Greek Islands by Rail – An Odyssey Through the Cyclades

With pine-clad mountains rising above impossibly blue seas, a trip to the Greek islands is a once-in-a-lifetime adventure. But, with so many enchanting isles spread across both the Aegean and Ionian Seas, it can be tricky to plan the perfect island-hopping itinerary.

Spring is a wonderful time to see popular destinations like Santorini and Mykonos without the summer crowds. Plus, the weather is warm but not hot.

1. The Cyclades

The dazzling isles of the Cyclades, scattered through the heart of the Aegean Sea, are known for their cosmopolitan blend of beauty and history. From the clifftop opulence of Santorini to the party-mad energy of Mykonos and the serene tranquillity of Naxos, each island in this stunning archipelago offers something unique to visitors.

It is easy to see why the islands attract all types of holidaymakers, from intrepid explorers to young couples and families. There is no shortage of things to do in the Cyclades, from scuba diving in crystal-clear waters off of Ios to hiking in the smouldering mountains of Milos. And, as well as the crystalline beaches and awe-inspiring sunsets, there are also ancient ruins to explore and a culture steeped in mythology.

Thankfully, it’s easy to travel around the islands by ferry and bus. Ferries connect the most popular islands, while local buses and taxis can be used to reach the smaller spots dotted across the Aegean. The only thing to be wary of is that ferries operate less frequently during the winter.

Once you have your ferry tickets, it’s just a matter of planning the best itinerary for you. If you are after a beach lover’s route, start by visiting Naxos and its sweeping white-sand beaches, then move on to Ios and its spectacular east-coast coves. Then finish your journey with the volcanic island of Paros and its deluxe cave hotels.

Alternatively, head to Corfu for its UNESCO-protected Old Town and the pristine beaches of the north coast. Then, visit the lesser-known Paxos, with its three charming bays and satellite island, Antipaxos, which boasts iconic blue waters. Or, visit Kefalonia, with its woodland villages and Shipwreck Beach, or Zakynthos, which welcomes scuba divers with its underwater wreckage. And then there’s tiny Ithaka, the home of Odysseus, which enchants with its wild forests and scenic coastlines. It’s a true island-hopping Odyssey. Just make sure to pack your sunscreen!

2. The Ionian

With its sun drenched islands and ancient sun bleached ruins, Greece has inspired romance and heroism through the ages. From Homer’s Odyssey to Zorba the Greek, there is no shortage of tales of legendary journeys and daring deeds. But today, you don’t need to be Odysseus or a billionaire to travel the Greek Islands. With a little thought, patience and the right ferry schedule, an island-hopping odyssey across the 6,000+ Greek Islands can be a truly memorable experience.

The best time to go island hopping in Greece is between spring and summer, when the weather is warm but not scorching, and the crowds haven’t yet descended. We recommend a trip in April or May to see the highlights of the Cyclades, like Santorini and Mykonos, before the season gets going. Or plan a trip in late June or July to experience the iconic Ionian Islands, including Corfu, Cephalonia, and Kefalonia.

Rule Number One: Choose a ferry route with good connections to the mainland. This will be your back-up in case of adverse weather or other unavoidable delays. Rule Two: Make sure your ferry ticket is booked in advance. Especially during high season, there are often limited ferry seats available, and they can sell out quickly.

The easiest way to book a ferry is directly through Blue Star Ferries and Hellenic Seaways. They have online ticketing systems that allow you to easily check availability and to book your tickets in advance. You can also reserve your ferry seat with a Eurail Pass, though this option is only available for non-European residents.

With Great Rail Journeys planning your train travel from the UK as well as your ferry tickets, you can relax and enjoy every mile of your island hopping adventure. Get in touch and we can start planning your perfect journey through the heart of Greece.

3. The Dodecanese

There are 6,000 Greek islands to explore, and each has its own character, from whitewashed houses lining a secluded cove to bustling harbor towns brimming with tavernas. But it’s the Greek landscape itself that draws you in, with a sun hardened panorama sculpted by wind and waves.

The Dodecanese, a cluster at the southeastern edge of the Aegean Sea, serve as a bridge between Europe and the East. Here you’ll find evidence of the Minoan and Mycenaean trade that drove the archipelago’s earliest inhabitants, as well as successive waves of European settlers – Ionians, Romans, Byzantines, Venetians and Ottomans. This rich legacy is evident throughout the island chain, from Rhodes’ ancient acropolis and stadium to the medieval structures in Lindos and Ialyssos.

In the modern era, the Dodecanese have been ruled by Greece (since 1912) and Turkey (since 1949). Today, they are a bridge between Europe and Asia, with a vibrant economy based on tourism. The islands are known for their beaches and cuisine, and a variety of cultural and archaeological sites.

A group of 24 inhabited islands and 220 total isles, the Dodecanese offer some of the best-known Greece island destinations – Mykonos, Santorini and Kos – as well as lesser-known gems like Astypalea, Kalymnos and Karpathos. It is here you’ll find pristine beaches backed by lush forests and awe-inspiring cliffs, as well as medieval cities full of cobblestoned streets.

Countless archaeological excavations and surveys have been carried out on the Dodecanese, especially on the larger islands of Rhodes and Kos, but the archipelago’s past is still unfolding. For example, recent discoveries suggest that the Dodecanese served as a meeting point for Western and eastern traders in the late Bronze Age and early Iron Age.

The beauty of island hopping in the Greek Islands is that there’s something for everyone, from hikers and naturalists to culture seekers and history buffs. A trip to the Dodecanese is also a great choice for families. Children under 4 travel free and do not need a Greek Islands Pass, however you will need to add a Child Seat to your booking.

4. The Cypriots

The most famous of Greece’s island groups, the Cyclades are home to the awe-inspiring cliffs and sunsets that the country is known for. Start the trip off right in Santorini, where you can rub lines from your bucket list at the Parthenon and walk the quaint cobbled streets of its capital city. From there, it’s on to Ios, a party-centric island where you can take in the raucous nightlife before crossing over to Paros, a laid-back oasis where you can slow down and savor fresh seafood by the sea.

Aside from a handful of larger islands, most of the Greek Isles are served by ferries that operate year-round. The best option is to fly into Athens’ main international airport, Eleftherios Venizelos, and then transfer to the local metro system for a ride to Piraeus port, which is where all inter-island ferries leave from. The best times to visit the islands are in early spring, late summer and autumn.

The Peloponnesian Islands lie south of Athens and retain a strong cultural identity influenced by neighboring countries. Aside from the gorgeous beaches, they also boast historic ruins and beautiful architecture. One of the best ways to explore this island group is on a scenic rail line that runs from Katakolo in the west to Olympia, birthplace of the Olympic Games.

The smallest of the Ionian Islands, car-free Hydra is a small island with pretty blue-and-white houses and lush pine trees. Spetses has a Nantucket-like charm with horse-drawn carriages and yachts parked in the harbor, while family-friendly Poros offers a large town crowned by a clock tower and tree-shaded beaches. Finally, Aegina, the closest island to Athens, has a lovely waterfront and its own ancient temple.

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