Rethymno Province

Basking between the commanding bastions of its 15th-century fortress and the glittering azure waters of the Mediterranean, Rethymno is one of Crete’s most enchanting settlements. Its Venetian-Ottoman quarter is a lyrical maze of lanes draped in floral canopies and punctuated with graceful wood-balconied houses, ornate monuments and the occasional minaret.

Crete's third-largest centre has lively nightlife thanks to its sizable student population, some excellent restaurants and a worthwhile sandy beach right in town. The busier beaches, with their requisite resorts, line up along a nearly uninterrupted stretch all the way to Panormo, some 22km away.

Located 25km southwest of Rethymno, Argyroupoli is built on the ruins of the ancient city of Lappa, one of the most important Roman cities in western Crete, though very few remnants of it survive. Argyroupoli's network of atmospheric cobblestone alleyways lined with Venetian-era stone houses and Byzantine churches makes it a lovely place to stroll. As it's in the foothills of the Lefka Ori (White Mountains), the town is a useful gateway to some fine hiking trails.

At the bottom of the town is a watery oasis formed by springs from the Lefka Ori that keep the temperature markedly cooler here than on the coast, making it a good place to escape the summer heat. Running through aqueducts, washing down walls, seeping from stones and pouring from spigots, the gushing springs supply water for the entire city of Rethymno.

The 16th-century Arkadi Monastery, 23km southeast of Rethymno, has deep significance for Cretans. As the site where hundreds of cornered locals massacred both themselves and invading Turks, it's a stark and potent symbol of resistance and considered a catalyst in the island's struggle towards freedom from Turkish occupation.

Arkadiou’s impressive Venetian church (1587) has a striking Renaissance facade topped by an ornate triple-belled tower. The grounds include a small museum and the old wine cellar where the gunpowder was stored.

Set beside a sweeping sandy crescent and accessed via two scenic gorges – Kotsifou and Kourtaliotiko – Plakias gets swarmed with package tourists in summer (when it can be very windy) but otherwise remains a laid-back indie travellers’ favourite. While the village itself isn’t particularly pretty, it's an excellent launch pad for regional excursions and hikes through olive groves, along seaside cliffs and to some sparkling hidden beaches.

Tiny Margarites, 26km southeast of Rethymno, is famous for its pottery, a tradition that can be traced back to Minoan times. The village has only one road, and no bank or post office, but it boasts more than 20 ceramics stores and studios. Most studios source their clay by hand (the area is known for its clay), and offer unique, bright and good-quality usable pieces. This is the perfect place to pick up a keepsake.

If possible, try to avoid mornings and lunchtime, when droves of tour buses flood the town. By afternoon all is calm, and you can explore the atmospheric alleyways, wander through the studios and enjoy wonderful valley views from the eucalyptus-lined taverna terraces on the main square.

Perched beside Mt Psiloritis, 37km southwest of Iraklio, Anogia is a wonderful spot to slow things down and glimpse authentic rural Cretan life. It's the perfect base for excursions up to the Nida Plateau (1400m) and Zeus' cave.

Here locals cling to time-honoured traditions, and it’s the norm to see men gossiping in the kafeneia (coffee houses), flicking komboloïa (stringed beads) in their hand, and dressed in traditional black shirts with vraka (baggy pants) tucked into black boots. Elderly women, meanwhile, keep busy selling traditional woven blankets and embroidered textiles. The town's turbulent history – in WWII and under Ottoman rule – has instilled a legacy of rebelliousness and a determination to express an undiluted Cretan character.

The town's also famous for its stirring music and has spawned many of Crete’s best-known musicians, such as Nikos Xylouris.

• Start Rethymno
• Finish Rethymno
• Length 150km; one day

The Amari Valley is a quilt of unspoilt villages punctuated by Byzantine churches and framed by olive groves and orchards. Mt Psiloritis looms grandly above the landscape. You'll need a good map to navigate around here; a map app on your phone or GPS will do the trick. Given that the villages here have tight, narrow, one-way lanes, hiring a small to medium-sized car will generally make life easier.

Begin with a visit to the ever-impressive Moni Arkadiou. To reach it, head east from Rethymno, take the turn for Adele and follow the signs. Continue south to Thronos, whose Agia Panagia has extraordinary, if faded, 14th-century frescoes (the key is available at the cafe next door, whose owner will give you a quick rundown). The mosaics on its floor are even older, remnants of the 4th-century basilica that Agia Panagia was built upon. Drop by nearby Taverna Aravanes for wonderful valley views, good local info and traditional Cretan food that's cooked in a wood-fired oven; cooking classes (€6 per person) can also be arranged. From here, head downhill and turn left for Fourfouras.

Follow the signs to Amari, an enchanting medley of Venetian buildings and a square filled with cafes and overflowing flowerpots. Climb the 19th-century bell tower to share beautiful views with the pigeons. Continue on to Monastiraki, home to a Minoan site. It's badly signposted, so ask locally for directions, and keys if it's locked. Carry on through Lamiotes, turning east after Petrochori. Pass through olive groves, stopping at the remains of the 7th-century Bizari Basilica, destroyed in 824 by the Arabs.

In Vizari, visit olive-woodworking shops, then head east to pretty Fourfouras, where trails climb up Mt Psiloritis and you can refuel at the gas station and bakery. Head south to Apodoulou, for the ruins of the manor of Kalitsa Psaraki, named for a girl abducted by Turks and rescued by an English traveller (who then married her). Also here are more stone remains, of a Minoan settlement. Follow a dirt track west of town to Agios Georgios, with its still-colourful 17th-century frescoes.

Return north, taking the turn for Agios Ioannis, through the western valley. Turn north for Anomeros and on to Gerakari, which was totally destroyed during WWII by the Germans. Today it's a modern, colourful market town famous for its cherries and wild tulips and its nicely frescoed 13th-century Church of Agios Ioannis. Its main strip has a string of tavernas if you're feeling peckish.

Complete the loop in Meronas, where the 14th-century Church of Maria and its frescoes are a highlight of the trip. Carry on to Agia Fontini, from where you can continue north to Rethymno.

About 2km outside the village of Melidoni is this stunning cathedral-like cave, an evocative underworld of stalactites and stalagmites. A place of worship since Neolithic times, it also carries heavy historical significance as the site of a massacre in 1824 during the Turkish occupation. Here 370 villagers and 30 soldiers sought refuge from the Ottoman army; after a three-month siege, the Turks lit a fire and asphyxiated the people inside, including 340 women and children.