Greece is famous for its islands and many visitors are looking to arrange the perfect Greek island-hopping trip. And rightly so, because Greece has more than 6000 of them, in all shapes and sizes. Of these islands, only around 230 are inhabited. When visiting Greece, island-hopping is highly recommended but choosing which ones to visit is a challenge.
The islands are divided into six different island groups: Saronic, North Aegean, Spades, Ionian, Cyclades, and the Dodecanese. Each of the island groups has its culture and vibe, and each island within the grouping is different. In addition to the island groups are the large Aegean islands of Crete and Evia which do not officially belong to any of the groups. The islands are connected by ferry service. The largest islands have airports.
Most islands have a main town "Hora" but also have smaller towns and villages scattered. There's usually some sort of public transportation, but that might be donkey-taxi or a tired bus that makes one trip an hour (or so). Most islands will have a very laid-back kind of taxi service. The busiest islands are better served by multiple bus routes and may offer scooter or car rentals.
I would suggest breaking down your research into chunks by first deciding on an island group(s) best suited for your needs. Then look into individual islands and towns. Whether you choose an island or two within each island group or spend all your time in one, you are sure to find exactly what you are looking for. Ferries can get expensive especially if you choose the fast ferries. Budget travellers can save money by choosing slow ferries and fewer islands.
For Venetian/Roman/Greek history, the Dodecanese Islands which include Rhodes, Kos, and Palmos, have lots to see. Located on the southeast side of the Aegean between the Cyclades and Turkey, the Dodecanese are a cluster of 165 large and small islands, but only 26 are inhabited.
These islands are famous for their medieval architecture. Rhodes is especially medieval with its fortified port, seven gates, and palace of the Grand Master. The history can be felt as you meander through the streets of the old town. Kos is also famous for its medieval character but also attracts those looking for beaches. In Kos, you can even enjoy sitting under the same tree where Hippocrates used to hold classes for his students. Each island has its own unique character deserving of your time.
The Ionian Islands
The 14 inhabited Ionian Islands include the popular islands of Corfu, Paxos, and Keflonia. These islands are more Renaissance/Baroque in atmosphere and tend to be greener. Like most Greek islands these islands have wonderful beaches. Expect to see neoclassical towns with Venetian forts and castles and the remains of Ottoman fortifications.
The Cyclades Islands
This is the island group with the iconic blue/white buildings and amazing classical history and archeology. Some of the best known islands are part of the Cycladic group including Santorini, Mykonos, Naxos and Andros. (Check the links for posts on the individual islands). Some islands attract the luxe crowd and feature shopping or nightlife (Mykonos, Santorini) while others are much more laid back (Naxos, Andros)
There are approximately 220 islands in this group, all clustered in a rough circle in the Aegean. Visitors can easily spend their entire trip just in this island group. Beyond the amazing beaches, the Cyclades Islands are home to the iconic blue/white buildings, windmills, and stunning beaches. Santorini includes an archeological site called Akrotiri which calls itself the Greek Pompeii.
Famous Santorini (Thera) is a volcanic island, with unique black and red sand beaches and stunning sunsets. Mykonos is a cosmopolitan island attracting the jet set crowd while Tinos attracts religious pilgrims. Delos has all the ancient archaeology to fill a nerdy heart. Andros is warm and friendly and has some of the tastiest food in the islands... which is really saying something.
The Saronic Islands
The Saronic Islands are closest to Athens and are very quiet. For travellers on a shorter trip should consider this island group for a couple of days or as a daytrip from Athens. These islands have become increasingly popular since the 1960s. Hydra, once the home of wealthy marine captains, is pedestrian-only and quite lovely. It has a rich history and was very important during the Greek War of Independence in the early 1800s and was the vacation home of the late Leonard Cohen for many years.
Aegina is quite popular, especially for boaters and family trips. It is known for its spectacular beaches and excellent fishing. The beaches aren't as great but nearby Moni island has a private beach with regular water taxi service.
Poros is extremely popular with locals who flock to the beautiful beaches and local hotels and resorts. Summer weekends should be booked well in advance.
The Sporades, or scattered islands almost in the center of the Aegean. The Sporades are comprised of many islands but the most well known are Skiathos, Skopelos, Skyros, and Alonissos. These islands offer stunning natural landscapes and beautiful views of the surrounding sea. Although each island has its own unique character visitors can expect vast pine forests, olive groves and cypress groves. According to legend, the islands were formed when a couple of the young gods threw rocks into the sea.
Skiathos is the island where the movie Mamma Mia! was filmed. It has a strong tourism industry with plenty of excursions and a thumping nightlife. Skopelos is virtually untouched by tourism, offering the perfect location for those looking to chill and enjoy nature. Alonissos is even quieter but has a reputation for fantastic food and stunning sunsets. Skyros, with lots of greenery and smooth sandy beaches, is the most popular with locals.
North Aegean Islands
Situated very close to the coast of Turkey, the North Aegean Islands have a charm of their own. These islands have a long naval history and were very important during the War of Independence. These islands are the setting for several Greek myths and are mentioned in the works of famous ancient writers such as Homer. Some of the best-known of these islands are Ikaria, Lemnos, Samos, and Fournoi. Each is surrounded by crystal clear waters and stunning beaches while the interior of the islands are populated by villages scattered in amongst the lush green hills and valleys.
Ikaria is the island where Icarus took his deadly flight too close to the sun and fell. There are several important archaeological sites there, as well as hot air springs for soaking. Lemnos is volcanic and is renowned for its lakes and vibrant villages. Samos has the Pythagoreion dedicated to the mathematician, Pythagoras and Heraion dedicated to the goddess Hera. The former pirate hideout of Fournoi is now known for birds, seals and sea turtles.
Crete is the biggest and most populated island in Greece. It is considered by many to be the most beautiful of all the islands. Crete is large enough to spend one's entire trip exploring. The rare pink-sand beaches, forests, snow-capped mountains, and medieval cities will ensure everyone has plenty to explore. Most famous are the ancient Minoan palaces.
Evia is the second-largest island of Greece after Crete and is mentioned in several Greek myths. It is also the only island you can drive to from Athens, via the town of Halkida. Similar to Crete, Evia has plenty of archeological and historical significance and sites.