Lecce isn’t just about baroque architecture and charming streets — it’s also a fantastic place to enjoy the sea. The Salento coast offers crystal-clear waters, dramatic cliffs, and quiet bays that are perfect for sailing adventures. While Lecce itself isn’t directly on the water, the nearby ports and bays make it a prime launch point for unforgettable marine experiences. We especially love the Private Yacht Tour in Gallipoli, which combines comfort, exclusivity, and a thoughtfully designed itinerary. Exploring the Bronze Age island of Sant’Andrea or swimming in Punta della Suina’s turquoise waters provides a memorable taste of the region’s natural beauty.
Whether it’s a full-day private cruise, a laid-back sunset sail, or a day spent exploring caves and coves, there’s a sailing experience here suited for every traveler. Some tours focus on private luxury, while others offer more relaxed, social atmospheres. Below, we’ve rounded up the top options, highlighting what makes each one special and helping you choose the perfect match for your trip.
Types of Sailing Tours in Lecce
This list includes private yacht charters, guided sailing excursions with snorkeling, shared boat trips with swimming stops, luxury yacht rentals, and sunset sails. Each offers a different vibe, from intimate and exclusive to social and leisurely. To explore one of these experiences, check out the full details via the links provided, like the Private Yacht Tour in Gallipoli or the Sunset on a Sailing Boat in Gallipoli.
1. Private Yacht Tour in Gallipoli
At number 1, the Private Yacht Tour in Gallipoli offers a luxurious way to see Salento’s coastline. This 8-hour experience is perfect if you’re after privacy, comfort, and a customized itinerary. The yacht can take you to destinations like Gallipoli, Porto Cesareo, Otranto, and Ugento, giving you a tailored taste of Salento’s most scenic spots. With up to 9 people sharing the cost, it’s a fantastic option for families or small groups seeking exclusivity.
The tour includes stops at Isola di Sant’Andrea, a flat Bronze Age island with archaeological sites, and the Parco Naturale Regionale Isola di S. Andrea e Litorale di Punta Pizzo, where you can soak in the view of Punta della Suina, a stunning stretch of beach where the sea and sky blend seamlessly. You’ll enjoy the sea breeze, romantic sunsets, and the scent of salt and Mediterranean herbs. The boat is equipped to ensure comfort, and the guide can tailor your itinerary based on your interests.
Bottom Line: If privacy and flexibility matter most, this is the top pick. It’s ideal for groups wanting a private, comfortable day on the water with personalized stops.
2. Sailing boat tour with lunch and swimming stops
For around $138.82 per person, the Sailing boat tour with lunch and swimming stops delivers a rich, active experience. This 6-hour trip departs from Santa Maria di Leuca, skimming along both the Adriatic and Ionian sides of the coast depending on the skipper’s discretion. It’s a great choice if you love exploring caves, snorkeling, and enjoying fresh seafood in a relaxed setting.
The itinerary includes visits to Grotta delle Tre Porte, with its impressive three-entrance cave, and other caves like the Dragon Cave and Lovers’ Cave, where swimming is encouraged. The crew is attentive and the on-board lunch — a fresh fish-based meal — is a highlight, with reviewers praising the high quality of the food. The trip is ideal for travelers who want active exploration with plenty of time for swimming and relaxing.
Good to Know: The reviews mention an enthusiastic crew and beautiful scenery. It’s suited for those comfortable with a 6-hour boat trip, and the price includes snorkeling gear and lunch.
Bottom Line: Perfect for water lovers who want a mix of adventure, relaxation, and good food in a friendly atmosphere.
3. Sailing boat excursion in Salento
At number 3, the Sailing boat excursion in Salento offers a flexible, personalized experience from Gallipoli. This 7-hour trip combines visits to Isola di Sant’Andrea, Lido Pizzo, and the old town of Gallipoli from the water. The boat is a classic Sun Odyssey 37, providing comfort and style for day trips, sunset outings, or private events like dinners or team-building activities.
What makes this tour stand out is its customization. You can choose whether to focus on snorkeling around the island, enjoy a leisurely cruise around Gallipoli’s historic coastline, or simply relax with a drink on deck. The itinerary includes stops for swimming in La Grotta delle Tre Porte, and the crew is known for their friendly, unpretentious approach.
Review insight: Travelers mention the “fantastic staff” and the “perfect surroundings,” emphasizing the intimate, high-quality experience. It’s especially good for couples or small groups seeking a stylish, relaxed day.
Bottom Line: Ideal if you want a tailored day on the water with a stylish vessel and flexible itinerary options.
4. Yacht Private Tour Gallipoli Porto Cesareo
Number 4 on our list is the Yacht Private Tour Gallipoli Porto Cesareo, which balances luxury and exclusivity. This 8-hour cruise features the Cranchi 50 Atlantique, a yacht with generous outdoor spaces, sunbathing areas, and a large cockpit. It’s perfect if you’re after a high-end experience but want to avoid the crowds.
The itinerary includes stops at Punta della Suina with its sand dunes and Mediterranean scrub, and Isola di Sant’Andrea for swimming and relaxing. The crew provides prosecco and local delicacies, making it feel like a true indulgence. It’s priced at $768 for the whole boat, which makes it a good deal for a small group seeking privacy and style.
Review insight: The single review mentions a high level of satisfaction, especially regarding comfort and scenic stops. The tour is best suited for travelers wanting a luxurious, all-day escape on the sea.
Bottom Line: This tour is for those wanting a premium, private experience with personalized service and scenic stops.
5. Yacht Rental in Otranto with Captain
For a flexible, customizable experience, consider Yacht Rental in Otranto with Captain. Priced at $989.03 for up to 8 people, this 5-hour private charter puts you in the captain’s hands. You choose your route, whether that’s staying close to the shoreline or venturing further out.
This experience is ideal if you prefer a more hands-on approach — selecting your stops, enjoying fresh fruit and water, and perhaps adding an onboard lunch. It’s perfect for families or friends who want a personalized day at sea without fixed itineraries or group tours. The flexibility allows you to avoid busy tourist spots and spend quality time on your terms.
Review insight: Although only one review is available, it mentions a seamless, relaxed day with the captain tailoring the experience. It’s best for travelers who appreciate customization and privacy.
Bottom Line: A versatile choice for those who want control over their sailing day, with the comfort of a private yacht and captain.
6. Sunset on a Sailing Boat in Gallipoli
Finally, for a shorter but unforgettable experience, the Sunset on a Sailing Boat in Gallipoli offers a 3-hour journey from 17:00 to 20:00. This trip is perfect for those who want to enjoy the coast’s breathtaking sunset without committing to a full day or longer. You’ll sail along Punta della Suina, the Island of Sant’Andrea, and other scenic spots, with ample time to relax, swim, and take photos.
The highlight is watching the sky turn fiery hues over the sea — a truly relaxing way to end a day. The intimate setting and warm colors make it a favorite for couples or anyone seeking a peaceful, scenic end to a day in Salento.
Review insight: The one review mentions an “unforgettable sunset experience,” emphasizing its serenity and beauty.
Bottom Line: Ideal for those wanting a short, romantic escape into the Salento evening with memorable views.
How to Choose the Best Sailing Experience in Lecce
When selecting a sailing tour, consider your budget, time available, and what kind of experience you’re after. Private yacht tours like the Gallipoli private yacht are perfect for celebrating special occasions or enjoying exclusive privacy. If you prefer a more active day with swimming and exploring caves, the sailing boat with lunch and swimming stops offers a combination of adventure and good food. For a romantic sunset, the shorter Gallipoli sunset sail provides a memorable, peaceful experience.
Budget-wise, shared trips like the sailing boat tour in Salento offer excellent value, while private options deliver more comfort and customization. Booking early is advised, especially in summer months, to secure your preferred date and boat.
Final Thoughts
The range of sailing options around Lecce is impressive — from private, luxury yachts to relaxed sunset sails and active snorkeling trips. If you’re traveling with family or friends and want total control over your day, the private yacht in Gallipoli or Porto Cesareo tops the list. For those seeking a more social, laid-back experience, the shorter sunset trips and guided excursions fit the bill.
No matter your choice, these experiences promise a special way to see Salento’s coast and enjoy its stunning waters. Book early, plan your preferred type of outing, and prepare to make some sea-based memories you won’t forget.
