Greek Island Hopping Itinerary: History Meets Paradise

This post may contain affiliate links. Read our Disclosure Policy here

Greek Island hopping is as dreamy as it sounds. With ancient history meeting spectacular beaches, these islands are a place where you can step back through time as you stumble upon ruins, but later in the day relax on one of the many picturesque beaches that dot the hundreds of inhabited islands that make up the Greek archipelago.  

In fact, because of the vast 4600 mile coastline, it is home to a diverse landscape made of up of volcanic soil, sandy beaches and coastal caves just to name a few.

Even though only 227 islands are inhabited, there are actually over 6000 islands scattered in the Aegean and Ionian Seas. With this being said, choosing which islands to visit can be a tad overwhelming.

Most of the islands are found in the Aegean Sea and are divided into seven groups – the Northeastern Aegean Islands, the Sporades, the Evia, the Islands of Argosaronic, the Cyclades, the Dodecanese and Crete.

Best time for Greek Island Hopping

The busiest and most expensive month to go island hopping would be August. High season runs from mid June to mid September. This is when ferries run more regularly, more shops and restaurants are open and of course the weather is warmer.

Shouldering the high season might be the most optimal time to go as you don’t have to deal with as many crowds and prices tend to drop.

Island Hopping in the Cyclades 

Hands down, the most popular group of islands are the Cyclades because they are close to Athens and include the iconic destination of Santorini. The name Cyclades refers to the islands forming a circle around the sacred island of Delos.

If this is your first time visiting Greece I highly recommend planning your itinerary around the Cyclades as they complete every checklist on a Greek island hopping adventure.

Greece Island Hopping - Mykonos


Known as the ‘Island of Winds’ Mykonos is an island like no other. It is centered around its cosmopolitan flair with nightlife and beach parties. If partying is not your thing there are plenty of quieter beaches and of course so much history to dive into.

Mykonos town is called the Chora and is a typical Cycladic village. The narrow streets form a labyrinth and are closed off to traffic during most of the day.

Whitewashed houses with colorful doors satisfy any photographers pallet and stumbling upon the three iconic windmills that date back to the 1600’s just solidify how picture perfect this island really is.

Little Venice is located on the peak of the island and is where you can find all the trendy shops and cafes. Discovering both the Archaeological Museum and Folk Museum is also a great way to spend some time.  You might even wander into the island’s token pelican who likes to pose for pictures!

Greece Island hopping - Mykonos

Another iconic landmark worth seeing in the Chora is the church complex of Panagia Paraportiani. The Church of Agios Efstathios is at the center of the complex and the others are built either on top or beside one another.  The oldest church dates back to the 14th century and the entire complex overlooks the sea.

You can’t visit Mykonos without spending a day at one if its pristine beaches. There truly is something for everyone. From family friendly beaches, to nude beaches to beaches with a plethora of water sports.

Mykonos is like a beach buffet and you don’t have to search very hard to choose your ideal flavor.

Greek island hopping - Delos
Delos Island

Finally the other must-see activity to check off your list is visiting the island of Delos. Take a day trip to Delos either on a ferry or on an organized tour.

The island itself is a UNESCO World Heritage Site and is one of the most important mythological, historical and archaeological sites in the country. Nowhere else in the entire world is there an island archaeological site of this size and importance.

According to Greek Mythology Delos was the birthplace of Apollo and Artemis. The island’s ruins are home to Doric temples, markets, an amphitheater, mosaics and the famous Terrace of the Lions statues.

There is also an Archaeological Museum that hold antiquities from the Archaic, Classical and Hellenistic periods. Visiting Delos is an experience in itself. The landscape is breathtaking and the history makes you feel like you have been thrown into an enchanting story.

Paros - Greek Island Hopping


Paros sometimes gets dwarfed by its cousin Mykonos, however don’t be fooled into thinking it is any less glorious. Some say it is what Mykonos was about 20 years ago, therefore a little less crowded and a little more affordable.

Located in the heart of the Cyclades it is known for its golden sandy beaches, buzzing nightlife and charming traditional villages.

Parikia is the main town in Paros where all the hustle and bustle takes place. Like most Cycladic architecture there is so much character in the whitewashed houses and blue-domed churches.

There is no shortage of restaurants and cafes in Parikia, and all the amenities needed can be found in this center. For this reason, Parikia is a great location to stay in if you want to be close to everything.

Paros - Greek Island Hopping

Peering over Parikia is the hill of Kastro (meaning castle). This castle was built in 1260 by the Venetians and is situated on the highest point of town. Although material and columns from an ancient temple were used to build this once standing castle, the only part that still remains is part of a wall and a tower.

There are several churches that surround the area of Kastro and are definitely worth a visit. One of the most important Byzantine monuments still standing is the Monastery of Panagia Ekatontapiliani (Our Lady of the Hundred Gates).  

The original church was constructed in 4th century A.D. and consisted of a three-aisled basilica. In 6th century A.D., the Byzantine Emperor added a dome to the church.

Throughout the centuries more reformations were performed and today the Church is complex of Paleochristian, Byzantine and post-Byzantine elements.

Paros Greece

Windsurfing and kite-boarding are popular activities in Paros. The main beaches for sports activities are Pounda on the west side, as well as Santa Maria Golden Beach and New Golden Beach on the east side of the island.

The winds are so reliable on New Golden Beach that the Windsurfing World Cup has been held at this location numerous times over the years.

Although Paros has an abundance of its own beautiful sandy beaches, taking a day trip to either Antiparos or Despotiko Island is another activity that can fill your day.

Both islands are adorned with secluded beaches where you can find that slice of paradise that you can truly call your own. Antiparos also has an impressive cave that you can visit that highlights the natural beauty as well as holds historic significance.

There are approximately 400 steps leading down to the heart of the cave where you will be able to view stunning stalagmites and stalactites.

Santorini - Greece Island hopping


Your Greek island hopping adventure wouldn’t be complete without a trip to the stunning island of Santorini. Hands-down the most well-known island, Santorini bears its uniqueness by how the island was actually formed.

In 1600 B.C. a massive volcano erupted leaving the center collapsing into the sea. Now what remains is a crescent-shaped caldera where white-washed villages cling to the rocky edge.

Tourists flock from near and far to catch a glimpse of one of the world’s most glorious sunsets. Oia is the town on the northern tip of the island where the famous sunsets are most visible.

You may be jostling shoulder to shoulder with other sunset seekers, however, watching the fiery ball sink into the turquoise sea truly is an experience like nowhere else in the world.

Santorini - greek island hopping

Hiking along Santorini’s caldera is a great way to see the beauty of the island. You don’t have to be in tip-top shape to do this hike as the paths are well-marked and there are lots of stops along the way.

The hike itself begins in Fira (the main town) and ends in Oia. The hiking trail is about 6.5 miles and takes approximately 3 to 5 hours depending on how fast you walk.

A good pair of shoes and a bottle of water is all you will need. It is also recommended to start earlier in the morning during the summer months to avoid the heat of the day.

Not only is Santorini one of the most visually appealing places in the world, but it is also the home to the Greek version of Napa Valley. Wine-making dates back at least 3000 years on Santorini, yielding 40 native varieties of grapes.

If you consider yourself a wine buff, taking part in a wine tour is a must. There are plenty of tours to choose from a wide variety of wineries. Tours tend to book up during the summer months so booking in advance is recommended.

Santorini volcano Greece

One of Santorini’s most popular excursions is a trip to the volcano. Right now this volcano is an underwater active volcano but you can take a boat tour departing from either the port of Athinios or the old port in Fira.

The first stop is Nea Kameni where you will get to hike up the lava rock and at some points be able to feel the heat of the volcano right under your feet! Next, you will be taken to Palea Kameni which is known for its hot springs. The water contains sulfur and is said to have therapeutic effects, so kick back and soak in the healing hot springs.

If a little more history is what you are looking for then look no further than the Akrotiri Ruins. Right at the southern tip of Santorini are the ruins of one of the Bronze Age’s most sophisticated settlements.

The settlement itself was a prosperous town until it was wiped out by the giant volcanic eruption. Like the Roman ruins of Pompeii, Akrotiri is extremely well preserved.

When the volcano erupted the volcanic debris-covered Santorini which preserved Akrotiri’s buildings and contents. Interestingly enough when the volcanic earth was excavated to provide building material for the Suez Canal an entire pre-historic village was found, preserved and unscathed by nature.

Greece Island Hopping

How to island hop in the Cyclades 

The most cost-effective way to do some Greek island hopping is by ferry. There are small airports on many of the popular islands, however, the ferry system is very easy to use and a great way to enjoy the beauty of the sea.

A great website to book your ferry tickets is through Ferry Hopper, as it provides ferry services and tickets for 36 companies. Just remember that your online booking receipt is not your ticket. You will have to pick your ticket up at the port of call so getting there early is recommended.

Piraeus is the main port of call in Athens and is where the majority of departures leave. There are a few options that take you from the airport directly to Piraeus Port.

The most convenient is by taxi. Standard yellow taxis charge a flat rate and take approximately 40 minutes. You can expect to pay between 54-70 Euros depending on the time of day.

The metro station is a more affordable option at 10 Euros (children under 6 are free), but you do have to change lines. The station itself is only a 10 minute walk from the arrival gate, but the time in transit takes closer to an hour and half.

You would need to take the Blue Line (line 3) to Monastiraki Station and then transfer to the Green Line (line 1) to Piraeus Station.

If you’re not up for figuring out ferry schedules, booking your own accommodation and generally going it on your own on your Greece Island hopping adventure, I highly recommend you check out this epic 10 day sailing trip

Other Greece Island hopping you shouldn’t miss

Beyond the islands that I have been to there are a few others that stand out and are definitely on my must-see list when I have the chance to go back!

Typically catching a ferry to the different islands is easiest if you choose locations within the same group. It could take days of travel time if you are hopping from one group of islands to the next. Therefore sometimes it may be more beneficial to look into cheap flights.

HOT TIP: Don’t assume that flying would be more expensive. Cheap flights are often released between January – March, before the peak season starts. Finding a one way flight to the furthest location might be a better option and then you can ferry hop back to Athens at your leisure.

Hydra - Greece Island Hopping


Part of the Argosaronic Islands, Hydra is a gorgeous island within close proximity to Athens. Just a short 2 hour ferry ride, Hydra impresses its visitors with its simplicity.

There are no motor vehicles allowed on the island, therefore other than by foot donkeys are the key source of transport.

Enjoy the hiking paths in the countryside, the beautiful stone mansions that peer over the harbor and the secluded crystal-blue coves. Step away from the hustle and bustle of everyday life and enjoy true bliss on this cute Greek island full of so much character.

Samos Greece


Separated from Turkey by only 0.8 miles at its narrowest point, Samos is a Greek Island in the Aegean group worth exploring. Although the island itself is quite large, it hasn’t been hit with mass tourism just yet.

Visit the old town in Ano Vathi that is full of architecture with influences from neighboring Macedonia and Anatolia, Turkey. The town itself was created in the 17th century when its residents moved away from the coast to prevent pirate attacks.

Samos is also home to the Temple of Hera which has been deemed a UNESCO World Heritage Site. Samos is also known for its exquisite beaches.

Due to the size of the island, there are no shortages of sandy havens – Potokaki and Lemonakia are among the top of the list to visit. Lastly don’t leave Samos without visiting one of its award-winning Vineyards.

Milos Greece


Part of the Cyclades, Milos is said to be a photographer’s paradise. Its unique appearance is characterized by its lunar-looking landscape. Formed by volcanic activity, the white calcareous rock is a stunning contrast against the turquoise waters.

Not only are there many unmarked caves to discover but Milos is home to one of the world’s most prominent catacombs. These fascinating marks of history date back to the 1st century and are thought to be older than the catacombs of Rome.

Don’t leave Milos without spending some time at one of its 70 beaches. Some even boast red, pink and orange hues.

Rhodes Greek Islands


If you are looking for sunshine Rhodes is the place to go. Being one of the most southerly islands in the Greek Archipelago, Rhodes summer season starts as early as April.

Being the largest of the Dodecanese islands, it is also known for its impressive preserved medieval architecture. Visiting the Medieval City of Rhodes is a must. It is another UNESCO World Heritage Site and is one of the world’s most beautiful urban ensembles of the Gothic period.

Mixed with other buildings that date back from the Ottoman period, the Medieval City is truly a sight like no other. Visiting the Lindos Acropolis is another highlight of Rhodes.

At the top of a steep rock stands the centuries-old Acropolis that is said to compete with Delphi as the second most visited archeological site in all of Greece. Like so many of the Greek islands, Rhodes has no shortage of gorgeous beaches.

Head to Saint Paul’s Bay which is located in the historic village of Lindos.  Nothing could be more picture-perfect than laying on a beach with views of the Acropolis up the rockface, twinkling blue waters of the ocean at your toes and to top it off a cute Greek Orthodox Chapel right in the cove.

Corfu Greece


Situated on the western side of Greece, Corfu is the greenest of the Greek islands. It is actually closer to Albania than it is Greece and is part of the Ionian group. This stunning island is quite different from most as it is heavily influenced by the Venetian, Byzantine and British.

With an island so lush it is suggested to explore Corfu by foot or bicycle. Hike up Mount Pantokrator or discover the saltwater lakes of Korission or Antinioti. Heading to the north part of the island you will discover plenty of hidden gems – secret coves and secluded beaches.

Recommended Tours
Athens to Mykonos
8 days
Small Group
6-8 People
Mykonos to Mykonos
10 days
Small Group
6-8 People
15 days,
Athens to Santorini
Small Group
16-8 People
Check PriceCheck PriceCheck Price

More on Greece:

Did you like this story? Share it!


Looking to get started on your trip planning process? Let us help!

Travel Gear & Packing: Check out our packing lists and travel gear guide to ensure you're bringing the right items on your trip.

Book Your Flight: Ready to fly? Check out our tips for finding cheap flights.

Find A Car Rental:We use Discover Cars to compare car prices, find deals and book rentals.

Book Your Hotel: Compare prices and book with our recommended hotel search engine. You should also check out our tips for finding cheap accommodation.

Find Vacation Rentals: Search vacation rentals & apartments on VRBO for the best prices and options.

Protect Your Trip:Don’t forget your travel insurance! Protect your investment and yourself. Read Is Travel Insurance Worth It?

If you need more help planning your trip, be sure to check out our Step by Step Trip Planning Guide where we break down our process for getting the trip planning process right every single time.

About Heather Halpern

Based in Edmonton, Canada - I caught the ‘travel bug’ many years ago when I was a competitive rhythmic gymnast and haven’t been able to quench the thirst for exploring the world. Even though I live a pretty regular life with a full time job, I aim to take at least one overseas adventure a year. This means, I skimp, save and try to live the happiest life possible throughout the year so that I can experience my one true love…travel!

We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites. We are also a member of other affiliate programs. For more info please read our disclosure page

Leave a Comment

Divergent Travelers- Adventure Travel Blog