Greece is really a choice of islands: the Santorini caldera, quieter Paros and Milos, the gorges and palaces of Crete.
Greece has more than a hundred inhabited islands and each has its own character, so choosing well is most of the work. Santorini is the famous caldera view and the busiest island. Paros and Antiparos are relaxed and easy with children. Milos is all boat days and strange white rock, and Crete is big enough for a week of its own.
We usually pair Athens with two islands at most, linked by ferry or a short flight. Mainland Greece is underrated: the Peloponnese has Mycenae, Epidaurus and the old town of Nafplio, and it stays quieter than the islands in high summer.
The honest caveats are August and the wind. August is the busiest month by far, and the meltemi, a strong northerly wind, blows across the Cyclades through July and August, making smaller boats uncomfortable and sometimes cancelling them. June and September are warmer in the sea and calmer on the water.
The experiences we plan most often, with the months they are at their best.
Stay on the caldera rim in Imerovigli or Firostefani rather than Oia, which fills with visitors at sunset. Walk the cliff path from Fira to Oia early in the morning, then spend an afternoon tasting assyrtiko at a winery in the island's interior. A private catamaran at sunset avoids the crowds on the terraces. Cruise ships make the middle of the day busy from spring to autumn.
Much of Milos can only be reached by water. A day boat takes you to the sea caves and rock arches at Kleftiko, with swim stops in water so clear the seabed looks close enough to touch. On land, Sarakiniko is a moonscape of pale volcanic rock, best seen early. Plaka, the hilltop village, is the place for sunset and dinner.
Paros is the easy island: good beaches, short drives and the harbour at Naoussa lined with fish tavernas. Walk the old Byzantine path from Lefkes to Prodromos in the cooler hours, and take the short ferry to Antiparos for a quieter beach day. It suits families and couples who want a base with little driving.
Crete could fill a fortnight. Walk the Samaria Gorge in the White Mountains, which opens only in the warmer months, and spend time in the Venetian harbour at Chania. Knossos is best early with a guide. Cretan food is its own cuisine: dakos rusks with tomato and mizithra cheese, snails, wild greens and raki after dinner.
Two hours from Athens, Nafplio is an old port town and a good base for Mycenae and the theatre at Epidaurus, where a coin dropped on the stage is heard in the back row. Further south, Monemvasia is a walled Byzantine town on a rock joined to the mainland by a causeway. It is a quieter alternative to the islands in August.
Climb the Acropolis at opening time, then spend the hot middle of the day in the Acropolis Museum, where the top floor looks straight across to the Parthenon. Eat souvlaki in Monastiraki and meze in Koukaki, and finish on a rooftop facing the floodlit temple. Two nights is right before the islands.
On the islands, choose between a village hotel with tavernas on the doorstep and a quieter property with its own beach. On Santorini the caldera side has the view and the other side has the beaches. In Crete, the northwest around Chania has the old towns and tavernas, and the east has the larger resorts.
Stone pavilions on a Peloponnese hilltop, each with its own pool, and a beach club ten minutes down the hill.
Sea-view suites with plunge pools and jetted tubs at Megali Ammos, a short stroll from Mykonos Town but out of its noise.
Whitewashed suites stepped down the Oia cliff, with caldera views from every veranda and the village lanes on the doorstep.
Low bungalows and pool villas along 2 km of Cretan shoreline, with a sculpture garden and a short walk into Agios Nikolaos.
A small hotel in a restored early 20th-century building, with a rooftop pool and restaurant looking straight at the Parthenon.
A large seafront resort among Messinian olive groves, with golf, tennis, a 4,000 square metre spa and a kilometre of beach.
Sample routes to start from. Every one can be changed.
Three nights in Athens for the Acropolis and the museums, then a drive west via the Corinth Canal to seven nights on the Messinia coast, where a kids club, an aqua park and ancient Olympia keep every age busy.
Two nights in central Athens below the Acropolis, four on the caldera cliff at Oia, and three at Megali Ammos, close enough to walk into Mykonos town for dinner. Island hops by ferry, with a Delos day included.
The Greek island season runs roughly from Easter to October, and most smaller hotels close outside it. June and September are the sweet spots, with warm water, long days and less wind than high summer.
July and August bring heat, crowds and the meltemi, which keeps the Cyclades cooler but makes ferry crossings rough. In winter, Athens and the mainland make a good cultural trip; the islands mostly sleep.
A classic first trip that keeps travel short: two nights in Athens, then two islands linked by one ferry crossing. 7 nights.
Arrive and settle into a hotel near the Acropolis. A private guide for the Acropolis at opening, then the museum and dinner in Koukaki.
Ferry from Piraeus to Paros. Beach days, a walk from Lefkes on the old stone path, and a boat trip to Antiparos.
Ferry on to Santorini and a caldera-view room in Imerovigli. A winery lunch, then a private catamaran at sunset.
A last swim, then fly home from Santorini via Athens or direct on a seasonal London flight.
Practical notes checked against their sources. For entry and safety, the FCDO advice for Greece (opens in a new tab) is always the authority.
Athens is about three and three-quarter hours direct from Heathrow. Island connections are by ferry from Piraeus or Rafina, or by short domestic flight. We leave slack in the plan in July and August, when strong winds can delay smaller boats.
UK passport holders can visit Greece without a visa for short stays, and new Schengen border checks are being introduced. Read the FCDO entry requirements for Greece (opens in a new tab) before you book and again before you travel.
Read the FCDO entry requirements for Greece (opens in a new tab)
See the TravelHealthPro page for Greece (opens in a new tab) and the FCDO health page before travel. Summer heat is the main risk: sightsee early, rest in the afternoon and drink plenty of water.
Greece uses the euro. Cards are accepted in hotels and most restaurants, but keep some cash for small tavernas, beach bars and island taxis.
Surcharge-free roaming in the EU is no longer guaranteed for UK customers, so check your provider's charges. Ofcom warns that phones can connect to costly satellite networks at sea, so switch off data roaming on ferries.
There is no set percentage. In tavernas, rounding up or leaving a few euros in cash is normal. The small cover charge on the bill pays for bread and water, not service.
It depends on what you want from the days. Santorini for the view and a sense of occasion, Paros for beaches and village life, Milos for boat days, Crete for variety and food. Pairing Santorini with a quieter island gives you both sides of the Cyclades.
Large ferries are generally dependable, but high-speed catamarans and small boats can be delayed or cancelled when the meltemi blows in July and August. We avoid tight connections on the day you fly home and prefer to end a trip with a night in Athens or on an island with an airport.
Yes, especially Crete, Rhodes and the southern islands, where the sea stays warm and the days are still long enough for the beach. Smaller Cycladic islands begin closing towards the end of the month, so check that the hotels and tavernas you want are still open.
Very easily. Greek families holiday with children and tavernas welcome them. Choose islands with short transfers and sandy beaches, such as Paros, Naxos or parts of Crete, and avoid the cliff-edge hotels on Santorini, which are rarely suited to small children.
Tell us a little and a specialist will reply with ideas, dates that work and a price. Best months: June and September.
Italy rewards choosing one region well: lemon terraces at Amalfi, Tuscan hill towns, lake villas and the lagoon light of Venice.
Croatia is the Adriatic by boat: Roman Split, the walls of Dubrovnik and islands such as Hvar, Vis and Korčula in between.
Cyprus has a beach season that runs into November, Roman mosaics at Paphos and painted mountain churches in the Troodos.
Turkey joins Istanbul, the balloons over Cappadocia and a wooden gulet on the Turquoise Coast in a single, varied week.
