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Carried by the wind: Salento by sailboat

A sailing holiday in Salento, between the Adriatic and Ionian Seas, sailing from Gallipoli to Otranto and back

Get ready to experience a week on a sailboat in Salento, where the wind charts the course and the sea sets the pace. We set sail from Gallipoli, amid golden light and Ionian waters, and sail down to Santa Maria di Leuca, the meeting point between the Adriatic and Ionian seas. The voyage continues along the Adriatic coast, among white cliffs, sea caves, and secret bays, to Otranto, with its timeless charm. The days pass by with slow sailing, swimming in crystal clear waters, snorkeling, and sunsets enjoyed from the deck. The nights alternate between quiet anchorages and ports rich in history, with the scent of Salento cuisine accompanying the evenings. An essential and intense journey, made up of sea, wind, and freedom. Here, Salento is discovered from its best vantage point: the sea.


Travel code
SALSL
When are we leaving?
Based on the date
When are you coming back?
Based on the date
How long does it last?
7 days 6 nights
Per person
500 €

WHERE ARE WE GOING?

Program

First day

Welcome to Salento
We will meet in the morning at the port of Gallipoli: we'll get to know each other, then set sail. Our route takes us to the iconic Isolotto di Sant'Andrea, with its solitary lighthouse, or towards the wild nature of Punta Pizzo. The first dip in the sea marks the start of the holiday. At sunset, we sail past Santa Maria di Leuca, where the Adriatic and Ionian seas meet: golden light, white cliffs, the silhouette of the lighthouse slowly lighting up. Aperitif on board, light breeze, and laughter. Night in port, with free time to explore the city.

Second day

From Leuca to Castro Marina
We leave behind Santa Maria di Leuca and begin sailing along one of most spectacular coasts of Salento. The sea guides us between white cliffs, sea caves, and secret coves: we stop for long swims, snorkeling in turquoise waters, and moments of pure silence, lulled by the wind. We pass by the most iconic caves, where the light enters obliquely and the sea seems to shine from within. We arrive in the afternoon at Castro Marina. We spend the night at anchor: dinner on board, stars above us and the sound of the sea as our only soundtrack.

Third day

From Castro Marina to Otranto
We set sail calmly from Castro Marina, following a coastline that surprises at every mile. We sail under high cliffs, skirting legendary caves such as the Zinzulusa Cave , and enjoy leisurely stops to dive from the boat, swim to emerald coves, and dry off in the sun. Those who wish can explore the water with a mask and snorkel, while others can stay on deck and watch the landscape go by. In the late afternoon, we enter Otranto offers one of the most beautiful views of the trip. Stop at the port and enjoy a free evening among the alleys, lights, and scent of the sea.

Fourth day

From Otranto to Tricase Porto
We leave Otranto with our bow pointing south, along a bright and wild coastline. We sail between white cliffs, transparent water, and bays that are perfect for slowing down: diving from the boat, slow swims, moments of relaxation on deck while the Salento flows to the rhythm of the wind. We sail along iconic stretches and open views of the Adriatic, until we reach Tricase Porto. Here we choose whether to stop in the harbor or remain at anchor for an intimate evening under the stars, lulled by the sea.

Fifth day

From Tricase to Torre Vado
We start again from Tricase Porto , following a coastline where nature and history meet. From the sea, we admire ancient watchtowers, signs of a past made up of routes and defenses, and cliffs sculpted by the wind. We sail in front of the picturesque Ciolo Channel, a deep crack in the rock that opens onto emerald waters, perfect for swimming and snorkeling. Stops alternate between sea caves, diving, and moments of absolute tranquility. In the afternoon, we arrive at Torre Vado, where we stop in the harbor: dinner on board, the sky lit up with stars and the sea still all around us.

Sixth day

From Torre Vado to Gallipoli
We leave Torre Vado and follow the Ionian coast, which is gentler and brighter. From the sea, you can see ancient coastal towers and long stretches of sand interrupted by low rocks, ideal for stopping to bathe and swim in warm, transparent waters. We stop among sheltered bays and small sea caves, where the sea changes color and invites you to slow down. In the late afternoon, we enter the port of Gallipoli marks our return to civilization. The evening is to be enjoyed in the historic center: a stroll through white alleys, music filling the squares, seaside bars, the scent of Salento cuisine, and that summer atmosphere that makes Gallipoli unforgettable.

Seventh day

Disembarkation
Breakfast on board in the port of
Gallipoli and last glances at the sea. It's time to say goodbye, looking back on a sailing holiday in Salento between the Adriatic and Ionian seas: from Santa Maria di Leuca to Castro Marina, from the cliffs of Otranto to the caves and canyons of the Canale del Ciol, to the Ionian bays of Torre Vado. A journey of crystal clear sea, wind, authentic landing places, and freedom. Disembarkation scheduled for 10 a.m.

  • accommodation in double cabins
  • mini introductory sailing course
  • skipper and sailor
  • health and baggage insurance
  • use of SUP and tender
  • final cleaning
travel to the embarkation point, tourist tax where applicable, excursions, and anything not mentioned under "Includes."
Please note that provisions, marina fees, and fuel are not included as they depend on the group's management and are handled locally with a shared fund; they usually amount to around €50-60 per person per day.
Good to know
Where
boarding/disembarking
Porto Gaio in Gallipoli or neighboring ports - LE. You will be aboard a 13-meter sailboat with 3 double cabins and 2 bathrooms on board. Triple cabins available upon request. Participants: boat for 6/7 people.
discover the boat
Tour guide
Skipper and sailor. The skipper is the captain of the boat and an expert on the itinerary. For safety reasons, his decisions regarding navigation are final. The sailor assists the skipper in maneuvering and managing the boat and, together with the guests, organizes and collaborates in cooking and cleaning the common areas.
Itinerary information
Daily sailing hours: 2 to 4 hours Type of sailing: along the coastPossibility of overnight anchorage/buoy: 3 out of 6. The actual number of nights at anchor/in port will depend on the group's wishes, weather conditions, and any need for supplies/provisions.
Notes
Extra night: Check-in is scheduled for the morning of your departure; if you need to arrive the night before, you can request an extra night on board for an additional €40 per person at the time of booking.
Important
A sailing vacation is, by definition, a vacation in freedom: for this reason, the itinerary is tentative and may be subject to change depending on weather and sea conditions, boat traffic, the availability of ports, anchorages, and landing sites, as well as the need to restock water and food supplies. The crew will evaluate every decision in the interest of safety, navigation, and the overall harmony of life on board, taking into account, whenever possible, the needs of the participants as well. For this reason, routes, stops, and overnight anchorage points may vary during the trip.
Train

Reference station: Gallipoli, where regional trains from Lecce arrive.

Airplane

Reference airport: Brindisi.

Other

From Lecce station and Brindisi airport, you can consider using the shared shuttle service (€29 per person from Lecce station and €40 per person from Brindisi airport).

After booking, we provide all the contact details so you can make your own reservations.

Do you need more information?

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