Lecce isn’t just famous for its baroque architecture and charming streets; it’s also a fantastic base for sailing adventures along the Salento coast. The region’s clear waters, hidden caves, and picturesque ports make it an ideal place to explore by boat. We especially love the Private Yacht Tour in Gallipoli because it offers a luxurious, customizable experience that takes you to some of the most evocative spots in the area. Imagine cruising past the Isola di Sant’Andrea or enjoying a sunset from the deck—these moments are truly special. For those looking for a more social experience, the Sailing boat tour with lunch and swimming stops provides a fun, interactive day with plenty of opportunities to cool off in crystal waters. And if you’re after a flexible, private outing, the Yacht Rental in Otranto with Captain lets you tailor your route and pace, which is perfect for a relaxed day on the water.
In this guide, we’ll cover five top sailing experiences around Lecce, each offering a unique way to enjoy the sea—from private yacht cruises to guided boat tours with swimming and snorkeling. Whether you’re seeking a romantic sunset sail or an active day exploring sea caves, there’s something here that can match your travel style.
1. Private Yacht Tour in Gallipoli
Living the sea life in Salento is a highlight for many visitors, and at number 1, the Private Yacht Tour in Gallipoli stands out for its exclusivity and flexibility. This tour is perfect if you want a luxurious, personalized experience that’s all about your group. You can rent a comfortable yacht and choose your destinations, with Gallipoli, Porto Cesareo, Otranto, and Ugento all within reach.
What makes this tour unique is the detailed itinerary that takes you to archaeologically significant sites like Isola di Sant’Andrea, with its Bronze Age settlements, and the Parco Naturale Regionale near Punta Pizzo, a stunning spot where land and sea merge. The 8-hour experience allows plenty of time to soak up the scenery, watch the romantic sunset, and breathe in the scent of the Mediterranean. This trip is ideal for travelers seeking privacy, comfort, and a curated day out on the water. The reviews praise the yacht’s comfort and the unforgettable moments created onboard.
Bottom Line: If you want a private, full-day escape with tailored stops to explore Salento’s coast, this is your best bet.
2. Sailing boat tour with lunch and swimming stops
At number 2, the Sailing boat tour with lunch and swimming stops offers a more interactive and social experience. This 6-hour trip is designed for those who want to enjoy the sea, snorkel, and relax with their friends or family. The boat, Morgana Sailing, sails along Santa Maria di Leuca’s coast, exploring caves, inlets, and beautiful beaches.
What sets this tour apart is the combination of caves like Grotta delle Tre Porte and Lovers’ Cave, with stops for swimming in crystal-clear waters. The boat’s crew prepares a delicious, fish-based lunch on board, making it a true culinary treat. The reviews highlight how well-organized and friendly the crew is, and many remark that the caves and scenery make for a “beautiful and unforgettable” day.
This tour is perfect if you want to combine adventure with good food and don’t mind sharing the boat with other travelers. It’s a balanced option for those seeking a day of exploration with plenty of opportunities to swim and relax.
Bottom Line: Ideal for travelers who want a fun, social day on the water with excellent snorkeling stops and a tasty onboard lunch.
3. Sailing boat excursion in Salento
If you’re after a more flexible, customizable experience, the Sailing boat excursion in Salento might be just right. Operating out of Gallipoli, this trip uses an elegant Sun Odyssey 37 sailboat for a 7-hour adventure that can include snorkeling, sightseeing, and private trips. The itinerary can be tailored to your preferences, whether you want to stay close to shore or venture further out.
Highlights include exploring Isola di Sant’Andrea, with its flat landscape and archaeological sites, and cruising around the Old Town of Gallipoli from the water. The boat can be used for sunset sails or special events like dinners or team-building activities, which makes it versatile. The reviews reflect this flexibility, with travelers praising the crew’s professionalism and the chance to see hidden spots from the sea.
This trip suits travelers who want a more personalized outing—perfect if you enjoy planning your route or celebrating a special occasion on the water. It’s a slightly more intimate experience that emphasizes comfort and customization.
Bottom Line: Best for those who want a private, tailored sailing experience with options for snorkeling and scenic cruising.
4. Yacht Private Tour Gallipoli Porto Cesareo
For around $768, the Yacht Private Tour Gallipoli Porto Cesareo offers a luxury private experience that balances comfort and scenery. This tour features a Cranchi 50 Atlantique yacht, equipped with spacious outdoor areas, sunbathing spots, and a large stern bridge—perfect for relaxing and taking in the views.
The itinerary includes stops at the Punta della Suina, a stunning beach area where the sea meets the sky, and the Isola di Sant’Andrea. The crew offers prosecco and Salento delicacies onboard, adding a touch of indulgence. The 4-hour schedule is ideal for travelers who want a quick yet luxurious escape with enough time for swimming, sunbathing, and sightseeing from the water.
This tour appeals to those seeking luxury and privacy without a full-day commitment. It’s especially suited for travelers celebrating a special occasion or those who prefer a more upscale outing.
Bottom Line: Perfect for a shorter, high-end boat trip that emphasizes comfort and exclusivity.
$768
5. Yacht Rental in Otranto with Captain
Finally, the Yacht Rental in Otranto with Captain provides the ultimate freedom and flexibility. For about $989 per group, you can rent a yacht for around 5 hours—completely guided by your chosen route. The captain manages navigation while you relax, enjoying scenic views, close shoreline cruising, or anchored out at sea.
This experience is ideal for travelers who want to design their own day and include optional extras like lunch. The crew offers complimentary fresh fruit and water, and you can decide to anchor in quiet spots or explore coastal caves at your leisure.
It’s suited for those who prefer an intimate, customizable adventure with minimal pre-planning. The focus here is on your preferences, making it perfect for family groups or couples looking for a private, relaxed day at sea.
Bottom Line: The best choice for travelers who want control over their itinerary and a peaceful, private boat experience.
$989.03 per group (up to 8)
How to Choose the Right Sailing Experience
Choosing the best sailing experience depends on your budget, timeline, and what you want to get out of your day on the water. If luxury and privacy are your priorities, the Private Yacht Tour in Gallipoli or Yacht Rental in Otranto are excellent options. For a fun, social day with plenty of swimming, the Sailing boat tour with lunch and swimming stops offers great value and lively scenery. If you crave a tailored experience, the Salento sailing excursion provides flexibility and intimacy.
Consider your fitness level and interest in exploring sea caves or archaeological sites. For some, the idea of a private, luxury cruise might be more appealing, while others might prefer a group tour with snorkeling. Booking early is recommended, especially in peak summer months, to secure your preferred date and boat.
Lecce’s coastline offers a variety of sailing experiences that cater to different tastes and budgets. Whether you want a luxurious private yacht, a guided tour with snorkeling, or a customizable day at sea, this region’s waters won’t disappoint. We encourage you to pick a tour that matches your style, and don’t forget to book well in advance—these wonderful sea days fill quickly.