Syrmata & Sunsets

Discover blue-domed chapels, pristine waters and lost cities on this 10-day island-hopping itinerary of the southern Cyclades. Answer the siren Instagram call of Milos with its blindingly blue bays, chalk-white villages, kaleidoscopic beaches and early Christian catacombs. Explore the spectacular moonscape cliffs at Sarakiniko, the bottle-green swimming hole at Papafragas, and the colourful, rickety syrmata gazing out to sea.

Next head to Folegandros, the finest spot for daydreaming this side of Athens. Discover Byzantine hiking trails, rocky footpaths leading to secluded coves and ancient sea caves. Settle into charming cafés in clifftop Hora, catch up on local gossip, and adjust to the languid pace of life. With 85 Greek Orthodox chapels on the island there’s little division between soul, noise and spirit here.

The final stop on your itinerary is Santorini, the superstar island of the Cyclades, home to whitewashed houses, volcanic slopes and shimmering blue seas. Take a boat trip to the smouldering crater of Nea Kameni, stop by Akrotiri to view ancient ruins, enjoy freshly caught seafood at Ammoudi Bay, visit wine caverns adorned with artworks, and join cooking classes celebrating Santorini’s gastronomic delights. In the evening, settle down on the caldera edge to watch a showtime sunset.

Family Adventure Holidays - Trip Duration

Family Adventure Holidays - Departure Dates
Greek Islands Family Adventure Holiday - Syrmata & Sunsets trip map
Family Adventure Holidays - Minimum Age

Family Adventure Holidays - Activity Level

What's included

  • Flights: Direct return flights from UK regional airports to Athens (ATH)
  • Transport: Inter-island ferries, car hire from port pick-up to port drop-off
  • Accommodation: 10 nights in a B&B, hotel, apartment or villa
  • Meals: Breakfasts where stated
  • Trip Pack: Key family-friendly information about the country you are visiting with recommended activity links, places to eat and fun facts.

Trip highlights

  • Explore ancient catacombs and Roman amphitheatres on Milos
  • Discover the incredible lunar landscape of Sarakiniko
  • Enjoy lazy lunches in colourful fishing villages such as Mandrakia & Klima
  • Immerse yourselves in a Greece of the past on Folegandros
  • Hike the jaw-dropping Fira to Oia coastal path
  • Discover Akrotiri, the Greek ‘Pompeii’, a beautifully preserved ancient city
  • Experience the spectacular Santorini sunset

Key facts

  • When can we go? April to October
  • What type of tour is it? Private self-drive, island hopping tour
  • Who is it suitable for? For geography geeks, history buffs, food connoisseurs and adventurous families with a penchant for coastal capers, traditional island life and jaw-dropping sunsets
  • What is the minimum age? We would recommend a minimum age of 7 years for this trip but this is just a guide; our itineraries can be adapted, no problem, for families with younger children

Guide price

We publish ‘guideline prices’ for both the high and low season to give a reasonable estimate of what you might expect to pay per person based on a family of four (two adults, two children). To get an accurate price based on your estimated departure date and party size please contact us directly.

Guide Price: Apr & Oct - £955pp

Guide Price: May to Sept - £1,298pp

Greek Islands Adventure Holiday - Trip itinerary

DAY 1: Milos – Statues & Souvlaki

On arrival in Athens, you will be met and transferred to the port of Piraeus. From here, it is a 3-hour ferry ride to the tiny volcanic island of Milos, home to whitewashed fishing villages, cliff-ringed coves, invigorating hot springs, Venetian castles and early Christian catacombs. Fall in love with the undulating cliffs at Sarakiniko, the bottle-green swimming hole at Papafragas and waters so blue at Kleftiko you’d think they’d been photoshopped.

Formed around a central caldera and characterized by lunar-like rock formations, Milos has the highest concentration of beaches in the Cyclades (over 70 such sandy shores!). Despite all of this natural wealth, Milos remains delightfully untrodden. For those seeking more action adventure activities Milos does not disappoint; sea-kayaking, scuba diving, hiking and mountain bike riding are all available.

We would recommend spending the remainder of your day acclimatizing to your new surroundings.

In the early evening we would suggest heading to Plaka, the island’s capital over 200-metres above sea level. This pretty town offers winding cobblestone streets, an archaeological museum and café-bars whose sunset views rival Santorini. There are also funky boutiques and artisan stores specialising in handmade jewellery. Expect to see creative, assured and gimmick-free Mediterranean menus offering fabulous Greek food (we’ll get to the chocolate pudding later!)

Fun Facts: In 1820, amateur archaeologist Olivier Voutier discovered the marble statue known as the “Venus de Milo.” The celebrated work now lives at the Louvre in Paris.

DAY 2: Milos – Bakeries & Boulders

Today is dedicated to the south of the island. Start your day at Adamas, where you’ll find independent boutiques and a pretty harbour view. Along the way, grab some yummy pastries at the local bakery - the spinach pockets are especially good!

Afterwards, drive south along the coast, marvelling at the brilliant aquamarine sea, before stopping at Firiplaka, a sandy beach with freestanding sea caves just wide enough to squeeze into and some perfectly placed rocks where you can practice your cannonballing! If you are feeling even more adventurous, next door is Tsigrado beach, accessible by shimmying down a rope ladder and recommended for surefooted individuals only.

Travelling east, Paleochori boasts a stunning coastline of burgundy cliffs and huge boulders. This painterly landscape was shaped by minerals that bubble up in the undеrground springs along the shore (one of the bеасh taverna’s uses an especially warm patch to bake local dishes). Finish your day on the east coast at Pollonia, where you can eat sushi next to the sea or mouth-watering meatballs accompanied by live music and Greek dancing. The milk chocolate pudding, served out of a warming drawer at the local bakery is out of this world! The ferry to Kimolos (25-minute ride) also leaves from Pollonia and is well worth the trip if you have time. Every restaurant here is family-run and the coastline is filled with colourful fisherman’s houses stacked up like jewels.

Fun Facts: Milos was invaded by Germans between 1941 and 1945, During World War II. A network of tunnels underneath Adamas that was used as a bomb shelter still exists to this day.

Optional Activities: Ferry to Kimolos

DAY 3: Milos – Lunar Lagoons & Boat Sheds

Up and at ‘em at early light! Grab some beach towels and set off to explore the northern coast. Your first stop is Papafragas, a hidden cove with a caved arch that leads to the sea. Next, on to spectacular Sarakiniko, with its lunar landscape, horizontal rock formations and hipster vibe - very 1970’s James Bond! Spend time swimming in lagoons, cliff jumping and snorkelling on one of the most unique beaches in the world.

Just along the coast is Mandrakia, a charming fishing village lined with colourful houses and turquoise waters. We would recommend stopping for an authentic Greek lunch at the popular taverna above the syrmata (colourful boat sheds). The grilled octopus and riganato washed down with cool white wine are an excellent choice. A little further along the coast, Firopotamus boasts gorgeous blue waters guarded by a white little church and quirky beach bean bags.

Afterwards, take a break from the beaches to appreciate some of the island’s history. We would recommend parking at the medieval mountainside town of Trypiti where a single mile-long hiking path passes the early-Christian catacombs and the ancient Roman amphitheatre down to the village of Klima. The catacombs date back to the 1st and 5th century and are a well-preserved example of a communal burial site. The fifteen-minute tour is well worth the small fee.

End your day at the seaside fishing village of Klima, where authentic tavernas offer blinding sunset views.

Fun Facts: Sarakiniko is named for the Saracen pirates who would hide their boats under the white cliffs that resemble massive folds of whipped cream.

Optional Activities: Hiking, Christian catacombs museum

DAY 4: Milos – Blue Caves & Swimming Holes

Your final day on Milos is free to either relax on the beach or enjoy some additional activities. If you would like to explore the island a little more, we would recommend spending the day at sea as many parts of the island are only accessible by boat. There are some excellent local companies offering half or full day sailing trips often with a fabulous BBQ and a Greek dance lesson thrown in.

Sailing tours set out past Cape Vani, where free climbers scale cliffs that look like Scylla and Charybdis, before reaching Kalogries Bay, the perfect spot for swimming. From here, it is on to the deep blue cave of Sikia and the jaw-dropping Kleftiko with its towering, limestone rocks sprinkled like jewels in an aquamarine sea. The caves at Kleftiko used to be a famous hiding spot for pirates. Day tours usually sail on past Paleochori, the Thiorichia sulphur mines and the much-revered island of Polyaigos, encapsulated by crystal-clear waters, perfect for snorkelling.

Alternatively, you could join a full day kayaking trip that includes 3-4 hours paddling and 2-3 hours relaxation time for swimming, cliff jumping, hiking and snorkelling. A fabulous way to explore sea caves, rock gardens and secluded coves.

Fun Facts: The Thiorichia sulphur mines brought prosperity to Milos in the 1930’s, but they closed their doors in 1960. You can still see the carriages on their rails, rusty tools and abandoned offices.

Optional Activities: Sailing tour, sea kayaking, scuba diving

DAY 5: Folegandros – Church Bells & Raki Bars

From Milos, you’re headed to an island that is considered even more off-the-beaten-path. Its name is Folegandros and boy, are you in for a treat! Only a mere 12 square miles, Folegandros will transport you to a Greece of the past; low-key tavernas run by black-clad grandmothers, the idyllic sound of church bells, locals knocking back shots of rakomelo and children scampering among billows of crimson bougainvillea.

The main town and top sightseeing spot, Chora, teeters atop 200m volcanic cliffs in a blazing intensity of sugar-cube architecture, indigo sky and emerald sea so translucent you can count the fish swimming by. The town’s hugger-mugger of lanes, heavy with the scent of oregano and wriggling with cats, lead to three interlocked squares, rammed with tables and lined with olive trees, tavernas and dinky raki bars.

For the rest of today we would recommend exploring the town, stopping intermittently to top up on Greek coffee or fresh fruit smoothies, adjusting to the languid pace of life. Don't miss the handmade matsata pasta, karavoli (snails), orange pies, and amygdalota almond sweets. If you need to walk off some of your indulgences, zigzagging steps lead up to the town’s only real landmark, Panagia church. We would recommend making the pilgrimage at sunset to enjoy the amazing island views.

Fun Facts: The 2011 census counted only 765 people living in the municipality of Folegandros.

DAY 6: Folegandros – Donkey Tracks & Secret Coves

Folegandros is made for rambling; stone-paved donkey tracks criss-cross the island over sage-and thyme-scented hills. If you don't know where to begin, there are two classic routes to choose from, either independent or guided. The return route from Ano Meria to Agios Georgios is roughly 90 minutes on foot, but broken up by some of the island's best scenery and a refreshing dip at Agios Georgios beach. Ano Meria also boasts an Ecological and Folk Museum with primitive wine and olive presses. The alternative, stonier route from Chora to Agios Nikolaos takes less time and leads to the Insta-worthy church of Agios Nikolaos gazing out to sea - prepare to have inquisitive lizards and the occasional obstreperous goat for company.

We would recommend spending the afternoon relaxing on the beach. The island's finest is sandy Agali with its bright smattering of tavernas serving exquisite fresh fish. Alternatively, head to pretty Katergo beach with its gently shelving turquoise waters or dramatic Voreina with its rocky cliffs. The only way to reach many of the island’s secluded beaches is by little fishing boats from the main port or an adjoining beach. Livadaki is one such dazzling, white-pebble beach that is blissfully deserted when you arrive by boat from nearby Agali. Watch out for the teeny fish that nibble your toes as you bathe.

Fun Facts: There are at least, 85 Greek Orthodox chapels on Folegandos - under the Ottoman Empire, if you built a chapel, you were exempt from property taxes.

Optional Activities: Hiking, Ecological and Folk Museum

DAY 7: Folegandros – Groupers & Lobsters

There are a variety of options for your final day on Folegandros. The island is an underwater paradise for scuba divers and free divers with caves, reefs and walls such as Cathedral Cave and Poulioxeres Reef. Expect to see goldblotch groupers, slipper lobsters and sea anemones. Sign up for sessions with a local operator.

If you would prefer a less strenuous way to circumnavigate the island, we would recommend a boat tour where you can snorkel and swim in secret coves before feasting on a fabulous meze spread prepared by the captain’s wife. This is also a great way to see the high cliffs of Folegandros, so contoured that pirates called it ‘the island of iron’. A boat tour is the only way to see Chrysopilia, a magical cave lined with ancient inscriptions.

Spend your final evening enjoying fresh fish ceviche by the coast or mezze dipping plates in Chora against a magical backdrop of fairy lights.

Fun Facts: Archaeologists discovered hundreds of ancient names on the cave walls at Chrysopilia. These discoveries have given rise to the theory that the cave was a place of worship during the 4th century BC.

Optional Activities: Scuba diving, island boat tour

DAY 8: Santorini – Sugar Cubes & Lost Cities

Under an hour’s ferry ride from Folegandros, lies Santorini, one of the most insta-famous destinations in the world. The unique volcanic caldera, frosted with sugar-cubed houses, blue-domed churches and vertiginous cliffs in psychedelic hues, formed when the volcano flipped its lid around 3,500 years ago. There is no other island on earth where nature’s wrath resulted in such jaw-dropping beauty.

Santorini is undoubtedly paradise for couples but the island really does have something for everyone; adventurers can discover the Lost City of Atlantis and history buffs the prehistoric city of Akrotiri; hiking aficionados can embark on a breath-taking stroll from Fira to Oia and water babes an invigorating swim in the volcanic hot springs.

This afternoon, as a great introduction to the island, we would recommend visiting the Lost Atlantis Experience, dedicated to the volcanic explosion that blew out Santorini's heart. The exhibit features holograms, interactive representations and a 9D cinema. Afterwards, head to Profitis Ilias, the highest point on the island where a quaint monastery provides the backdrop to the most magnificent sunset view, a blazing spectrum of oranges, purples and pinks.

Fun Facts: Prior to the volcanic eruption that occurred on the island, Santorini was called Strongoli.

Optional Activities: Lost Atlantis Experience

DAY 9: Santorini – Panoramas & Hot Springs

This morning, lace up your walking boots, grab a freshly baked bougatsa and head to Fira, with its white-washed houses and cobbled alleys that make you feel like you have fallen into a fairy-tale. If you have the time and inclination, we would recommend descending the 587 stairs to the Old Port and hopping on the cable car back up.

The remainder of this morning is dedicated to the breath-taking 10km clifftop walk from Fira to Oia (age 7+ recommended). The trek takes at least 3 hours so we would recommend completing before the peak afternoon heat. The trail follows the rim of the caldera, passing through Firostefani and Imerovigli before arriving in the jaw-dropping town of Oia, adorned with narrow alleys and staircases that lead anywhere your imagination wants to go. It is the perfect spot for coffee & cake overlooking the sapphire blue Aegean. If you are a book lover, Atlantis Books, a whimsical bookshop with hobbit-like rooms, is a must visit.

After exploring Oia, make your way down the steps to Ammoudi Bay, a tiny fishing village with crystal-clear turquoise water. It’s a great place to enjoy freshly caught seafood and listen to the waves while nibbling tzatziki appetizers. If you are feeling adventurous, head east along the path, to a tiny island located just off the shore. This spot is super popular for cliff jumping and swimming.

From Ammoudi Bay, we would suggest joining a sailing tour, one of the absolute highlights of Santorini. Sail around the smouldering crater of Nea Kameni before stopping to swim in the natural hot springs. Discover caves and rock formations below Indian Rocks then continue to White Beach for the chance to swim and snorkel. End with a visit to Red Beach, a pure masterpiece of nature, before sailing back to land accompanied by traditional Greek mezedes and a sizzling BBQ feast.

Fun Facts: The name ‘Santorini’ was coined from two words ‘Santa’ which means ‘Saint’ and Irenene which means ‘Irene.’

Optional Activities: Cable car, hiking, sailing tour

DAY 10: Santorini – Windmills & Vineyards

This morning is dedicated to the historical sites of Santorini. At the very tip of the island lies the Akrotiri Archaeological Site, an ancient Cretan settlement. It was buried in volcanic ash 3,600 years ago, preserving the remains of sophisticated houses decorated with vibrant frescoes and even indoor toilets! Nearby, are the inland villages of Pyrgos and Emporio where you will find traces of the old Santorini with blue-domed chapels, windmills and vineyards.

Later this morning, gourmands among you might like to join a relaxed cookery class where you can participate in the creation of traditional Greek dishes and, of course, get to eat them afterwards. Alternatively, wine connoisseurs could join a local vineyard tour for wine tastings served with cheese, salami, and Greek olives. Wine production on Santorini dates back at least 5000 years with exceptional Assyrtiko grapes and Vinsanto wines.

This afternoon, we would recommend venturing out to sea on a kayaking tour. The bicep-busting itinerary journeys beneath rock faces and squeezes through sea caves before reaching Black Mountain and the Akrotiri lighthouse. On your final evening in Santorini we would recommend heading to the open-air cinema where popular Hollywood-style movies are screened against a memorable mountain backdrop.

Fun Facts: Archaeologists have unearthed poignant details of lives interrupted at Akrotiri - pots of barley, a basket of sea urchins and a golden ibex in a clay chest.

Optional Activities: Akrotiri Archaeological Site, cookery class, vineyard tour, sea kayaking, open-air cinema

Wandering Tribe has travelled to all of the destinations that we feature and we like nothing better than talking about them. If you would like further information about these tours or a tailor-made quote then please contact us on 07392 742333. Alternatively you can fill in the contact form and we will endeavour to get back to you as soon as possible.