Top Cyclades Islands Sailing Tours

[Up to 8 Guests] Private Cruise in Milos and across the Cyclades • Morning, Sunset, or Full Day options • Explore Kleftiko, Sarakiniko & more on a luxury open-yacht • Open bar and meals included Charter the entire yacht on a Private Cruise in Milos and the Cyclades, with three curated route options across Milos, Kimolos, and Poliegos. Our cruises cover more coastline than you'll find on a typical private charter. Your captain shapes the day around your preferences and confirms your meeting point 48 hours before departure. Hotel and villa pick-up available upon request. Every route is tailor-made. Discuss your preferred stops and durations directly with your captain. Half-Day cruises include 5 to 6 stops over 5 hours, Full-Day cruises include 7 to 8 stops over 8 hours. Stops may be adjusted on the day based on conditions. Book your Private Cruise!

Embark on a private sailing adventure around Santorini’s volcanic wonders. Perfect for couples or small groups, this exclusive experience creates unforgettable memories. Start with a visit to the volcanic islet of Nea Kameni, where you can swim in the healing hot springs, feeling the warmth of the waters as you admire the dramatic volcanic landscape. Next, enjoy a snorkeling adventure in the crystal-clear waters, then sail to Santorini’s famous beaches, exploring hidden coves and serene shores. As the day ends, savor a Greek dinner onboard, made with fresh, local ingredients, and sip on the finest local wine as the sun sets over the caldera. This private experience is the perfect blend of romance, adventure, and serenity. Book now for an unforgettable sunset sailing experience that captures Santorini’s beauty.

Close your eyes and create an image of setting sail towards the horizon with a glass of wine on hand, watching the sun dipping into the water. Right before the way back to the port , grab the chance to capture the breathtaking view of Little Venice during the time that the sky color transforms from blue into hues of orange and red. Taste our production of wine and `a plate with fruits and snacks.

Discover Santorini’s volcanic wonders, swim in natural hot springs, sail the Caldera, and enjoy a breathtaking sunset cruise experience.

Start or finish your vacation with a sailing cruise on a catamaran charter. Sail across and explore the Aegean with your own personalized sailing route to any location of your choice. Get the royal treatment with skippers, hostesses, private accommodation, and complimentary services made available to you. We can pick you up from any port you are in.

Enjoy two extended swimming stops in breathtaking turquoise waters. Swim, snorkel with the provided equipment, explore the coastline on a SUP, or simply relax aboard a comfortable sailing yacht while surrounded by the incredible scenery of Polyaigos. During your first swimming stop, enjoy a selection of traditional Greek meze, accompanied by water, soft drinks, local beer, house wine, and a small taste of traditional Greek ouzo—all included. At your second swimming stop, fresh seasonal fruit is served before sailing back to Kimolos. With a maximum of 12 guests onboard, this experience offers a relaxed, intimate, and personalized atmosphere, making it the perfect way to discover the hidden beauty of Polyaigos away from the crowds.

Board the "Thalassa" in the afternoon and depart to the small port of Nea Kameni volcano for a magical Santorini sunset cruise. Upon arrival at the volcano our guide leads you up to explore the rim of the volcanic crater. Leaving the volcano our sailing boat heads to the Hot Springs and their thermal sulfurous waters, where you can let yourself indulge in the natural-warm and soothing sea. During the remainder of our voyage, our sailing boat docks close to Thirassia giving you the opportunity to escape into the crystal clear and refreshing blue waters. In the meantime the crew prepares a delicious BBQ buffet and you'll enjoy the renowned white local wine. Next we depart for the northern tip of Santorini and the town of Oia. From our sailing boat we have a unique vantage point for viewing and photographing the lovely traditional settlement of Oia. Here you can relax and enjoy the beautiful scenery.

From Paros Piso Livadi Port - Exclusive Private Sailing Adventure Around the Koufonisia Archipelago and Naxos. Enjoy an exclusive sailing trip through the stunning waters of Koufonisia. Our first stop is Pezoulia Bay in Kato Koufonisi, where you can swim, snorkel, and enjoy a light snack. We then sail along the southern coast, admiring dramatic cliffs and sea caves before reaching Laki Bay, where a freshly prepared lunch awaits. After lunch, we pass Glaronisi, a stunning cave area, and continue towards Pano Koufonisi. Sailing along the coast, you’ll admire the island’s beauty and spot Chora. If conditions allow, we’ll also pass Pori, known for its crystal-clear waters and sea caves. Our final stop is Rina Cave in Naxos, where you can swim in a breathtaking setting and enjoy a sweet treat before sailing back along Naxos’ western coast to Piso Livadi in Paros Island. Book your private sailing tour with a maximum group of 10 people!

Our "West Side of Milos & Kleftiko" cruise offers a unique blend of natural beauty, historical exploration, and relaxation. Enjoy the privacy of the yacht by sailing through the Aegean Sea with our monohull sailing boat and our experienced crew. Explore the Mediterranean biodiversity, sunbathe under the Greek sun and make the most of now, now. Enjoy refreshing swims at Kalogries, Kleftiko, and Agios Dimitrios beaches, each offering crystal-clear waters and serene surroundings. Capture stunning images at Sykia Cave, Arkoudes Beach, and the picturesque village of Klima with its iconic "syrmata" boathouses. The calm waters and hidden sanctuaries of Milos provide a peaceful and relaxing environment. The itinerary may change based on weather conditions or your preferences, ensuring a personalized experience. This cruise is perfect for anyone that want to spend a great day on a sailing yacht seeing all the best parts of Milos.

Starting from Piso Livadi port, located at the South East coast of Paros we offer a half day sailing cruise, tailored for the traveller who wants to get the maximum of his stay on Paros. Highlights are the famous BLUE LAGOON, Despotiko, spectacular coast line of Antiparos and the sea caves of Tripiti. Greek dishes are served to enjoy mediterranean flavors and complete your experience

Spoil yourself with a private cruise around Santorini's islands and beaches! Spend 3-5 unforgettable hours! Swim and snorkel in the crystal clear waters of the Aegean Sea! Savor a tasty Greek barbecue made with local ingredients! Enjoy your own tailor-made journey!

Experience a private half-day cruise from Adamantas to Kleftiko aboard a luxurious sailing catamaran. Perfect for family, friends, special celebrations, with activities, dining, & breathtaking views.

Share with the experience of sailing on a luxury catamaran in the Aegean, set up for the passenger’s comfort and entertainment. Lounging on the comfortable cushions in the front and on the flybridge, seating in the outside living room, music, snorkeling gear and fins, noodles and 2 paddle boards invite to enjoy the sea during the extensive stops (4 hours cruise – more than 3 hours at anchor) Another focus is set on the food and beverage offer (included in the package) with Greek specialties, exquisite wine from Paros and local spirits The menu Greek specialties Cretan dako bites (dried rusk bread) with fresh Parian grated tomato with Mount Olympus feta cheese, local cherry tomatoes, olives, cucumber, Greek style marinated anchovies, Parian Gruyere, Myconian cured ham, fresh baked bread, fruits and sweets. Coffee tea, sodas, wine (white/rose), beer, souma (a local spirit Grappa style) and ouzo Your crew of two will keep you safe, entertained and spoiled beyond expectation.

• Sail along the iconic caldera, passing volcanic cliffs, the famous Red Beach, and the White Beach. • Swim in crystal-clear waters, explore hidden coves, or relax on deck with champagne in hand. • Enjoy a gourmet meal prepared with local ingredients, plus open bar service with wine, beer, and soft drinks. By the sea • Choose between a daytime adventure or a sunset cruise — with front-row views of Santorini’s world-famous sunset from the sea. Why Choose Us: • We operate the newest, most elegant yachts in Santorini. • Private and customizable – perfect for romantic couples, families, or small groups. • Professional English-speaking knowledgeable crew offering 5-star service. • Free hotel pickup and drop-off included.

Our cruises are one-way starting either in Agia Kyriaki beach and ending in Pollonia village or vice versa. We never sail back to our starting point in order for our passengers to have more time on stops and view more places along the way. We provide a transfer service included in the price in order for you to get back to the starting point of the cruise. Our crew is very well experienced and the Captain of the Veronica yacht is a permanent resident of Milos since he was born, he knows every hidden gem around Milos and he will make you feel comfortable onboard. Our cave exploration in Kleftiko is unique indeed, and our meals are always fresh and very well cooked and served by our hostess onboard. The Yacht itself is a unique Danish-made Moen 331 built to sail in the Aegean Sea providing safe and comfortable sailing. Join us, have fun onboard, and create memories that last forever.

The unique breathtaking sunset in the Greek sea accompanied with traditional local snacks and drinks is the best way to relax on your vacations.

Sail to the famous Blue Lagoon at sunset and experience the magic of turquoise waters surrounded by the islets of Panteronisi, Tigani, and Glaropounda. Perfect for swimming, snorkeling, or simply relaxing with a glass of rosé and light finger food. This short, unforgettable cruise brings you to the island’s No.1 hidden gem — only accessible by boat — just in time to catch the golden glow of the Aegean sunset.

Exclusive Private Cocktail Sailing Tour in Santorini! Set sail on a private adventure through the stunning waters of Santorini with our Cocktail Sailing Tour! Enjoy the island’s beauty, unwind, and indulge in expertly crafted cocktails, all in the privacy of your own boat. Begin with 3 complimentary cocktails of your choice from our exclusive cocktail menu, featuring a variety of refreshing drinks made with premium spirits. As you cruise the coastline, enjoy more cocktails at special prices. Whether you prefer a classic favorite or something unique, our curated cocktail menu has something for every taste. This private sailing tour offers the perfect mix of relaxation, adventure, and luxury, all surrounded by Santorini’s natural beauty. Perfect for couples, families, or friends, this exclusive tour promises an intimate, unforgettable experience. Book your private Cocktail Sailing Tour today and experience Santorini like never before!

Explore Santorini like never before on this full-day private cruise that blends stunning beaches with rich cultural experiences. Sail the caldera to visit iconic spots, including White Beach, Red Beach, and Black Beach for swimming and snorkeling. Discover hidden caves and take a refreshing dip in the Hot Springs near the Volcano. Cross to the serene island of Thirassia for a local winery visit and explore traditional villages. Enjoy a scenic walk to Korfos Bay before savoring an onboard meal. The day culminates with a spectacular sunset at the Akrotiri lighthouse, making this tour ideal for couples, families, and groups seeking a comprehensive Santorini experience. - Full-day private cruise featuring Santorini’s top beaches - Swim and snorkel at iconic beaches and hot springs - Visit a family-run winery and charming villages on Thirassia - Experience a stunning sunset while cruising back to Vlychada port

Experience a beautiful sailing day around the Small Cyclades & Naxos. We sail all the way to our destination, stopping at various breathtaking locations and some of the most stunning bays, where the landscape is unique, and the sea changes color. You can swim and snorkel, relax in the peaceful surroundings, and enjoy the refreshing sea breeze.

Embark on a 36-hour private sailing adventure aboard a fully crewed yacht with a professional captain and attentive hostess. Perfect for those seeking comfort, privacy, and authentic island life, this cruise reveals the wonders of Milos and its neighboring islands. Departing from Adamas, dive into Kleftiko’s legendary rock formations and snorkel in Sykia’s crystal-clear waters, then sail to charming Kimolos for an overnight stay amid its traditional village and local flavors. Day two brings the untouched beauty of Polyaigos, ideal for swimming and relaxation, before returning to Milos for a full circumnavigation—so you experience all three islands: Milos, Kimolos, and Polyaigos. The price thoughtfully covers all expenses, ensuring a seamless, unforgettable private cruise with breathtaking scenery and personalized service.

Immerse Yourself in the Beauty of the Small Cyclades Breathe in the fresh Aegean air and embrace the tranquility of the Small Cyclades. On this full-day sailing adventure, you’ll explore hidden bays accessible only by boat, dive into crystal-clear waters, and snorkel in the peaceful silence of nature. Our journey begins at Iraklia, where we’ll visit the remote beach of Alimia and snorkel above the wreck of a WWII hydroplane. Next, we set sail for the serene island of Schinoussa, inviting you to dive into its pristine waters and embrace its calming beauty. A freshly prepared lunch will be served on board as you unwind in the tranquil surroundings. On our return, we’ll explore Naxos’ southern coast, stopping for a sweet dessert and fresh fruit before a final refreshing swim. If luck is on our side, we may even spot dolphins playing in our wake as we sail back to Piso Livadi.

Escape the crowds and discover the hidden gems of the Small Cyclades on this 7-hour private cruise departing from the picturesque port of Ambelas in Paros (10:00 AM–5:00 PM). Cruise across the Aegean Sea to the peaceful islands of Heraklia and Lower Koufonisi, where you'll have plenty of time to swim in crystal-clear turquoise waters, snorkel, relax on secluded beaches, and soak up the breathtaking island scenery. Whether you're looking to unwind under the Mediterranean sun, explore untouched coastlines, or simply enjoy a memorable day with family or friends, this private cruise offers the perfect blend of relaxation, adventure, and authentic Cycladic beauty before returning to Paros in the afternoon.