2 Week Greece Itinerary: The Best Island Hopping Route

This is the only itinerary you need for your 2 week Greece itinerary and island hopping adventure! Island hopping in Greece is truly a bucket list experience.

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But with hundreds of islands to visit in Greece, which ones should actually make it onto your itinerary? This amazing two week Greece island hopping route has you covered!

Greece has hundreds, yes hundreds, of islands. The options are truly endless, and you can have an entirely unique and different experience from the next person depending on where you decide to go. 

We spent 3 weeks island hopping and we only scratched the surface of what the Greek islands have to offer. I’ve shortened our itinerary so you can see the best of the Greek islands in 14 days.

What Is The Best Time To Visit The Greek Islands?

High season: the high season in the Greek islands is June – August. These months will bring the highest temperatures, most days with full sun, and warmer water temperatures in the Mediterranean Sea. However, the high season also brings the most travelers along with higher prices for hotels, transportation, and activities.

Shoulder season: the ‘shoulder’ season are the months right before and right after the high season. In the Greek islands, this is May or September/October. This is when you’ll see lower prices for hotels and activities, and smaller crowds. However, the shoulder season also has a slightly lower likelihood of warm temperatures and sunny days. While May can be a toss up, September and October are often warm and sunny with fewer crowds.

I recommend visiting at the end of the summer and into Autumn for the best weather, prices, and availability. My personal favorite is the end of September or early October.

How To Get Around The Greek Islands: Ferries & Planes

There are a few methods of transportation to get around the Greek islands during your 2 week Greece itinerary. I’m going to go over how to get between the islands, how to get around on the islands, and how to get back home at the end of your trip.

Use my ‘Travel Resources’ page to help you plan your trip with tips for booking hotels, eSIM’s, and more!

Getting Around the Greek Islands By Ferry

Hands down the best way to travel from island to island while in Greece is using the Greek ferry system. 

Others may tell you to fly between islands, and in some cases that is possible. But, often there are limited and expensive flights between the islands. It’s much easier to hop on a ferry and be at your destination in just a few hours. 

The ferries in Greece are run by multiple companies and there are a few different options of types of boats, as well. I’m going to give you a quick rundown of how to use the ferries so you can navigate the Greek islands. 

Use Ferryhopper to book all of your ferries during your 2 week Greece itinerary. It’s the easiest way to search, book, and track your ferry journey. 

I recommend you book your ferry trip as far in advance as you can, just to be sure you can get on the ferry you want. As soon as you know your travel plans, book the ferry.

There are two main types of ferries in Greece: the big slow ones, and the small fast ones. Both have their benefits. 

The small jet boats are often faster, but don’t do quite as well when the seas are rough. The large car ferries take longer, but are generally a bit more stable and provide you with more space on your journey. There is often also a price difference, as well. 

It’s really a personal decision which of these boats you prefer!

How To Get Around The Greek Islands By Plane

While traveling between islands by plane is not my first recommendation, it’s an option for those worried about traveling by ferry. The ferry system can often be delayed and somewhat unreliable. 

But, more often than not people are more worried about sea sickness. So, planes can be another option.

There are a few downsides to traveling between the islands by plane, though. First, there are often not direct flights between islands. This means making a stopover and prolonging your journey.

Not to mention, many of the smaller islands either don’t have airports or have very limited flight options. 

It isn’t a bad idea, however, to fly from Athens to your first island if you plan on going to one of the further and larger islands first (like Santorini). After that, though, I would recommend ferries for the rest of your 2 week Greece itinerary!

Read Also: 10 Essential Items To Pack For A Trip to Europe

2 Week Greece Itinerary: Island Hopping Route

Let’s get into the perfect 2 week Greece itinerary, island hopping edition! On this itinerary you’ll visit Athens plus four of Greece’s most beautiful islands.

Day 1: Athens
Days 2-4: Naxos
Days 5-7: Paros
Days 8-11: Milos
Days 12-14: Santorini

Use this map to help visualize all of the points of interest mentioned in this blog post. I’ve noted recommended restaurants, hotels, and things to see & do.

Day 1: Athens

Begin your 2 week Greece itinerary in Athens, the magnificent capital of Greece with no shortage of history and culture to start off your trip. You could also fly into Athens, jump right onto a ferry and come back and explore the city on the tail end of your trip. However, I would recommend doing Athens first!

Stay in the neighborhoods of either Monastiraki or Plaka, which are close to the Acropolis and full of great restaurants and shopping. 

You’ll likely spend most of your time in Athens in these two neighborhoods as they are the most tourist friendly and boast a majority of the major sights in Athens. 

How To Get Around Athens, Greece

The easiest way to get around in Athens is just by public transportation and walking. I promise you do not want to rent a car, nor do you need to. The roads are very narrow, parking is a nightmare, and everything you’ll want to see is within walking distance of each other or easily accessible by metro. 

To buy a metro ticket, you can purchase tickets in the metro station. There are 1 day, 3 day (tourist ticket), and 5 day options. Choose which one works best for you. The tourist ticket includes one roundtrip to and from the Athens airport.

We always use Google Maps to plan our usage of public transport. Just search your destination on Google Maps, and it will show you exactly where to enter the metro, which train to catch, how many stops, and where to exit the metro. Google Maps makes it really easy to navigate public transportation everywhere!

The Acropolis (Parthenon)

If there is one thing I know about visiting the Acropolis, it’s that it WILL be busy. So just expect it. An estimated 3 million people visit the Acropolis every year, so it will be you and everyone and their mother, and that’s okay. 

To avoid the crowds as best as possible, visit first thing in the morning when the gates open. And, buy your tickets in advance so you can breeze on through the gates as soon as you get there. 

A guided walking tour of the Acropolis is also a great idea, since there is just so much history here. We used an audio guide we found online, and it was fine. But I’m sure we missed a lot of the best information, so I wish we had done a tour.

I would personally book this walking tour because its only 2 hours long. I think anything longer than that would be very tiring.

If you plan to go on your own, purchase your Acropolis tickets in advance here.

The Acropolis is more than just the Parthenon, and yes they are different. ‘Acropolis’ in Greek means ‘high city’ or ‘city on a hill’. It’s simply the highest point in Athens where the ancient Greeks built their most important structures. 

The Parthenon is a former temple built on the Acropolis to honor the goddess Athena. Surrounding the Parthenon are other temples, sanctuaries, and altars. There is a lot to see, and it can be a little overwhelming especially with the crowds. I recommend you come with a plan of what you’d like to see and what you’re okay with skipping.

I recommend you listen to the free Acropolis walking tour on the Rick Steeve’s Audio Europe app if you don’t get a guided tour. The app is free to download and listen to! You can find in here or in the App Store. This way, you can stay as long or as short as you want at the Acropolis.

Recommended Acropolis Guided Tours:
– First Access Acropolis and Parthenon Guided Tour (4.7 )
– Acropolis, Parthenon, & Acropolis Museum Guided Tour (4.8 )
– Acropolis & Mythology Highlights Small Group Tour (4.8 )

Hill of Ares (Areopagus Hill)

Right next to the exit from the Acropolis area is Areopagus, or the Hill of Ares. In Ancient Greek times it was the site of the Council of Nobles and the Judicial Court. Today, it’s a fantastic viewpoint to see the city of Athens. It’s especially popular at sunset for views of the Agora and Athens. 

It is free to access as it is just outside of the Acropolis area, so you can come here without purchasing a ticket to the Acropolis. 

Do note, the rock has become very slippery over the years as people climb all over it, making it a bit treacherous to navigate!

Wander Through Plaka & Anafiotika

The most picturesque neighborhoods in Athens that are perfect for strolling and taking pictures are Plaka and Anafiotika. Located below the Acropolis and near the busy restaurant and tourist areas, you can get lost wandering the streets here. 

Plaka is a wonderful mix of ancient ruins and modern Athens. You’ll walk past the Roman Forum and gaze up at the Parthenon, all while winding through restaurant tables and trinket shopping. Walk around Plaka to get the busy, bustling feel of Athens, and then keep walking until you get a little lost and end up in Anafiotika.

Anafiotika is a small neighborhood nestled between the Acropolis and Plaka. Once you get to these residential areas, the restaurants and crowds fade away. As you wander, you’ll find little hidden viewpoints of Athens, cats running about your ankles, and narrow walking paths that feel like secrets.

This was my favorite spot in Athens, as it felt quiet and serene compared to the business of Plaka. Please keep in mind, this is a residential area and people do live here, so be respectful and don’t enter any areas that are private property. 

Days 2-4: Naxos

The island of Naxos is the largest in the Cyclades island group and has some wonderful history and culture. It’s the closest to Athens of all the islands in this itinerary, making it a logical first stop. 

You can either take a ferry or fly to Naxos, depending on your preference. 

Chalki & Filoti

Naxos has some charming little towns that are great to walk around and shop in. Chalki and Filoti were my two favorites that I recommend you check out!

Each has it’s own charm, with boutique shopping and adorable cafes. These are really the type of little towns to just wander around for part of a day and grab some food or drinks, so be sure to stop by. However, you likely won’t spend the entire day here, so just keep that in mind as you plan!

Temple of Apollo (Portara)

Located right next to the ferry port is the Temple of Apollo that sits out on a small peninsula overlooking Naxos town (Chora). 

These ancient ruins overlook the beautiful white washed buildings of town and show a beautiful juxtaposition of the old and new in Greece. You can sit here and watch the ferries come and go while enjoying a picnic or just admiring the handiwork of the ancient Greeks.

It’s a great place to watch sunset and enjoy the stunning views of Naxos. There are also a handful of cute little swimming spots around the peninsula as well.

Venetian Castle of Naxos

The Castle of Naxos is an old venetian stronghold built centuries ago and that forms the structure for much of the main part of town. 

While there is no central location to visit per se, you should wander around this part of town and through the small passageways created by the castle. 

Restaurant Recommendation: our favorite dinner spot on Naxos was Taverna Naxos, located on the main strip. The restaurant location is tagged in the interactive map above!

Beaches of Naxos

Naxos has some of the best white sand beaches in the Cyclades. White sand beaches aren’t the most common in this family of islands, but Naxos is a great place to find some. 

Some of the best rated beaches on the island are Aliko (my personal favorite), Mikri Vigla, and Plaka beach. 

Day Trip To Koufonisia 

If you’re feeling adventurous, spend one of your days on a little trip to the small island of Koufonisia. The island is located off the southeastern coast of Naxos. 

Koufonisia is a much smaller island than Naxos with not many residents. A day trip to Koufonisia will take you to explore the small islands off the coast of Naxos and give you a great perspective of the island from the sea. 

Personally, I would book this Rina Cave-Koufonisi Cruise & Rina Cave Swim with BBQ that has great reviews.

How to Get Around Naxos

The best way to get around Naxos, since it’s quite large, is renting a car, quad bike, or scooter. 

We rented a car and scooter while on Naxos and enjoyed both. However, a car is much more comfortable, so that’s something to consider. Also, a motorcycle distinction is required on your license to rent a scooter. But, it isn’t required for a quad. 

If you’re renting a car, you can search for availability here. But, if you want to rent a scooter or a quad, there are lots of small local rental shops on the island. 

You can reserve ahead of time on their websites, or you can book in person once you arrive. Just note that rentals can be hard to come by last minute, especially in the high season of Summer!  

Days 5-7: Paros

Paros was one of my favorite islands for its picturesque villages and classic Greek island charm. The island is also well known for its lively nightlife and delicious seafood! 

I recommend that you rent some wheels in Paros, whether a car, quad, or scooter. To get to all of the little villages and beaches you’ll want to see you will need transportation, but choose your method of transport wisely based on your comfort level. 

Parikia

The main town of Paros is Parikia, and it’s a great place to base yourself while on Paros. It’s also a cute town with a lot of restaurant options, shopping, and rental car shops. Most likely, this is where you will arrive if you come to Paros by ferry.

Restaurant Recommendation: One of the best meals we had in all of Greece was at Bountaraki. It’s a small seafood restaurant with incredible fare and super welcoming staff.

Naousa

One of the most popular spots on Paros, and for good reason, is the adorable town of Naousa. This is the picturesque little town you think of when you picture the Greek islands. 

Here you’ll find wonderful shopping, hopping bars and restaurants, and a beautiful port. It’s also one of the best places to stay on the island!

Naousa is a great place to walk around, have lunch or a drink, and do some shopping. 

And while there is no main beach in Naousa, just around the corner is the beautiful Kolympethres beach – one of my favorites on Paros! 

Lefkes

The little town of Lefkes is located up in the hills of Paros and is such a cute town to walk around, grab some gelato and espresso, pop into little shops, and just explore. Some of the most beautiful photo spots on the island are in Lefkes, so it’s definitely worth the stop.

Aliki 

On the south side of the island is the town and port of Aliki. This is a small port where many boat trips leave to explore around the island for the day. In fact, we picked up our license free rental boat here that we had all to ourselves for the day. It was amazing!

Aliki is also a great place to stay on the island as well. It’s a bit quieter and less expensive than Naousa when looking for a place to stay, so it’s a great option. And, its only about 20 minutes by car from the main ferry terminal. 

Rent A Boat To Explore Paros & Antiparos (license Free Rental)

Hands down the best thing to do on the island of Paros is rent your own boat for the day. There is a company that offers these boat rentals without the need for a boating license. This is the one we booked.

They will give you a quick crash course on the boat, give you a map of the best spots around the island, and send you off! 

What we loved about doing this was the fact that we had complete control over our itinerary. We were able to explore the southern coast of Paros, and headed over to Antiparos as well. 

If you’re the adventurous type, I highly recommend renting your own private boat for the day in Paros! We booked with The Sailor’s Ride and loved them!

Book A Guided Boat Tour of Paros

If you’re not feeling quite so adventurous to drive your own boat, consider one of the classic boat tours of Paros. You’ll have a guide and skipper with you to show you around and handle all the details of the day. 

Seeing the island from the water is one of the best ways to experience the beauty of Paros. Plus, there are spots on the island that can really only be reached by boat, so I think this is a great activity to add to your itinerary.

I would book this one if I were booking a guided boat tour of Paros!

Take the Ferry to Antiparos for the day

Located just next door is the smaller island of Antiparos – the name comes from ‘anti’ meaning ‘opposite’ of the island of Paros. 

While Antiparos is a smaller island, there is plenty of beauty. While you’re there walk around the main town, check out the Venetian Castle, and take a trip to one of the island’s many beautiful beaches. 

Ferries leave from Pounta or Parikia, so you can choose which one works best for your location on the island. Find and book your ferry here. Find ferry times, price, and availability on Ferryhopper.

Beaches of Paros

Paros has lots of beaches to enjoy. Some of the most highly rated include Kolympethres, Santa Maria Beach, Aliki Beach, and Voutakos. 

However, there are tons of little beaches all over the island that are fun to explore! 

Days 8-11: Milos

Get ready to have a new favorite Greek island! I was blown away by the landscapes of Milos, as well as the adorable fishing villages. 

While Milos is getting more popular, it is still like a mini escape from the business of Santorini or Mykonos. However, it still has great nightlife and amazing views! I think it’s a must visit on your 2 week Greece itinerary.

Kleftiko Boat Tour

A non-negotiable activity while on Milos is a boat tour to Kleftiko. This area of the island is only accessible by boat, but it’s certainly the island’s most incredible landscape. 

This boat tour will take you through bright blue waters and hidden caves, all while stunning white cliffs tower overhead. And if you choose a full day tour, you’ll eat lunch on a sailboat surrounded by the most beautiful water you’ve ever seen.

The water is so clear here that you’ll see hundreds of colorful fish swarming your boat, and yes you most definitely can jump in and snorkel!  

On your tour, you’ll be taken into an amazing naturally formed cave and taught about the history of the island’s beauty.

Of our 5 days on Milos, our boat tour to Kleftiko was by far the highlight. This is the tour I’d recommend you book!

Sarakiniko Beach

While there are no white sands here, Sarakiniko beach is the most otherworldly and fascinating beach on the island. 

Imagine if Greece and Mars had a baby… you would get Sarakinko beach. 

Here you can cliff jump into the bright blue waters below, or swim in the shallow inlet if that’s more your speed.

Because the landscape is made up of these small canyons carved into the rock, you can also go exploring for some amazing spots to take pictures. Just be sure to bring some sturdy water shoes or sandals (I always bring my Teva’s for this reason). 

Firopotamos

One of the most charming fishing villages on the island of Milos is Firopotamos. Not only are the colorful homes built right onto the water just so picture perfect, but it’s also a great place to swim! 

The town itself is very small – there is one beach bar and no restaurants – but great for swimming and taking pictures. 

There are also many little rentals you can stay in here for a super secluded experience. Here are a few that are popular and adorable!

Plaka

The charming town of Plaka is one of the best places to stay on the island of Milos. But, if you aren’t staying up here, you can still visit for the day and experience the quaint beauty of Plaka. 

Here, you’ll find a handful of delicious restaurants with amazing views, cute little shops selling handmade and local items as well as clothes, and one of the best sunset spots on Milos. 

Walk up to the Venetian Castle of Milos for sunset for some of the most amazing views in the Cyclades. It’s about a 10 minute walk from the center of Plaka and gains some serious elevation. But, it’s absolutely worth it for the payoff. 

Mandrakia

My personal favorite little fishing village of Milos is Mandrakia. Mostly because my favorite restaurant on the island is here! 

Medusa is a seafood restaurant situated overlooking the Mediterranean Sea, with an intimate atmosphere and outstanding dishes. Ingredients are locally sourced from Greek farmers and fishermen, with many ingredients grown or caught right on Milos – like the octopus!

I recommend making a reservation ahead of time to be sure you get the chance to eat at this outstanding restaurant. 

There are also a handful of adorable rentals here to consider for your time on Milos. And, there are two small but beautiful beaches located just around the corner from the main area of town. 

Beaches Of Milos

Milos has some incredibly unique beaches, so here are a few of the best ones that I have not already mentioned above.

Firiplaka beach is a long and wide open beach on the south side of the island that is perfect to spend a day at. To get here, you will take a dirt road, but don’t worry a rental car can make it! You can also rent kayaks and license free boats here, as well.

Tsigrado beach is one of the most unique I’ve ever been to. You will need to descend a makeshift wooden ladder to get here – honestly it was really cool! But, it’s not the most accessible beach on the island, for sure. However, I found the swimming here to be amazing.

Papafragas Caves is a really cool spot that has both a beach, and cliffs like Sarakiniko. This is a really cool swimming spot on calm water days!

Days 12-14: Santorini

The last few days of your 2 week Greece itinerary will be spent on the beautiful island of Santorini. This is likely the most popular of the Cycladic islands, and for good reason. 

Because of its popularity, you’ll find that out of the islands on this itinerary, Santorini is the busiest and most expensive. But, I do feel that it’s worth visiting for a few days if it’s your first time in Greece, so here is the rundown of how to visit Santorini in 2 days. 

Oia

The most iconic town on Santorini is Oia (pronounced ee-uh). Think blue domed churches, white washed buildings built into the hills, and gorgeous views of the caldera and Mediterranean sea. 

While in Oia, wander through the walking streets that create the maze of Oia. There are many popular photo spots where tourists pile up to take pictures, but there are even more little corners with amazing views to explore if you just keep wandering. 

Oia is the most popular spot to stay on Santorini, with incredible views of the caldera (the volcano the island was formed from). 

While in Oia, walk down to the beautiful Ammoudi Bay for dinner. Just around the corner from the restaurants is also a ‘hidden’ swim spot to check out. 

Read Also: Packing For One Week In Europe, Summer & Winter

Marvel at the beautiful blue domed churches that Santorini is known for. There are multiple in the heart of town. 

Oia also has tons of boutiques and art galleries to spend time wandering around. While I felt that many of the clothing stores were selling the same thing, there are a couple hidden gems here and there – make it a point to try to find your favorite!

Fira (Thira)

Another common place to stay on Santorini is the town of Fira. This is where we stayed as it was a slightly less expensive option but still has the whitewashed cliffside town feeling like Oia. In fact, I secretly like Fira better than Oia (shh, don’t tell anyone!)

In Fira, take the cable car to the Old Port for amazing views of town, visit one of museums like the Archaeological Museum of Thera, or even attempt the 10k long walk from Fira to Oia for incredible views of the sea and Caldera. 

Akrotiri

The Akrotiri of Santorini is an ancient city ruin you must visit while on the island. It’s the cite of a Cycladic Bronze Age settlement founded between 5000-4000 BC. 

When you visit you’ll see excavations of homes, pottery, and other artifacts from the time this settlement was inhabited. Archaeologists found that the society was destroyed by the eruption of the volcano in the 16th century BCE. 

If you enjoy history and want to learn more about the island, Akrotiri is the best place to do so on Santorini. I recommend this guided tour if you want an in depth experience of the ruins.

Akrotiri Tour Recommendation: Akrotiri Prehistoric City Private Guided Tour

Visit A Winery

Santorini produces wonderful wine, and there are multiple wineries you can visit to learn more about the process. 

I think this is one of the best activities to do on Santorini to learn more about the history and culture of the island. It’s a plus that you get to try some great Greek wine!

2 Week Greece Itinerary Final Thoughts & Options To Extend

There it is, the perfect 2 week Greece itinerary for your first time island hopping in Greece

As always, this itinerary can be adjusted according to your needs and preferences. It’s meant to serve as a guide to help your planning and give you ideas for things to do, how to get around, and where to stay.

If, however, you have longer than 2 weeks and want more places to visit and things to see, here are a few options. Add the islands of Ios, Sifnos, or Folegandros to your itinerary for a slow-paced island experience. One of my personal favorites that we visted but that didn’t make it into this 2 week Greece itinerary is Crete!

Or, simply add more days to the islands in the itinerary above to extend your trip.

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I hope you enjoy your perfect two week trip to Greece using this itinerary & make some amazing memories! <3