Island hopping through the Cyclades is one of the most unforgettable travel experiences you can have in Greece. After exploring this region multiple times, I’ve crafted what I believe is the perfect 14-day Greece island hopping itinerary.
This route blends the most iconic islands of Greece like postcard-perfect Santorini with hidden gems that most travellers miss like the dreamy, laid-back island of Koufonisia. You’ll wander charming whitewashed villages, swim in crystal-clear waters, eat fresh seafood by the sea, and discover the unique personality of each island.
I designed this 2 week Greek island hopping itinerary to follow the most efficient ferry route through the Cyclades. It’s carefully planned to maximize travel flow while giving you plenty of time to soak in the highlights of each destination. From the vibrant energy of Paros to the slow pace of Iraklia, this itinerary will show you both sides of the Cyclades: the famous spots and the lesser-known gems.
Whether it’s your first trip to Greece or your fifth, this route will surprise and inspire you. Keep reading to discover the perfect island order, how long to stay in each spot, and the top experiences that you can’t miss along the way.
The beautiful island of Paros
Table of Contents
The Ultimate 14 Day Greek Island Hopping Itinerary – Discovering the Best of the Cyclades
The best way to book ferries between the Greek islands is online. I always use the FerryHopper app when island hopping in Greece to book my ferry tickets, compare routes, prices, and travel times. Be sure to download this app for your 2 week Greece trip to make booking ferry trips easy to do on the go.
High-speed ferries are faster but more expensive, while regular ferries are slower but smoother and more scenic. I recommend always booking your journey in advance during high season (June–September), and print or download your tickets before boarding.
Greek Ferry Tips:
Aim for morning ferries when possible as they’re less prone to delays and you’ll have more time to enjoy your next destination.
If you’re prone to sea sickness, don’t forget to take a Dramamine tablet before boarding if it’s a windy day.
To avoid a rough journey, you can choose to book a larger ferry that accommodates cars which means it will be less bumpy when faced with big waves. The FerryHopper app shows you photos and information about the type of boat to make it easier to choose.
Book a flight to Santorini to start the trip and then take ferries between the islands.
I had an unfortunate experience with a very rough ferry ride on a small, foot passenger-only boat from Athens to Santorini. I made that mistake so that you don’t have to! Flights from Athens to Santorini are often the same price and much shorter than the ferry which took me 7 painful hours.
Swim in the stunning turquoise bays of the Cyclades
SIM Cards in Greece
I would highly recommend getting a SIM card for this 14 day Greek island hopping itinerary. It will help you easily stay connected, book ferry tickets, and navigate walking routes or public transport on each island.
Vodafone is a top choice for travellers offering good coverage even on smaller islands like Koufonisia and Iraklia. You can pick up a prepaid tourist SIM at the airport or in most main towns, with affordable data packages that usually last 10 – 30 days.
If your phone supports it, consider using an eSIM for even more convenience, no need to find a physical store. Providers like Airalo or Holafly let you set everything up online before you arrive, so you’re connected the moment you land in Greece.
Explore the prettiest white-washed villages on this 2 week Greece itinerary
Where to Start Your Trip
Santorini has an international airport (JTR) with direct flights from major European cities like London, Paris, Rome, and Amsterdam plus frequent domestic flights from Athens. This makes it one of the easiest Cycladic islands to reach by air, saving you the hassle of a long ferry ride at the start of your trip.
By flying directly into Santorini, you can start your trip with a bang: epic caldera views, world-famous sunsets, and a true sense of arrival. It also positions you perfectly to island hop northward with minimal backtracking.
Tip: Try to arrive early in the day so you have time to explore and catch the sunset in Oia on your first evening. If you’re flying into Athens first, book a separate domestic flight to Santorini rather than taking the long, bumpy ferry ride!
A traditional Greek taverna on Paros
What to Pack for 2 Weeks in Greece
It’s best to pack light when island hopping in Greece as cobblestone streets aren’t luggage-friendly and it’s not fun to drag a large suitcase on/off ferries. Instead, I would recommend travelling with a backpack for this type of trip. Essentials include:
Google Translate – Handy for menus and signs on more remote islands
Booking.com – Best for finding/booking accommodation for all budgets
GetYourGuide – Perfect for finding/booking day trips on the go. Download the GetYourGuide app through this link and receive 5% off your first booking with my discount code: 5 (offer only available to new app users).
Enjoy dining by the sea on your Greek island hopping adventure
Best Time of Year to Go
The best time for Greek island hopping is May to early October. I went island hopping through the Cyclades mid May and had mostly sunny/warm weather with minimal crowds (except for Santorini which was still busy). It was warm enough to swim in the sea everyday of my trip.
June & September are ideal: warm weather, swimmable seas, and fewer crowds.
July & August are peak season: expect full ferries, higher prices, busy beaches/towns and limited accommodation choices.
May & October offer a quieter, more authentic experience but some ferry routes and beach services may be limited.
Koufonisia, Small Cyclades
Getting Around the Greek Islands
This itinerary recommends renting a car or scooter to navigate some of the islands. This is the best way to explore and see the highlights at your own pace, without relying on bus schedules which can be unreliable and infrequent.
However if you are a solo traveller who doesn’t feel comfortable driving in a new country then you can either take the local bus or book organised sightseeing tours. I always use GetYourGuide to find and book tours on the go.
When it comes to locating car rental shops on each island, I found them easily with a quick Google search. There are always small shops conveniently located in the main port town so you can walk to them from the ferry or your accommodation.
During high season, this is something you might want to arrange beforehand but when I did my Greek island hopping trip in May, I did it on the go. For those who want to compare prices and book your rental cars online before your trip, check out the link below.
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Arrival: Fly into Santorini (JTR), ideally arriving in the morning or early afternoon, explore the town and have dinner in Oia.
Day 2: Explore Santorini
What to do: Spend the full day seeing the sights of Oia, wake up early to photograph the 3 domes, walk down to Ammoudi Bay, watch the sunset from Oia Castle.
Day 3: Explore Santorini
What to do: Hike the Fira to Oia Trail, visit a winery, explore more of the island like the black sand beach of Perissa.
Day 4: Travel to Naxos (2 nights)
Travel: Take the ferry from Santorini (~1.5–2 hours).
What to do: Explore Naxos Town (Chora), walk up to the Portara at sunset and have dinner in the Old Town.
Day 5: Explore Naxos
What to Do: Rent a car for the day and explore the island. Go beach hopping, visit Halki and Apeiranthos villages, stop at the Temple of Demeter and return to the Chora for dinner and a sunset stroll.
Day 6: Travel to Iraklia (1 night)
Travel: Take a small ferry from Naxos (~1 hour).
Afternoon: Relax, swim, and enjoy the peaceful, remote vibe. Hike to Livadi Beach or the Cave of Agios Ioannis if you want some adventure.
Evening: Dinner at a local taverna with sea views.
Day 7: Travel to Koufonisia (1 night)
Travel: Ferry from Iraklia to Koufonisia (~1 hour).
What to Do: Spend the day beach-hopping on foot. Fanos, Italida, and Pori beaches are stunning. Relax and swim in the clear turquoise waters.
Evening: Sunset dinner by the water in the main village.
An iconic scene of Naoussa, Paros
Day 8: Travel to Paros (2 nights)
Travel: Ferry from Koufonisia (~1.5-2 hours), take a local bus or rental car to Naoussa (25 min from the port).
Afternoon/Evening: Explore Naoussa, enjoy beach time, sip sunset cocktails at a seaside bar.
Day 9: Explore Paros
What to Do: Rent a car to visit Lefkes Village, Golden Beach, and the charming fishing village of Piso Livadi.
Optional: Take a boat trip around the island to secluded beaches and bays of Paros and Antiparos.
Day 10: Travel to Sifnos (2 nights total)
Travel: Ferry from Paros to Sifnos (~1.5–2 hours).
Afternoon: Check into your hotel in Kamares, hit the beach in town, and enjoy a peaceful evening watching the sunset and having dinner in a local seaside taverna.
Day 11: Explore Sifnos
What to Do: Rent a car or take the bus to hike one of the island’s scenic trails, relax at Vathi or Faros Beach, explore Kastro and see the impressive Church of the Seven Martyrs.
Evening: Dinner at a local taverna, Sifnos is known for its excellent Greek cuisine!
Day 12: Travel to Milos (2 nights)
Travel: Ferry from Sifnos to Milos (~1–1.5 hours).
Afternoon: Visit Sarakiniko Beach for moon-like landscapes and cliff jumping.
Evening: Wander through Plaka for sunset views and dinner.
Day 13: Explore Milos
What to Do: Take a boat tour to Kleftiko, rent a scooter/car to explore colourful fishing villages like Klima, or visit Firiplaka and Tsigrado beaches.
Evening: Enjoy a final sunset dinner overlooking the sea to end your Greek island hopping adventure.
Day 14: Depart from Milos
Option 1: Fly from Milos to Athens (40-minute flight).
Option 2: Ferry from Milos to Piraeus Port (Athens) (~3–5 hours depending on ferry type).
Tip: If you have a flight from Athens, plan to arrive the evening before or book a later flight to avoid tight connections.
Temple of Apollo – Portara of Naxos
14 Day Greek Island Hopping Itinerary – How to Spend 2 Weeks in Greece
Santorini – Days 1 – 3 (3 nights)
There’s no better way to kick off your Greek island hopping adventure than with the jaw-dropping beauty of Santorini. This island truly lives up to the hype and yes, the sunsets really are that good! From the iconic whitewashed buildings of Oia to the lively streets of Fira, Santorini delivers an epic start to your journey.
Keep in mind that Santorini is one of the top destinations in Greece so you can expect to see crowds and higher prices no matter what time of year you visit. The fact that it’s also a cruise ship port means that there are very few times when the narrow streets of Oia aren’t full of people. There is a reason for Santorini’s popularity and in my opinion it is absolutely worth including it on your 2 week Greece itinerary!
Aim to arrive in Santorini by flight and book the first 3 nights of your trip here, spending two full days soaking up the beauty of this iconic Greek island.
Breathtaking scenery in Oia, Santorini
Highlights of Santorini
Oia – Spend your days wandering the narrow, winding lanes of Oia, where every corner looks like it belongs on a postcard. Come sunset, head to the ruins of the old castle in Oia to watch the sky light up over the caldera, it’s magical (but be ready for crowds). Securing your spot well before sunset is a must.
Ammoudi Bay – One of my favourite memories from Santorini was taking a small hike down to Ammoudi Bay from Oia. There you can find crystal-clear water, fresh seafood tavernas, and a unique perspective of Oia from below. It’s a great spot for a late lunch or even a quiet sunset dinner if you want to avoid the crowds above. It’s a bit of a workout on the way back up, but totally worth the effort.
Fira – In Fira, enjoy buzzing cafés, cliffside bars, and sweeping views of the volcano. If you’re up for it, walk the Fira to Oia trail, a scenic 10km coastal hike boasting spectacular caldera views from start to finish. Don’t miss a visit to the black sand beaches of Perissa or a wine tasting at one of the island’s local wineries.
Soaking up that perfect morning light in Oia
Best Photo Spots in Santorini
It’s no secret that Santorini is one of the most photogenic places on earth, I’m sure your Instagram feed is already full of the iconic blue-domed churches. Whether you’re a professional photographer or just love a good Instagram moment, these Santorini photo spots are unmissable:
Oia Castle at Sunset – This is the classic Santorini shot. Make your way to the ruins of Oia Castle about an hour before sunset to claim a good spot. The view over the windmills and whitewashed rooftops glowing in golden light is unreal. Yes, it gets crowded, but it’s so worth it.
The Blue Domes of Oia – Tucked down a small alley just off the main pedestrian street in Oia, you’ll find the famous trio of blue domes. Early morning is best to avoid the crowds and catch soft lighting.
Fira to Oia Hiking Trail – There are countless epic photo opportunities along this coastal trail, think rugged cliffs, quiet churches, and uninterrupted views of the Aegean Sea. The hike is fairly long, wear good walking shoes and expect it to take you the better part of the day.
Imerovigli – Often overlooked, this village between Fira and Oia offers equally incredible views with way fewer people. The Skaros Rock viewpoint is especially dramatic.
Sunset at Oia Castle, Santorini
Where to Stay on Santorini
Oia – If it’s your first time in Santorini, staying in Oia is the better choice. This is where you can wake up to the those idyllic blue dome and caldera views right at your doorstep. It’s more romantic and peaceful than Fira which is perfect if you’re here to soak up the views and unwind.
Fira – If you’re after more nightlife, shopping, and easier access to transport, Fira is a better and often slightly more affordable base. You’ll also be closer to the port and public bus routes if you’re planning on exploring the rest of the island.
Mid-Range – Marcos Rooms: Lovely rooms in the heart of Oia with a large terrace for watching the sunset. Very friendly couple running this place, within walking distance from the bus stop, restaurants and main attractions of Oia.
Luxury – Three Domes Oia: Treat yourself on a special occasion with a stay at this stunning property overlooking the blue domes and the caldera. Relax in your private hot tub with a glass of champagne while gazing out at a magical Santorini sunset.
After the buzz and incredible views of Santorini, arriving in Naxos feels like a refreshing change of pace. It’s the largest island in the Cyclades, yet it has a down-to-earth vibe that instantly makes you feel more relaxed. With its golden beaches, small mountain villages, ancient ruins, and amazingly good food, Naxos is a highlight of any Greek island hopping itinerary and it’s surprisingly underrated.
Unlike Santorini, Naxos isn’t swarming with crowds, even in high season. It’s more laid-back and authentic, with fewer cruise ships and more opportunities to experience everyday Greek island life. It also happens to have some of the best beaches in the Cyclades, plus a rich history that can be seen as you arrive at the port, greeted by the iconic Temple of Apollo.
Take a ferry from Santorini to Naxos and spend two nights soaking up everything this gem has to offer. From gorgeous beaches and traditional tavernas to ancient landmarks and hilltop villages, Naxos is sure to be a highlight of your Greece itinerary!
Exploring Naxos Chora
Highlights of Naxos
One of the best ways to experience Naxos is to rent a car for the day and explore the island at your own pace. The roads are easy to navigate, and the scenery changes dramatically as you move from coast to mountains and back again. It’s one of the few Greek islands where you can visit ancient ruins, hike through olive groves, and swim at stunning beaches all in a single day.
With a car, you can easily see all of these places in one day, stopping wherever catches your eye along the way. Naxos is full of roadside surprises, from tiny chapels to local bakeries and stunning viewpoints. During my time on Naxos, I really loved Plaka Beach, Halki Village and the Old Town (Naxos Chora).
Plaka Beach – This long stretch of soft golden sand and crystal-clear water is my favourite beach on Naxos. It’s perfect for swimming, relaxing, and grabbing lunch at one of the casual beachfront tavernas. Nearby Agios Prokopios and Agia Anna are also beautiful, with a slightly more lively feel.
Halki Village – Nestled in the heart of the island, this dreamy village is full of neoclassical architecture, shady squares, and local craft shops. Be sure to stop at the Vallindras Distillery to sample Naxos’ famous citron liqueur. This tiny village was one of my highlights of Naxos.
Apeiranthos – Perched high in the mountains, this marble village is one of the prettiest spots on the island. Wander its narrow alleys, visit a local museum and stop for a traditional lunch with panoramic views over the countryside. I ate at the cutest place called Taverna Platanos Apeiranthos.
Strolling through the pretty streets of Halki, Naxos
Temple of Demeter – Make a stop at this ancient temple hidden away in the countryside of Naxos near the village of Sangri. Built in the 6th century BC and dedicated to the goddess of agriculture, this beautifully restored marble temple sits among rolling hills and farmland.
It’s an easy and worthwhile stop if you’re exploring the island by car, especially for history lovers or anyone looking for a quiet detour off the beaten path. The Giroulas Museum here is small but gives an insightful look into the temple’s past.
Portara (Temple of Apollo) – You can’t miss this famous landmark, it’s the first thing you’ll see as the ferry pulls into Naxos Town. Set on a tiny islet just off the harbour, the massive marble doorway is all that remains of an ancient temple. It’s especially magical at sunset, with the sea and sky glowing behind it.
Naxos Old Town (Chora) & Castle (Kastro) – Don’t leave the island without spending some time exploring the Old Town of Naxos, just steps from the port. It’s easy to lose track of time as you wander the medieval maze of narrow stone alleys with its whitewashed walls and hidden archways.
Start at the base of the old market street and slowly make your way up toward the Kastro (castle), a Venetian fortress dating back to the 13th century. Along the way, you’ll pass local artisan shops, cozy cafés, and rooftop bars with incredible views over the Aegean.
With many great tavernas in and around the Old Town, this is a fantastic place to enjoy a delicious Greek meal. I had dinner at Scirocco Restaurant and the food was truly incredible!
View of Naxos Chora
Where to Stay on Naxos
For a short stay like this, the best place to base yourself is Naxos Town (Chora). It’s close to the port, filled with great restaurants, and puts you within walking distance of the Old Town, the Portara, car rental shops and the main bus routes if you’re not renting a car.
Recommended Naxos Hotels
Budget – Vakhos: Simple, clean and well located rooms only a 5 minute walk from the town with AC and private bathrooms. Ideal for the budget traveller.
Mid Range – Sweet Home Naxos: Bright, spacious apartments in an excellent location with attentive staff and a great breakfast included.
Luxury – Anapollo Boutique Hotel: An oasis right in heart of Naxos Chora featuring beautiful, modern rooms with private balconies, an outdoor pool and an exceptional breakfast served every morning.
After exploring the larger and more famous islands like Santorini and Naxos, stepping onto Iraklia feels like time slows down in the best possible way. This tiny, off-the-radar island is part of the Lesser Cyclades and it’s the perfect place to pause, unplug, and simply breathe.
With only a handful of villages, a few quiet beaches, and no big resorts or tourist infrastructure, Iraklia offers a glimpse into the slower, more authentic side of Greek island life.
You won’t find long lists of must-see attractions here and that’s exactly the point. Iraklia invites you to disconnect, wander without a plan, swim in crystal-clear waters, and enjoy peaceful moments that are hard to come by on the more famous islands. Even in peak summer, it’s never crowded, and you’ll often feel like you have the place entirely to yourself.
Catch a ferry from Naxos (usually the Express Skopelitis or Blue Star Ferries) and spend one slow, relaxed night on this hidden gem. It’s an ideal mid-itinerary breather before continuing on to the equally dreamy but slightly livelier island of Koufonisia.
Arriving at the port of Agios Georgios, Iraklia
Highlights of Iraklia
While Iraklia is small, there are a few attractions that make your short stay here truly memorable. You won’t need a car as most things are walkable or accessible via taxi/short hikes.
Livadi Beach – Just a 15–20 minute walk from the port town of Agios Georgios, this quiet beach has soft sand, shallow turquoise water, and very few people. It’s the perfect place to throw down a towel, read a book, and go for a peaceful swim.
Panagia Village – This small and sleepy village is set on a hillside of central Iraklia and is home to just a few traditional tavernas and houses. You can visit the blue domed Church of Panagia and stop for a cold drink in a taverna. This village is the starting point for the Cave of Agios Ioannis hike.
Cave of Agios Ioannis – If you’re up for a hike, this is one of the largest caves in the Cyclades and holds both geological and spiritual significance. Bring a head torch and proper shoes, it’s a rugged but rewarding adventure with spectacular island views along the way.
You can take a taxi from the main port town of Agios Georgios and ask him to drop you off in the village of Panagia. Download an app like Mapy.com to easily navigate the trail to the cave. The hike is 2.7 km and takes around an hour to complete one way. Bring enough water, I ran out of water during my hike to the cave and it was a very hot day!
Local Tavernas – With only a few on the island, each one feels personal and welcoming. I had a lovely Greek feast at Akathi Restaurant, it was fresh, simple, and full of flavour. Sitting outside with the sound of cicadas and views of the Aegean at sunset is a magical memory from my Greek island hopping trip.
Views along the hiking trail to the Cave of Agios Ioannis
Where to Stay on Iraklia
For a one night stay, the best place to base yourself is in the port town of Agios Georgios. It’s the island’s main hub (though still tiny!), and staying here puts you within walking distance of the ferry, tavernas, and Livadi Beach.
There are only a handful of family-run guesthouses and rooms available, so it’s best to book ahead especially in July and August. Look for places like Anna’s Place or COSMOS Studios, both of which offer warm hospitality, a traditional vibe, and serene views over the sea.
Staying in Agios Georgios means you can drop your bags and start relaxing right away, no transfers, no stress, just simple island living!
On day 7 it’s time to move on to another slice of Cyclades paradise: Koufonisia. Despite its growing popularity, this little island still feels wonderfully relaxed and unspoiled.
With turquoise waters that rival the Maldives, golden sandy beaches, and a walkable coastline, Koufonisia instantly takes your breath away. The island is compact and everything is close together so you won’t need a car or even a bike unless you want to explore further.
A single day on Koufonisia is enough to experience its dreamy beaches, chilled out beach bars, and cute Cycladic village vibe. That said, don’t be surprised if you find yourself wanting to stay longer!
Take the ferry from Iraklia whenever it’s available and you’ll have the rest of the day to soak up the sun, swim, and enjoy this island gem. If you don’t feel like leaving the main port village to explore, you don’t have to. Ammos Beach, right in town, is just as beautiful as the others!
Take in the spectacular scenery of Koufonisia
Highlights of Koufonisia
Beach Hopping – One of the best things to do on Koufonisia is simply walk the coast from the port to Pori Beach, stopping at Fanos and Italida along the way. The beaches are small, stunning, and easy to access on foot, bike or boat taxi. Each cove has its own vibe, some have music and beach bars, while others are totally quiet.
Pori Beach – The most famous beach on the island, Pori Beach is a wide, curved bay with electric-blue water and soft sand. There are a couple of casual tavernas nearby for lunch or a drink, and the water here is some of the clearest I’ve ever seen. You can easily take a boat taxi here from the port or walk for 45 minutes.
Sea Caves & Natural Pools – On your walk toward Pori, make sure to stop at Devil’s Eye, a natural rock pool perfect for a quick dip or photo stop. The sea caves along this stretch are also worth exploring.
Evening in Chora – Koufonisia’s main port village is small but full of traditional charm. Enjoy a seaside dinner at one of the tavernas near the port, then wander the whitewashed lanes of the Chora, where bougainvillea spills over balconies and the vibe is slow and magical.
Go for a dip in the natural rock pools
Where to Stay on Koufonisia
The best place to stay is in or near the main village of Chora, close to the port. This keeps everything within walking distance, beaches, restaurants, ferry, and shops so you can make the most of your short visit.
Great options include Asterias Studios and Hotel Posidonion, or one of the many cozy guesthouses near the waterfront. Many offer simple Cycladic-style rooms with balconies overlooking the sea or garden.
Just like Iraklia accommodation here is limited so it’s best to book ahead, especially in high season!
Enjoy the more authentic side of Greece on Koufonisia
Paros – Days 8 – 9 (2 nights)
With its idyllic whitewashed villages, golden beaches, and easy-going vibe, Paros stands out as a favourite from my days of island hopping through Greece. Paros has so much to offer, you can spend your time beach hopping, wandering the most beautiful towns, or taking a boat trip around hidden coves.
Whether you’re after a quiet village or something a little more vibrant, Paros delivers. It’s lively without being overwhelming, with great food, a fun nightlife scene, and plenty of culture and nature to discover.
Take a morning ferry from Koufonisia (likely via Naxos), and settle in for two fun-filled nights on this Cycladic gem. On day 9 of your Greek island hopping itinerary, I suggest renting a car to see the best of the island, ticking off some of the top highlights of Paros below!
Naoussa – This picturesque fishing village on the northern coast is one of the highlights of Paros. With its lively waterfront lined with tavernas, stylish boutiques, and whitewashed alleys full of charm, Naoussa perfectly balances tradition and modern. It’s a great place for dinner and a cocktail by the sea.
Parikia Old Town – The port town of Parikia is often overlooked but it’s worth exploring. Stroll through its winding streets, visit the impressive Panagia Ekatontapiliani (a Byzantine-era church), and grab a coffee at one of the hidden courtyard cafés. It’s less polished than Naoussa but a bit more authentic.
Lefkes Village – Nestled in the hills of central Paros, Lefkes is an enchanting village that feels worlds away from the beach crowds. A place where every alley appears as a scene from a fairy-tale. Wander its quiet bougainvillea-filled streets, admire the pretty Cycladic architecture, and enjoy lunch in the shady town square.
Kolymbithres Beach – One of the most unique beaches in the Cyclades, Kolymbithres features smooth, sculpted rock formations that create little private coves for swimming. The water is crystal clear and shallow, ideal if you’re craving a chilled out afternoon.
Dine at a seaside tavern in Naoussa, Paros
Marpissa – Marpissa is a quiet and charming village on the eastern side of Paros. Built on a hill, it’s full of whitewashed houses, flower-filled alleys, and peaceful squares. Unlike the busier towns, Marpissa feels authentic and serene; the ideal spot for a peaceful stroll before heading to nearby places like Golden Beach or Piso Livadi.
Golden Beach – Located on the southeastern coast, Golden Beach is one of the longest and most beautiful beaches on the island. It’s lovely for swimming, sunbathing, and especially windsurfing, it’s actually one of the top windsurfing spots in Europe. You’ll find beach bars, sun loungers, and plenty of space to relax, even in peak season.
Piso Livadi – This small fishing village on the eastern coast is a low-key spot that feels more local than touristy. With its cute seaside tavernas, moored fishing boats, and vibrant turquoise water, Piso Livadi is worth a short stop. It’s also a great base if you prefer staying somewhere smaller and more relaxed than Naoussa or Parikia.
Boat Trip to Antiparos – If you have time, consider booking a boat trip to the beaches and bays around Paros and the neighbouring island of Antiparos. Because nothing says summer in Greece like a boat day!
This was one of my favourite activities during my stay on Paros. I booked this exact boat trip online the day before, they offer half day boat tours. We stopped to swim at the most spectacular bays, ate fresh fruit and connected with other travellers on the boat. Overall, it was an epic day and I highly recommend it if your schedule allows.
Where to Stay on Paros
For 2 nights on Paros, I recommend choosing either Naoussa or Parikia, I stayed just outside of Naoussa and it was perfect. Some great options include Ragoussis Sweet Rooms, Kanale’s Rooms & Suites (luxury), or Siroco’s Rooms in Parikia for more budget-friendly stays.
Naoussa is great if you want to be close to the action with trendy restaurants, nightlife, and boutique hotels. It’s postcard-perfect and walkable. Parikia is great for convenience. It’s near the ferry port, has easy transport links, and still offers plenty of charm and great dining options.
Tucked quietly into the western Cyclades, Sifnos is often forgotten in favour of its larger neighbours like Paros and Milos. With towering hills, unspoiled beaches and timeless beauty, Sifnos has a remote yet familiar vibe to it.
You’ll immediately feel a slower change of pace after the buzzing energy of Paros, relaxed but with just enough to do without ever feeling rushed.
Sifnos offers the kind of true, authentic Greek culture that you search for but don’t find on touristy islands like Santorini or Mykonos. It’s the perfect island to unwind, indulge in some of the best Greek cuisine in the Cyclades, and discover a mix of quaint villages, amazing beaches, and stunning hiking trails.
Catch a ferry from Paros to Sifnos (about 1.5 hours) and spend two nights soaking in the peaceful rhythm of the island. On your full day here, I recommend renting a car or scooter so you can easily explore the best of Sifnos.
View from the ferry as you approach Kamares, Sifnos
Highlights of Sifnos
Kastro – One of the most beautiful villages on Sifnos, Kastro (meaning “castle”) sits perched on a hill overlooking the sea. It’s like stepping back in time with its medieval architecture, sea views, and quiet stone alleyways. Don’t miss the Church of the Seven Martyrs, which sits dramatically on a rocky outcrop, the island’s most iconic photo spot.
Apollonia&Artemonas – These neighbouring villages are the beating heart of Sifnos and offer everything you’d want from a classic Cycladic setting. Just picture winding stone lanes, whitewashed houses with bright blue shutters, and pretty flowers blooming around every corner.
Take a stroll along Apollonia’s pedestrian street lined with boutique shops, traditional tavernas, and cozy cocktail bars that come alive after dark. It’s the perfect place to wander in the evenings, grab a delicious local meal, or enjoy a relaxed drink under the stars.
Just up the hill, Artemonas offers a quieter, more elegant charm. This village is a maze of cobbled alleys that wind up the hill, passing blue-domed churches, pretty courtyards, and family-run bakeries. It’s ideal for a peaceful morning stroll, a scenic photo walk, or a lazy afternoon spent people-watching in a shaded square with a Greek coffee in hand.
Church of the Seven Martyrs as seen by drone
Hit the Beach – One of the best beaches on Sifnos, Platis Gialos is a long stretch of golden sand with calm, swimmable waters. Lined with tavernas and cafés, it’s ideal for a relaxed afternoon by the sea with all the comforts nearby. For something quieter, head to Vathi Beach, a wide bay surrounded by nature and a handful of tavernas. It’s peaceful, shallow, and invites you to float for hours.
Go For a Hike – If you’re into walking, Sifnos has some of the best hiking trails in the Cyclades. One of the most scenic is the trail to Chrisopigi Monastery, which sits on a dramatic headland over the sea. The walk is peaceful and the views are stunning but it’s a longer trail at 5.5 km (2 hours) each way.
For those wanting a shorter adventure, I would suggest simply walking down to the Church of the Seven Martyrs from Kastro which offers equally dramatic views and stunning photo opportunities.
Kamares – The port of Sifnos is a lovely beach town worth spending time in. I loved grabbing an ice cream cone and strolling along the wide, sandy beach and then hopping in for a swim to cool down. The water here is shallow and inviting!
As the sun sets, grab a seaside table at Agianemi or Camaron for dinner with a view, the sunsets here are some of the best on the island. With its great selection of tavernas and chilled beach vibes, Kamares is the best place to end a day of sightseeing.
Kamares is the perfect base for your two night stay on Sifnos with everything you need a short walk away – beach, restaurants, shops, car rentals, ferry port.
Recommended hotels in Kamares:
Myrto Hotel – A cozy, beachfront hotel just steps from the sand, tavernas and port.
Sifnos Sunset – Comfy rooms with balconies and great views over the bay.
Filadaki Villas (luxury) – Perched on a hillside with a private pool and panoramic views of the port.
As the end of your 14 day Greek island hopping adventure approaches, you might be wondering if Milos will live up to everything you’ve seen so far and the answer is yes, absolutely. Arrive by ferry from Sifnos (just under 2 hours) and enjoy two nights uncovering the highlights of this volcanic gem.
Home to surreal landscapes, colourful fishing villages, hidden coves and the most unique beaches you’ve ever seen, Milos is the perfect end to your Cycladic adventure. Here, you’ll find the perfect mix of relaxation and exploration, simply rent a scooter or ATV and enjoy discovering at your own pace.
The relaxed vibe of Milos is exactly what you’ll crave at the end of this epic Greek island hopping adventure. A contrast to the busier islands, Milos offers quiet beaches, authentic Greek villages, and stunning coastal landscapes that invite you to slow down and savour every moment.
Colourful village of Mandrakia, Milos
Highlights of Milos
Sarakiniko Beach – You’ve never seen a beach like this before. With its smooth, white volcanic rock formations and bright turquoise water, Sarakiniko feels like you’ve transported to another planet. Come early or late in the day to avoid crowds and capture some incredible photos.
Kleftiko – Only accessible by boat, Kleftiko is a must-see! These magical sea caves, sparkling turquoise water and white cliffs were supposedly once a hideout for pirates. Book a boat tour that includes swimming stops, this is the best one to go with, stopping right at these epic caves.
Plaka Village – The charming hilltop capital of Milos is full of winding lanes, pretty scenes, and unbeatable sunset spots. Don’t miss the panoramic views from the Venetian Castle above the village, it’s epic at sunset but gets crowded so come early!
Klima & Mandrakia – These colourful fishing villages are picture-perfect. Klima is known for its traditional “syrmata” houses, little boathouses painted in bright colours right on the water’s edge. Mandrakia is smaller, but equally charming and home to one of my favourite lunch spots, Medusa Taverna.
Firiplaka & Tsigrado Beaches – For more beach time, head to the island’s southern coast. Firiplaka offers stunning scenery and clear, swimmable water. Tsigrado, just next door, is a bit of an adventure to reach (you’ll climb down a steep set of ladders), but it’s beautiful and well worth the effort.
The otherworldly Sarakiniko Beach
Where to Stay on Milos
Milos offers several great areas to stay depending on your vibe, but for a short visit, the best options are Adamas (the port town) and Plaka (the hilltop capital). Both areas are great so it really depends on whether you want to be seaside or tucked into a picture-perfect village.
Adamas is perfect for convenience, close to the ferries, car rentals, restaurants, and the main bus hub. It’s a great base if you’re planning to explore the island by boat or bus.
Plaka, on the other hand, is full of classic Cycladic charm with narrow lanes, sunset spots, and traditional tavernas. It’s quieter and more atmospheric, best if you want that authentic hilltop village feel to end your trip.
After two unforgettable nights in Milos, it’s time to make your way back to Athens. You have two main options: ferry or flight, depending on your schedule and travel preferences.
Ferry – Milos is well connected to Athens (Piraeus Port) by both high-speed and regular ferries. High-speed ferries take around 3.5–4 hours, while the slower (and usually cheaper) options take about 6–7 hours.
I recommend booking in advance as seats can sell out quickly, especially in summer. Ferries typically depart in the morning or early afternoon, making it easy to reach Athens by evening.
Flight – If you’re short on time or prefer flying, Milos also has a small airport with daily flights to Athens. It’s the quickest way to return to the mainland as the flight takes only 40 minuets. Be sure to book early, as seats are limited and fill up during peak season.
Whichever option you choose, give yourself a little buffer time in Athens (at least one night if your international flight is the next day) to wind down, reflect on your trip, and enjoy one last Greek meal with an Acropolis view!
Discovering unbelievably clear water on a day trip to Antiparos from Paros
Final Thoughts on Island Hopping in Greece
Island hopping in Greece is truly a bucket list adventure that everyone should experience at least once in their life. It’s the kind of trip that stays with you long after it ends, forever reminiscing on those slow sunset dinners by the sea and lazy afternoons at the beach.
In my opinion, the Cyclades islands of Greece are home to the most beautiful towns and natural scenery in all of Europe. If you’ve ever found yourself dreaming of whitewashed villages, crystal-clear seas, and unforgettable sunsets, there’s no better time to start planning your trip.
No matter how many times you’ve been to Greece, this 2 week island hopping itinerary offers the perfect balance between famous hotspots and quiet island escapes, giving you a trip that’s both exciting and soul-soothing.
Trust me, once you experience the magic of the Greek islands, you’ll be counting down the days until you can return!
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Island hopping in Greece should be on everyone’s bucket list. Using this information packed post to plan the trip would be a great starting point to get there!
Island hopping in Greece should be on everyone’s bucket list. Using this information packed post to plan the trip would be a great starting point to get there!