If you’re dreaming of combining stunning scenery, a touch of adventure, and a relaxed seaside vibe, a sailing excursion in Salento might just be your perfect escape. Based out of Gallipoli, this experience offers a full day on an elegant Sun Odyssey 37, exploring some of the most beautiful spots along Italy’s southern coast. Whether you’re a seasoned sailor or a curious first-timer, this tour promises a blend of scenic cruising, swimming, and local flavor that’s hard to beat.
What we particularly love about this trip is its emphasis on small-group intimacy and personalized attention. With a maximum of six travelers, you’re unlikely to feel lost in a crowd, which allows for a more tailored experience. The boat itself is described as elegant and well-equipped, and the itinerary thoughtfully balances active pursuits like snorkeling with relaxing moments on deck. A second point of appreciation is how the tour showcases different facets of Salento, from natural islands to historic coastal towns. But a possible consideration? The weather can influence the experience — no wind, for instance, might mean less sailing and more motoring.
This tour suits travelers who enjoy outdoor adventures, scenic views, and a touch of local life. If you’re after a relaxing day with plenty of opportunities for swimming or soaking up the sun, this is it. Families, couples, or small groups looking for a flexible, intimate outing will find it especially appealing. Now, let’s take a detailed look at what makes this experience so worth considering.
Key Points

- Personalized and intimate with a maximum of 6 travelers, ensuring attentive service.
- Diverse itinerary including snorkeling, swimming, coastal viewing, and historic sea views.
- Flexible options for full-day, sunset, or weekend trips, catering to different interests.
- Quality vessel: An elegant Sun Odyssey 37 designed for comfort and style.
- Good value for money considering the variety of activities and personalized service.
- Ideal for outdoor lovers who want a mix of adventure and relaxation on the water.
An Introduction to the Salento Sailing Experience

This sailing trip in Salento offers a chance to see the coast from a different perspective — from the deck of a well-maintained, comfortable sailboat. Based in Gallipoli, a city famous for its lively old town and stunning waterfront, the tour gives you a break from crowded beaches and tourist traps. Instead, you’ll find yourself floating gently along the Ionian Sea, with the chance to explore hidden coves and historic sites.
What makes this experience stand out is its attention to detail. The itinerary isn’t just a list of stops; it’s designed to give travelers a well-rounded taste of the area’s natural beauty and seaside charm. The boat’s crew, led by friendly skippers Diego and Gina, are committed to making each trip unique, whether you’re on a full-day adventure or a romantic sunset sail.
A big plus is the variety of stops. You get to snorkel in crystal-clear waters, enjoy a leisurely lunch on board at Torre Pizzo, and circumnavigate Gallipoli’s old town from the sea. Even if weather conditions aren’t perfect, the crew is flexible, and you might find yourself simply cruising or enjoying a peaceful sea breeze instead of sailing against the wind.
You can also read our reviews of more boat tours in Lecce
The Itinerary: What to Expect at Each Stop

Stop 1: Isola di Sant’Andrea
Our journey begins with a visit to the Isola di Sant’Andrea, a small island known for its pristine waters and snorkel-friendly reefs. The review highlights the water’s incredible clarity — “at least 10 meters deep” — making it a perfect spot for swimming and underwater exploration. The boat anchors here for around two hours, giving everyone ample time to don masks and fins, and enjoy the quiet beauty beneath the surface. The included snorkeling gear means you won’t need to bring much except your curiosity and swimsuit.
Stop 2: Torre del Pizzo
Next, the boat moves to Torre Pizzo, a historic watchtower with an inviting, crystal-clear bay. This is a popular spot for swimming, and the crew often sets up a lunch on board here, allowing you to relax with freshly prepared snacks or light meals. The review mentions a “lousy” lunch, but also clarifies that what they called a “lunch” was more like an aperitif with local delicacies such as Spelled salad, tomatoes, olives, and rocket. The emphasis is on local, simple flavors, perfect for a mid-day break after some water activities. You’ll spend about three hours here, soaking in the sun and enjoying the sea.
Stop 3: Il Centro Storico di Gallipoli
The final highlight is a sea circumnavigation of Gallipoli’s historic old town. This two-hour cruise offers breathtaking views of its ancient walls and buildings from the water — a perspective many visitors miss when exploring on foot. It’s a calm and scenic way to cap off the day, and as one reviewer put it, it’s a chance to see Gallipoli from a different angle, adding depth to your understanding of the town’s maritime history.
You can also read our reviews of more sailing experiences in Lecce
Practical Details: What You Need to Know

Meeting Point and Timing
The tour starts at the Marina Yachting Portolano in Gallipoli at 10:00 am. The meeting point is conveniently accessible near public transportation, simplifying your arrival. The activity ends back at the same spot, making logistics straightforward. A key point to remember is that the tour lasts approximately 7 hours, giving plenty of time to enjoy each stop without feeling rushed.
Group Size and Atmosphere
With a maximum of 6 travelers, the experience maintains an intimate atmosphere. This is ideal if you prefer personalized attention, asking questions, or just relaxing in a small group. The reviews reflect this, with guests praising the crew’s hospitality and the chance to interact more closely with the skippers.
Pricing and Value
At around $142.30 per person, the price includes snorkeling gear, a well-maintained vessel, and scenic stops. While it may seem on the higher side, many find the value justified by the personalized service, the variety of activities, and the chance to see Salento’s coast from the sea. The tour also offers the flexibility of choosing a sunset sail or a weekend adventure, catering to different preferences.
Weather and Cancellation Policy
Since the experience relies on good weather, cancellations due to poor conditions are possible but generally come with a full refund or rescheduling. You can cancel up to 24 hours in advance without penalty, giving some peace of mind if your plans change unexpectedly.
What the Reviews Reveal: Authentic Insights

Most reviewers speak highly of the stunning views and friendly crew. Duncan called it “worth every cent,” highlighting the “fantastic staff” and “perfect surroundings.” Veronica appreciated the hospitality of skippers Diego and Gina, who “coccolato” (spoiled) guests with an appetizer and fun sailing experiences.
One critique came from Jeannette, who was disappointed with the food — describing it as “lousy,” but also clarifying it was more an aperitif than a full meal. She noted the water was beautiful to swim in, and the snorkeling was a highlight. This points to an important aspect: expect simple, local snacks rather than gourmet cuisine.
The tour’s small size and flexible itinerary seem to be its strengths, making it a very personal and memorable experience. Travelers appreciated the beautiful waters, relaxed pace, and informative commentary from skippers.
The Sum Up: Who Should Consider This Sailing Tour?

This Salento sailing adventure offers a blend of scenic beauty, cultural perspective, and personalized service that appeals most to those seeking an authentic, laid-back experience on the water. It’s perfect for outdoor enthusiasts, couples celebrating special occasions, or small groups wanting a private escape from crowded beaches.
The experience is a great value for those who appreciate quiet snorkeling spots, stunning coastal views, and local flavors. Keep in mind, if your priority is gourmet food or extensive sailing, you might want to look for other options. But for a memorable day of gentle sailing, swimming, and relaxing in the company of knowledgeable hosts, this trip hits the mark.
Frequently Asked Questions

How long does the tour last?
The full experience lasts approximately seven hours, starting at 10:00 am and returning to the meeting point around 5 pm.
What is included in the price?
The price covers the use of the sailboat, snorkeling gear, and stops at key locations. Light snacks or aperitifs are provided during the stops.
Is this tour suitable for children?
While most travelers can participate, the tour’s intimate size and water activities suggest it’s best suited for children comfortable with swimming and boat trips. Check with the provider for specific age recommendations.
What should I bring?
Bring swimwear, a towel, sun protection (hat, sunscreen), and possibly a light jacket for cooler moments. Everything else, like snorkeling gear, is provided.
Can I cancel if the weather is bad?
Yes, the tour offers free cancellation up to 24 hours in advance. If canceled due to weather, you’ll be offered a different date or a full refund.
Is the tour customizable?
While the itinerary covers key spots, the crew aims to make each trip special. You might find some flexibility, especially on private bookings or weekend excursions.
What’s the boat like?
It’s an elegant Sun Odyssey 37, designed for comfort and style — perfect for a relaxing day at sea.
How many people will be on the boat?
The maximum group size is six travelers, ensuring a cozy, intimate atmosphere.
In summary, this sailing trip in Salento is ideal for travelers who want a personalized, scenic experience on the water with opportunities for swimming, relaxing, and enjoying local flavors. It’s a chance to see Gallipoli and its surroundings from a peaceful sea perspective, making it a worthwhile addition to any Italy itinerary focused on natural beauty and local charm.
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