Greece Sailing Tours

Destinations - Greek Islands

Monobrow Sailing Tours: Explore the Greek Islands by Sea - Day and Multi-day tours
Set sail on an unforgettable adventure through Greece’s most stunning islands with Monobrow Sailing Tours. Whether you’re seeking relaxation or adventure, our bespoke sailing experiences offer a unique way to explore Greece’s crystal-clear turquoise waters, charming coastal villages, and hidden gems that are often overlooked by traditional tourists.

We offer both day and multi-day sailing tours to give you the flexibility to explore the Greek islands in the way that suits you best. Whether you’re looking for a quick getaway or an extended adventure, our tours are customized to provide the ultimate island-hopping experience.

The following tours offer a sample of the many sailing tours available. Contact us to discuss the perfect wine tour for you.

    Santorini

    Caldera Sunset Cruise 

    Time 15:30 to after sunset

    Our famous Sunset Cruise begins from Oia and the picturesque Ammoudi bay. Our first stop is Thirassia Island, where we can enjoy a refreshing swim and snorkel in its crystal-clear waters. We then continue sailing towards the Volcano and the Hot Springs. Discover the magic of geothermal energy while swimming in the volcanic thermal springs.

    Sailing along the stunning Caldera coastline, your host will explain the historical and geological facts that formed Santorini’s complex of islands. You will be charmed by the unique cliffs and the spectacular colours of the soil on the horizon!
    Enjoy your dinner at the hidden coves of the Black Mountain and sail close to the impressive White Beach and Red Beach, experiencing the most famous sunset in the world just before your disembarkation at the port of Vlychada.

    Santorini - Ios - Mykonos Cruise

    10-Hour Full Day Cruise

    Set sail on a captivating journey through the Greek islands, starting with Ios. Enjoy a half-hour stop at Maganari Beach, where you can relax on golden sands and swim or snorkel in the crystal-clear waters. Next, head to Mykonos, the world-famous "Island of the Winds," where you'll have four hours to explore. Stroll through the charming streets of Mykonos Town, visit landmarks like the Windmills, and discover the vibrant nightlife or relaxing beaches, including Psarou and Paradise Beach. Whether you want to shop, dine, or simply unwind, Mykonos offers something for everyone.

    In the afternoon, return to Santorini and be treated to one of the most iconic experiences of the Aegean: a sunset over the Caldera. As the sun sets behind the cliffs, you’ll enjoy breathtaking views of the caldera and the surrounding islands, with vibrant hues filling the sky. This unforgettable moment will mark the perfect end to a day of island-hopping, offering both relaxation and adventure. Whether you’re capturing the moment or simply taking in the beauty, the Santorini sunset is an experience you won’t want to miss.

    Santorini - Milos - Polyaigos - Kimolos

    10-Hour Full Day Cruise

    Milos Leaving Santorini, we first head to the stunning Klestiko in Milos, a hidden gem known for its dramatic rock formations and the mesmerizing hues of the sea. Explore this unique spot, where the deep blue waters meet towering white cliffs, offering a perfect setting for relaxation and photography.

    Polyaigos Next, we sail to Polyaigos, the largest uninhabited island in Greece. Here, you’ll have half an hour to immerse yourself in the island’s natural beauty. Swim in the azure waters, explore the magical sea caves, and discover its peaceful, untouched beaches. Polyaigos is a paradise for nature lovers and those seeking solitude.

    Kimolos Our journey continues to Kimolos, a picturesque island known for its striking white landscapes. Named after the Greek word “Kimolia” (chalk), Kimolos is famous for its white rock formations. Spend half an hour swimming in its pristine waters, and don’t miss the Syrmata—traditional, colorful boat houses carved into the rocks by fishermen. The island’s quaint charm and tranquil atmosphere make it a perfect stop.

    Milos Pollonia The final stop of the day is Pollonia, a charming fishing village on Milos. Spend three hours soaking in the beauty of this peaceful village, nestled around a small inlet with a picturesque harbor. Pollonia combines traditional Greek charm with modern comforts, making it one of the island’s main tourist resorts. Enjoy the serene atmosphere, stroll along the waterfront, and savor fresh seafood at one of the local tavernas.

    In the afternoon, we return to Santorini, where you’ll witness the breathtaking sunset over the Caldera, completing this unforgettable journey through the Aegean islands.

    Mykonos

    Half Day or Full Day Cruises

    Let’s set together a day on board. Gather the group of your preference, choose one of our luxurious yachts and spoil yourself.

    Embark on a relaxing sail cruise around Mykonos and its surrounding islands, exploring secluded coves and hidden beaches. Use the provided snorkeling equipment to discover the vibrant underwater world, and swim in the crystal-clear, blue waters that surround the island. Spend your day unwinding on the yacht’s spacious deck, basking in the warm sun while taking in breathtaking views. With a semi-private itinerary, you’ll enjoy a personalized, exclusive experience, allowing you to explore the best of Mykonos in a private, leisurely mode.

    Indulge in a traditional Greek BBQ on board, savoring freshly grilled fish or meat, a true taste of Greece’s rich culinary heritage. During the cruise, you’ll have the opportunity to visit the historic island of Delos, known for its ancient ruins and sacred significance. Choose from a variety of cruise options: a sunset cruise lasting 3-4 hours, offering breathtaking views as the sun dips below the horizon; a daily cruise of 6-8 hours, providing a more extensive exploration of the islands; or a full-day cruise of 12 hours, allowing you to immerse yourself in the beauty of the Aegean. Throughout your journey, enjoy a selection of food and drinks, from refreshing beverages to delicious Greek dishes, ensuring a perfect and unforgettable experience on the water.

    Muti Day Cruises

    Experience the ultimate Greek escape on a private multi-day island sailing cruise, crafted for couples, families, or small groups. Enjoy exclusive access to secluded beaches and charming villages, with a dedicated crew catering to your every need. Dive into crystal-clear waters, savor Mediterranean meals onboard or at local tavernas, and unwind under star-lit skies. This intimate cruise blends relaxation and adventure, offering an unforgettable way to explore Greece’s natural beauty and timeless allure.

    This experience can be personalized and can accommodate your preferred number of days and islands to visit.

    Some Suggestions

    Cyclades islands
    Sea path: Mykonos, Delos, Paros, Naxos, Ios, Santorini

    The proven favourite islands. The distinctive blue green waters and exceptional unique architecture set the Cyclades blue oasis. Follow the Blue sea path for an unforgettable week on board and visit the top- notch islands of Greece. Popular islands for their characteristic vivid waters, sandy beaches, sunset, small roads, food and nightlife.

    Dodekanisa islands
    Sea path: Samos, Agathonisi, Lipsi, Arkii, Patmos, Fourni, Ikaria.

    The lesser-known islands to suit those seeking ‘something different.’ Deserted islands with white rocks and light blue waters. Enjoy the sea breeze and experience the greatness of an on board vacation on the White root. Follow the white sea path for an exceptional week on board, discover isolated and traditional Greek islands with few residents. A series of small and different islands. Tranquility and authenticity in every rock that you ll step on.

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