Vlichada, on the southern coast of Santorini, offers some of the most memorable sailing experiences in Greece. Known for its dramatic cliffs, volcanic beaches, and crystal-clear waters, Vlichada’s unique landscape makes it an ideal launch point for exploring by boat. Whether you’re after a luxurious private cruise, a sunset adventure, or a multi-day island-hop, the options here cater to a wide range of tastes. We’re particularly fond of the private catamaran tours, which combine comfort, flexibility, and fantastic views, and the longer crewed charters, perfect for those wanting to truly unwind and explore at a leisurely pace. For instance, the 7-day Cyclades cruise offers a deep dive into Greece’s iconic islands, with plenty of time to relax and soak up the scenery.
The list below covers six of the best sailing experiences in Vlichada, from intimate private tours to extensive multi-day charters. Each one offers something distinctive—whether it’s gourmet food, stunning vistas, or the chance to swim at volcanic beaches—and all are designed to help you make the most of your time on the water.
1. Santorini:Catamaran: private cruise with food & drinks
At number 1, this private catamaran cruise stands out for its personalized approach and the fact that it’s run by a family business. For around $1,004 per group (up to 2 people), you get a 5-hour experience that includes a Greek lunch buffet, drinks, and plenty of chances to swim and snorkel in Santorini’s famously clear waters. The captain and host focus on making your day comfortable and tailored to your preferences, which means you can enjoy a trip that’s as relaxed or active as you like. One of the best features is the boat’s ability to approach hidden spots within the Caldera—places larger boats often can’t reach—providing exclusive swimming and photo opportunities.
The boat cooks your meal on board, which adds a personal touch many visitors appreciate. Plus, the trip can be adjusted to suit your needs, making it perfect for couples seeking romance or small groups after a private, intimate experience. The limited number of guests ensures a quieter atmosphere, and the focus on personalized service makes this a strong choice if you want a memorable, hassle-free day.
Bottom line: For a private, flexible, family-run experience that combines excellent cuisine and unique access to hidden caldera spots, this cruise is hard to beat.
2. Santorini: Motor Yacht Sunset Cruise with 5-Course Dinner
At number 2, this sunset cruise on a motor yacht offers a luxurious way to end your day in Santorini. Limiting the group size to 14 ensures a semi-private feel, and what we love about this tour is its five-course dinner served onboard—an unusual feature for a sunset cruise. As you sail across the Aegean, you’ll enjoy unlimited wine, beer, and soft drinks, along with stunning views of the caldera and hilltop villages.
The itinerary includes stops at volcanic islands like the Volcano and Mesa Pigadia, allowing for swims in warm waters with fewer crowds. The boat surveys the breathtaking vistas of Santorini, making it an ideal choice for those wanting a combination of scenic beauty, fine dining, and comfort. The quality of the meal on this cruise elevates it above simpler sunset sails, making it perfect for special occasions or food lovers.
Good for: Travelers seeking a luxury experience with gourmet food and relaxed atmosphere, combined with sightseeing. The limited guest count enhances the intimate feel.
Bottom line: If you want a sunset cruise with a gourmet dinner and spectacular views, this cruise offers a chic, memorable experience.
3. 3-Day Crewed Charter “The Relaxing” – Lagoon 42 catamaran
Number 3 on our list takes you beyond a typical day trip with a 3-day crewed catamaran cruise exploring the Cyclades, including Ios and Folegandros. For about $6,439 per group (up to 6), this experience is all about living at sea with a crew making everything smooth and comfortable. It’s perfect for travelers wanting to unwind and escape busy tourist spots, with the freedom to customize your stops and enjoying the serenity of the open water.
The journey begins in Thera and includes multiple stops at the Vlichada Marina—a convenient hop-on, hop-off point. Highlights include swimming at volcanic beaches, exploring charming villages, and relaxing onboard a luxurious Lagoon 42. Guests love the chance to experience island life with the help of a passionate crew who handle all logistics. The itinerary includes overnight stays on islands, giving you ample time to explore or simply relax aboard.
Bottom line: Ideal for those seeking a multi-day sailing adventure with a focus on comfort, flexibility, and exploring lesser-known islands like Folegandros and Ios.
4. 7-Day Crewed Charter “The Cosmopolitan” – Lagoon 42 catamaran
Sitting at number 4, this luxury 7-day cruise offers a comprehensive exploration of the Cyclades, including the famous Mykonos. For about $15,025 per group (up to 6), this trip is perfect for travelers who want to enjoy Greek island life without the hassle of planning each detail. The cruise departs from Santorini and takes you across the most popular islands, with plenty of time for swimming, relaxing, and sightseeing.
You’ll stay onboard a luxury Lagoon 42, with an experienced crew ensuring everything runs smoothly. Highlights include discovering iconic windmills and charming alleyways of Mykonos, enjoying onboard gourmet meals, and relaxing on deck as the sun sets over the Aegean. It’s a deep dive into Greek island culture, with the convenience of a fully crewed vessel making it accessible even for those new to sailing.
Bottom line: Best suited for travelers looking for an extended, all-inclusive luxury experience that combines sightseeing with relaxation and gourmet dining.
5. Santorini: Motor Yacht Private Cruise with 5-Course Meal
Number 5 features a private motor yacht cruise lasting between 5 and 10 hours, with a focus on personalized service. For a similar experience to the private catamaran, this tour includes a full meal, unlimited alcohol, and hotel transfers. It’s perfect for travelers who want flexibility—whether you prefer a half-day or full-day trip.
The cruise allows you to survey Santorini’s caldera and hilltop villages, with stops at volcanic sites like Mesa Pigadia. You’ll enjoy homemade 5-course meals, paired with unlimited wine, spirits, and beers, plus a welcome Prosecco and fruit salad. The stops for swimming and snorkeling add a fun element, with the boat providing a chance to relax while taking in the scenic vistas.
This tour’s personalized approach makes it ideal for couples or small groups who want a tailored experience with all logistics handled.
Bottom line: A flexible, private cruise that combines sightseeing, excellent cuisine, and luxury for those wanting control over their day.
6. Santorini: Private Catamaran Tour with BBQ & Unlimited Drinks
Rounding out the list at number 6, this private catamaran with BBQ provides a laid-back, customizable experience. For around 5 hours, you’ll enjoy a BBQ meal onboard paired with wine, beer, or soft drinks. The tour includes hotel transfers, which simplifies logistics.
The focus here is on relaxing in style—visiting picturesque spots at your own pace or with the captain’s suggestions. You can swim and snorkel at two beaches, avoiding crowds, and the sunset option offers a stunning view as the sun dips below Oia. The boat’s flexible route and private setting make it ideal for couples, small groups, or families seeking a personalized day on the water.
Guests appreciate the casual, social atmosphere and the opportunity to enjoy a delicious BBQ with unlimited drinks. Watching the sunset from the water is the perfect way to end a day in Santorini.
Bottom line: Perfect for those who want a private, relaxed experience with a focus on good food, drinks, and scenic views.
How to Choose the Best Sailing Experience in Vlichada
When deciding between these options, consider your budget, time available, and what type of experience you prefer. If you seek a luxury private cruise, the Santorini: Catamaran: private cruise with food & drinks or the Private Catamaran Tour with BBQ & Unlimited Drinks are excellent choices. For those wanting an extended adventure, the 7-day Cyclades cruise offers in-depth exploration with all the comforts of a luxury vessel.
If you prefer a more intimate and flexible experience with gourmet dining, the Motor Yacht Sunset Cruise with 5-Course Dinner provides a balanced mix of sightseeing and fine food. Budget-conscious travelers or those seeking a shorter trip might find the private catamaran with food & drinks or the private BBQ tour more suitable.
Consider also the group size—smaller groups mean more personalized service, while larger groups can be more social. Booking early is advisable, especially for popular dates, to ensure availability.
Final Thoughts
Vlichada offers a fantastic variety of sailing options suited to different tastes and budgets. From the luxury private catamaran cruises perfect for romantic getaways or special occasions, to multi-day island-hopping adventures ideal for explorers, there’s something for all. Two standout choices are the private cruise with food and drinks for its exclusivity and personalized touch, and the 7-day Cyclades cruise for travelers wanting an in-depth Greek island experience.
Whether you want a quick afternoon sail, a sunset dinner, or a lengthy voyage across the Cyclades, booking ahead will help you secure your spot. Embrace the laid-back charm of Santorini’s water routes and enjoy a truly memorable sailing adventure.
