If you enjoy the sparkling of the crystal blue sea dancing with the sun, the fresh breezes, white-washed villages, blue-topped churches, and seafood off the hook and grill, you NEED to plan that next trip to Greece and the Greek Islands. With islands that dot the Aegean sea, it will feel extremely challenging to figure out where to go if you have limited number of days. Having gone through this exact same experience, I wanted to put together this detailed 14 day Greek island itinerary that has a perfect balance of islands in the Western Cyclades.
14 Day Greek Island Hopping Itinerary Highlights
Island hopping the Western Cyclades is one of those trips that you have to do in your lifetime. From hidden beaches, the freshest octopus, glorious sunsets, and the laid back vibes, Greece is a traveller’s paradise in more ways than one. You’ll find the full 14 day Greek island hopping itinerary further down below but to get you hyped up, I’ve picked out my 5 favourite things whether experiences, sights, beaches, activities, or meals from the trip that you’ll no doubt want to fit in for a 2 week adventure.
Here were my top 5 highlights of the Greek Islands:
- Naoussa in Paros
- Vorina Beach in Folegandros
- Caves of Antiparos
- Oia Sunset
- Tsigrado Beach in Milos
Curious where our favourite place we stayed was? More on that below but I highly recommend the Prekas Apartments in Imerovigli, Santorini which is has the perfect view of the sunset! The thing is, you’ll want to book this at least 6 months out so get on it ASAP!
Read more about Greece
- The Comprehensive Greek Islands Travel Guide
- How To Get From Athens to Santorini
- Is Santorini Worth It?
- How Many Days Do You Need In Santorini?
- Greece Travel Guide
Where to stay in Greece?
- The two of our favourite properties on our island hopping adventure were Prekas Apartments in Santorini and Giannoulis Hotel in Milos where one had epic views and the other just blew our expectations in terms of comfort and space.
Table of Contents
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Here's what we're covering:
- 14 Day Greek Island Hopping Itinerary Highlights
- Table of Contents
- Your 14 Day Greek Island Hopping Itinerary
- Trip Planning Map
- Day 1 – Paros – Planes, Buses, and Ferries
- Day 2 – Paros – Exploring Naoussa and Beaches
- Day 3 – Antiparos – A Hop Over
- Day 4 – Santorini – Famous Fira
- Day 5 – Santorini – Drive & Explore
- Day 6 – Santorini – Oia Sunset
- Day 7 – Folegandros – Slowing it Down
- Day 8 – Folegandros – ATV Beach Hopping
- Day 9 – Folegandros – Katergo Beach
- Day 10 – Milos – Catacombs & Castles
- Day 11 – Milos – Surface of the Moon
- Day 12 – Milos – Tsigrado Beach
- Day 13 – Athens – Odeon of Herodes Atticus
- Day 14 – Athens – A History Lesson
- Day 15 – Athens – Time To Head Home
- What About the Other Islands?
- A Quick Greek Island Travel Guide
- How Much Does a 14 day Greek Island Trip Cost?
- The Whole Greek Island Hopping Experience
Your 14 Day Greek Island Hopping Itinerary
This breakdown of 14 days in Greek island hopping from one beautiful island to another and ending off with an archeological discovery in Athens is a great way to plan a trip if you’re working with 2 weeks of vacation time. Focusing on the Western Cyclades, it gets the chance to fully experience 4 islands that are completely different in size and vibe and whether you know it now or not, will give you a good idea of which ones you want to go back to because they are just that magical.
The key to having a good trip though is knowing how to plan piece it together and getting down to the nitty gritty details that were honestly hard to find together in one spot online and so the goal of this itinerary is to arm you with everything you need to know before you go.
For this 2 week Greek island itinerary guide, I’ve kept it high level with a summary of each of our days similar to my itineraries for Puerto Rico, Iceland, and Cape Town. For those of you that are looking for a more detailed breakdown of what I suggest and personal anecdotes of how it worked for our trip, jump into the individual island itineraries.
BEFORE YOU CONTINUE
You need to read the Greek Islands travel guide where I’ve compiled in detail a lot of what I learned personally on the trip. These are the kind of things that a lot of listicles and guides don’t talk about. Click on the button below to open a new tab to use as a companion to this article.
Trip Planning Map
A critical part of how I approach trip planning now is to create a custom map of where I’m going. I find it helps big time because you start getting a clearer picture of where things are in proximity to one another and it also acts as your real GPS map when you’re on the road.
Tip: View the Greek Island Hopping 14 Day planning map in full screen and create a copy for yourself. Make tweaks for your own trip and in Google Maps, you’ll be able to view it by going into the menu, selecting “My Places” and the “Maps” tab.
Day 1 – Paros – Planes, Buses, and Ferries
Your first day in Greece is going to be largely uninteresting but will be quite eventful because you’ll be arriving in Athens, figuring out how to get to your ferry, and then finally getting to your first island of Paros.
Going from your plane to a bus and then ferry can often be the most out-of-your-comfort-zone activity you’ll do on your trip.
You can go directly from Athens to Santorini but based on ferry schedules, it made more sense to start with Paros.
Read the full 2 day itinerary of Paros
If you’d like a more detailed breakdown of each day, be sure to not miss reading this guide to help in your trip planning.
Day 1 Summary
Where you’ll eat:
- Dinner – Aromas Traditional Tavern – A traditional Greek restaurant that serves a wide selection of seafood in downtown Parikia.
Where to stay:
As with my previous trips, I was able to find everything I needed through Booking.com because of their massive inventory and variety in terms of types of accommodations. Here, I share with you where I personally stayed but also recommended alternatives that I think you’ll like based on different budgets.
I STAYED HERE
Not located in Parikia directly, this was a super reasonably priced hotel that has small budget-sized rooms but balanced out with large property grounds, a pool, and free breakfast. It’s under 50€ and walkable into town.
BUDGET
Located in Naoussa, this property is priced as budget but offers as much as most properties on the island with AC, private bathroom, wifi, balcony, and comfy beds. There’s a shared kitchen available here.
MID-RANGE
This is a Cycladic-style property located near Naoussa and close to Angii Anargiri Beach. Rooms are spacious with patio or balcony and equipped with AC, fridge, and TV. Free street parking nearby.
LUXURY
This is an incredible family-run hotel where villas have stunning views of the sea and picturesque courtyard. Rooms are spacious, modern, and clean. Wifi and breakfast is included. Friendly staff often quoted as one of the best features.
Day 2 – Paros – Exploring Naoussa and Beaches
One day to explore the entire island of Paros is a tall order but you’ll be able to see a lot of it because it’s not that big. In a matter of a day, you’ll be able to see all the top highlights and also have some time set aside for suntanning at a beach.
This is an island that has a lot of beautiful rocky features to it as they slope down into the shimmering turquoise water. As you make your road trip, you’ll remark how laid back the island is and while you do see tourists around, it’s never overwhelming.
If you’re feeling ambitious, you can try to do the full loop but from personal experience, I’d recommend that you not rush it, enjoy the northern end of Paros including Naoussa and cut back through the mountains.
Day 2 Summary
What you’ll see:
- Paros Park
- Monastiri Beach
- Kolymbithres Beach
- Naoussa
- Santa Maria Beach
- Lefkes
- Ancient Marble Quarry
What you’ll do:
- Santa Maria Beach – You’ll have to put your foot down on deciding which beach to hang out at and the timing will likely be best on this part of the island.
Other places to consider:
- Moraitis Winery
- Itria Cocktail Bar
- Taverna Glafkos
Where you’ll eat:
- Breakfast – Eri Hotel – Complimentary Greek continental breakfast at the hotel.
- Snack – Ragoussis Bakery – Popular bakery that has amazing pastries, fresh juice, cakes, and cookies.
- Lunch – Siparos – No joke that this was our favourite restaurant on the entire trip. The squid was unbelievable and so was the fresh fish linguine.
- Dinner – Trata Fish Taverna – Located right next to Aromas and serving up similar food but equally as good.
Where to stay: Staying in the same accommodations as Day 1 in Paros.
Day 3 – Antiparos – A Hop Over
Normally I’d recommend spending two days focused just on Paros but because of how you need to make 14 days in the Greek Islands fit together, your third day is going to be mostly on the adjacent island of Antiparos.
If you enjoy Paros, you’ll love Antiparos even more because it’s even quieter, more chill, and just as strikingly beautiful with its rocky outcrops, Aegean Sea vistas, and amazing cave.
It’s Antiparos that makes a trip to Paros so incredible because you get to do two islands in one.
Day 3 Summary
What you’ll see:
- Paros Cave
- 3 Windmills
- Castle of Antiparos
- Parikia
- Church of Panaya of Ekatontapiliani
- Frankish Castle
- Agios Konstatinos
What you’ll do:
Other places to consider:
- Glyfa Beach
- Panagia Beach
- Yemeni Wine Restaurant
- Kakao Cafe/Cocktail Bar
- Distrato Cafe
- Bebop Rooftop Bar
Where you’ll eat:
- Breakfast – Eri Hotel – Complimentary Greek continental breakfast at the hotel.
- Lunch – Captain Pipinos – There’s not too much in Ag. Georgios in the south of Antiparos but if there’s a reason to go, it’d be to eat lunch here.
- Dinner – To Souvlaki Tou Pepe – This is your casual Greek gyro joint that has seats but if you take gyros to go, it’s only 2.60 EUR.
Where to stay: Staying in the same accommodations as Day 1 in Paros.
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Day 4 – Santorini – Famous Fira
As the most well-known of all Greek Islands, the beauty of Santorini is unmatched when it comes to the crescent wall that forms the sunset facing caldera, the city of white-washed Cycladic architecture hanging on precariously, beaches formed from the volcanic activity that gave birth to the island, and finally the most epic of sunsets.
Make your way to the island from Paros and once you get settled in your hotel spend the rest of your day exploring the capital of Fira, its winding streets of retail therapy, the ringing from the trains of donkeys that come up, and labyrinth of stairs that lead to bars, restaurants, and hotels.
If you’re coming straight from Athens, find out how to get from Athens to Santorini in our detailed guide.
You might be wondering, is Santorini worth it? Read more to find out why we ended up adding it to our itinerary.
Read the full 3 day itinerary of Santorini
For a more detailed look of each day in Santorini, make sure to click into the itinerary.
Day 4 Summary
What you’ll do:
- Ferry from Paros to Santorini
What you’ll see:
- Virgin Mary Catholic Church
- Fira
Other places to consider:
- Skaros Rock – Next to Imerovigli is a giant piece of land that juts out into the water like the bow of a ship. From a distance, you can see people hiking and climbing up to the table top where the views must be pretty amazing. We were hesitant to do it because it was so windy and our hotel mentioned that it’s harder than it looks especially when you need to take the ladder back down.
Where you’ll eat:
- Breakfast – Eri Hotel – Free breakfast at the hotel before leaving Paros.
- Lunch – Avocado – Modern eatery in Imerovigli with traditional Greek and Mediterranean fare. Highly recommended!
- Dinner – Ouzeri – A traditional Greek taverna in the heart of Fira with reasonably priced dishes but lacks the cliffside view.
Where to stay:
I know you will have different requirements so I’ll try to break down a few recommendations that you can look at in your research that are solid picks but aren’t ridiculously expensive.
If you want to learn more, make sure to read more about the best area to stay in Santorini.
I STAYED HERE
You might be surprised by the price but this is honestly one of the most reasonably priced hotel in Imerovigli with this kind of view. The suite is comfy and well-equipped since it has its own kitchen. The caldera view simply can’t be beat.
ANOTHER IN IMEROVIGLI
Located in Naoussa, this property is priced as budget but offers as much as most properties on the island with AC, private bathroom, wifi, balcony, and comfy beds. There’s a shared kitchen available here.
MODERN FIRA
If you’d like to be in a super convenient location and don’t care for the cliffside caldera view, this is a perfect property that boasts 900+ reviews, high rating, super modern decor, and incredibly spacious. A true gem in Fira.
FIROSTEFANI
If you’d like to be closer to Fira but still looking for epic caldera views, the area of Firostefani is also worth a look. It’s in between Fira and Imerovigili and prices are quite reasonable. The only downside is Skagos blocks your view of Oia.
Day 5 – Santorini – Drive & Explore
With the help of a car rental, you’ll spend the day exploring the far reaching places of the island that you wouldn’t be able to do easily by foot or even the local bus.
You’ll get a chance to spend time discovering the various towns of the island that are jammed packed with authenticity, history, culture, and charm. Places like Pyrgos, Megalochori, and Emporio are often skipped but are definitely worthy of your time and gets you away from the hectic crowds.
This is also a day where you’ll get a chance to enjoy the two famous beaches of Red Beach and Perissa Beach (aka Black Sand Beach).
Finally, accounting for the fact you spent all of your money in a beautiful villa with a caldera view, you’re going to want to take advantage so dedicate this day to enjoy it from your Santorini home. Toast the beautiful sunset with a glass of local wine.
Day 5 Summary
What you’ll do:
What you’ll see:
- Pyrgos
- Megalochori
- Emporio
- Perissa
- Red Beach
Other places and activities to consider:
- Akrotiri – Somewhere I had planned to go but simply ran out of time. Akrotiri is was a settlement that was burned down and covered in volcanic ash in the 16th century. As a result, there’s quite the incredible excavation here for those interested in archeology and history.
- Ancient Thera – On the ridge of a steep mountain is this ancient village where you’ll find a number of ruins to explore. This is not far from Perissa. It was originally part of the plan but we spent a little too much time at the beach.
- Small-Group Santorini Wine Tasting and Vineyard Tour – Yes, Santorini has quite a number of vineyards so if you’re a fan of wine, this is a great experiential tour to consider that lasts 4.5 hours and takes you to 3 wineries and includes 12 samplings of wine.
Where you’ll eat:
- Breakfast – Grab some snacks from your local grocery store and eat them in the car or find a cafe in one of the villages you’ll visit.
- Lunch – Mama’s Food – Serving traditional Greek dishes, this is a hidden gem by Perissa Beach
- Snack – Santa Irini Bakery – A 24 hour bakery in Perissa that bakes homemade sweets and savouries that’s perfect for a snack on-the-go.
- Dinner – Anogi – Possibly the most popular restaurant in Imerovigli and for good reason. Their prices are reasonable, service is great, and food is excellent.
Where to stay: Staying in the same accommodations as Day 4 in Santorini.
Day 6 – Santorini – Oia Sunset
While not necessarily off-the-beaten-path, the trail that connects Fira with Oia and follows the lip of the caldera is a must-do for anyone that loves to hike. Spend most of your day making your way and taking in the breathtaking views.
Once you get to Oia, you’ll have many options to explore the picturesque town whether it be Ammoudi Bay down below, walking the posh streets, or taking photos of the blue-domed churches.
Close out your time in Santorini with the grand finale of the Oia sunset from your spot on the Byzantine Castle Ruins.
Day 6 Summary
What you’ll do:
What you’ll see:
- Oia
- Ammoudi Bay
- Oia’s famous sunset
Other places and activities to consider:
- Volcanic Islands Cruise with Hot Springs – This is the classic cruise to the volcanic island of Santorini that includes a swim in volcanic hot springs, the city of Thirassia, and be able to make it in time for sunset in Oia.
- The Santorini Catamaran Red Cruise with Meal & Drinks – This is a 5 hour catamaran sailing experience that you can choose to do in the morning or for sunset. It includes swimming/snorkelling in front of the Red Beach and White Beach, a stop at the hot springs, and a bbq meal with wine, water and drinks.
- Santorini Gems: Small Group Sailing Cruise on a Catamaran – A “lagoon and shine” experience where you’re on a small catamaran that is similar to the above but is slightly more expensive because of the smaller size.
- Santorini Catamaran Cruise with Greek buffet and drinks – Another 5 hour catamaran cruise option that has a size of 20 or fewer. Includes hotel pick up and drop off.
Where you’ll eat:
- Breakfast – Food you stocked up from the grocery store
- Lunch – Ammoudi Fish Tavern – Serving traditional Greek dishes, this is a hidden gem by Perissa Beach
- Dinner – PitoGyros – Possibly the most popular restaurant in Imerovigli and for good reason. Their prices are reasonable, service is great, and food is excellent.
Where to stay: Staying in the same accommodations as Day 4 in Santorini.
Day 7 – Folegandros – Slowing it Down
From the busiest of islands in the Western Cyclades to the quietest, arriving in Folegandros will be a refreshing change. Instead of camping out for sunset, you’ll be taking naps and taking leisurely strolls in what has to be one of the most authentic and lovely towns.
There’s not a whole lot planned other than the optional climb up to the church to watch the sunset. Enjoy your “day off” and explore the Chora after the town wakes up from its own siesta.
Read the full 3 day itinerary of Folegandros
Want to know how to plan how 3 days in Folegandros looks like including real travel tips, make sure to read the full itinerary and island guide.
Day 7 Summary
What you’ll do:
- Hike up to the Church of Panagia
What you’ll see:
- Chora
- Pounta Square
- Church of Panagia
Where you’ll eat:
- Breakfast – Food you stocked up from the grocery store
- Lunch – Araxe – Personally, I think this is the best restaurant in town with great service, food, and cozy square setting with the perfect foliage.
- Snack – “The Uncle” – Homemade Italian ice cream that’s the only game in town but is actually good.
- Dinner – Piatsa – In the adjacent square to Araxe, this is another open seating area
Where to stay:
I STAYED HERE
We picked this for its affordability and central location to Pounta Square that’s family run and offered port pick-up. Rooms were clean and included everything we needed including table for my laptop, small fridge, and great little front porch with a view.
AFFORDABLE
This is a sister property to the Meltemi and across the street. Rooms are a bit more modernly renovated to Meltemi but overall similar style and equally friendly staff.
RESORT & SPA
Idyllic resort that has the largest outdoor swimming pool on the island that’s in the heart of Chora that’s just far away that it’s also very quiet and tranquil. Rooms are huge and staff is extremely friendly.
LUXURY
This is in the town of Ano Meria which means it might not be as central but this is a beautiful luxury villa boasting sea views and open terrace. Rooms are extremely well renovated, breakfast is included, and transfers to port are free.
Day 8 – Folegandros – ATV Beach Hopping
On your second day in Folegandros, pick up your ATV and go from beach to beach to see the true beauty of the island. You’ll hike down to the super secret Vorina Beach where you might be the only one down there. Take your ATV off-road and go to the beaches of Ambeli and Agios Georgios.
Finish off your day back in Chora, enjoying another spectacular sunset and perfect meal.
Day 8 Summary
What you’ll do:
- Hike down to Vorina Beach
What you’ll see:
- Vorina Beach
- Ano Meria
- Ambeli Beach
- Agios Georgios Beach
Other activities to consider:
- Island Spirit Cruises – Instead of doing your own tour of a few beaches on the island, you can instead book a boat tour. This one goes from Agkali to Livadaki and Agios Nikolao.
- Diaplous Travel – They run a beach-hopping boat tour with several routes to choose from. You’re able to see up to 5 beaches with an experience such as this.
Where you’ll eat:
- Breakfast – Pounda – Breakfast and lunch restaurant serving freshly made dishes in its beautiful garden courtyard.
- Lunch – Pounda – Order packed lunch and eat it on the beach.
- Dinner – O Kritikos – Taverna specializing in fresh meat. Their restaurant is located in the most romantic and charming part of Chora.
Where to stay: Staying in the same accommodations as Day 7 in Folegandros.
Day 9 – Folegandros – Katergo Beach
Most people will tell you that hiking to Katergo Beach isn’t possible but it totally is. You’ll have your ATV for a second day and after a short hike, you’ll find yourself on the islands most popular beach that features a wide stretch of sand. It’s incredibly scenic here because of the rock formations that surround including the long spine that sticks out in the water, slicing the beach’s water in half.
If you have time, you’ll see the port town of Karovastasis and Vardia Beach.
Day 9 Summary
What you’ll do:
- Hike down to Katergo Beach
What you’ll see:
Other activities to consider:
- Katergo Beach Water Taxi -If you’d rather take a water taxi to Katergo beach from Karavostasis, that is available from the port and only costs 10 EUR per person. This isn’t something that can be booked and is in a drop-in basis.
Where you’ll eat:
- Breakfast – Pounda – Same awesome breakfast spot that you’ll just fall in love with.
- Lunch – Souvlaki Club – The local grill shop that’s always busy and confirmed to be pretty awesome.
- Dinner – Blue Cuisine – Certainly the fanciest restaurant on the island. While we had high hopes for this restaurant, it fell a little bit short of expectations despite its zen and modern outdoor seating.
Where to stay: Staying in the same accommodations as Day 7 in Folegandros.
Day 10 – Milos – Catacombs & Castles
Milos and wildly unique and even though you’re headed into Day 10 of this Greek island itinerary, going to your final island of your Greek islands adventure, you’re going to discover so many new things here.
For your first day on the island, get settled in and you’ll be exploring the area around the old capital of Plaka. Nearby is a fishing village named Klima and this is where you’ll see what’s known as a “syrmata” where they carve into the rock wall to create these fishermen dwellings on the beachfront. They’re quite the sight to see because all of their garage doors are painted in bright colours.
You’ll also find remains of a Roman village that was here as well which is why the Catacombs and Ancient Theatre are so historically significant.
Finally, head to the city on a hill, Plaka, and watch a ridiculously beautiful sunset by the Kastro’s church.
For dinner, you’ll be eating at the famous Oh! Hamos! which not only was highly reviewed but also recommended to us locals all the way in Folegandros.
Read the full 3 day itinerary of Milos
For the detailed itinerary of how to spend 3 days in Milos including what to see, do, where to eat, and best places to stay.
Day 10 Summary
What you’ll see:
- Klima & its colourful fishing village
- Catacombs
- Ancient Theatre
- Trypiti, Pera Triovassalos, and Triovasalos
- Plaka
- Kastro sunset
Other activities to consider:
- Archeological Museum Milos – A charming small museum for a small island that’s open from 9AM – 4PM (closed Monday and Thursday) if you’re interested in learning more about the history of early settlements in the area
- War Museum – While in Plaka, another often not visited place is this small museum that focuses on the German occupation during World War II.
Where you’ll eat:
- Breakfast – You’ll probably need to skip a proper breakfast. Instead you can pick up some food the night before or grab something on the ferry.
- Lunch – Astakas – Perfectly positioned along the Klima waterfront. Their squid ink risotto was quite unique. Loved their complimentary Greek yogurt dessert.
- Snack – Coffee Time – We found this coffee shop along our drive and loved that they gave us a free cookie with our coffee.
- Dinner – Oh Hamos (or O! Hamos!) – Easily the most popular restaurant on the island. In the summer time, it’s said the lines go fully out the entrance and onto the main street. During the off-season, you can drop in easily to get a spot but in high-season make sure to come here early and expect to wait for a table. No reservations are taken so come here for early lunch or dinner.
Where to stay:
Milos is a large island with a lot of accommodation options. That said, I personally think Adamas is the most convenient place to stay but Pollonia is another option for its serene spot on the island and high-end hotels.
I STAYED HERE
An unexpectedly awesome hotel in Adamas that was super spacious with its living space with kitchenette and couch plus separated bedroom. Wifi is available throughout and there is parking available for cars and ATVs. Airbnb listing available.
BUDGET
You can’t beat the price for this property in Pollonia. These are Cycladic-style rooms just 50m from the beach and tavernas. Wifi is free throughout and all units have air condition with balcony or patio. No frills and great location.
UNIQUE WINDMILL
A full two bedroom house at an affordable price in Plaka that is truly a unique experience. The garden, patio, and terrace overlooking the sea and mountain is truly a highlight. Fridge is stocked with breakfast foods too.
LUXURY
Located in Pollonia, this hotel is perched on a cliff offering panoramic views. Features an infinity swimming pool, modern Cycladic-style rooms, and included breakfast will spoil you every day.
Day 11 – Milos – Surface of the Moon
On your second day in Milos, you’ll be hitting the road again and this time exploring the northern shore of the island.
Volcanic activity creates all sorts of wonder and mysterious landscapes. Milos is blessed with a collection of beaches in the north that are some of the most unique you’ll ever see. One is Papafagras and the other is Sarakiniko.
Eventulaly make your way to the village of Mandrakia and have a memorable meal at Medusa.
Day 11 Summary
What you’ll see:
- Pollonia
- Papafragas Beaches
- Sarakiniko Beach
- Firapatamos
- Mandrakia
Other activities and places to consider:
- Fourkovouni – The fishing village we weren’t able to make but with better planning, perhaps it’s possible to go there on Day 10 or before heading out to Pollonia. Out of all the fishing villages, this one is perhaps the most off-the-beaten-path which is why it doesn’t even show up on TripAdvisor.
- Plathiena Beach – A beautiful secluded beach that’s a bit more traditional than the other ones you’ll see on this day but if you’re looking for this, consider slotting this into your Greek island hopping itinerary.
Where you’ll eat:
- Breakfast – Eat breakfast with supplies purchased from the local grocery store in Adamas.
- Lunch – Enalion – One of the many seafood restaurants you can find in Pollonia that are similar but serve up great dishes.
- Snack – Kivotos ton Gefseon – Restaurant that is popular for breakfast but if not for that, come here for the Greek pastries, dessert, and honey.
- Dinner – Medusa (Medousa) – Simply remarkable restaurant you have to go to in Milos. Whereas Oh Hamos is more well-known for its meats, Medusa takes the cake when it comes to seafood.
Where to stay: Staying in the same accommodations as Day 10 in Milos.
Day 12 – Milos – Tsigrado Beach
It’s time to explore the South and make it another memorable beach day. Tsigrado Beach is your target and you’ll need to be prepared to work a little to get down there. With the assistance of rope and ladder, descend into a narrow trench that leads to another wooden ladder that drops down to the beach.
Next door is Firiplaka Beach, another beach that you can check out while you’re there. Make sure to walk all the way to the end to see the pastel colours of the rock.
Day 12 Summary
What you’ll see:
- Adamas
- Tsigrado Beach
- Firiplaka Beach
Other activities and places to consider:
- Paliorema Old Sulfur Mine – Let’s just say I didn’t really quite figure out how to get here. What made me nervous was the fact that this area of the island is technically off limits to cars in that there’s a line you cross to get here that makes the vehicle uninsured because it’s mostly off-road. Now if you read the reviews, it’s totally do-able as tons of people go but I didn’t want the trouble and also didn’t make time in the schedule to make it work.
- Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch – Perfect yacht sailing trip for those that want to leave from the Adamantas Port. You’ll visit several beaches along the way and the hideout of Kleftiko.
- Milos Sailing Tour with Snorkeling and Lunch – One of the most popular tours and a great way to see the coastline from a luxury catamaran. Includes a snorkel safari, breakfast, lunch, afternoon tea and snacks. Ideal for families and leaves from Pollonia.
- Poliegos, Firligos and Kleftiko Caves Full Day Cruise – This is a full day catamaran cruise that takes you two 3 beaches that are not easy to get to. This leaves from Pollonia.
Where you’ll eat:
- Breakfast/Lunch – Artemis Bakery – This is a corner-store Greek bakery where you can grab your choice of bread, pastry, cookies, ice cream, coffee, and orange juice at a really good price.
- Dinner – O Zygos – We wanted to walk to dinner and so we picked a local spot that wasn’t one of the big ones. While it didn’t blow us away, we still ended up having a great souvlaki meal while watching the sun set over Adamas.
Where to stay: Staying in the same accommodations as Day 10 in Milos.
Day 13 – Athens – Odeon of Herodes Atticus
It’s time to head back to the main land. After your ferry back to Athens, you’ll likely be in the port of Piraeus. Take the subway into the city and get settled.
For your first of two days in the capital, use the time to get orientated and educated. The Acropolis Museum is a must because it’ll give you the base knowledge of what the heck you’ll be looking at the next day. Trust me, it’ll empower you to explore the Acropolis on your own without the need for a guide.
If the timing works out (realistically you’ll need to arrange your days to fit it in), you’ll be watching a classic Italian opera on the hallowed grounds of the classic Greek theatre at the footsteps of the Acropolis hill. Even for those that aren’t fans of opera, this is truly a treat.
Read the full 2 day itinerary of Athens
Despite only having two days, your days are going to be packed with the classics of Athens. Find out the nitty-gritty details about planning that 2 day itinerary by continuing to read the separate guide.
Day 13 Summary
What you’ll see:
Where you’ll eat:
- Breakfast/Lunch – On the go – Since you’ll have an early start with the ferry which’ll blend between both meals, this is up to you where you want to grab food. You can buy food from the grocery store to eat on the ferry or you can try to eat a big breakfast before you board.
- Dinner – Herodeon Atticus – I know, not really a real dinner but this is a good fall back if you don’t have time to get a proper dinner and need to make a show.
Where to stay:
There are plenty of places to stay in Athens but depending on your budget, you’ll have to find a real balance between location and type of accommodations. One thing you’ll notice with Athens is that there are a ton of B&B/homestay properties in the city and that is really the sweet spot when it comes to affordable accommodations. Luckily, Booking.com has a really awesome portfolio of places to stay. Let me show you where I stayed and a few others that I strongly considered.
I STAYED HERE
This is a budget apartment we booked in a very convenient area that’s walking distance to all the main attractions (1.3km away from the Acropolis Museum). The room is comfortable and clean but the only draw back was the shared bathroom and kitchen as this is only one room within an apartment.
SIMILAR B&B
Along the lines of Athens having so many great apartments available, this is one that’s only 400m from the Acropolis Museum. Featuring free wifi, city views, balcony, AC, and fully equipped kitchen, for the price you really can’t beat it. This stay is for the whole unit.
MID-RANGE HOTEL
If you’re okay with being a little bit further away but a short metro ride from the historical core, this gives you the comfort of a beautiful property with a pool, comfortable and spacious rooms, and excellent service. This is close to the Panormou metro station.
LUXURY
If you want top end luxury, quality, and insanely good location, this has to be it. This hotel puts you steps away from Hadrian’s Arch, and the Acropolis Museum. Beyond that view, the rooms are hyper modern, comfortable, and luxurious. Breakfast is included as well!
Day 14 – Athens – A History Lesson
This is an all-out kind of day where you’ll have one day to see all the main attractions and highlights of Athens. It’ll seem overwhelming but it’s totally do-able.
Everything will eventually culminate in watching the sun descend on the Acropolis and the Parthenon. Marvel at all the ruins from numerous empires gone by.
Day 14 Summary
What you’ll see:
- Hadrian’s Gate
- Temple of Olympian Zeus
- Panathenaic Stadium
- Plaka
- Monastiraki
- Hadrian’s Library
- Ancient Agora of Athens (including Temple of Hephaestus)
- Acropolis
Other places and activities to consider:
- six d.o.g.s – Near Monastiraki, this is a highly rated cafe that is an alternative choice to A for Athens where you can chill in their outdoor patio with a beer or coffee, and sandwich.
- National Archaeological Museum – There simply wasn’t enough time to fit this in but one of those things that I keep missing every time I come to Athens.
- O Thanasis – In Monastiraki Square is this kebab shop that might look run-of-the-mill but is actually very good.
- Andero Viewing Platform – This is on Filopappou and where you want to be for sunset to get that perfect shot of the Acropolis.
- Herodion Hotel – If you want to do another rooftop bar, this hotel actually came highly recommended.
- Hydra, Poros, and Aegina Full-Day Cruise with Lunch – If you wanted to do something totally different in Athens, a day trip like this might be right up your alley. Taking you to the famed Hydra, Poros, and Aegena, this is a cruise excursion that is pretty amazing.
- Cape Sounion: Sunset Tour from Athens – See the Temple of Poseidon and Cape Sounion which is known for its epic sunsets.
- Delphi Guided Day Trip from Athens – Take a trip to the center of the Ancient Greek universe on a full-day tour of Delphi, site of the oracle, and heart of the classical Greek world.
Where you’ll eat:
- Breakfast – On the go – Depending on where you’re staying, you’ll pass by many bakeries and cafes along the way. Pick up something quick or eat inside.
- Lunch – A For Athens – It’s labelled as a cocktail bar but this is a spot that carries a refined and modern selection of entrees, many drinks as you can expect from a bar, and finally a two level establishment that allows you to be on the roof or indoors that both have the best view of Monastiraki Square and the Acropolis.
- Dinner – Sfika – A casual cafe/bar/restaurant that serves popular Greek grilled dishes and is best known for their mixed meat plate.
Where to stay: Staying in the same accommodations as Day 13 in Athens.
Day 15 – Athens – Time To Head Home
14 days island hopping through Greece is one hell of a trip but as they say, all good things come to an end. This day doesn’t really count towards the 2 weeks because that would be cheating right?
From your hotel you’ll need to find a way to the airport and from there it should be smooth jetting back home. For us, we made it back to Toronto with Air Transat which is the same airline we took to get to Athens. Air Canada also has direct flights.
Day 15 Summary
Where you’ll eat:
- Breakfast/Lunch – On the go – Grab something in the morning as you make your way to Syntagma Square or find something to eat at the airport.
What About the Other Islands?
I won’t go into too much detail here because naming off every single other island in the Western Cyclades would not be a good use of your reading but what I wanted to do here is walk you through my trip planning process and other islands I considered in this 2 week Greek island itinerary.
Naxos
- What I liked about it – Naxos was an island that seemed to be one of the more popular routes when it came to the Western Cyclades but at the same time felt underrated as well. It’s attractive for its size, monuments, greenery, and ease of planning ferry routes around.
- Why I didn’t pick it – With Paros high on our list, I wasn’t sure if we wanted to hop over to an adjacent island and ultimately it just didn’t make the cut.
Mykonos
- What I liked about it – Second to Santorini, this is probably one of the best known islands of the region. Having done the research, I learned that there were a ton of great hiking options here, beaches, and of course windmills to explore.
- Why I didn’t pick it – You could say the “party” reputation it has was a bit of a turn off as that wasn’t the reason why we were going to Greece. I’m glad we didn’t go though because I fear that it would be closer to that Santorini experience than something like Folegandros.
Crete
- What I liked about it – While technically in the Western Cyclades, there was strong pull to include this in just because of how popular it is when you look at sample itineraries. There are a lot of attractive places to explore here including Heraklion, Chania and the plethora of outdoor gems to find.
- Why I didn’t pick it – Ultimately, there was no way that we could effectively see it because of how giant the island is. We could’ve flown in to pop our head to see one town and bounced out but it didn’t seem worth it.
Sifnos
- What I liked about it – From Milos, there’s a perfect way to line up Sifnos via the SeaJets ferry and I really wanted to fit it in because it had the same vibes as Folegandros but with a slight different focus on pottery.
- Why I didn’t pick it – Just couldn’t fit in the schedule!
A Quick Greek Island Travel Guide
For a more thorough breakdown of what you need to know to go island hopping in the Western Cyclades, make sure to head over to the full travel guide on the Greek Islands which covers in depth all the things you need to know before planning your trip to the Western Cyclades and beyond.
That said, I’ve compiled a quick list of tips that apply to most of all the places that are covered in this 14 day Greek island hopping itinerary to get you started.
Money – To my surprise, there were more places that accepted credit cards than my first trip to Greece many years ago. That said, it’s still advisable to have cash on you because there were plenty of smaller shops that didn’t so I’d say overall it’s 50/50. One thing that we constantly had to consciously do was break change for tips because in Greece, most credit card machines don’t have a tip option when you pay at say a restaurant. You always want to make sure you have coins available.
Tipping – The general rule of thumb for tipping in Greece is 10%. In the case of taxis, don’t feel the need to tip extra because they’re handling your luggage, this is usually already added to your rate. For hotels, 1 to 2 EUR per day is the norm.
Meals – There is something unique to the Greek Islands that I love. When eating meals at restaurants, if you don’t order dessert, many restaurants will provide a complimentary plate of Greek yogurt with honey or something else. It got to the point where we almost felt like it didn’t make sense to order a real dessert because when we did, we never got the complimentary one.
Ferry – I’ve shared my specific ferry tips above but one I didn’t get to mention was that if you can, make sure to put a legitimate phone number on your ferry booking because you will get important text messages. When we landed in Greece, we got a message that our ferry had mechanical issues which is why we knew about it even without checking online. Delays and schedule changes also come through via SMS. Ideally this is your home cell number or if you know you’re going to switch to a different number when you land (i.e. with KnowRoaming), then use that number instead.
Use this Ferry Planning Tool
FerryHopper allows you to find out what ferry companies are operating to and from Santorini. We recommend using this to help with trip planning.
When it comes to booking ferries, you don’t always need to book far in advance since they aren’t the kind to sell out quickly but I would advise you to make your reservations as soon as you’re confirmed because it’s not like ferry ticket prices drop as the date gets closer. With limited number ferries, you also don’t want to get screwed because the one you wanted sold out. FerryHopper is an excellent tool to figure out what ferry companies can take you where. Use the widget below to get started!
Lastly, ferries in Greece are rarely on time so don’t expect Japanese-like efficiency but it’s always best practice to assume they are and to show up at the port 1 hour ahead of time at least to get settled and ready to board.
For ferries in Athens, remember there are two ports – Piraeus and Rafina. Rafina is closer to the airport and easier to get to so take that into consideration when planning.
ATV – This is incredibly easy to drive and a ton of fun. Personally, I loved doing it on the small islands but not sure if I’d recommend the same for Santorini. A few tips that we learned along the way:
- Navigation – The rear passenger on the ATV is going to have to be responsible for navigating. You can use your phone or a paper map
- Fuel – I’ve mentioned this above several times but fill up a lot less than you think. ATV’s don’t chug through gas as much a regular car. If you have a full-ish tank, don’t fill up until the very end and from there go by 2-3 EUR increments.
- Inspect the ATV before you go – Basic insurance is usually included but you want to make sure the ATV you’re taking out is in good shape. Do a full walk around of the vehicle before you go and if there are any problems with it, make sure they mark it down so you’re not liable.
When is the best time? – Much of the Greek Islands shuts down in the winter months so that only leaves the summer. However, since the middle of summer is both too hot and way too crowded, my recommendation is to go during the shoulder seasons of May – June and September – October.
Getting here – Athens International Airport (ATH) is going to be your primary hub coming in and out of the country. From there, it’s either ferries or additional flights. When it comes to the Greek Islands, the bigger ones have them such as Paros (PAS), Santorini (JTR), and Milos (MLO). This means that in theory you could skip the long ferry to and from Athens and just take flights instead and ferries in between. To put alerts on the flights and find the best deals, I recommend using Skyscanner.
Where should I stay? – We did almost all of our hotel reservations through Booking.com and it’s because they have such a good inventory of properties that range from hotels, hostels, guesthouses, and resorts. I love that cancellation is easy for most properties and the booking management is seamless. Plus, if you get up to Genius Level 2, you can save up to 15% off on top. As an alternative, there’s also Agoda, VRBO, and Airbnb.
Do I need travel insurance? – As always, travel insurance is highly recommended. My philosophy is that you want to make sure you’re covered in case the unknown happens. Make sure to read our guide on choosing the right travel insurance for you. Overall, World Nomads has the best balance of price and coverage.
How Much Does a 14 day Greek Island Trip Cost?
This is a question that I get a lot and with good reason because as amazing as all of this looks, how deep do your pockets have to be and how much money should you save to have a similar experience?
For 14 days, here are a table of our costs for two people. The one thing it doesn’t include is flights.
This means this trip cost $2,318.82 per person. Breaking this down by 14 days, that means that we paid $165.63 per person per day.
To see this in pie-chart form, this is what it looked like:
Everyone’s budget is going to be different for a trip like this and there are many ways that this could have been done even more luxurious or more cost conscious. I feel like this is a very down-the-middle type of trip where we splurged on a few things here and there but overall tried to keep costs manageable.
The Whole Greek Island Hopping Experience
Words can’t describe how incredible this trip was.
When I started planning for this trip, I was truthfully not very confident about how I would be able to figure out how to organize this 14 day Greece itinerary. The ferry schedule looked daunting, there were too many islands to choose from, and I didn’t know how to break down 2 weeks into something where we would have a variety of things to see and do but also not go overboard with moving around.
Overall, I have to see that things turned out really well. Every single island was unique in its own way, we got a chance to beach a ton which was one of our main goals, and eat ridiculously good seafood. I seriously can’t have gyros, souvlaki, tzatziki, or grilled squid ever again. I’m ruined.
So what was our favourite island?
Another question we’ve gotten a ton of since coming back. Here’s my honest assessment of each of them:
- Paros – First one is always special and I thought this was the most well-rounded island because there was a lot to explore on the main island but you could also pair it with Antiparos and get away from the already small crowds of Paros.
- Santorini – The thought was that you couldn’t do the Greek Islands without doing Santorini and to that I say that I’m glad I was able to show my wife around (this was my second time there) but we both agreed that the cruise and tour bus crowds are just too much. The island is beautiful with those caldera views and the hike was awesome but you think about how ridiculous Oia has become, you just yearn to get away from all of those people. Plus it was expensive there.
- Folegandros – If we had to pick, this was our favourite island and maybe that makes us anti-social but I loved how there was just the one main town to see, you didn’t feel like you had to see every corner of the island, the people were hyper local, and you could literally be on a beach by yourself.
- Milos – The second largest island we went to that was again just so uniquely different. Every single beach was memorable and every single fishing village was as well.
The only black mark of the trip was when I was pick-pocketed on the subway in Athens to which I say that I feel like an idiot for not spotting it when the team of 3 came onboard, and to warn all of you that the city is definitely now on the top of my list in Europe where you have to be extra careful.
Got questions for your own trip to the Greek Islands or Greece in general? Let me help by simply dropping a comment down below!
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