Two Weeks in the Cyclades with Teenagers: A Car-Free Family Island-Hopping Route to Santorini, Sikinos, Ios & Naxos
This two-week Cyclades family itinerary covers Santorini, Sikinos, Ios and Naxos in a circular ferry route returning to Santorini. Best time: May to October. Highlights: caldera views from Pyrgos and Fira, unspoilt gem of Sikinos, beach life on Ios, golden sands and beaches and mountain villages of Naxos. No car rental needed.
Introduction
This trip had been over two years in the making. Originally planned as a special journey with one granddaughter to celebrate her exams, Covid struck and all our plans went up in smoke. When the world reopened, our travelling party had expanded – my husband Peter and two more grandchildren joined us, making five in total. Three teenagers aged 14, 17 and 18, none of whom had ever been to Greece despite having travelled to far-flung places around the world. It was my duty to show them what this beautiful country has to offer.
Think of Greece and what do you see? That picture-postcard image of white cubist buildings and blue-domed churches. To give my grandchildren that quintessential Greek experience, the Cyclades was the obvious choice. But I also needed to consider that three teenagers might want something a bit more lively than my usual off-the-beaten-track adventures. This itinerary was designed to give them a flavour of island hopping – a whistle-stop tour that balanced the unspoilt with the accessible, the quiet with the vibrant.
What Makes This Itinerary Special
A Perfect Introduction to Island Hopping
This route showcases the extraordinary range of the Cyclades. From the caldera drama of Santorini to the untouched tranquillity of Sikinos, from the youthful energy of Ios to the varied pleasures of Naxos – each island offers something different. It’s designed to give first-time visitors a true taste of what Greek island hopping can be, without overwhelming them.
The Circular Cyclades Route
The very name “Cyclades” means “encircling islands” – they surround the sacred island of Delos. This itinerary embraces that circular nature, departing from and returning to Santorini. Flying into and out of the same airport simplifies logistics enormously, and the ferry connections between these islands are reliable and frequent.
Multi-Generational Appeal
This route works for families spanning different generations. Teenagers will love the beaches and the liveliness of Ios. Parents and grandparents will appreciate the cultural richness of Naxos and the peaceful authenticity of Sikinos. The variety means everyone gets something they love without anyone feeling dragged to places that don’t interest them.
Balance of Famous and Hidden
Santorini and Naxos are well-known destinations with excellent infrastructure. Sikinos remains one of the least-visited islands in the Cyclades – a hidden gem that rewards those who make the effort to reach it. This combination gives first-timers confidence while introducing them to the magic of discovering lesser-known places.
Excellent Public Transport Throughout
Every island on this route can be explored without a car. Naxos has particularly good bus services reaching the mountain villages. Ferries connect efficiently, and the Blue Star and local ferry services are reliable. With a large family group and luggage, not needing to worry about car hire is a genuine relief.
The Route at a Glance
Route: Santorini (Pyrgos) → Sikinos (Alopronia) → Ios → Naxos (Stelida) → Santorini (return)
Duration: 2 weeks as travelled: Santorini 1 night, Sikinos 3 nights, Ios 3 nights, Naxos 5 nights, Santorini 2 nights. Could easily be extended with longer stays on each island.
Transport: Flights to Santorini; inter-island ferries including Dionisios Solomos and Blue Star Chios; excellent local bus services on Naxos.
Best Time: May through October for reliable ferries and swimming weather. Note that July is peak season with busy beaches and crowded buses. June or September offer similar weather with fewer crowds.
Who It’s For: Families with teenagers, first-time island hoppers, those wanting a mix of famous and hidden destinations, beach lovers, and anyone seeking an authentic introduction to the Cyclades.
Throughout this post, you’ll find links to excerpts from my travel diary. Feel free to click through and follow the journey exactly as it unfolded.
The Island-by-Island Itinerary
Day 1: Arrival on Santorini (Pyrgos)
Santorini wasn’t my first choice for extended exploration – I know how busy and crowded it gets in peak season. But as a gateway island with the best-value flights, it made perfect sense for starting our adventure. Besides, one of my granddaughters was heading to university to study geography in September – a visit to the volcano was an absolute must.
Getting There: Direct flights from the UK land at Santorini Airport. Our hotel arranged airport transfer for €45 (for all five of us). The transfer to Pyrgos took around 20 minutes.
Getting Around: We chose Pyrgos as our base rather than the more famous (and more crowded) Fira or Oia. From Pyrgos, the walk to Fira takes around 50 minutes – the hotel optimistically suggested 25, but with teenagers in tow and heat to contend with, allow longer. Buses also connect the villages.
Where to Stay – My Personal Recommendation: Symphony Suites in Pyrgos sits on the cliff edge directly above the port, about a 10-minute walk from Santo Wines. We stayed in their 2-bedroom apartment called Phaedra – the only option that could accommodate five of us. Fantastic views over the volcano, fluffy robes, slippers, and complimentary wine. Breakfast delivered to the suite at our chosen time. The hosts Georgia and Katerina were wonderful.
Don’t Miss:
● The walk from Pyrgos to Fira for sunset and the classic Santorini experience
● Views over the caldera and volcano
● Santo Wines for a wine tasting with caldera views (just 10 minutes from Symphony Suites)
● The quieter charm of Pyrgos village itself, away from the cruise ship crowds
The Reality Check: Santorini in mid-July is overwhelmingly busy. Cruise ships disgorge thousands of passengers daily, creating queues three-deep at the cable cars. If you prefer a more peaceful experience, consider Santorini at the beginning or end of your trip when you can better cope with crowds, or visit in shoulder season. For us, one night was enough to give the grandchildren the iconic Santorini experience before escaping to quieter islands.
Onward Travel Connection: Ferry to Sikinos on the Dionisios Solomos. Note that this was the only ferry on our itinerary that required physical tickets rather than e-tickets – we picked them up from an office in Fira. The ferry ran over 2 hours late but rewarded us with a spectacular sunset view from the water.
🏩 Book Symphony Suites in Pyrgos here
→ Read about planning this family island hop
→ Read about our arrival on Santorini
Days 2-4: Sikinos (Alopronia)
Sikinos was a revelation – a real little gem of a place. After the overwhelming crowds of Santorini, arriving here felt like exhaling for the first time. This tiny island, one of the least visited in the Cyclades, offered exactly what we needed: crystal-clear water, genuine tranquillity, and a pace of life that allowed us all to decompress. My granddaughter Macy declared it “the most beautiful place she has ever seen.”
Getting Around: Sikinos is small enough to explore on foot. A bus connects the port of Alopronia to Chora (the main village) perched on the hillside above. Walking is the primary mode of transport here – embrace it.
Where to Stay – My Personal Recommendation: Ostria Studios in Alopronia, run by Margarita and her daughter, sits right on the port with terraces overlooking the sea. We had a family setup with the adults in one apartment and the grand-adults in a triple studio next door. Waking to the gentle rhythm of lapping waves and watching ferries come and go from our terrace was pure bliss. The bright blue painted shutters and immediate beach access made this feel like authentic Greek island life.
Where to Eat: Dining options are limited but excellent. The single taverna in Alopronia served fantastic fava, Greek salad, skordalia, and dolmades with local white wine. In Chora, Klimataria offers traditional village charm whilst Sellada at the village entrance offers sunset views and a menu that appeals to the teenagers – pasta dishes, burgers, and even Mexican burritos alongside Greek classics. We arrived early enough to explore the village before dinner.
Don’t Miss:
● The natural plunge pool on the other side of the port – crystalline turquoise water popular with families
● The climb to Chora for sunset views over neighbouring islands from the windmills
● Watching the tiny ferry Santorini arrive – one of the few boats serving this quiet island
● Walking to the eastern beaches – Dialiskari and Agios Giorgios offer seclusion and stunning scenery
● Simply sitting on your terrace watching the sea – this is what Sikinos is for
The Reality Check: The Meltemi winds were fierce during our visit. At its worst, the Meltemi delivers a free, first-class exfoliation treatment right there on the beach. Swimming spots need to be chosen for shelter. Sikinos has very limited ferry connections, which keeps it unspoilt but requires careful planning. We left wishing we’d stayed longer – three nights wasn’t enough for this lovely island.
Onward Travel Connection: Ferry to Ios departs at 10:40am. Set alarms for 8:00am and advise teenagers to pack the night before! Leave the apartments by 9:30am to be safe.
🚌 Check noticeboard at bus stop for schedules
→ Read about arriving on Sikinos – a breath of fresh air
→ Read about our last day on Sikinos – over all too soon
Days 5-7: Ios
Ios has a reputation as a party island, but there’s far more to it than nightclubs and beach bars. The stunning Chora with its labyrinthine white alleys, the beautiful beaches, and the legendary tomb of Homer all offer substance beyond the party scene. For teenagers, the energy and beach life proved irresistible; for the adults, there was enough culture and beauty to keep us engaged.
Getting Around: Buses run regularly between the port (Gialos), Chora (the main town), and Mylopotas Beach. The walk from Chora to Mylopotas takes about 15-20 minutes downhill. Taxis are available but buses are efficient and inexpensive during high season.
Where to Stay – My Personal Recommendation: For families, a good budget option is Galini Pension a few minutes walk from Paralia Gialos. Look for accommodation that gives easy beach access but enough distance from the nightlife zone if travelling with mixed ages.
Don’t Miss:
● Mylopotas Beach – one of the best beaches in the Cyclades with golden sand and turquoise water
● The climb to Chora at sunset for spectacular views
● Panagia Gremiotissa Church above Chora for panoramic island views
● Homer’s Tomb at Plakoto in the north of the island (for those interested in mythology)
● Simply enjoying the beach life that draws visitors from around the world
The Reality Check: Ios in July is busy with young party-goers, particularly in the evenings. If travelling with teenagers, this might be exactly what they want; if you prefer peace, choose accommodation away from the main party areas and enjoy beaches during the day. The port cafes were packed with departing passengers on the day we left.
Onward Travel Connection: Ferry to Naxos via Blue Star services. The crossing gives wonderful views of the Cycladic islands as you travel north.
→ Read about our arrival on Ios
→ Further exploration on Ios and not a party in sight
→ Last day on Ios – beaches and more beaches!
Days 8-12: Naxos (Stelida)
This was my first time back on Naxos in seven years, having first visited around 1995 – nearly 27 years ago. I’ve always sold this destination to clients as “an island that has it all,” and it proved the perfect place to unwind towards the end of our trip. Five nights allowed us to properly unpack for the first time and settle into a rhythm. The grand-adults discovered the pool was their “new favourite thing” while Peter and I explored beaches and villages.
Getting Around: Naxos has an excellent bus service connecting the port and main town to the beaches (Agios Prokopios, Agia Anna, Plaka) and mountain villages (Halki, Koronos, Apiranthos). Buy tickets at the bus station before boarding. Be warned: buses can be chaotic and overcrowded when ferries arrive, so our boarding mantra was essential – “Stick together and show no mercy!”
Where to Stay – My Personal Recommendation: Hotel Proteas in Stelida, close to Agios Prokopios Beach, proved perfect for our family. This is also a firm favourite with my clients. A 2-bedroom apartment with an extra bed accommodated all five of us. The pool was a genuine luxury that the grandchildren adored. Our host Andreas was wonderfully welcoming, and the breakfast was excellent. The hotel is about a 10-15 minute walk from the Lagos bus stop, mainly downhill to the beach.
Where to Eat: Kavourakia near Stelida serves excellent gyros – our first of the trip. Niko’s Taverna on Agios Prokopios beach offers tables on the sand and a cowboy guitarist who was busking during our visit. The mountain villages have traditional tavernas serving local specialties.
Don’t Miss:
● Agios Prokopios and Agia Anna beaches – famous golden sand, though increasingly developed with sunbeds
● The “shark rock” at Agia Anna – now sporting a white beard after years of weathering
● Maragkas Beach and Plaka for longer, less developed stretches of golden sand
● The atmospheric Kastro quarter in Naxos Town – my favourite place to stay on past visits
● The Portara – the massive marble gateway visible from the harbour
● A bus trip to Koronos or other mountain villages for dramatic scenery and traditional life
Day Trips from Stelida: The bus to Naxos Town takes around 20 minutes. The mountain village of Koronos makes a dramatic half-day trip – the bus departs at 1:30pm and returns at 4:30pm (approximately 1 hour each way). Be warned: the bus journey involves hairpin bends and can be standing-room-only when ferries have just arrived. Pretty Halki village is another excellent option for exploring traditional Naxian life.
The Reality Check: Naxos in mid-July was almost unrecognisable from my previous visits. The beaches have become heavily commercialised with sunbeds arranged in different “classes” based on row position – a trend I find dispiriting. The bus service simply couldn’t cope with demand, leading to a rather poor experience for our family on the Koronos trip. Despite loving this island for nearly three decades, I wouldn’t be in a rush to return after this experience. Visit in shoulder season if you can.
Onward Travel Connection: Ferry back to Santorini for the final two nights. Blue Star services make the crossing efficiently.
→ Read about returning to Naxos after seven years
→ Read about the bus journey from hell to Koronos
→ Mikri Vigla, Portara Sunset and Grandma Loses her S***!
→ Quite a Lazy Day – Grotta Beach and Agia Anna
→ Naxos Villages and South Beach Bus Tour Ending with a Surprise!
Days 13-14: Return to Santorini
Returning to Santorini at the end of the trip allowed us to catch our flights home without stressful last-minute ferry connections. Two nights gave time to explore more of the island, perhaps take that volcano boat trip for the geography student, and enjoy the caldera views one more time before heading home.
Getting Around: Buses connect the main towns and villages, though they can be very crowded. Taxis are available but expensive. Consider pre-booking transfers for airport journeys with luggage.
Where to Stay – My Personal Recommendation: Villa Kavallaris in Mesaria. Good budget accommodation with a lovely swimming pool. Although still touristy, Mesaria and Katerados are just far enough from Fira to escape the cruise crowds but still close enough to all amenities.
Where to Eat: Taverna Paradosiako is a fabulous taverna in Mesaria – also close to great bakeries. In Katerados I highly recommend Katerinas Taverna.
Don’t Miss:
● Volcano sunset boat trip on the Aphrodite – essential for anyone interested in geology
● Oia at sunset (though expect crowds)
● The quieter villages of Pyrgos, Megalochori, or Emporio for caldera views without the masses
● Wine tasting at one of the island’s many excellent wineries
Final Departure: Santorini Airport is small and can be chaotic during peak season. Allow plenty of time and consider using the hotel’s airport transfer service for a stress-free departure.
Practical Information
Budget Notes: 2022 was a bumper year for Greek tourism, with prices reflecting high demand. For a family of five, expect to pay more for accommodation than solo or couple travellers. We chose slightly better accommodation than I’d normally book as a budget traveller – the priority was comfortable family rooms rather than basic pensions. Hotel pools proved worth their weight in gold with teenagers.
Booking Ahead: Unlike my usual “make it up as you go along” style, this trip required advance booking throughout. July is peak season and hotels fill quickly, especially family-sized rooms. Book ferries in advance too – popular routes sell out.
Ferry Tips: The Dionisios Solomos serves the Santorini-Sikinos route but required physical tickets collected in Fira – check this for your specific ferries. Blue Star ferries served us well for other crossings. Our boarding mantra for chaotic ferries: “Stick together and show no mercy!” The grandchildren heeded this advice brilliantly.
Travelling with Teenagers: Set alarms for early ferries and insist they pack the night before. Pool access at accommodation keeps everyone happy during downtime. Mix beach days with cultural excursions to maintain variety. Accept that their Instagram feeds will be full of cats.
Disclaimer: This itinerary reflects our July 2022 trip. Ferry schedules, accommodation availability, and prices will have changed. Always check current information before travelling.
Is This Trip Right for You?
This itinerary is perfect if you:
- Want to introduce family members to Greek island hopping for the first time
- Travel with teenagers who need a mix of beach time, culture, and some liveliness
- Appreciate variety – from famous to hidden, from busy to tranquil
- Value a circular route that simplifies logistics (same airport in and out)
- Prefer excellent ferry connections and reliable public transport
- Want those classic Cycladic white-and-blue photo opportunities
- Can manage without a car on all islands
Think twice if you:
- Hate crowds – peak July brings overwhelming numbers to Santorini and popular Naxos beaches
- Prefer undeveloped beaches – many have become commercialised with tiered sunbed pricing
- Want extended time on each island – two weeks across four islands is a whistle-stop tour
- Travel with very young children – some ferry connections can be rough and unpredictable
- Seek nightlife beyond Ios – other islands are quiet after dark
- Dislike early starts – ferry schedules sometimes require dawn departures
Final Thoughts
This trip had been two years in the making, delayed by a pandemic that changed everything. What started as a special journey with one granddaughter became a multi-generational adventure with five of us navigating ferries, beaches, and the beautiful chaos of Greek island hopping together.
Was it the way I’d usually travel? No. My preferred style is longer stays, slower exploration, time to feel the essence of a place rather than ticking boxes. But watching my grandchildren discover Greece for the first time – seeing Macy declare Sikinos “the most beautiful place she has ever seen,” watching them chase cats for Instagram, observing them navigate ferry boarding with the mantra “stick together and show no mercy” – made every compromise worthwhile.
Sikinos stole all our hearts. That tiny, unspoilt gem reminded us why we travel to Greece in the first place. Naxos, despite being overwhelmed by mid-July crowds, still showed flashes of the island I fell in love with nearly three decades ago. Ios gave the teenagers exactly what they needed. And Santorini, for all its tourist intensity, delivered those iconic views that draw millions.
Island hopping in Greece isn’t a tick-box exercise. It’s an experience. This trip gave my gorgeous grandchildren a taste of this beautiful country, and I hope it planted seeds for their own future adventures. As for me, I’m already planning where to go next – probably somewhere quieter, smaller, and decidedly off the beaten track. But that’s a story for another time.
