Cyclades, Greece Sailing trips & boat tours

Our most recommended Cyclades, Greece Sailing trips & boat tours

Santorini: Luxury Small Group Catamaran w/ Meal & Open Bar

1. Santorini: Luxury Small Group Catamaran w/ Meal & Open Bar

Drop anchor on a luxury catamaran tour around the Santorini caldera while enjoying a delicious traditional meal with refreshing drinks from the open bar. Sail in the morning or at sunset on a cruise with a maximum of 20 guests. After being picked up from your hotel, unwind as you’re taken straight to the port. Take advantage of the snorkeling opportunity with a half-hour stop off the coast of Red Beach, plus 1.5 hours to snorkel in the sea caves of White Beach. Bathe in the lagoon’s hot springs and snorkel in clear waters. Taste the flavors of Greece on board a menu of local Santorini delicacies for lunch or dinner, depending on the time of day you choose, with meat and vegetarian options. The menu includes barbecue skewers, dolmadakia (rice-stuffed vine leaves), Greek salad, and other local dishes. Sit back and unwind with a post-meal cocktail and music. Stay refreshed with unlimited drinks on board, including local white wine, Greek beer, and soft drinks. Continue past the two uninhabited volcano islands of Palia Kameni and Nea Kameni and take in other sights such as Aspronisi island and the Akrotiri lighthouse. Later the cruise sails in the caldera below the town of Fira and past the old port. If you chose the late afternoon option, stop below the village of Oia and be wowed by the striking sunset lights adorning the skies with vibrant, pastel colors. This is sure to be an unforgettable highlight to an already unforgettable cruise experience. At the end of your Santorini excursion, relax as your minibus driver conveniently drops you back at your hotel.

Santorini: Catamaran Cruise with Meal and Open Bar

2. Santorini: Catamaran Cruise with Meal and Open Bar

Cruise aboard a spacious and luxurious catamaran and experience views of Santorini’s landscape. Stop at the day at the famous Red Beach Start with pickup and travel by minibus to the marina of Vlychada where the half-day cruise begins. Meet the crew and be welcomed on board with a glass of wine or a soft drink. Set sail towards the island's colorful beaches while the guide on board will share insights into the history of Santorini and the geological events that created Santorini’s rugged landscape and its surrounding islands. Your first stop of the day will be at the famous Red Beach. Enjoy time to swim, snorkel, and take pictures of its reddish hues and wild cliff formations. The first mezedes (finger food) are offered when you get back on board to continue your trip. Admire stunning views of the sandy shores of White Beach, surrounded by bright limestone cliffs, followed by a short stop for pictures of the caves and impressive rock formations of the Indian Rocks, which can only be reached by boat. Cruise past the 18th-century Venetian Lighthouse of Akrotiri, located on the southwestern tip of the island, and continue your sailing journey by entering the waters of Santorini’s caldera. Head towards the renowned volcano for the second stop of the day at the sulfur-rich hot springs. Take a relaxing dip into its healing and detoxifying waters. Back on board, enjoy the view of Santorini, a postcard-perfect portrait of the villages on the cliff. Set sail again towards the last stop for another swimming and snorkeling opportunity in the crystal-clear waters of Mesa Pigadia. Meanwhile, the crew will be setting the table for the delicious lunch for you to enjoy after your swim. The menu features BBQ chicken, Neapolitan pasta, Greek Salad, Vegetarian meals such as Greek Ratatouille, a traditional Greek dessert, and an open white wine bar that also serves unlimited soft drinks, and water. Then, sail back to Vlychada where your driver will be waiting to take you back to your accommodation in Santorini.

Santorini: All-Inclusive Luxury Catamaran Small Group Cruise

3. Santorini: All-Inclusive Luxury Catamaran Small Group Cruise

Explore the clear Mediterranean waters of the Santorini Caldera on a brand new Lagoon 450 catamaran. Make 2 swimming and snorkeling stops, then feast on a barbecue meal.  Once out on the water, the first stop of the tour will be a 30-minute visit to Red Beach, so named for its bright sand. After some relaxed swimming and great snorkeling, get back aboard the sailboat and continue to White Beach, featuring equally striking rock colors and more excellent swimming and snorkeling.  After swimming, the crew members will serve a delicious barbecue meal onboard. From there, take some time to take in the views from the beach before sailing past the beautiful uninhabited islands of Aspronissi and Akrotiri.  The tour's last stop will be at the hot springs for 30 minutes of relaxation, with the chance to go for a soak in the springs. The tour finishes at the port where you'll board a minibus for a transfer.

Adamas: Milos and Polyaigos Full-Day Cruise with Lunch

4. Adamas: Milos and Polyaigos Full-Day Cruise with Lunch

Spend your day exploring Milos Island and the uninhabited island of Polyaigos. Enjoy lunch and drinks and stops to swim in crystal clear blue waters. Your journey from Adamas and make your way to the colorful fishing villages of Adamas Gulf and Arkoudes. On the northern side of the island, admire the famous lunar landscape of Sarakiniko and the volcanic islands of Glaronissia. Stop for a swim on Polyaigos Island before sailing to eastern Milos to learn about the history of the Sulfur Mines at Thiorichia. Stop for a swim in the emerald waters of Gerakas and then head to the famous Kleftiko, an old hideout for pirates to snorkel in its caves. Before leaving Kleftiko, enjoy lunch in its unique landscape. Next, see the Cave of Sykia, with its collapsed roof, as well as the western side of Milos, which is only accessible by boat. See the old manganese mine of Cape Vani before returning to the port of Adamas around 7 PM.

From Adamas: Kleftiko Sailing Cruise with Snorkeling & Lunch

5. From Adamas: Kleftiko Sailing Cruise with Snorkeling & Lunch

Discover the coastline and beaches of Milos on a full-day guided cruise from Adamas. Swim and snorkel around the old pirate bay of Kleftiko with the gear provided. Savor a Greek lunch with drinks, and make another swim stop at Agios Dimitrios before admiring the sunset from the deck. Start from the port of Adamas, and admire the traditional fishing villages as the boat sails. Look out for the Bears, two large bear-shaped rocks at the entrance to the port. Cross the cape of Vani, with its volcanic rock. Sail past the west coast of Milos with its rare flora and fauna, the picturesque beaches of the Agathia, Triades, and Ammoudaraki, and the monastery of Saint John Siderianos.  Enjoy your journey as the ship arrives at Kleftiko with its towering, white limestone rocks of different-colored caves and tunnels lit in differing colors by the reflecting sun. Let the captain drop anchor, put on your masks and fins, and go for a swim in this unique place. Feast on a delicious meal on the return trip as you enjoy the views. There will also be a swim stop at the little church at Agios Dimitrios or at Klima. Admire the sunset across the bay of Adamas as your boat heads back to port and the end of your sailing adventure.

Santorini: Sunset Cruise with Swim Stops, Dinner, and Drinks

6. Santorini: Sunset Cruise with Swim Stops, Dinner, and Drinks

Explore the coastline of Santorini on this sailboat sunset cruise. Soak in the volcanic hot springs and swim through the waters of Red beach. View White Beach and the Black Mountain Beach. Watch the sunset over the sea while eating an authentic Greek dinner.  Sail along the southern coastline of Santorini and admire the lunar-like coastline of the island. At the picturesque Red Beach, dive into the crystalline waters for a swim or snorkel to explore the rich seabed. Continue sailing with views of White Beach, the Black Mountain Beach, and the Venetian lighthouse south of the Caldera. Next, stop to take a relaxing dip in the therapeutic volcanic hot springs.  Admire the impressive beauty of the sunset, while a dinner of traditional Greek mezzes, barbeque, and plenty of vegetarian options is served. Sip on local wines and finish your meal with a sweet dessert. Return to your accommodation in Santorini at the end of your tour. 

Santorini: Catamaran Cruise with Meals and Drinks

7. Santorini: Catamaran Cruise with Meals and Drinks

Be driven to the luxury catamaran and take a 5-hour cruise off the coast of Santorini. Hop aboard the catamaran and explore Santorini from the water on this relaxing cruise adventure. Choose from the daytime or evening option, and feast on delicious food as you go. Experience the beauty of the island as you set sail from the southern port of Vlychada. Follow the coast to the red sands of Red Beach. Take a swim in the shallow waters of a private beach.  Venture below the Indian Rocks and marvel at the sea caves and rock formations close to an old Venetian lighthouse. Admire the volcanic landscape as you travel through the middle of the caldera. Visit the hot springs for a healing mud bath before going to a private bay at Palea Kammeni Island. For the sunset option, journey out to open waters after dinner and watch a magnificent sunset in the middle of the Aegean Sea. Then, sail back to port, where a driver will wait to take you back to your hotel.

Santorini: Premium Catamaran Cruise with Fresh BBQ & Drinks

8. Santorini: Premium Catamaran Cruise with Fresh BBQ & Drinks

Climb aboard the 74-foot Ocean Voyager or the 80-foot Tahiti catamaran for a 5-hour cruise around Santorini in the Aegean Sea. Set off on a journey of discovery that will first take you to the hot springs, then the Red Beach, and finally the White Beach. Swim and snorkel and tuck into a delicious meal onboard. Start your adventure with a comfortable hotel pickup and set sail for beautiful Red Beach to swim and snorkel for 30 minutes. Continue to a secluded White Beach, only accessible from the sea, for more swimming and snorkeling in the shadow of the towering white cliffs. Onboard the catamaran, savor a barbecue supper of salads and grilled meat and veggie options. Continue sailing inside the crescent-shaped Caldera, close to the volcano, and enjoy a final dip in the Hot Springs, before sailing back to Oia as the day ends with a spectacular sunset.

Adamantas: Milos Sightseeing Sailboat Cruise

9. Adamantas: Milos Sightseeing Sailboat Cruise

Embark on a full-day cruise to west Kleftiko from Adamantas. Visit Cape Vani, and Sykia cave, and enjoy Greek tapas on board with plenty of swimming and snorkeling stops en route. You will start your journey from Adamantas and sail close to the east coast of the bay, passing the Christian catacombs, the colorful villages of Skinopi, the capital of ancient Milos, and the place where the famous statue of Venus de Milo was discovered. Sail to Cape Vani, an impressive 30-meter tall rock, home to one of the first mineral mines in Milos. You will see the mines' quay before jumping in for the first swim of the day in the crystal-clear waters of Kalogries. After returning to the boat, relish some homemade snacks and refreshments while moving to Sykia, the biggest and most impressive cave of Milos. Snorkel the clear green waters of Sykia before taking a small dinghy under a rock passage and into the cave. Explore a salt lake with a small beach, illuminated by a natural skylight in the rock above. Upon returning to the boat enjoy some delicious snacks accompanied by soft drinks or local wine, beer, and greek traditional liquor. Finally, you will reach Kleftiko, the old pirates' lair. Take the dinghy to uncover the unique beauty of Kleftiko caves and find the perfect photo-opt with the underwater cameras. You will also enjoy a delicious meal in Kleftiko. On the return journey, relax on the deck or join the cockpit to help steer the boat. Dive in for one final swim in the bay of Agios Dimitrios, a tranquil spot inaccessible by car which offers an amazing view of Plaka and Tripiti and all the colorful villages across the bay.

Santorini: Private Catamaran Cruise with BBQ Meal and Drinks

10. Santorini: Private Catamaran Cruise with BBQ Meal and Drinks

Explore the shores of Santorini on this cruise from Ammoudi Bay. Admire sights like Indian Rock and the Venetian Lighthouse. Have the option to choose between a sunset tour with dinner or a day tour with lunch. Sip on delectable local wine with your meal. Sail in a comfortable catamaran to the warm therapeutic waters of the volcanic hot springs. Head towards Aspronissi Island and pass by the Indian Rock formation and the 19th-century Venetian Lighthouse. Stop at Mesa Pigadia which is next to the unique White beach. Indulge in a Greek barbecue lunch or dinner and pair your meal with fine regional wines. Dive into the dazzling waters of the famous Red Beach and capture pictures of its reddish sand.

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What people are saying about Cyclades, Greece

Overall rating

4.4 / 5

based on 4,908 reviews

Excellent cruise for a short period of time we stayed in Santorini. Staff are very accommodating and always making sure they meet our needs. We had a great time sailing around the island. Highly recommended while in Santorini! I will surely book this again on my next visit to Santorini.

Fabulous from start to finish. From the very fun bus journey when collected (especially when they have to free fall backwards to go to the port !) to the beautiful meal and stunning sunset . The crew on board were so friendly .

Very helpful and friendly staff! The boat was comfortable, the views were fantastic, and the food was delicious. Highly recommend this boat experience!

The food was great, the tours was great and the staff was very friendly. I'd highly recommend this tour!

Lovely day out - beautiful scenery, fantastic crew and delicious food.