There’s nothing quite like island-hopping in Greece: bouncing over Homer’s “wine-dark” seas aboard a stately ferry; longing to jump ship at every pine-stippled isle – each more beautiful than the last; watching black-clad grannies holding bags of honey-doused baklava and old men clutching time-worn komboli worry beads as they jostle to get aboard. 

The journey itself is half the fun, but best of all is the chance to discover not one but several destinations on a single itinerary, from lesser-known outposts where ships dock a few times a week to lively party islands that greet hundreds of new visitors several times a day. Every Greek isle has its own character – and with more than 227 inhabited options to choose from there’s enough to keep you busy for a lifetime. 

So where to start? I could have suggested a dozen options, but this 11-day itinerary is perfect for first-time Greek island-hoppers, featuring a combination of both headline-grabbing and lesser-known destinations. 

You’ll visit the marble-pillared Parthenon in Athens and the city’s yacht-lined Riviera, Santorini’s blue-domed churches and spectacular caldera, Crete, renowned for its wonderful scenery, cuisine and hospitable locals, and Karpathos, an island of spectacular sandy beaches, hidden coves and time-warped villages. Think of it as a Greek meze, designed to give you a taste of the country’s dazzling array of flavours in one sitting.

Board a morning flight to Athens, Greece’s colourful and chaotic capital (BA, easyJet, Ryanair, Jet2, Wizz and Aegean all fly there from the UK). For the smoothest experience possible, reserve a ride with local firm Greece Private Transfers to arrive in air-conditioned style at your base for the next two days: Divani Palace Acropolis. Situated in the shadow of the city’s most iconic monument, this elegant hotel, clustered around a plant-lined courtyard pool, is quite literally part of the fabric of Athens, built as it is atop the old city walls (you can see them in the basement).

Follow the leafy streets of the Plaka district to Melina Mercouri, a cosy cafe stuffed with photos and memorabilia dedicated to the actress and star of classic Greek film Never On A Sunday. Fill up on manitaropita (mushroom pie), before tackling the steep slopes to The Acropolis, home to the 2,400-year-old Parthenon temple. After exploring the citadel, admire the marvels in the Acropolis Museum before wandering down bougainvillea-adorned alleys to traditional kafeneion Glykis for meze. End your perfect Athenian day with cocktails on the rooftop terrace at Odos Lysiou. 

Greece is rightly renowned for its delicious and (mostly) healthy cuisine, and Athens has a fantastic variety of restaurants, from little family-run koutoukia and simple ouzeris to more modern fine-dining venues. Note that Greeks eat late, with lunch typically taken around 2pm and dinner at 10pm, so you’ll have plenty of time to work up an appetite.

To snaffle the city’s most superlative souvlaki, seafood and handmade pastries, sign up for a local-led neighbourhood tour with Culinary Backstreets. Its guided trips showcase the edgy northern Exarchia district, with its murals and record shops, and – more conveniently for guests at Divani Palace Acropolis – Plaka, among others.

If you prefer to go solo, make a beeline for American-style diner Gastone, near the Varvakios food market, where the Liakos brothers’ tweaked versions of Greek street food (like tzatziki made with creamy gorgonzola cheese) are making waves, or Dopios, run by creative chef Christoforos Peskias, where highlights include shrimp popcorn.

For more on what to see and do (and where to eat and drink) in Athens, see our guide. 

Once little more than a grungy ferry hub, Piraeus is now a destination in its own right, so set aside a few hours to explore its cutting-edge art galleries housed in repurposed warehouses (a new metro link from Syntagma Square whizzes you there in 15 minutes). Fill up on freshly grilled octopus and yellow split pea fava at family-run kafeneio Riris (127 Klisovis St).

There is no shortage of departures for your first island – Mykonos – with most services leaving early in the morning and taking around four hours. Opt instead for the mid-afternoon high-speed ferry, which takes a shade over two (getting into Mykonos at 5pm). 

Take a taxi to your digs for the night, Bill and Coo Suites, a sophisticated design hotel with wraparound sea views and a restaurant serving succulent Mediterranean fusion treats. Ditch your bags, take a peek at the five famous Kato Mili windmills, and then find a table at one of the bars in the waterfront-facing Little Venice for a sundowner. 

Later, if the mood takes you, join celebrities dancing until (almost) dawn in the string of hip clubs that line the silky sands of mega yacht-spiked Psarou Bay. 

For more on what to see and do (and where to eat and drink) in Mykonos, see our guide.

Greece’s party island is fun for a night, but spectacular Santorini deserves more of your time. Hop on one of Seajets’ high-speed catamarans and it is only an hour’s ferry ride away; the leisurely glide into the volcanic isle’s high-sided caldera, topped by a snowy ruff of villages, is magical – and sure to cure any lingering hangover.

From Canaves Oia Epitome to the new Santo Pure, Santorini is littered with lovely hotels, but for the perfect base away from the crowds (but close to the main sights) it has to be Magma, a luxurious complex with a cocoon-like spa, vast suites with private pools and a gourmet restaurant, near Oia. From here it’s a 20-minute ride (by bus or taxi) to Akrotiri, the fascinating Minoan site known as the ‘Greek Pompeii’, which was buried under volcanic ash around 1500BC. 

Santorini is famed for its sunsets, but don’t bother battling with Oia’s crowds. Instead, hop on one of Santorini Yachting Club’s smart catamarans for a sunset cruise (book in advance). They leave from Vlychada’s pebble beach, a 10-minute bus ride from Akrotiri. After swimming in hot springs, you’ll end your day in Ammoudi Bay, where your bobbing yacht is the perfect place to watch the sky turn pink over the world’s most famous volcanic caldera.

Back on dry land, head for no-frills restaurant To Psaraki in Vlychada, where chef Thanasis Sfougaris serves up some of the island’s best seafood.

Just 10 minutes’ water taxi from Santorini’s bustling Ammoudi harbour, the tiny island of Thirasia is a blast from the past. Described by locals as like Santorini 50 years ago (before mass tourism arrived), there’s only one road connecting its five villages and most locals get around by moped or mule.

You’ll get a good overview of this time-warp island on a hiking tour with Explore Thirasia, who’ll lead you along overgrown paths to discover Agrilia’s abandoned cave dwellings, clamber the 270 steps to Thirasia’s lofty capital of Manolas, with its epic views over to Oia, and snack on meze served with brimming tumblers of raki punch in one of the tavernas lining the waterfront of Korfas, the island’s tiny port.

Back on Santorini once more, eschew Oia’s expensive restaurants and head for local-loved taverna Tou Steki Tou Nikou in Imerovigli, where you can enjoy home-cooked food, including crunchy ntomatokeftedes (tomato fritters), for half the price.

With its lost-in-the-past mountain villages, world-class beaches and near-deserted archaeological sites, Crete, just two hours’ ferry ride from Santorini, provides a striking contrast to the first half of this itinerary. Known to Greeks as the megalo nisi (big island), it’s a seven-hour drive from tip to toe, so you’ll need wheels: Cretarent can arrange to have a car waiting for you in Heraklion’s bustling port. 

Head west along the potholed palio dromos (old road), which loops between lofty mountains and beach-lined coast to Chania. Dump your bags in one of the spacious top-floor suites at the central Samaria Hotel, and then head out to shop for silver jewellery, traditional stivani leather boots and other souvenirs in the labyrinth of shopping streets surrounding Chania’s Venetian harbour. 

When hunger hits, grab a harbour-side table at family-run mezedopoleio Ta Xalkina, where you’ll be serenaded by the wild sounds of live Cretan music as you snaffle xochloi (snails) in a garlicky sauce and other succulent meze snacks.

Rouse yourself early, check out, and then drive along a nail-biting mountain road to Hora Sfakion, where boats will be waiting to whisk you over to the remote beach of Agia Roumeli. The beach lies at the southern entrance to the 10-mile-long Samaria Gorge. Follow the trail for as long as you wish, keeping your eyes peeled for mountain goats, soaring eagles and massive griffon vultures, before retracing your footsteps back to the coast. Reward yourself with a refreshing dip in the crystal-clear waters. 

Return by boat to Hora Sfakion and drive across the island’s forested spine to Rethymnon (Second World War buffs should pause to visit Askifou’s relic-packed war museum). Lunch on claypot-baked tsigariasto lamb at family-owned Othonas, in Rethymnon’s bougainvillea-lined old town, and then stroll the jasmine-scented streets in search of the town’s beautifully preserved Ottoman mosques and Venetian loggias. Grab a honey-drizzled slice of baklava at the workshop of Crete’s last traditional phyllo pastry master, Giorgos Hatziparaschos (on Vernardou Street). Spend a restful night at Kapsaliana Village Hotel, a lovingly restored, stone-built complex that once belonged to Crete’s 16th-century Arkadi monastery. 

After a lazy breakfast of bougatsa (custard pie) in the hotel’s delightful olive tree-shaded restaurant, follow the winding coast road to Heraklion. 

Whatever your opinion about its controversial restoration, the palace of Knossos, mythical home of King Minos and the Minotaur, is well worth a morning of your time. After your visit to the site, just south of Heraklion, marvel at the Minoan frescoes in the city’s beautifully renovated archaeological museum, and then make a beeline for Kritamon, in the busy little village of Archanes, nine miles south of Heraklion, where chef Dimitris Mavrakis has a deliciously innovative take on Cretan classics.

From here it’s an easy two-hour drive via a string of remote mountain villages to Sitia. With its unspoilt beaches, steep streets and low-key tavernas lining the waterfront, this town is a slice of real Crete. There are only a handful of small hotels, with the best of the bunch being cosy Porto Kaza, with stunning harbour views. 

Drop off your luggage and descend to Meraki, where you can snaffle kalamari swimming in a rich wine sauce, local pasta kritharoto served with asparagus and lashings of nutty Cretan graviera cheese, and other sumptuous dishes as you watch locals enjoying their leisurely evening volta (walk) along the waterfront.

For more on what to see and do (and where to eat and drink) in Crete, see our guide. 

The ferry from Sitia to Karpathos usually leaves in the early afternoon, so if the weather’s good get up early and make the half-hour drive to Vai beach, where you can lounge on the same idyllic palm-fringed sands that once featured in the Bounty chocolate bar ads. Back in Sitia, head for Savoidakis bakery to buy spinach-stuffed spanakopita and wild greens-packed hortopita pies to sustain you for the five-hour crossing. 

Stretching some 30 miles from the little port of Diafani in the north to the windsurfing beaches of Makrigialos and low-key capital Pigadia in the south, this dazzling Dodecanese island is way off most tourist radars. 

Call in advance to arrange a hire car via the genial Mixalis Reisis from local company Karpathos Travel, and drive for an hour along vertiginous mountain roads to Afoti Beach Hotel, a boutique beauty overlooking one of the island’s most popular strips of sand, which also has a small taverna serving seafood, burgers and snacks, along with a great range of cocktails.

Karpathos has some of Greece’s loveliest beaches, but be warned: many of those idyllic, pine-fringed shores can only be reached via steep dirt roads. Spend the day lounging on Apella’s sandy beach, backed by a tiny 13th-century church, or swimming from dune-strewn Diakofti’s remote coves.

In the afternoon, make your way to the mountain village of Olympos. Cut off from the outside world until a road was built in the 1980s, it offers a trip back in time, and women – who still dress in colourful traditional costumes – are said to rule the roost. You won’t get luxury here, but Olympos Archipelagos has clean and comfortable two-storey villas teetering above the wide expanse of Fisses Bay.

End your epic island-hopping trip with a sunset supper at O Mylos, in a former windmill, where traditional dishes (try the hand-rolled makarounes, slathered with goat’s cheese) are as good as the views.

There are daily flights from Karpathos Airport, eight miles from Pigadia, to Athens. From the Greek capital it’s easy to find connecting flights to all the main UK airports.

Although ferries still travel the main routes during colder months, connections tend to be less frequent – so it’s best to travel between May and mid-October.

June or September is your best bet: the weather is generally good (bring a light raincoat just in case) and not too hot, ferries and accommodation – the busy Easter period excepted – are cheaper than in high summer, and it’s far less crowded. 

Most ferries included in this itinerary run at least once a day between May and October, but secure your tickets in advance (ferryscanner and ferryhopper are among the best booking sites). The Sitia to Karpathos ferry only runs twice a week, however (usually Wednesdays and Saturdays), so check carefully and plan the rest of your itinerary around these dates. 

Don’t fancy doing all the legwork? While different from the holiday described here, Sunvil has a range of island-hopping itineraries, such as its two-week Western Cyclades itinerary, which features Santorini, from £1,041pp. For something stylish (but sustainable), tall ship sailing company Star Clippers offers seven-night island-hopping cruises in the Sporades from £2,249pp, including flights. 

Greece is pretty laid back when it comes to sartorial style: swimwear, shorts, T-shirts and an extra layer for those cooler evenings should be more than enough (plus something to cover shoulders and legs if you plan to visit churches). Out of season you’ll need a few jumpers, jeans and a raincoat.

Must-read books include Victoria Hislop’s The Island, Nicholas Gage’s wonderfully gripping Eleni and Nikos Kazantzakis’ Report to Greco.

Diesel-powered ferries are often pretty filthy so have some grungier clothes for travel days. It can also get chilly on deck, so bring a warm shawl or coat. Ferries also have an incredibly fast turnaround, so grab your luggage and get ready to leave as soon as the boat docks. 

Ferries are generally very reliable, but they’re sometimes cancelled due to strikes or weather conditions – make sure you have good travel insurance so that you’re covered just in case.

Knossos will be one of the highlights of your trip to Crete, but if you want to get the best out of this sprawling site it’s best to book a guided tour.

Despite rising prices due to inflation, eating out in Greek tavernas is still pretty cheap, especially in less touristy parts such as Karpathos or eastern Crete. If you’re on a tight budget you can easily get by on Greek street snacks such as the ubiquitous gyros, a pita stuffed with meat, chips, chunks of onion and tomato, and tzatziki.

Although crime is almost non-existent on the islands, overcharging can be an issue at bars and restaurants in Mykonos – check carefully both prices on the menu before ordering, and your bill. Cover charges at clubs like Nammos can also be exorbitant.