Top Cyclades Islands Sailing Tours - page 5

Explore the beautiful caldera of Santorini with your very own chartered catamaran. This full-day cruise sails around the popular Greek island allowing visitors to take in the famous sights such as the lighthouse of Akrotiri, the steep caldera cliffs, the Red Beach, and much more. Swim, snorkel, and soak up the sun and enjoy a traditional Greek dinner, including an open bar and dessert, on board the vessel.

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing at the secluded and pristine beaches of the uninhabited island of Rhenia with a visit to Delos island – one of the most important archaeological sites of Greek history and a UNESCO world heritage landmark.

Enjoy a relaxing day of sailing, swimming, and island-hopping on a private cruise from Mykonos to the southern beaches. As this is a private tour you can choose your own beaches, including Ornos, Platys Gialos, Elia, Agrari, and more. Snorkeling gear will be provided so you can explore the underwater world without bringing your own equipment.

Our adventure begins at Kini, a charming fishing village on Syros' west coast. We board a boat and leave behind everyday life, cruising toward the island’s most hidden and untouched beaches. Expect turquoise waters, rocky landscapes, and the peaceful stillness of the Aegean. We disembark at Amerikanos Beach, a quiet, storied cove with raw beauty — the perfect setting for a refreshing swim and brief relaxation. From there, we begin a coastal hike leading to Grammata, a site of mystery and deep meaning. Etched into the rocks, you’ll find ancient inscriptions — words of sailors and travelers carved more than 2,000 years ago. Messages of longing, hope, and survival await your discovery. A picnic and a swim, in crystal-clear waters, recharges us before we return by boat to Kini. Perfect for νature lovers & hiking enthusiasts, τravelers seeking authentic local experiences, ψouples, families, and small groups.

A peaceful romantic trip with the essence of a cruise to be unforgettable. Embark on this afternoon excursion!

Choose Your Perfect Half-Day Cruise Experience Enjoy a unique escape on the sea with one of our three half-day cruises Morning Cruise – 09:30 to 12:30 Start your day in paradise! Enjoy a delicious breakfast, light snacks, and 3 drinks per person as we sail to the breathtaking Blue Lagoon and Faneromeni Bay. ️Midday Cruise – 13:00 to 16:00 Soak up the sun with snacks, fresh fruits, and 3 drinks per person on board. Explore the turquoise waters of the Blue Lagoon and Faneromeni Bay — the perfect midday getaway. Sunset Cruise – Around 18:00 to 21:00 Experience the magic of the golden hour at sea. Departure time may vary slightly with the season (you’ll be informed in advance). Sail through the Blue Lagoon and the Fira Channel, where you’ll enjoy a spectacular sunset view. Includes snacks, 3 drinks per person, and unforgettable memories. Choose from beer, wine, soft drinks, or one of our cocktails: Aperol Spritz Piña Colada Mojito Mojito with Mastiha Margarita Strawberry Daiquiri

Our first stop is an hour away, the renowned Big Delos island. While there, you will have the opportunity to visit one of the most famous archaeological sites in Greek history : the birthplace of the Olympian God Apollo and the Olympian Goddess Artemis. You will have approximately one hour to explore the grounds of this significant cult center of Ancient Greece. Rhenia is a popular meeting point for yachts cruising the area due to its spectacular waters, which range in color from a stunning emerald green to a beautiful turquoise blue. Upon arrival, we will anchor in a secluded bay where you will enjoy the privacy of a white beach with no crowds. You will have plenty of time to swim in the crystal waters, put on a pair of goggles and see underwater life up close. Back on the boat, we will treat you to a traditional Mykonian lunch while you enjoy a drink of your choice,

Set the sails to the wind and explore the exclusive beauties of Mykonos on a sailing yacht with the onboard buffet of Greek flavors and complimentary wine, beers, and soft drinks. Enjoy a beach safari to the most beautiful and famous south-coast beaches. Relax and swim in a secluded bay of Rhenia Island. We sail back to Mykonos by watching the breathtaking landscape of yellow, orange and red colours while the sun goes down in the very blue Aegean Sea

Spend the morning swimming, snorkelling and sunbathing around Santorini on this 5-hour cruise. Along the way, see landmarks such as Indian Head Mountain and the Old Venetian Lighthouse; visit the Red and White Beaches; and take a dip in the Hot Springs. Tour includes hotel pickup and a delicious BBQ lunch on-board.

Sailing around the Aegean Sea doesn’t have to break the bank. Instead of arranging a costly private charter, explore both the coastlines of Milos and the uninhabited island of Poliegos during this cost-effective, small-group excursion. Spend the day swimming, snorkeling, or paddle-boarding in secluded bays and caves—or simply relax on the crew-staffed boat with a drink in hand.

Spend an evening sailing along southern Mykonos and taking in the beauty of its beaches during this sunset cruise. Spend the late afternoon discovering idyllic locations where you can swim and snorkel in the azure waters or simply relax on the wide deck. Indulge in delicious finger food and sip on drinks and refreshments while you sail and witness a stunning Mykonian sunset to cap off the evening.

That semi private sailing tour is a family friendly sunset tour, due its small number of maximum participants and allows you to enjoy The idyllic Parikia Sunset under relaxing music , while swimming as you passing through some of nicest sea locations. Our experienced captain will choose the most protected areas from winds and occasionally might change the route of trip, in order to be more enjoyable- as safety comes first . She is so polite and ready to provide details about passing through locations or sea stops. Snorkelling equipment is available and swimming allowed in all sea stops. Prepare your camera and get ready to fall in love one more time!!

Although not a day trip, this experience provides the perfect ending to a day in beautiful Mykonos. Set sail towards the horizon, with a glass of wine in hand, and watch the sun is dipping into the water, as the blue sky transforms into hues of orange and red. Let the summer breeze free you of all your worries, and enjoy the majestic view, while the gentle waves rock you to the rhythm of nature at its best.

Every side of the island has complete different things to offer you! There are caves and stories about pirates . There are huge piles of lava that have been standing there for thousands of years , longing to be admired and little fisherman villages ,like nothing else you have seen before, built by the water. Swimming in exotic colorful and transparent water with a completely different scenery each time we make a stop and it always goes with an open bar with drinks and beverages and a freshly cooked Mediterranean meal onboard . We provide you with snorkeling gear and a waterproof camera so you may take unique pictures for these wonderful memories that last forever ! Trust us as we love the water and what comes with it! We sail all year long as we can’t escape the passion of feeling the wind on our faces and the water under our feet and through the boat! Come fall in love with the island that still surprises each and everyone one of us and has been doing it for the past several years!

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port of disembarkation. Relax on a wooden traditional Greek boat and visit the active volcano of Santorini, a unique geological park built of lava. Swim in the mud baths created by the many volcanic eruptions. visit traditional Thirassia that will take you back in time 30-40 years and swim in its deep blue waters. Returning you can take pictures from the unique landscape of the village of Oia with its white houses and blue domes from the boat. Is a value for money trip aimed at visitors and families who want to enjoy nature and landscapes and avoid the hustle and bustle of the city. Post unique landscapes and the crystal clear waters of the Caldera.

Set sail on a private full-day cruise aboard a luxurious sailing catamaran from Adamantas Port, Milos, for an unforgettable journey to Kleftiko Bay and Polyegos Island. Relax with unlimited beverages as you explore stunning destinations, starting with swims in the crystal-clear waters of Triades Bay and Kalogries Beach. Continue to the iconic Kleftiko Bay for snorkeling, SUP surfing, and fishing, followed by a freshly prepared Mediterranean meal onboard. Sail onward to pristine Polyegos Island, with brief stops at Fyriplaka, Tsigrado, and Gerakas beaches, before reaching the serene Galazia Nera Bay. Here, dive into turquoise waters or simply unwind in this untouched paradise. Return to Adamantas Port with cherished memories of a luxurious and adventurous day exploring Milos and Polyegos. *Note: The itinerary may vary based on weather conditions.

A rare balance between elegance and performance! Oceanis 46.1 possesses all the features of a large cruising yacht. Its stepped hull and a large number of clever customizable fittings make it easy to sail and pleasantly comfortable. The magic of the island unfolds in front of you, giving you the chance to have a completely personalized trip by visiting the nicest spots of the island and living a unique experience. Arrange a private day or sunset cruise or a full day in the Caldera of Santorini and discover the beauty of the Aegean Sea in a completely different way, relax and enjoy the sun and the sea breeze.

Experience the freedom of the open ocean on a private cruise when you book this stylish Lagoon 450 catamaran. Transfer direct from your accommodation in air-conditioned comfort with onboard Wi-Fi, then board your craft, which comes with snorkel gear, and set sail for Thirasia. Savor a Greek feast, washed down with unlimited beer, water, white wine and soft drinks: choose between morning or sunset cruises to fit your schedule.

See some of the most popular spots on Mykonos, Little Venice and Agios Stefanos, on this group day-cruise. You’ll stop at each spot, once for brunch, and next for swimming and lunch. You don’t need to organize a thing. Just be ready to enjoy the water and explore two of Mykonos’s top attractions.

A sailing cruise is the perfect way to experience Santorini, but costs can rack up quickly. Keep finances under control when you book this all-inclusive cruise, with hotel pickup and drop-off, snorkeling basics, a seafood and barbecue feast, and free-flow local wine, beer, and soft drinks. You'll visit either Red Beach or White Beach (weather dependent), see the Lighthouse, and stop at Palea Kameni and Nea Kameni islands, including the hot springs.

Many of Paros’s most popular sights can only be explored by boat. On this full-day tour, hop aboard a boat in the village of Pounda and set sail into the vibrant waters of the Aegean Sea. Explore off the coast of Antiparos and navigate the Padieronissia island complex, stopping at several sites for a refreshing swim in the warm ocean.

Explore the stunning volcanic coastline of Milos—and enjoy three swim stops plus a stop in Kleftiko—during this full-day sailing excursion. Enjoy close-up views of Milos' attractions, from the colorful fishing village of Klima to the rock formations of Cape Vani. Other highlights include a swim and snorkel stop at the ancient pirate hideout of Kleftiko, and swimming at Kalogries Beach and Agios Dimitrios.

Some of Milos’ most beautiful spots can only be reached from the sea. Soak up the views in style on this small-group cruise by charming sailboat. Discover Kleftiko Beach’s sculptural formations, drop anchor at cliff-framed Gerakas beach, and swim in the turquoise waters of Poliegos, an uninhabited island. Your day includes both breakfast and lunch with drinks for maximum comfort.

Enjoy a premium sailing experience on a semi-private catamaran cruise in Santorini, limited to a maximum of 15 guests for a more comfortable and personalized atmosphere. Choose between a refreshing morning cruise or a magical sunset experience and sail along the stunning Caldera. Discover Santorini’s most iconic locations, including Red Beach and White Beach, with stops for swimming and snorkeling in crystal-clear waters. Continue your journey to the Volcano Hot Springs, where you can enjoy a unique swim in warm, mineral-rich waters. Along the way, take in breathtaking views of the cliffs of Oia, Imerovigli and Fira. On board, relax and enjoy a freshly prepared BBQ meal, drinks and friendly service from the crew in a relaxed and welcoming environment. The sunset cruise ends near the Akrotiri Lighthouse, offering one of the most breathtaking sunset views in Santorini. Perfect for couples, friends and travelers looking for a high-quality shared experience with limited group size.