Compare Cyclades Islands Adventure by Trails Beyond vs Sail Greece: Mykonos to Santorini by Intrepid Travel

Day 1: Athens – Naxos 

Meals: Dinner

Accommodation: 3* Hotel in Naxos

Walking duration: 1 – 1.5 hours

Distance: 2 – 2.5 km

Level of difficulty: easy

Early in the morning, we meet at Piraeus port, where you will be welcomed by your tour leader! We board the ferry to Naxos island, the largest of the Cyclades islands (approx. 5 hrs by ferry).  Upon arrival and check in at the hotel, you will have free to relax at your hotel, spend some time at the beach or enjoy a cup of coffee in one of the front side cafes. In the afternoon, we will enjoy a welcome tour in Naxos town (Chora). We will visit the Venetian castle and the old town, while our guide will give us a good insight on the history and culture of the island.  Before dinner, when the sun goes down, we will not miss the chance to walk through the paved footpath towards the islet of Palatia and admire the impressive marble gate of Portara and the stunning sunset views it offers. In the evening, we will enjoy a welcome dinner during our first day all together!

Day 2: Naxos inland hiking 

Meals: Breakfast

Accommodation: 3* Hotel in Naxos

Hike duration: 3.5 – 4 hours

Distance: 6.5 km

Level of difficulty: easy to moderate

Enjoy a good breakfast today, as we will explore hiking the best of Naxos inland, with its fertile valley, olive groves, vineyards and traditional villages.

Starting from the village of Moni, crossing old marble paths and the Tragea plateau, we will end up in the picturesque village of Chalki after approx. 3.5 hours and we’ll visit the traditional citrus distillery, where will be able to sample their famous locally produced liqueurs.

After lunch, we will visit the picturesque villages of Filoti and Apeiranthos, the most well – known and traditional villages of mountainous Naxos.

Day 3: Daily sailing to Small Cyclades

Meals: Breakfast

Accommodation: 3* Hotel in Naxos

Today we will set off on a daily sailing tour with destination Iraklia and Schinousa islands, two secluded earthly paradises in the Aegean Sea that will captivate you for their crystal clear, turquoise waters and their calmness! A day full of surprises, fun and adventure! Snorkeling, diving with a sea scooter, kayaking and much more will definitely give you an unforgettable experience!

Day 4: Naxos – Santorini

Meals: Breakfast

Accommodation:  3* Hotel in Santorini

Nobody can resist the charm of the never-ending, golden Naxos beaches and its clean, greenish blue waters. So today get ready to explore some of them on a horse ride*!  Depending on the season and the weather, we will also have plenty of time to enjoy swimming and snorkeling in the crystal clear waters of the Aegean Sea. Alternatively, you can enjoy your last morning in Naxos leisurely, go to Chora for shopping or simply walk around the narrow alleys and enjoy your coffee in one of the charming cafes across the side front.

 In the afternoon, we will take the ferry to Santorini. Prepare yourself for this striking, magical, volcanic island and feel its unique and inspiring aura! The views from the boat once we enter the caldera are simply stunning and captivating…

Our first day in Santorini includes a wine tasting experience of signature local wines and a walk around the capital city of the island, Fira.

*Horseback riding/ mountain biking are optional activities. You may consult your tour leader for options, prices and availability.

Day 5: Hike Fira to Oia & Sunset Sailing cruise

Meals: Breakfast and Dinner (BBQ on board)

Accommodation:  3* Hotel in Santorini

Hike duration: 3 – 4 hours

Distance: 9 km

Level of difficulty: easy to moderate

Today we will take the hiking trail that leads from Fira to Oia, all the way along the Caldera cliff edge. It is a scenic route with no particular difficulties, offering spectacular views over the caldera. Passing by Firostefani, Imerovigli and Skaros, we will finally reach the picturesque settlement of Oia in approx. 3 hours. Once in the picturesque village of Oia, you will have free time to walk around its picturesque streets, visit the tiny beautiful shops or relax in one of the numerous cafes/restaurants with roof top terraces offering fantastic caldera views and enjoy your lunch.

Later on we’ll follow the steps down to Ammoudi bay, where we’ll board a beautiful catamaran yacht and enjoy a memorable sailing cruise inside the caldera. You will have the chance to swim in the Hot Springs, discover more of Santorini’s beauties and enjoy BBQ dinner on board, prepared by the crew.  On top of that, you will enjoy Oia’s famous sunset right from the deck!

Day 6: Santorini South Discovery

Meals: Breakfast

Accommodation:  3* Hotel in Santorini

Today we will enjoy a fantastic day in Santorini, discovering the natural and historical beauty of the south! In the morning, we will first visit the traditional village of Pyrgos, which was declared as a “protected settlement” in 1955. Pyrgos is a typical Fortress Settlement of the Cyclades islands and on its hilltop you can find ruins of Kasteli Castle, one of the five 'kasteli castles' on the island. We will afterwards head towards the monastery of Prophet Elias, located on the highest hill of Santorini, offering 360 panoramic views of the island! From there a breathtaking, yet slightly rough, descending trail begins that will take us to the archaeological site of Ancient Thera. Located at 360m height, on Messavouno mountain, it was named after the mythical king of the island, Theras, and was inhabited since the 9th BC century.

From there, we will follow the descending hiking path towards Perissa. Once there, you will have free time to relax, enjoy swimming, water sports, scuba diving or a walk along the long black sandy beaches of Perissa and Perivolos and lunch in one of the seaside restaurants.

We will afterwards head south and visit the archaeological site of Akrotiri, also known as the “Greek Pompeii”, one of the most important prehistoric settlements of the Aegean*. Unique findings, two-storey prehistoric buildings and houses, dated back to the Bronze Age, will definitely amaze you! 

*For those of you who love sea kayak, we can arrange an unforgettable sea kayak experience, instead of visiting Perivolos beach. Starting from Akrotiri, you will paddle by the Red and White beaches, discovering the south coast of the island beyond the ordinary way! Views of the spectacular rock formations, swimming and snorkeling in crystal waters, beautiful beaches and a light picnic are all part of this amazing adventure!

Day 7: Santorini – Athens

Meals: Breakfast

This is the last day of our weekly adventure in the Cyclades islands. You have the morning free to explore the town of Fira, purchase any souvenirs you may want, before we take the ferry back to Athens. Depends on your schedule

Day 1 Mykonos

Welcome to Mykonos, Greece. Your adventure begins with a welcome meeting at 4 pm at a restaurant called Asian food Sushi & Coffee Bar - Cantina Street Food Mykonos located at Marina Tourlos, Mykonos. The first port of call is the local supermarket to buy supplies for your trip as a group. The starter pack will include provisions for some breakfasts, lunches and/or snacks. If you have any special dietary requirements, please make sure you notify us at the time of booking so we can accommodate your requests. Before and after the meeting, perhaps head out to enjoy Mykonos and unwind on one of the island’s sandy beaches. Navigate the town's narrow streets, visit the Church of Panagia Paraportiani or browse chic galleries, restaurants and boutiques. In the evening, perhaps wander down to Little Venice to enjoy a cocktail by the water at sunset. You'll spend tonight aboard the boat. Notes: The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we are flexible on the day's itinerary. The itinerary is subject to change and may vary depending on weather. Your skipper will make the final call to ensure your safety at all times.

Day 2-7 Sailing the Greek Islands

Naxos This morning we head for the Bay of Gaidharos for breakfast and a swim, before making our way across the glistening water to Naxos. Discover the beautiful beaches, fragrant olive groves and charming villages of Hora, the capital of Naxos. As the largest Cycladic island, Naxos also has one of the most colourful mythological histories. The old town areas of Hora are perfect for a stroll or to partake in the vibrant nightlife. The best beach choices are to the south, where water sports are also on offer. Follow a pathway up to the impressive Venetian Kastro where mansions, monuments and churches all retain their medieval spirit in a mass of winding laneways. Stop by the old Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. The massive Portara stands as the gateway to the unfinished Temple of Apollo on the islet of Palatia, just to the north of the marina. Perhaps even join an optional jaunt out into the countryside for a glimpse local rural life, visit one of the oldest temples in Greece, then chill out up in the hills with lunch at a family tavern. Get a taste of the local brew with a shot of Kitron (best described as a lemon liquor) and top it off with a wander along the beach. Syros Sail to the island of Syros (approximately 3 hours), dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek revolution made it a safe haven for the persecuted. Perhaps catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here). Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square. Small Cyclades It's time to feel the wind in our hair once again as we sail along the coast of Naxos. After around 5 hours we drop anchor in the Small Cyclades. While all the islands harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Shinousa and Donousa have permanent residents, with the largest population said to be somewhere around 300. Featuring clear waters, great beaches, friendly locals and sleepy tavernas all built around quaint fishing villages, the islands are an ideal overnight anchorage. Explore the town, sample some fresh seafood in a waterfront taverna, then sit back and simply enjoy the magic of the Mediterranean. Amorgos Next is a brief sail (approximately 3 hours) to the rugged, mountainous island of Amorgos – known to the world as the stunning location of Luc Besson's film, 'The Big Blue'. Katapola, the island's main port, boasts classic Cycladic architecture with windmills and an old Venetian castle. The waterfront is an excellent place to relax in restaurants, cafes and bars. Or take some time to explore the ancient Minoan Settlement nearby. We will take a drive up to the spectacular 11th-century monastery, Moni Hozoviotissis. Built gripping the cliff-face, it boasts spectacular panoramic views across the Aegean Sea. Filled with historical relics, it's often a highlight for those visiting Greece. Also worth a visit is the village of Hora (Amorgos town) which sits high up on the rocky mountainside. Stroll through the labyrinth of narrow stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower, one of the few remaining towers on the island. Ios Continue to Ios, an island inhabited since early Cycladic times, proudly claiming to be the burial place of epic Greek poet Homer. Ios has managed to retain some allure from the abundance of beaches and preservation of its classic cube houses packed around the laneways of Hora. A short walk from the harbour, Hora's shops, restaurants, nightclubs, bars and cafes all come alive in the evenings. If you are seeking a more authentic taste of the old town, try to explore during the day while the masses are beachside. The popular beaches of Gialos and Milopotas are also lively at night with a range of water sports on offer during the day. Valmas, Kolitzani and Tsamaria are all options if you're looking for something a little quieter; they are within easy walking distance of town. Sunset views can be enjoyed from atop the hill where Panagia Gremiotissa, or Church of the Virgin, sits. The distinctive single palm tree next to the church makes it icon you can always see from many places throughout town. On the afternoon of day 7 we sail towards Santorini, spending the final night of the trip in Thirasia which is a small island about 1/2 hour from Oia, Santorini. Santorini Formed by a huge volcanic explosion, Santorini is instantly recognisable with its blue and white buildings, fascinating ruins and stunning natural beauty. After making our entrance by sailing through the remarkable caldera, all the hubbub of this beautiful island is there for the taking. The exuberant capital of Fira, perched on the edge of the caldera, has an exciting range of restaurants, shops and bars. Perhaps make the most of the great scenery by taking a walk along the rim to Firostefani, Imerovigli and Oia. Santorini's volcanic beaches are a must-see: Red Beach's tiny red and black pebbles are hemmed in by spectacular red lava-rock cliffs, while the pick of the black beaches are Perissa, Vlhada, Perivolos and Agios Georgios. The white-washed Cycladic houses and old Venetian- and Byzantium-inspired architecture pack a real picturesque punch. Check out the Orthodox Metropolitan Cathedral, Catholic Cathedral and Dominican Convent. The Megaron Gyzi Museum, Museum of Prehistoric Thera, and Archaeological Museum are all also worth a visit.

Day 8 Santorini

Your adventure comes to an end this morning in Santorini at Athinios Port. If you plan to depart today, please don’t book a flight until after 16.00 in case the boat’s arrival is delayed due to weather conditions. Your skipper can assist with organizing a taxi to drop you off at your hotel or Santorini Airport.