Cyclades, Greece Romance & special occasions

Our most recommended Cyclades, Greece Romance & special occasions

Santorini: Highlights Tour with Wine Tasting & Sunset in Oia

1. Santorini: Highlights Tour with Wine Tasting & Sunset in Oia

Embark on a full-day guided tour of Santorini's highlights. Visit the iconic blue-domed churches of Oia, admire the views from Profitis Ilias, and relax on the shores of Perissa Beach before some well-deserved wine tasting. After pickup from your hotel, board the luxury coach and drive to Profitis Ilias, the highest point on the island. Take in an incredible panorama of the entire island of Santorini, and the stunning deep blue color of the Aegean Sea while learning about the island´s fascinating volcanic history. Wander around the courtyard of the 18th-century monastery that sits on top of the mountain. Then visit the Saint Nektarios chapel and enjoy the tranquility of your surroundings. Continue to the village of Pyrgos, a hidden gem of Santorini. Wander through its winding alleys and immerse yourself in its traditional atmosphere. See typical houses, blue-domed churches, and quaint shops. Walk up to its imposing castle for beautiful vistas of the surrounding area. The next stop is Emporio, where you will join a guided walk and visit the small Venetian fortress. Feel like you’re on the set of Mamma Mia as you discover the many doorways, windows, alleys, and arches of this picturesque medieval village. Continue to Perissa Beach, also known as Black Beach. Here, there will be plenty of free time to go swimming in the sea or have lunch at one of the Greek tavernas facing the beach. Take the opportunity to taste local Santorinian wine, one of the most famous products of the island. Learn about the winemaking process and enjoy a private wine tasting session of 3 wines made of local grape varieties. In the early evening, arrive at the cliff-top village of Oia with its famous blue-domed churches. Embark on a guided walk from Saint George's Church in the most peaceful part of Oia. Learn about Oia´s glorious maritime past and admire elegant captains' mansions and cave-like houses along the way. Once at the bustling castle area, enjoy some free time to take some photos, shop, or have a relaxing drink. Finally, watch an incredible sunset before meeting up with your guide opposite Platsani Church. Board the bus for a relaxing evening journey with drop-off back at your hotel.

From Adamas: Kleftiko Sailing Cruise with Snorkeling & Lunch

2. 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: 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.

Santorini: Greek Wine Tasting Experience with 3 Winery Visits & Transfer

4. Santorini: Greek Wine Tasting Experience with 3 Winery Visits & Transfer

Discover Santorini's wine culture on a guided wine-tasting tour. Visit 3 traditional wineries, sample as many as 12 different wine varieties paired with local delicacies, and enjoy the convenience of a pickup and drop-off service from your accommodation. Explore volcanic vineyards and distinctive wine cellars alongside an expert guide. Learn about the island’s distinct viticulture that produces some of the crispest and seductively sweet wines in the Mediterranean. Be treated to pairings of cheeses and snacks, including local treats, as you taste the major wine styles of Santorini, such as Assyrtiko, Nykteri, and Vinsanto Admire beautiful seaside and countryside landscapes. If your tour is in the late afternoon, be rewarded with striking sunset views. At the end of this unique tour experience, sit back and relax as you are driven back to your hotel or accommodation.

Santorini: Catamaran Cruise with Meal and Open Bar

5. 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: Catamaran Caldera Cruise with Meal and Drinks

6. Santorini: Catamaran Caldera Cruise with Meal and Drinks

Enjoy the spectacular beauty of the Caldera and the beautiful Santorini sunset, while sailing with a luxury catamaran. Select from the Day Cruise or Sunset Cruise options which both offer a unique chance to admire Santorini’s beauty, sailing through the deep blue waters of the island. Start your Day Cruise journey from the old port of Ammoudi and head to Thirassia Island, a fishermen’s island ideal for swimming and admiring the unique view of Manolas village. Explore the unmanned volcanic beaches or sunbathe on the deck. Feel the energy of the volcano while heading to the hot springs. Sail towards the Black Mountain and the big light house south of the Caldera, as you head to the White Beach and the Red Beach for a swim when anchored, a delicious lunch is served onboard with wine and dessert. The Sunset Cruise begins with a stop at the Red Beach for a refreshing swim and stops at all the same locations as the Day Cruise. On the Sunset Cruise, enjoy dinner with wine and dessert served onboard.

Adamantas: Milos Sightseeing Sailboat Cruise

7. 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.

Mykonos: Sunset Cruise with Drinks

8. Mykonos: Sunset Cruise with Drinks

Come onboard and enjoy the breathtaking Mykonian sunset! Set sail and enjoy the magnificent view of Little Venice and Mykonos. Drop anchor to watch the "Dreamy Sunset" over the ocean, islands, and distant shoreline. Enjoy drinks and snacks on-board, before setting out on the return journey, where we relish the mesmerizing light of the sun setting over the Aegean Sea. This is a cruise that you will make memories to last a lifetime, as it is ideal for couples, families, friends or people who just want to have a relaxing and memorable time.

Santorini: South Sea Kayaking Tour with Sea Caves and Picnic

9. Santorini: South Sea Kayaking Tour with Sea Caves and Picnic

Spend an unforgettable day experiencing the Greek island of Santorini from a kayak. Discover the south coast of the island and marvel at the views of spectacular rock formations, crystal-clear waters, and beautiful beaches. See Santorini’s Red Beach turn white! Learn to handle a sea kayak and have it adjusted before heading out on this adventure. Beginners aged 14 and above can participate in this activity. You need to be able to swim and be in reasonable physical condition. You’ll cover up to 4 miles in your kayak over a 3-hour period. Along the way, you’ll stop for a break at the famous White beach, where you can enjoy some snorkelling.

Adamas: Milos and Polyaigos Full-Day Cruise with Lunch

10. 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.

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What people are saying about Cyclades, Greece

We had the best time with Nicholas during our time in Santorini. He found out what our interests were and created an unforgettable day for us which included everything from wine tasting to sight seeing to food recommendations and everything in between. We didn’t want our day to end! My mom will be visiting next summer and we will definitely be sending her to spend the day with our new Greek friend in Santorini!

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.

This really was value for money. Learned so much about Santorini and Greece in General. The guide Elena was extremely knowledgeable, passionate and eloquent. Highly recommended! Thank you so much!

What a great tour! Our tour guide and tour were one of the best tours I've ever been on. She provided such great information that made the places come alive. Cannot recommend this highly enough!

Great tour of Santorini that shows you some of the authentic non touristy areas of the island. Our tour guide on the day was outstanding. Knew her history and made it interesting.