Top Cyclades Islands Sailing Tours

200+ results

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Milos Luxury Sailboat Cruise to Kleftiko Bay with Meal and Drinks

Set sail on an unforgettable luxury cruise aboard a Jeanneau 57 sailing yacht and discover legendary Kleftiko, one of Milos’ most iconic natural wonders. Departing from Adamas Port, this experience blends relaxation, adventure, and local storytelling in true Cycladic style. Sail along the stunning coastline, passing colorful Klima and the impressive Sykia Cave before reaching Kleftiko’s dramatic white rock formations, sea caves, and crystal-clear turquoise waters. Once a pirate hideout, the area is rich in history and volcanic beauty, with fascinating stories shared by your skipper along the way. Anchor in secluded coves for swimming, snorkeling, and stand-up paddleboarding, with time to explore caves and arches from the water. Back on board, enjoy a freshly prepared Mediterranean meal with unlimited drinks as you relax in comfort. Designed for small groups and authentic island vibes, this cruise is perfect for couples, friends, and travelers seeking a refined yet fun sea adventure.

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Milos Luxury Sailboat Cruise to Kleftiko Bay with Meal and Drinks

5 hours 30 minutesFree Cancellation

5.0

(38)

from $142

Boat Trip to the Pirate Cave & Blue Lagoon

Experience the best of Paros on a half-day boat tour to two of the island’s most breathtaking and unique locations! Swim and explore the mysterious Pirate’s Cave with its dramatic cliffs and legends, and unwind in the crystal blue waters of the Blue Lagoon. This unforgettable family friendly journey blends adventure, relaxation, and stunning natural landscapes. Designed for explorers, sea lovers, and those chasing the extraordinary – this tour is the ultimate island escape. Reserve your spot and let the Aegean work its magic! I

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Boat Trip to the Pirate Cave & Blue Lagoon

3 hours 30 minutesFree Cancellation

5.0

(19)

from $77

Santorini Sunset Cruise in Caldera

5 hoursFree Cancellation

4.9

(37)

from $53

Escape the crowds on land and admire Mykonos from the water on a luxury catamaran cruise that takes you off the beaten path to Rhenia, an uninhabited island surrounded by crystalline waters and home to ancient Greek ruins. Enjoy free time to relax as you wish—swim in the crystal-clear waters, soak up the sun, and enjoy refreshing drinks on board. Note: the itinerary is subject to weather conditions and might be adjusted to explore the southern coast of Mykonos.

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Mykonos: Brand-New Catamaran Cruise with Meal, Drinks & Transport

5 hoursFree Cancellation

4.9

(1,219)

from $141

Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

5 hoursFree Cancellation

4.6

(648)

from $93

Special Offer

Marvel and take photos next to the Red Beach Cliff . Drop anchor at Santorini's best! Our top-of-the-line Lagoon catamaran will take you to Red Beach.

Santorini stuns at any angle, but its most magical destinations are often only reachable by water. Experience its rugged coastline and volcanic islands by boat on this catamaran cruise. Choose between daytime and sunset bookings; snorkel equipment is available for swim stops, and you'll enjoy a BBQ buffet lunch or dinner washed down with local white wine and soft drinks—as well as swimming to the Santorini Hot Springs.

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Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers

5 hoursFree Cancellation

Experience one of the best Milos boat tours with a sailing cruise to Kleftiko along the island’s stunning west coast. Departing from Adamas, sail past volcanic landscapes, hidden coves and sea caves, with multiple stops for swimming and snorkeling in crystal-clear waters. Visit Kleftiko, swim at Kalogries Beach and explore Sykia Cave, some of Milos’ most iconic locations. Relax on deck and enjoy breakfast, lunch, drinks, seasonal fruits and traditional sweets served on board. With a small-group setting and experienced local crew, this sailing cruise offers a comfortable and unforgettable way to discover Milos. Highlights Full-day experience (10:00–17:00) Visit Kleftiko, Sykia Cave & Kalogries Beach Swimming, snorkeling and cave exploration Breakfast, lunch, drinks, fruits & sweets included Small-group experience with local crew Important Note: The itinerary is indicative and may be adjusted depending on weather, sea conditions, or for the safe operation of the cruise.

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Milos Kleftiko Sailing Cruise with Lunch, Drinks & Snorkeling

7 hoursFree Cancellation

4.6

(14)

from $130

Discover a side of Santorini that few other visitors get to experience—and make exploring beyond the mainland easy—on this half-day tour. Look forward to visiting Santorini's unique volcanic landscapes, and head to two islets accessible only by boat. Sail to Nea Kameni to hike up to the crater of the active volcano (entry tickets own expense), and to Palea Kameni, where you can soak in natural hot springs.

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Santorini Volcano and Hot Springs Cruise Tour from Fira Old Port

3 hoursFree Cancellation

4.2

(1,305)

from $35

Santorini Oia: Luxury Day Cruise with Fresh Fish BBQ & Drinks

4 hoursFree Cancellation

4.9

(38)

from $142

Make the most out of your time in Santorini aboard this tranquil catamaran tour. Enjoy the splendid views from the boat as it sails around Santorini, and discover a side of the island many other visitors miss. Swim and snorkel in the blue sea and indulge in a delicious barbecue dinner prepared onboard, complemented with local drinks. You see the best of the island in one relaxing getaway.

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

5 hoursFree Cancellation

4.5

(1,214)

from $93

Milos oneiro-kleftiko sailing experience with local guide

Milos is famed for its stunning, otherworldly coastal scenery, including the lunar-like Sarakiniko Beach— but the most impressive views aren’t reachable by land. On this small-group sailing tour, explore the island’s remoter west coast—a side of Milos most travelers miss—as you explore by boat. Along the way, listen to your skipper explain the island’s history and unique geology.

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Milos oneiro-kleftiko sailing experience with local guide

7 hoursFree Cancellation

5.0

(476)

from $166

Santorini 3 Islands Trip by Sailing boat

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.

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Santorini 3 Islands Trip by Sailing boat

5 hours 30 minutesFree Cancellation

4.5

(8)

from $41

Catamaran Day & Sunset Cruises with meals Drinks and transportation

Go on a half-day, small-group sailing adventure in the Aegean Sea. Select your preferred departure time—morning or afternoon—and set sail for Mykonos’ south coast or to the mythical birthplace of Apollo on the island of Delos. Relax at the beach, snorkel in beautiful turquoise water, and marvel at Delos’ ancient archaeological site. Enjoy lunch or dinner, wine, and hotel pickup and drop-off included in the tour price. Upgrade to a private boat for a personalized experience.

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Catamaran Day & Sunset Cruises with meals Drinks and transportation

5 hoursFree Cancellation

4.9

(1,238)

from $130

Likely to Sell Out

Milos and Polyaigos Full Day Cruise with Meals and Snorkelling

9 to 10 hoursFree Cancellation

4.8

(379)

from $148

Experience the volcanic beauty of the Aegean without having to line up for selfies on land during a catamaran cruise. Stop to bask on Santorini’s red- and white-sand beaches, snorkel, and soak in volcanic hot springs. Choose to sail in the morning or at sunset when the scenery is washed in golden sun. With included hotel transport plus a fresh Greek barbecue and soft drinks, beer, and local wine served onboard, it's a decadent way to enjoy the island’s famous sights.

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

5 hoursFree Cancellation

4.8

(1,327)

from $130

Likely to Sell Out

Half day Catamaran Morning Cruise in Kleftiko

6 hoursFree Cancellation

5.0

(47)

from $171

Santorini Caldera Cruise Tour (Volcano, Hot Springs, Thirassia)

6 hoursFree Cancellation

4.4

(1,417)

from $41

Special Offer

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks, and the historic Venetian Akrotiri Lighthouse. Our first swim stop is at Mesa Pigadia Beach or Red Beach. Here, you can dive into the crystal-clear waters for a refreshing swim and some snorkelling fun. The real highlight of our journey lies ahead as we venture into the awe-inspiring Caldera. Our next stop? The renowned Hot Springs of the volcano, where you can enjoy a rejuvenating swim in the therapeutic waters. For our third stop, we offer you the chance to visit and swim in Thirasia, the island adjacent to Santorini. After your swim , indulge in our elaborate lunch with stunning views of the surrounding seascape. As we sail back to Vlychada, don't miss the perfect opportunity to capture the breath-taking beauty of the Caldera. The ideal conclusion to your cruise, offering you the best views of Santorini.

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Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers

5 hoursFree Cancellation

Daily Boat Trip Antiparos & Despotico

6 to 7 hoursFree Cancellation

4.9

(99)

from $136

Special Offer

Sunfos Sailing Yachts at the archaeological site of Delos Island

Set sail on an adventure that combines history and relaxation. Cruise from Mykonos to Rhenia, admiring the sea views along the way, then explore the ancient ruins of the Archaeological Site of Delos on a guided tour. Take the opportunity to swim or snorkel in Rhenia’s turquoise waters. Everything you need is included: a freshly prepared Greek lunch, beverages, snorkeling gear, and floatation devices.

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

5 to 6 hoursFree Cancellation

Santorini’s most dramatic beaches and volcanic coves are best reached by boat. This half-day catamaran cruise from Oia lets you explore the island’s coastline from the water, with stops for swimming and snorkeling along the way. Sail past scenic islands and beaches before settling in for a sunset meal—a BBQ dinner onboard, paired with local wine—as the caldera glows at dusk. Hotel pickup is included for added convenience.

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Santorini Oia: Small Group Sunset Cruise with BBQ Fish & Drinks

6 hoursFree Cancellation

5.0

(111)

from $171

Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches like Psarou and Super Paradise, while enjoying refreshing swims in crystal-clear waters. Onboard, indulge in a freshly prepared Greek ΒΒQ meal, featuring delicacies, salad, and authentic local flavors, paired with refreshing drinks. As the sun begins to set, experience the magic of the Aegean sky transforming into shades of gold, pink, and purple, creating a truly unforgettable moment. With a premium catamaran, expert crew, and intimate atmosphere, this is more than just a boat tour, it’s a once-in-a-lifetime Mykonos sunset experience. Book now and let the Aegean’s beauty take your breath away! *Route may be adjusted by the captain based on weather conditions to ensure safety and comfort. This cruise operates using a fleet of two or more premium catamarans.

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Mykonos Catamaran Sunset Cruise with Meal, Drinks & Transfer

4 hoursFree Cancellation

4.8

(122)

from $148

Cruise around Santorini on this half-day catamaran tour departing from Vlihada Marina. Observe famed sights such as the Venetian Lighthouse, the Indian Rocks, the Red Beach, and the White Beach as you glide atop clear blue water. Enjoy a swimming and snorkeling excursion, then take in panoramic views of Thirasia Island and, if you've chosen an evening tour, sail past Oia during sunset—a must-do for any Santorini trip.

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Premium Small-Group Catamaran Cruise with BBQ, Open Bar, Transfer

5 hoursFree Cancellation

4.9

(7,863)

from $142

Santorini Gold Catamaran Cruise with BBQ, Drinks and Hotel Pickup

5 hoursFree Cancellation

4.9

(881)

from $118

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Top Cyclades Islands Sailing Tours

200+ results

Top Attractions in Cyclades Islands

Delos (Dilos)

Santorini Volcano

Oia

Church of Panagia Paraportiani

Red Beach

Mykonos Town (Chora Mykonos)

Delos (Dilos)

Santorini Volcano

Oia

Church of Panagia Paraportiani

Red Beach

Mykonos Town (Chora Mykonos)

Delos (Dilos)

Santorini Volcano

Oia

Church of Panagia Paraportiani