Il Giro dei Venti
Il Giro dei Venti
Il Giro dei Venti


Between land and sea

Leuca-Otranto: the coast of marvels

The first stage of Il Giro dei Venti takes us from Santa Maria di Leuca to Otranto, and back.

We start from the southernmost point of Puglia, the tip of Italy’s heel, where one of its most enchanting villages is situated: Santa Maria di Leuca. Nestled between Punta Meliso and Punta Ristola, the two rocky headlands that hug the promenade boast an ancient history full of myths and legends. Right off the coast, the Adriatic and Ionian seas meet. And yet, because of their different salinities, they never mix, creating a play of colors of remarkable beauty.

After about 100 km of cycling along the spectacular Adriatic coast, you arrive in Otranto, the first city to see the sunrise in Italy, hence its nickname: “Gate of the East”. Olive groves, stone walls, fortresses and pastel-colored houses characterize the village, one of the prettiest in Italy, and are the turning point for your return to Leuca.

Corfu: island of royalty and artists

Our cyclotourism itinerary in Greece is set amidst the scenery of Corfu, the “capital” of the Ionian Sea.

Seaside villages and tree-lined avenues, monasteries and castles, hidden coves and breathtaking bays. The same views that have bewitched writers and aristocrats for centuries – such as the Empress of Austria, Sissi, who loved spending her holidays here, and the English poet, Lord Byron – will accompany us along the way.

Leuca-Gallipoli: towards the pearl of the Ionian Sea

The second Italian stage brings us from Santa Maria di Leuca to Gallipoli.

Pedaling for about 100 km through Salento, between cities, hilltop hamlets and nature, you arrive at Gallipoli, the “Beautiful City” (from Greek, Kale Polis). Situated on the Ionian coast about forty kilometers from Lecce, the ancient village is perched on a limestone island and connects to the new city by an arched bridge dating back to 1600. The walls, ramparts and towers, which once protected the city from invaders, today shelter it from storm surges and exude historic charm.

Between two seas

The crystal-clear waters of the Adriatic and Ionian Seas will be the theatre for the three inshore sailings, each lasting (around) 3-4 hours. The wind – an essential element for every sailor – will define the routes. Depending on the conditions, Roberto Ferrarese, multiple times World Champion and Head of Sailing section “Il Giro dei Venti”, will evaluate day by day which sea to sail, whether the Adriatic Sea, in the Leuca-Otranto route, or the Ionian Sea, in the Leuca-Gallipoli route. It will sail (as well) between the coasts of Corfù. The destination will be reached by each crew in an overnight sailing (with motor).


8 days of discovery

May 27th – Kissed by Fortune

Meeting in Santa Maria di Leuca (LE) and check-in by 4 p.m.

8 p.m. Meeting at the Leuca Yacht Club and welcome drink, event overview and drawing of teams  – composed of a pair of cyclists and a pair of sailing enthusiasts – plus handout of the racing packages.

Overnight on boat.

May 28th – The Adventure Begins

Cyclists: wake-up at 5 a.m., breakfast and meeting at the start line for the first ciclotouristic stage from Leuca-Otranto, and back.

Sailors: wake-up, breakfast, briefing with Roberto Ferrarese.

Lunch in Leuca.

In the late afternoon, the first sail along the coast with sailors and cyclists.


Overnight on boat.

May 29th – Glimpses of Salento

Wake-up, breakfast and meeting. Transfer by bus to the stretch of coast between Porto Badisco, to the south, and Torre Sant’Emiliano to the north, where we will visit the natural park “Otranto-Santa Maria di Leuca,” stretching for about 57 kilometers along the east coast of Salento. The itinerant activities will introduce you to various local businesses, allowing you to experience Salento’s most authentic traditions.

  • 10 a.m. – Welcome to The Land of Surprise
  • Welcome drink at Agriturismo Grotta dei Cervi
  • 11 a.m. – The Walk
    A meditative and relaxing walk lasting approximately 2 hours.
  • 1 p.m. – Social Lunch
    Local tastes and stories at the table with regional producers Theme: good food and sustainability.
  • 3 p.m. – Live Music & Art Performance
    An artistic and musical performance.
  • 4-7 p.m. – Waiting for the Sunset
    An evening of relaxation and wellness with workshops dedicated to food, the art of stone and ceramics, dance and music, as well as massages, treatments, meditation and yoga.

Dinner and dancing. 

Return to Leuca by private transfer. At night, each crew will sail their boat to the island of Corfu (Greece). All participants must be on board with their bicycles loaded.

[For those renting a boat, the presence of a skipper on board is expected throughout the entire experience (the skipper cannot participate in the sailing events along the coast)].

Overnight on boat.

May 30th – Mysterious Corfu

Wake-up and breakfast at the Gouvia port. Departure for a guided tour of Corfu – an ancient crossroads of traditions and civilizations – amidst beaches, olive groves and picturesque villages.


In the afternoon, the second sail along the coast.


Overnight on boat.

May 31st – Wind on your Face

Cyclists: Early wake-up, breakfast at the Gouvia port and meeting at the start line for a cycling tour of Corfu.

Sailors: Wake-up and breakfast. Briefing with Roberto Ferrarese.

Transfer by private boat from Gouvia to Corfu (Kerkyra) and stop for a refreshing dip in the beautiful coves.


Aperitivo, buffet and dance show.

Return to Gouvia by private transfer. At night, each crew will sail their boat to Leuca. All participants must be on board with bicycles loaded.

June 1st – Towards the finish

Wake-up and breakfast at the Leuca Yacht Club. 

Meeting at the port and transfer by bus to some of the best wineries in Salento where we will taste internationally renowned local wines.


Return to Leuca by bus for the last afternoon sail.  


Overnight on boat.

June 2nd – And the winner is…

Cyclists: early wake-up and final ride from Leuca-Gallipoli, and back.

Sailors: wake-up and breakfast.


Afternoon transfer by private bus to the city of Spongano for the closing party: a large party dedicated to all the participants with an awards ceremony for the first three qualifying teams held at the Workness headquarters, an eighteenth-century Filograna building in Spongano.

Return to Leuca by private bus and overnight on boat.

June 3rd – See you soon!

Wake-up, breakfast and farewells.

*This program is subject to change and modification to ensure the safety of all participants and the successful outcome of the event.


The victories to be won

Il Giro dei Venti


The winning crew will be awarded a 7-day holiday (from May 25 to June 1, 2024) at Palazzo Maresgallo, a historic five-star resort immersed in the heart of Salento (or another equivalent structure). The prize is valid for each of the 4 crew members, plus one companion each.

Il Giro dei Venti


The silver medal crew will be awarded a 7-day holiday (from May 25 to June 1, 2024) at Naturalis Bio-Resort, an elegant five-star resort surrounded by over 18 thousand hectares of nature (or another equivalent structure) in Martano (LE). The prize is valid for each of the 4 crew members, plus one companion each.

Il Giro dei Venti


The third-place crew will be awarded a 7-day holiday (from May 25 to June 1, 2024) at Tenuta Centoporte, a four-star resort (or another equivalent structure) in Otranto on the Salento coast. The prize is valid for each of the 4 crew members, plus one companion each.


Step into the adventure

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