Grand Crete: two bases, one island, three very different feels

Crete is so big it feels like several islands in one, which makes it perfect for a simple two‑centre holiday. I like to keep things easy with two main bases and one “journey day” that doubles as a sightseeing day.

Start in the Elounda / Agios Nikolaos area in the north‑east. Here the pace is gentle: calm bays, pretty harbours and relaxed resorts that are made for lazy mornings, boat trips across the bay and long dinners by the water. It is a lovely soft landing if you are travelling with children or just want that classic “holiday” feeling from day one.

When it is time to move on, check out and drive down towards Heraklion to break the journey at Knossos, the most famous of Crete’s Minoan sites. You can spend a few hours wandering the ruins, talking myths and legends, then continue west in the afternoon.

Your second base is near Chania in the north‑west, which has a completely different mood: a beautiful old harbour, narrow lanes and easy access to some of Crete’s most spectacular beaches. From here you can plan full‑day adventures to Balos, with its turquoise lagoon, and Elafonisi, with pale sand and shallow water that is ideal for children.

You only unpack twice, but you still get three distinct chapters to your holiday: bay‑side calm, ancient history and wild, photogenic beaches.

Practicalities: Most people will fly into and out of Heraklion, then use a private transfer or hire car. As a guide, driving between the Elounda area and the Chania area in one go is roughly 3–3½ hours, so even if you choose not to stop at Knossos you are looking at a single, manageable cross‑island journey between bases.

Dodecanese duo: Rhodes & Kos in one easy hop

If you are ready to try island hopping but do not want anything too complicated, Rhodes and Kos make a lovely, gentle pair. They sit in the same island group, the Dodecanese, and are joined by regular ferries, yet each island has a very different feel.

Rhodes Town makes a brilliant first stop. The medieval old town is wrapped in huge stone walls and feels almost like a film set: cobbled streets, arches, little squares and views down to the harbour. You can spend your days dipping between a nearby beach or pool and the old town itself, timing your exploring for late afternoon and evening when the heat eases and the lanterns come on. It is a wonderful place to wander with a camera and just see where the streets lead.

From Rhodes you then sail on to Kos, turning a simple transfer into part of the holiday. There is something special about rolling your suitcase onto the ferry, grabbing a spot on deck and watching one island shrink as the next one appears ahead.

On Kos, the mood softens into full beach time. It is a flatter island with long stretches of sand and an easy promenade feel in and around Kos Town and the main resort areas. Some families like to base themselves close to town so they can mix pool days, beach time and a wander along the seafront, while others prefer a more self‑contained beach resort and just dip into town when it suits them. Either way, it tends to be a very relaxed, “flip‑flops on, no rush” sort of island.

Practicalities: Rhodes and Kos both have their own airports, so you can usually fly into Rhodes and home from Kos (or vice versa). Local transfers from the airports to popular resort areas tend to be around 30–60 minutes by taxi or private transfer. Ferries between Rhodes and Kos Town are typically in the 2–3 hour range on the main routes, so you can comfortably treat it as a travel half‑day between bases rather than a full day lost in transit.

Corfu: two moods on one lush island

Corfu is a great choice if you like the idea of a twin‑centre holiday but do not want to factor in extra ferries. The island has a very atmospheric old town, plus a coastline of beaches, coves and olive‑clad hills, so simply changing base gives you two very different experiences.

A natural place to begin is Corfu Town and its surroundings. The capital has a distinctly Venetian feel, with pastel façades, fortresses and little streets that are lovely to wander in the cooler parts of the day. Staying nearby means you can dip in and out easily: perhaps a morning exploring the old town, a museum or a fortress, then back to your hotel for pool time and a quieter afternoon.

For the second part of the trip, head up to the northern coast. Here Corfu feels softer and more rural, with bays, headlands and hillside villages. You can choose between smaller coves and boat‑hire spots, or broader sandy beaches that are ideal for younger children. Either way, days tend to fall into a happy rhythm of swims, simple lunches and exploring the coastline at your own pace.

Practicalities: Corfu has a single main airport close to Corfu Town, so the island works well as a fly‑in, fly‑out option with one flight in each direction. Transfers from the airport to hotels near the old town are usually around 10–20 minutes by taxi or private car. Driving from Corfu Town up to popular northern resorts is typically 45–90 minutes depending how far along the coast you go, so it feels very manageable as a one‑way journey between your two bases. Car hire is optional rather than essential: near Corfu Town you can rely on taxis, walking and local buses, then decide whether to add a car for a few days in the north if you want to beach‑hop and explore more than one area.

Culture to caldera: Athens, Naxos & Santorini

If you like the idea of a slightly bigger adventure, a three‑stop route linking Athens, Naxos and Santorini gives you a mix of history, easy beach time and wow‑factor views, all joined together by ferries rather than lots of extra flights.

A natural starting point is Athens. Spending a couple of nights here turns a simple flight into a city‑plus‑islands trip. You can visit the Acropolis and its museum, wander through Plaka and the surrounding neighbourhoods, and enjoy the feeling of being in a working city with thousands of years of history layered underneath.

From Athens you sail out into the Cyclades and on to Naxos. On the faster catamaran services the crossing is roughly 3 hours 15 minutes. Naxos is often recommended as one of the most family‑friendly islands in the group, thanks to its long sandy beaches and more low‑key feel. Days here are about swimming, sandcastles and simple taverna lunches, with the option to head into the greener interior to explore traditional villages. For many people this is the “heart” of the holiday: relaxed, barefoot and easy.

To finish, you hop over to Santorini for that classic caldera view. Fast ferries from Naxos to Santorini are typically around 1½ hours, so it is a short, satisfying hop between islands. White villages spill down the cliffs, blue domes pop against dark volcanic rock, and sunsets can be spectacular. It feels a little more dramatic and grown‑up, which works particularly well for older children and teens.

Practicalities: Most itineraries work well flying into Athens and out of Santorini, with one ferry from Athens to Naxos and a second ferry from Naxos to Santorini in between. The timings keep the journey feeling like part of the experience rather than a big travel day, and you still only unpack three times for a holiday that includes city culture, soft‑sanded beaches and those famous caldera views.

Whether you end up on one island or a little hop between two or three, I hope this has given you a few new ways to think about your next Greek escape. I also work closely with some lovely Greek hotel brands, so any properties I recommend will always depend on who is travelling and how you like to holiday.