Inspiration for your own tailor-made trip
Greece - Cyclades - Sifnos - Santorini
100% customisable for you
Your Cycladic Island escape kicks off today with a four-hour flight to Athens. After landing in the Greek capital, take a private transfer to your hotel for the night. Depending on the time you touch down, spend this afternoon strolling the city’s vibrant streets before tucking into your first tasty Greek dinner. Then it’s off to bed for a good night’s sleep, as tomorrow the islands await...
Fuel up for today’s travel with breakfast at your hotel, then take a private transfer to the port of Piraeus ahead of the boat crossing to Sifnos. It’ll take between two and three hours depending on the ferry, so sit back and enjoy the ocean breeze. As you sail, ready yourself for pristine beaches, iconic whitewashed buildings and brilliantly blue waters.
After arriving at Sifnos’ shores, collect your hire car and drive to your hotel and home for the next four nights. This evening, celebrate the start of your island adventure in style with a delicious local dinner (your Concierge can point you in the right direction).
Spend the next two days exploring Sifnos in the southwest of the Cyclades. There’s a lot to see here: the charming harbour in Kamares, Apollonia’s traditional tavernas, the Venetian homes of Artemonas and the ancient defensive architecture of Kastro (a photo-worthy backdrop). Admire hills dotted with pistachio and juniper trees, thyme and caper bushes and blooming wildflowers in the spring.
Sifnos is hiking heaven, beautifully demonstrated in the trail from Agios Andreas to the Mycenae citadel – a hilltop archaeological marvel founded in the 13th century BC. It’s tricky to visualise the city that once sprawled here, but a small museum offers some insight with exhibitions of excavated artefacts. Continue along a Neolithic trail to reach the Firogia monastery, standing like a sun-bleached beacon above the sea. If you prefer, hike the trails alongside a local guide to learn fascinating stories of this intriguing isle.
Another day brings another opportunity to explore the wonders of Sifnos and its equally exquisite surroundings. With a local guide, head across the water on a private boat towards Polyaigos Island, located 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 the Mediterranean monk seals who make their home here, along with some incredible beaches, nature trails and hidden coves (perfect for a refreshing dip). After a day on the water, return to your hotel to freshen up before one last delicious dinner on Sifnos. Tomorrow, Santorini awaits...
Drop your hire car at the port this morning before boarding the boat to Santorini, which takes around two-and-a-half hours on the fastest ferry. After stepping off the boat onto Santorini’s sunny shores, a private transfer will take you to your hotel in Oia, where you’re spending the next three nights.
This coastal town on the north-western tip of Santorini boasts rugged clifftops and spellbinding views across the vast caldera, now filled with warm Grecian waters. There are plenty of hotel options here, offering the chance to relax and unwind between venturing out to explore the island.
Santorini might just be the ultimate Greek island. Its distinct character comes from its high cliffs, white villages capped with cobalt-blue church domes, fragrant, fruit-filled orchards and strong contrasts of light and shadow. After strolling the intertwining alleyways of Oia and the equally lovely village of Fira, enjoy a bowl of creamy fava (a dip made with yellow lentils), and a glass of Vinsanto, Santorini’s sweet dessert wine.
Later, as the day draws to a close, head down to the beach to ride horses along the scenic shoreline. Experience the sensation of the horses padding along soft sand as the sun sinks below the horizon. Not an expert rider? Don’t worry, a sunset walk is just as spectacular in such a special spot.
Today is an opportunity to discover more about Santorini's geographical origins as you explore its caldera by catamaran. This vast caldera was formed by the collapse of a volcano's magma chamber. It partially sank before being consumed by the sea, leaving behind the distinctive crescent shape and dizzying cliffs.
Sail through this unique landscape with a local skipper and enjoy a lovely lunch onboard. Plus, you'll have plenty of opportunities for swimming and snorkelling. Round off the day (and your time on the island) with a delicious Greek dinner that might make you fall even harder for the charm of the Mediterranean.
Sadly, it’s time to bid the Cyclades a fond farewell and head home. A private transfer will take you to the airport ready to catch your four-hour flight home – ample time to reminisce over a trip well spent.
Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.
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Our team of destination experts will get to know you and your unique requirements for your holiday
We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities
All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges
