Pick islands in the same group
Practical tipSantorini, Mykonos, Paros, Naxos, Ios and Milos are all Cyclades and connected by frequent boats. Mixing in Corfu or Crete means flying, not sailing.
Which islands to pick, how to island hop without wasting days, and where the good beach clubs, boat days and dinners are.

Greece is not one trip, it is a hundred different ones depending on which islands you choose. Santorini and Mykonos are famous for good reasons and expensive for the same reasons; the Cyclades around them are cheaper, quieter and in some cases prettier. This guide helps you pick two or three islands that suit the trip you actually want, then tells you what to do once you land — including the boat days that end up being everyone's favourite part.
Start here
Late May to mid June and all of September are the best weeks: hot sea, long days, everything open, and noticeably cheaper than August. Two islands in a week, three in ten days — any more and you will spend your holiday on ferries.
Ferry schedules, opening dates and prices change every season and boats are cancelled in high winds. Confirm everything directly and keep a spare day before any international flight home.
Santorini, Mykonos, Paros, Naxos, Ios and Milos are all Cyclades and connected by frequent boats. Mixing in Corfu or Crete means flying, not sailing.
The good hotels in Oia, Mykonos town and Milos sell out by February for July and August.
Ferries get cancelled for wind. Never plan to sail into your flight home on the same day — go back to Athens the night before.
Every island town is marble steps and cobbles, and most restaurants want more than a bikini at dinner.
Cards are widely accepted, but beach bars, small tavernas and some boat operators are cash only. Draw out at the port.
Planning
An honest comparison. Pick two or three that are near each other.
Cyclades
Cliffside villages, caldera views, black sand beaches, volcanic wine. Not a swimming island — the beaches are a drive away and the sea is deep and dramatic rather than calm.
Cyclades
Whitewashed old town, world-famous beach clubs, big nightlife, a young crowd and very high prices.
Cyclades
Gorgeous villages, good food, a real windsurfing and young traveller scene, still relaxed. Naoussa is the prettiest port town in the Cyclades.
Cyclades
The biggest beaches, mountain villages, farms and the cheapest good food. Family-friendly and unhurried.
Cyclades
Lunar white rock formations, a hundred small coves and the best boat day in Greece. Quieter nightlife.
Cyclades
Small, beautiful and famous for a very young party scene in the main town.
Separate group
Huge, with mountains, gorges, cities and pink-sand beaches. Needs a car and a week of its own.
Athens
Most trips start here. Two nights is plenty and it is a genuinely good city night out.
Athens
Go at opening or in the last two hours of the day. Forty minutes up top is enough in the heat.
Athens
Cool, modern, and it makes the hill make sense. An hour and a half.
Athens
Bougainvillea, tiny white houses built by island craftsmen, stepped lanes under the Acropolis.
Athens
Drinks with the lit Parthenon above you.
Athens
Athens is the cheapest food of the whole trip. Eat well before you get to the islands.
Santorini
Come for the caldera, the sunsets and the volcanic beaches. Stay in the right village and it is magic; stay in the wrong one and it is a car park.

Santorini
Same caldera view as Oia, a fraction of the crowds, and a 25-minute cliff walk into Fira.
Oia
The famous one. Thousands of people, and still beautiful. Watch from a bar terrace with a booking rather than the castle ruins scrum.
Santorini
Around 10km along the caldera rim, three hours at an easy pace, with views the entire way.
Santorini
Hot springs, the volcano, Red Beach and White Beach, lunch on board, sunset sailing back.
Santorini
Volcanic white wine grown in low baskets on the ground. Several wineries have terraces over the caldera.
Below Oia
Three hundred steps down from Oia to fish tavernas at the water, with a swim off the rocks.
Perissa and Perivolos
Long volcanic beaches with beach bars, on the opposite side of the island from the caldera.
Mykonos
Beach clubs, boat days, late dinners and the best nightlife in the Cyclades. Expensive, unapologetically.

Mykonos
Sunbeds, music, lunch and champagne through the afternoon at the clubs along Paraga, Platis Gialos and Super Paradise.
Chora
Whitewashed maze, boutiques, Little Venice and the windmills. Get lost deliberately.
Mykonos
Either the ancient site of Delos, or a private boat that hops between the quieter northern beaches.
Mykonos
Greek food done expensively and very well, in courtyards and rooftops across the old town.
North coast
Undeveloped beaches with one taverna and no music. The antidote to the clubs.
Mykonos
Sunbeds, transfers and drinks are priced well above the rest of Greece. Always ask the price before ordering a bottle or taking a bed.
Quieter islands
Where to go when you want the same water for half the price.
Paros
A fishing harbour turned into the best evening town in the Cyclades: bars on the water, small restaurants, boats coming in.
Paros
Smooth granite rock formations sheltering small sandy coves.
From Paros
A ten-minute ferry to a smaller, quieter island with good beaches and one lovely main street.
Naxos
A long sandy beach and a giant marble doorway on an islet by the port, best at sunset.
Naxos
Halki and Apiranthos: marble lanes, distilleries, cheese, and almost no other visitors.
Milos
White volcanic rock shaped like the surface of the moon, dropping into deep blue water.
Milos
Kleftiko sea caves, tiny coves you can only reach by water, swimming stops all day.
Milos
Fishermen's houses with brightly painted doors right on the water.
On the water
Build one full boat day into every island. It is always the best day.

Split between six to ten people, a skippered day boat is often no more than a beach club sunbed each — and you get the whole day, your own music and empty coves.
Reef-safe sun cream, a cover-up, a hat you can tie on, cash, a dry bag and motion sickness tablets if you are unsure.
Most clubs charge per bed or set a minimum spend. Reserve the day before, arrive by 12, and check whether the price covers an umbrella.
The meltemi wind blows hardest in July and August and can cancel boats at short notice. Book boat days early in your stay so you have a spare day to rebook.
Food
Greek food is simple and the best of it is cheap.
Greek salad, grilled fish by the kilo, tzatziki, fried courgette, lamb, house wine from the barrel. Order for the table and share everything.
A few euros, sold everywhere, and the best late-night food in the country.
Choose the fish, agree the weight and price before it is cooked. Grilled whole with lemon and oil.
Little honey doughnuts, usually with cinnamon or chocolate.
Iced Greek coffee, drunk slowly, all morning.
Nights
Dinner at 9pm, bars at 11pm, and in Mykonos nothing before midnight.

Mykonos
Bars with tables on the water's edge, spray included, sunset over the windmills.
Mykonos
Big beach clubs turn into parties in the afternoon; town clubs run until sunrise.
Paros
Cocktails on the harbour wall, a young crowd, no attitude.
Santorini
A run of bars and small clubs in the island's main town.
Island taxis are few and vanish after midnight. Agree a pickup with a driver in advance or use your hotel's transfer — do not plan to hail one.
For the camera
Sunrise on the islands is empty, warm and pink. Use it.
Santorini
The three domes above the caldera.
Santorini
White chapels and cliff edges with nobody on them.
Mykonos
Five windmills above the town at sunset.
Milos
Bright white rock and deep blue water.
Paros
Blue boats, white walls, ruined fort in the water.
Naxos
A marble doorway framing the sunset.
Logistics
The part of a Greece trip most people get wrong.
High-speed catamarans are roughly half the time and twice the price, and they are cancelled in rough seas more often. Conventional ferries are slower, cheaper and far steadier.
July and August routes sell out. Book online in advance, arrive at the port 45 minutes early, and watch for last-minute gate changes.
Santorini, Mykonos, Naxos and Milos have airports with flights via Athens. Usually only worth it to save a full travel day.
Rent a quad, a small car or a scooter. Buses exist but they are infrequent and you will lose hours waiting.
Take tablets before boarding, sit low and central on the boat, and look at the horizon.
Money
Per person, per day, excluding flights and accommodation.
25 to 40 euros per person on most islands.
60 to 120 euros per person with drinks.
20 to 40 euros on most islands; 80 to 200 for two beds at a famous Mykonos club.
25 to 75 euros depending on distance and boat speed.
30 to 60 euros a day.
90 to 150 euros per person per day on Paros, Naxos or Milos; 200 to 350 in Mykonos or Santorini in high season.
Neighbourhoods, restaurants worth booking, the cafés that actually photograph well, and how to see the city without queuing all day.
Read itHow many cities to do, how long to stay, where to eat, and the coastal days worth building the whole trip around.
Read itA capsule wardrobe formula, the full checklist, what to leave at home, and the carry-on that saves the trip if your bag does not arrive.
Read it