Greek Island Hopping: Which Islands to Combine, How to Get Between Them and How Long to Stay

Start in Athens, pick one island group, and stay inside it. Islands connect far better within the same chain than across groups, so a single-chain route is simpler to plan and smoother to travel. For a first trip, the Cyclades (Mykonos, Paros, Naxos, Santorini, Ios) are the easiest and best connected. Ten days there gives you time on several islands without spending your vacation on a ferry deck.

Which island group should you choose?

The ones people hop between fall into a few clusters, and each has its own character.

The Cyclades are the Greece of postcards: whitewashed houses with colorful windowsills and doorways, dry rocky hills, old windmills and plenty of beaches. They are also the busiest group. First-timers, honeymooners and groups of friends tend to land here, because the ferries run often and the islands sit close together.

The Ionian Islands, off the west coast, are greener and quieter, with fewer ferry links. The extra effort pays off. They suit families especially well, with calm, shallow water on Corfu's east coast, fewer party crowds and a cooler, more relaxed summer than the Cyclades.

The Dodecanese, in the sunny southeast near Turkey, are more rustic and less developed. Historic ties to Venice and the closeness of Turkey give them a blended Turkish and Venetian flavor, and the pace is slow and cultural. Most visitors pick one island and stay a week, but two or three islands work well. In Rhodes, the biggest island, spend a night or two inside the old town, a UNESCO World Heritage site of fortified walls and historic streets.

The Saronic Gulf islands, between Athens and the Peloponnese, offer island charm close to the capital. Hydra is an easy boat ride from Athens' port, under 90 minutes, and it offers pretty scenery, a car-free feel and a calmer pace than the better-known islands.

Combining groups, say the Cyclades and the Dodecanese, is possible but complicated. On a first trip, choose one.

What does a classic Cyclades route look like?

Picture the chain as a string of beads: Athens, Mykonos, Paros, Naxos and Santorini, with lively Ios as an add-on.

Mykonos runs on glamour and late hours. Days start slowly and nights run long, so early risers get the lanes almost to themselves until late morning. Hotels cluster mostly along the shoreline, which leaves the hilly, rugged interior largely empty. Beach clubs, nightlife and a social crowd set the tone, and a side trip to the ancient ruins on nearby Delos makes a good daytime break.

Paros feels like a smaller, calmer Mykonos with fewer visitors: whitewashed towns, hilltop villages, clear water and sandy beaches. Chilled cocktail bars line the streets of Naoussa and Parikia, and at sunset the harbor restaurants spill their tables into the lanes. By the next morning the same streets feel empty again. Spend a day on little Antiparos, just across the water, for secluded coves and caves. Paros makes an excellent first island, with the classic whitewashed Cyclades look at a gentler pace and a lower cost than Mykonos or Santorini.

Naxos is larger and more varied than Paros, with a greener, rugged interior. Paros has the edge for prettiness and atmosphere, and Naxos for variety and room to explore. The crossing between them is short, so it's easy to do both.

Santorini is the island of views and sunsets. Oia and Fira, the main bases, sit on the edge of a volcanic caldera, and Imerovigli is also worth a look. Evenings in Oia can get busy around sunset, so try wandering its streets at sunrise, long before most people are awake. Away from the busiest spots you'll find wineries, well-preserved ruins and quieter villages such as Pyrgos and Emporio.

How do you get between the islands?

Mostly by ferry. Plenty of passenger boats crisscross the Aegean, so getting from island to island is quick and fairly easy. Pinning down schedules takes some work, though, because several companies may run the same route and timetables change often. Look up sailings online before your trip, then confirm them at a local travel agency once you're in Greece. In high summer, book popular sailings in advance online instead of waiting until you reach the port, since they can sell out.

Rough crossing times in the Cyclades:

• Athens (Piraeus) to Mykonos: about 2.5 to 4 hours
• Mykonos to Paros: 40 minutes to 2.5 hours
• Paros to Naxos: 25 to 60 minutes
• Naxos to Santorini: 1 to 2 hours

The range reflects the boat. Slower conventional ferries cost less than high-speed catamarans.

Athens has two ferry ports. Piraeus is the better choice if you're spending time in the city, since the metro runs into the center. Rafina sits closest to the airport, which makes it handy if you're heading straight from your flight to the boat.

Flying saves time. Planes are much faster than boats and less likely to be delayed or canceled, though tickets often cost more. Mykonos and Santorini have their own airports. Paros, Naxos and Ios don't receive direct international flights, so reach them by ferry from Athens, or fly into Mykonos or Santorini and take a shorter ferry from there. Flights into Athens usually cost less than flights into an island, so price out Athens plus a ferry before booking.

The Ionian Islands have no ferry from Athens. Fly into Corfu, Kefalonia or Zakynthos, then use ferries between islands, since there are no flights between them. Ferry timetables often appear just a few weeks before the season begins, and sailings tend to be longer and less frequent than in the Cyclades, though fares run cheaper. A sensible chain runs Corfu, Lefkada, Kefalonia, then Zakynthos, with a short boat hop from Kefalonia to little Ithaca. The ferry from Corfu to Lefkada alone takes about 5 to 6 hours, though a 30- to 45-minute flight from Corfu to Preveza, very close to Lefkada, cuts that down.

In the Dodecanese, island hopping is straightforward and often quite cheap. Start in Rhodes because of its airport, then ferry outward to Symi, Kos and Patmos. Each hop takes from under an hour to a couple of hours.

Sailings can be canceled in bad weather, which is more likely off-season. In September and October, winds in the Cyclades can pick up considerably and disrupt crossings, so leave slack between connections.

How many days do you need?

Ten days is the minimum to do it properly. With less time, too much of the trip goes to ferries. Two weeks is the sweet spot: three or four nights on each island, with no sense of rushing. Allow more time in the Ionian Islands, where travel days add up quickly.

What are some sample routes?

Tour and package itineraries show how the islands usually link up:

• Athens, Naxos and Santorini, 10 days
• Athens, Mykonos, Paros, Santorini and Ios, 11 days, a fast-paced, social group-tour route
• Athens, Syros, Paros and Naxos, 12 days, a three-island Cyclades combination
• Athens, Milos and Naxos, 9 days
• Athens, Sifnos and Santorini, 10 days
• Athens, Serifos and Sifnos, 9 days, a quieter alternative
• Athens, Poros and Hydra, 10 days, for the Saronic islands

Milos is less crowded than the big names, though it has joined the tourist trail in recent years. It's a rugged island with more than 70 beaches, a few of them reached by a scramble, and a 4×4 helps for exploring. For a quiet Ionian stop, consider adding Ithaca, a short ferry ride from Kefalonia. It's small and unhurried, with no large resorts and no party scene.

When should you go, and what will it cost?

The season runs from roughly late April through October. July and August are peak season, with reliable heat and frequent ferries, and the Cyclades get extremely busy. Hotel prices hit their highest, and in Mykonos and Santorini even budget hotels can more than double. Car rentals and restaurant meals cost more too. Between July and September, with August the busiest, visitors can outnumber available beds, so reserve your rooms well ahead.

Early June is a sweet spot: warm without being overwhelming, the sea is good for swimming, and the peak crowds haven't arrived. In general, the weeks just before or after the July to September rush pair good weather with calmer streets and gentler prices. In September and October, hotel prices drop and the crowds thin out. The Ionian Islands have a shorter window, June through August. By October, ferries there run far less often and some smaller routes stop altogether.

To save money, take the slower ferries and base yourself on Paros or Naxos instead of Mykonos or Santorini. Check when cruise ships are due, too. Head to outlying sights or beaches while they're in port, and come back to town in the afternoon, when the cruise passengers are loading up to leave.

What should Americans know before they go?

U.S. citizens can visit Greece without a visa for up to 90 days for tourism or business. Your passport should have at least three months of validity beyond your planned departure date, and officers may ask for proof of sufficient funds and a return ticket or other evidence of departure. A passport reported lost or stolen won't get you in, even if you've found it again, so travel on a valid one.

Greece is generally safe, but petty crime is common at popular tourist sites and on public transportation, especially the metro. Strikes and demonstrations are common too, and transportation strikes can shut down seaports, airports, taxis and public transit, another reason to leave slack in your schedule.

To drive a rental car, Greek law requires a valid U.S. license, and insurance companies may require an international driver’s permit. Thieves in Greece break into rental cars to steal passports, valuables and luggage, so avoid leaving them in a parked car.