Itinerary Highlights
    • Discover these two islands, set in the world's bluest sea, which sum up the splendour and authenticity of the Cyclades

    • Head out on a boat trip from Sifnos to visit nearby Polyaigos Island

    • Go riding on the beach in Santorini and explore the caldera by catamaran

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Begin your Cycladic adventure in Sifnos, a secluded island fringed by sandy beaches and proud of its longstanding traditions. Expect to see men bobbing up and down on the backs of their trotting donkeys and traditional pottery adorning workshop windows. There must be as many churches in Sifnos as there are days in a year, making it hard to know which ones to visit, but we’d recommend heading to the Virgin of Poulati Church - surrounded by olive trees and found at the bottom of a creek, it’s as picturesque as it is tranquil. Across the phosphorescent waters lies Santorini, your next stop. This island owes its fame to the magnificence of its physical setting, along with the whitewashed houses and generous smattering of blue domed churches that sit precariously placed on its hillsides.
It’s a Grecian escape that encourages the slower pace of life, whether that’s trying local delicacies in the Melenio café in Oia, joining a celebration at the Dominican convent of Saint Catherine in Fira or visiting the old village of Emborio, you’ll no doubt find yourself falling for the charm and allure of this Eden-esq holiday spot.


Everything is 100% tailored to you


Your Cycladic Island escape awaits, with a short flight from London to Athens seeing you arrive in under four hours. Once you’ve landed, you’ll be transferred from the airport to the port of Piraeus, where you will cross by boat to Sifnos. Ready yourself for pristine beaches, iconic whitewashed buildings and brilliant blue waters.

DAYS 2 & 3


Spend the next two days exploring the island of Sifnos, which lies to the southwest of the Cyclades Islands, within the deep blue Aegean Sea. Its hills are dotted with pistachio and juniper trees, thyme, capers and more. In spring, the whole place is bursting with wildflowers, even the coastline, with sea lilies opening their white flowerheads along the shore. Things to see here include the charming harbour in Kamares, the taverns in the capital of Apollonia (which are open late), the Venetian homes of Artemonas and Kastro and its ancient defensive architecture, where the houses form a strong and photo-worthy backdrop. Opt to begin your days either with relaxed breakfasts at the beach or hikes in the country. You could even journey from Agios Andreas to the Mycenae citadel, where the former city’s archaeological site perches on the top of the hill. Take in the view before continuing the hike along a rural trail that was once cultivated by Neolithic civilisation, until you reach the Fyrogia monastery just above the sea at the end of a small path. We can arrange for you to explore these hiking trails with a private guide.



Another day brings another opportunity to explore the wonders of Sifnos and its equally exquisite surroundings, but this time it’s by private boat. With a guide, you will head out across the water towards Polyaigos Island, east of Kimolos. Its few inhabitants are nearly outnumbered by goats, who work hard to keep the vegetation closely cut. If you're lucky, you might even see one of the Mediterranean monk seals and their colony, along with some incredible beaches, nature trails and hidden coves (which are perfect for a refreshing dip).



Transfer to the port and take a boat to Santorini, where you’ll be spending three nights in Oia. This coastal town on the north-western tip of Santorini boasts rugged clifftops and views across the vast caldera, now filled with warm Grecian waters. There are plenty of hotel options here, offering the change to relax and unwind in between venturing out to explore the island.



Santorini might just be the ultimate Greek island. Its distinct character revolves around high cliffs, white villages dominated by churches with cobalt-blue domes, fragrant vegetation, citrus orchards and strong contrasts of light and shadow. Oia and Fira are just as bright and airy. After walking the intertwining alleyways of the villages, enjoy a bowl of fava (made with yellow lentils), and a glass of Vinsanto liquor. Adventure seekers can take to the beach, where horse riding awaits. Experience the sensation of the horses padding along soft sand just as the sun sinks below the horizon. Of course, you don't have to be an expert rider. If you are, great, but if not, just enjoy the walk - it will be equally spectacular.



Today is an opportunity to discover more about Santorini's geographical origins, by exploring the caldera by catamaran. This vast caldera was formed from the collapse of a volcano's magma chamber, and initially partially sank before being consumed by the sea, leaving behind the crescent shape and dizzying cliffs. Sail through this unique landscape with a skipper, and enjoy a lovely lunch onboard. Plus, you'll have plenty of opportunities for swimming and snorkelling. Round off the day with a romantic dinner, that will leave you falling even harder for the charm of the Mediterranean.



Sadly, it’s time to head home today. You will be transferred to the airport ready to catch your four-hour flight home, during which you can reminisce on a trip well spent.

A la carte


A beautiful trip starting from Agios Andreas hill leads to the Mycenae citadel founded in the 13th century BC. Perched on top of the hill, the archaeological site bears witness to a rich ancient heritage. It takes a bit of imagination to visualise the city that sprawled to the top of this mountain, but the small museum at the entrance of the site exhibits the discoveries made during excavations. Take in the view before continuing the hike along a rural trail that was once cultivated by Neolithic civilisation, until you reach the Fyrogia monastery just above the sea at the end of a small path. You can explore these hiking trails with a private guide.



Enjoy the sensation of the horses padding along soft sand just as the sun sinks below the horizon. The horse adds a sense of freedom to this spectacular moment which you won't get on foot. Riding is an epic adventure. You don't have to be an expert rider. If you are, great, but if not, just enjoy the walk - it will be just as spectacular.


A Rough Idea of Price

Dependent on season, accommodation and activities
The cost for this trip starts from £3,540 per person. The final cost of the trip depends on the way we tailor it especially for you. The final cost varies according to several factors, which include the level of service, length of trip and advance booking time. The exact price will be provided on your personalised quote. The average starting price for this trip is £4,375 per person.
  • International flights with a scheduled airline

  • Airline taxes and fuel surcharge

  • Piraeus to Sifnos and Sifnos to Santorini crossings by boat

  • Four-day car hire in Sifnos

  • Four-night stay in Sifnos in a double room with breakfast

  • Three-night stay in Santorini in a double room with breakfast

  • Polyaigos Island in a private inflatable boat

  • Catamaran ride in the Santorini caldera

  • A romantic dinner at your hotel in Santorini

  • Our local Concierge service

  • A GPS navigation service accessible from our app, loaded with your itinerary, hotel details and places to visit
A few of the benefits of travelling with us
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