the afternoon enjoy the sea breeze while sipping a fresh local white wine tasting and the famous “taralli”.
- Accommodation: hotel in Monopoli (Albergo Diffuso Monopoli or similar)
Day 2: Monopoli to Alberobello | 47km
Today’s ride is a gradual climb from the Adriatic sea to the gently undulating valley of Itria. through the typical Murgia landscape with olive groves and fields surrounded by low stone walls. Stop at Castellana Grotte for a rest and to visit an immense underground cave system, one of the largest in Europe. Continue on to the Trulli capital of the world: Alberobello. The trulli (whitewashed stone houses with conical roofs) are exceptionally intriguing and comfortable, as you will experience tonight when you sleep in one. The 1,000 trulli surrounding you will make you feel transported into another world.
- Cycling for the day: 47km, 4h, ↑500m ↓100m
- Accommodation: Trulli resort in Alberobello (Trullidea Resort or similar)
Day 3: Alberobello to Ostuni | 40km
Ride through the historical “Murgia” area, amongst olive groves, southern vineyards and classic “Masserie” farmhouses. Pass the medieval town of Cisternino with its brilliant DOC wine, then on to Ostuni, a stellar town on the Adriatic Sea. You enter the heart of the city, pass its protective walls and gaze your eyes onto the Gothic fifteenth-century cathedral. A majestic moment to experience.
- Cycling for the day: 40km, 3h, ↑300m ↓500m
- Accommodation: 4-star hotel in Ostuni (Relais Sant’Eligio or similar)
Day 4: Ride to Ostuni, train to Lecce, ride to Gallipoli | 52km
This morning you cycle down to Ostuni train station where you catch the train to Lecce (not included), taking your bike with you.
After leaving the train station in Lecce, you soon approach the countryside. The ride is gentle, mostly on secondary roads surrounded by olive trees. When passing through small historic towns such as Copertino and Nardò, take some time to visit the town centre or just stop for a coffee. Then, you can find some nice spots for a swim in the Ionian Sea on the way to Gallipoli.
- Cycling for the day: 52km, 4-5h, ↑240m ↓330m
- Accommodation: 4-star hotel in Gallipoli (Hotel 33 Baroni or similar)
Day 5: Gallipoli to Santa Maria di Leuca | 51km
A coastal road takes you to the southernmost point of Puglia, dividing the Ionian and Adriatic Sea. But first, take a swim in the turquoise waters at the Torre del Pizzo beach and lay along the fine white sands. Then continue south to Santa Maria di Leuca, a magnificent village of fantastic beaches and wacky, wild, colourful mansions.
- Cycling for the day: 51km, 4-5h, ↑200m ↓170m
- Accommodation: 4-star hotel in Santa Maria di Leuca (Hotel L’Approdo or similar)
Day 6: Santa Maria di Leuca to Otranto | 52km
Revel in the sea breezes as you ride along the high coastal route, winding your way along the gentle, undulating rift of the cliffs, and enjoying the phenomenal views. Stop for a glimpse of the spectacular cave, the Grotta Zinzulusa, and then on to Otranto, a Greek-then-Roman port town, often frequented by merchants and thrill seekers in the past.
- Cycling for the day: 52km, 4-5h, ↑520m ↓530m
- Accommodation: 4-star hotel in Otranto (Hotel San Giuseppe or similar)
Day 7: Otranto to Lecce | 53km
Today you visit the Alimini Lakes, which run parallel to the sea. Cycle your way through the Greek Salento countryside, where traces of the former colonies are still present in the dialect, cuisine and bright style of architecture. The whites shine against the euphoric blue of the sea. Arrive in Lecce, a brilliant city full of wonderful palaces which will enchant you.
- Cycling for the day: 53km, 4-5h, ↑120m ↓90m
- Accommodation: 4-star hotel in Lecce (Hotel Delle Palme or similar)
Day 8: Departure
The trip and our services end after breakfast unless you have booked extra nights in Lecce or a transfer to the airport.
What to expect
Accommodation
Standard accommodation for this trip is mostly in selected 4* hotels. On day 2, you will have the chance to stay in authentic stone trulli typical of Puglia, located in the heart of the city. Some accommodations have a swimming pool. All places have been carefully hand-picked by us, and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.
Click to view default hotels
- Albergo Diffuso Monopoli (Monopoli)
- Trullidea Resort (Alberobello)
- Relais Sant’Eligio 4* (Ostuni)
- Hotel 33 Baroni 4* (Gallipoli)
- Hotel L’Approdo 4* (Santa Maria di Leuca)
- Hotel San Giuseppe 4* (Otranto)
- Hotel Delle Palme 4* (Lecce)






























*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
Breakfast is included each morning. When no restaurant is available on the route, lunches and snacks can either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. For the evening meals, dinner is available either from the restaurant in your hotel or the restaurants in the town where you stay overnight.
Difficulty and terrain
The rides go mostly on well-asphalted country lanes and secondary roads with little traffic, however, note that sometimes you will have to cycle on more highly-trafficked roads when approaching and riding in the larger towns. Average daily distances vary between 30km and 50km, with daily elevation gain ranging from 120m to 550m. The trip is suitable for regular cyclists who have an active lifestyle (read more about difficulty grades). Once you arrive at your first hotel you will receive a detailed information package, including a destination manual, route notes, and maps. Prior to the start date, you will also be sent GPS tracks, which you can load on any Garmin device or smartphone application that you are used to working with.
When to go
The trip can start each Friday between mid-April and mid-July and between the beginning of September and mid-October (please note that it can be scorching in July). For groups of 4 people or more, the trip can depart on any day of the week, subject to availability.
Puglia enjoys a comfortable Mediterranean climate with hot sunny summers and mild winters. There is an average of 300 sunny days in Puglia. Spring is characterised by the quick return of warmer and sunnier weather. The average temperatures in April and May are 14C going up to a comfortable 18C by the beginning of June. Summer lasts from June through September and is hot and sunny with average temperatures of 21C in September and 24C in July and August. Days in October are still warm, with average temperatures of 17-21C.
Getting there
Click to view travel options
By plane
Our recommended arrival & departure airports for this tour are Bari (BRI) and Brindisi (BDS).
By train or bus
Arrival in Monopoli: From Brindisi (BDS) or Bari (BRI) airports, you need to reach the close city stations. Train connections are available to reach Monopoli.
Departure from Lecce: Departing from Lecce you can take the direct train to reach both Bari or Brindisi train stations, where you will find connections to the relative airports. For the most updated information about trains visit the website www.trenitalia.it.
Inclusions
Included
- 6 nights in 4-star hotels and 1 night in authentic stone trulli
- 7 breakfasts
- Luggage transfer on all cycling days (1 piece up to 20kg per person)
- A detailed digital information pack, route notes and maps with tracks. Please note that the info pack is emailed to you prior to departure, and no printed documents are mailed or provided locally
- 24/7 phone support by our local office/representative
Excluded
- Airfare and connecting land transfers
- Train ticket to Lecce on day four
- Lunches and dinners, drinks and snacks
- Bike rental
- Travel insurance (required – get a quote online)
- Local tourist tax and entry fees (payable on the spot)
- Personal expenses
- Any items not specifically mentioned as ‘Included’ in the programme
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- Supplement applies to members of a group who require a single room / single use of a double room
- This holiday is NOT available for solo travellers
- Bike rental, including delivery to Monopoli, theft insurance and collection from Lecce. Extending the bike rental is not possible
- Airport transfers
- Extra nights only in Monopoli and Lecce
- Other departure days are available for min. 4 people for the same price. If less than 4 people – there will be a supplement
- Printed tour materials at first accommodation
Bike rental
In case you would like to rent a bike from us, we can offer you a standard hybrid bike, trekking bike or e-bike. All our bikes are equipped with a phone holder, 1 rear side bag, 1 repair kit, odometer, and 1 padlock. Helmets are available upon request at extra cost.
Sample models: Longo Hybrid, FRW Trekking, Atala Bfree









































































