Vlichada, with its rugged cliffs and calm waters, offers some of the most appealing sailing experiences in the Cyclades. Unlike the more crowded ports, Vlichada is known for its quiet beauty and access to lesser-known spots, making it an ideal starting point for boat trips. We especially like the private catamaran cruise (see here) because it combines intimacy with personalized service — perfect for a romantic getaway or a relaxed family day. The boats can approach hidden coves and secluded beaches, giving you access to spots inaccessible by land. Plus, the on-board Greek lunch buffet and drinks keep you refreshed without the hassle of planning your own meals.
While shorter day trips are great for a taste of the sea, Vlichada also makes a perfect base for more extensive adventures. For those craving a longer escape, the 3-day and 7-day crewed charters (see here, see here) allow you to explore multiple islands at a leisurely pace. These trips offer a chance to truly unwind while discovering the stunning Cyclades, making them suitable for seasoned sailors or anyone ready to indulge in luxury.
Below, we’ll explore each of these memorable sailing experiences in detail, helping you find the perfect fit for your trip.
1. Santorini:Catamaran: private cruise with food & drinks
For a personalized sailing adventure around Santorini, the private catamaran cruise with food & drinks stands out. This five-hour tour is perfect for couples or small groups up to two people, making it one of the most intimate ways to experience Santorini’s coastline. The operator runs their boats personally, ensuring high-quality service, and they tailor the trip to your preferences, whether you want to swim, snorkel, or explore hidden caldera caves. One of the biggest draws is the on-board Greek buffet — the crew prepares the meal right there, adding a homey touch you won’t get on larger tours.
The boat approaches hard-to-reach spots that larger vessels simply can’t access, giving you a chance to see Santorini from a different perspective. During the cruise, you’ll enjoy swimming in clear waters, relaxing in the sun, and savoring drinks while taking in the views of the volcanic islands.
Bottom line: This tour offers a highly personalized experience and a chance to indulge in authentic Greek hospitality, making it ideal for romantic escapes or small groups seeking exclusivity.
2. 3-Day Crewed Charter “The Relaxing” – Lagoon 42 catamaran
At number two on our list, the 3-day Crewed Charter “The Relaxing” offers a longer, more immersive sailing experience. For around $6,439, up to six guests can enjoy a luxurious three-day cruise through the Cyclades. Starting from Thera, the trip includes visits to Ios and Folegandros, two islands known for their charm, beaches, and local tavernas. The itinerary includes a stop at Vlychada Marina, where you can hop on and off, and the crew takes care of the rest, cooking onboard and navigating the often tricky waters.
This tour is perfect for travelers wanting more than a day trip — it’s about living at sea. The boat is a Lagoon 42 catamaran, renowned for stability and comfort, with plenty of space to relax and enjoy the scenery. The crew, described as passionate and experienced, makes the journey seamless. Guests have praised the flexible itinerary and the ability to customize stops, allowing you to explore less commercialized spots or relax on quiet beaches.
Bottom line: Ideal for couples or small groups seeking a laid-back, multi-day adventure with gourmet meals and the chance to explore multiple islands at your own pace.
$6,439 per group up to 6
3. 7-Day Crewed Charter “The Cosmopolitan” – Lagoon 42 catamaran
For those ready to truly escape, the 7-day Crewed Charter “The Cosmopolitan” offers an all-encompassing experience of the Cyclades. Starting from Santorini, this week-long adventure takes you to iconic islands like Mykonos, along with others that are equally beautiful but less crowded. The luxury Lagoon 42 provides all the comforts of home, with a crew dedicated to making your journey smooth and memorable.
This tour is best suited for travelers who want to combine sailing with sightseeing, beach lounging, and authentic local life. The itinerary is flexible, with plenty of opportunities for swimming, sunbathing, or exploring charming towns ashore. Guests consistently comment on the quality of the crew’s service and the boat’s comfort. It’s genuinely a chance to experience the islands without the stress of planning each day.
Bottom line: Perfect for seasoned sailors or those looking for a luxury experience that blends adventure and relaxation, all while discovering the Cyclades’ most popular islands in style.
$15,025 per group up to 6
4. Santorini: Sailing Yacht cruise with full meal and drinks
The Santorini sailing yacht cruise with full meal and drinks is a wonderful way to enjoy the island’s beauty in comfort. Priced at just $118 per person for a five-hour trip, this tour is accessible and packed with highlights. It’s especially suited for travelers wanting a taste of the Aegean, with the chance to swim, snorkel, and savor a delicious meal.
The tour includes a full meal showcasing local flavors, served while you relax on the deck. You’ll sail around Santorini’s coast and watch the stunning sunset, making it ideal for sunset chasers. The experience emphasizes the scenic views and the joy of sailing, with options for swimming in the clear waters and enjoying drinks with friends or family.
Bottom line: This yacht cruise is a great option for those wanting a relaxed, mid-length trip that combines scenic sailing, swimming, and good food — wonderful for couples or small groups.
$118 per person
How to Choose the Best Sailing Experience in Vlichada
When selecting your ideal sailing trip, consider your budget, the length of time you want at sea, and how much you value luxury versus intimacy. If you’re short on time and want a quick but memorable experience, the Santorini private cruise (see here) offers personalized service without breaking the bank. For those craving a longer, more relaxed adventure, the 7-day Cyclades cruise (see here) provides unmatched immersion. Budget travelers can enjoy the yacht cruise with full meal (see here), which combines affordability with quality.
Factor in your fitness level and comfort with sailing. Longer cruises involve multiple days at sea, so be sure you’re comfortable spending extended time on a boat. The best time to book is during the warmer months, from late spring to early fall, when the weather in Vlichada is most favorable.
Final thoughts
Vlichada offers a fantastic range of sailing experiences, whether you’re after a quick romantic cruise, a multi-day escape, or an affordable day trip. For ultimate privacy, the private catamaran is hard to beat, while the longer crewed charters are perfect for exploring the full beauty of the Cyclades in style. If you’re short on time but want to experience sailing and local cuisine, the yacht cruise is an excellent choice.
No matter your preference, the key is to book early, especially for popular summer dates. These tours give you a chance to see the Aegean from a different perspective — on the water, away from the crowds, and with plenty of opportunities to relax and enjoy the moment.