Southern Europe · The Greek Islands

Greece

Greece is really two trips in one country. There is the mainland, with Athens and the classical sites most travellers know by name, and then there is the Aegean — a scatter of islands, each with its own pace, its own light, and its own reason to linger a day longer than planned.

May – SeptemberUnwindDiscoverReconnect

The most satisfying way to see it is slowly and in sequence: a few days in Athens, then island to island by small ship or ferry, with time built in for long lunches, harbour walks, and evenings that are not scheduled at all. An advisor's work here is mostly sequencing — choosing the right islands in the right order, so the trip feels unhurried from start to finish.

When to go: The Greek islands are at their best from May through September, when ferries run full schedules, the Aegean is warm for swimming, and island hotels and tavernas are fully open.

Highlights

  • The Acropolis and the museums of Athens, best seen early in the morning before the heat and the crowds
  • Santorini's caldera villages, including Oia and Fira, built into the cliff above a flooded volcanic crater
  • Mykonos for its old-town lanes, windmills, and beaches — lively in season, quieter at its edges
  • Crete, the largest island, with the Palace of Knossos, mountain villages, and a food tradition all its own
  • The quieter Cyclades — islands such as Naxos, Paros, and Milos — for beaches, small ports, and a slower rhythm

Ways to go

  • Windstar Cruises — Small sailing and motor yachts that call at smaller Greek ports the large ships pass by, with an emphasis on time ashore.
  • Azamara — Destination-focused voyages with late-night and overnight stays, well suited to Greek island itineraries where evenings in port matter.
  • Crystal — A refined ocean voyage through the Greek isles, pairing island calls with attentive onboard service and guided touring ashore.
  • Regent Seven Seas Cruises — All-inclusive luxury sailings in the eastern Mediterranean that include shore excursions, for travellers who want the details handled in advance.

In port, arranged

Days ashore and days out in Greece are arranged through the excursion specialists below — private, small-group and shared days, sized to your party. Your advisor confirms the details with the operator before you go.

Shore Excursions Group

4,000+ tours · 300+ ports · smaller groups · return-to-ship guarantee

The largest shore excursion company in this directory, with a portfolio of over 4,000 tours in more than 300 ports covering 99% of cruise itineraries, smaller group sizes and a return-to-ship guarantee.

Arrange it with your advisor ↗

Project Expedition

21,000+ experiences · 700 cities · private & custom days

Advisor platform for tours, activities, shore excursions and transfers, with more than 21,000 experiences in 700 cities worldwide and a concierge team for custom itineraries, private tours and group quotes.

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Viator

300,000+ tours & activities · worldwide

The largest experiences marketplace in this directory, with more than 300,000 tours and activities worldwide, bookable by advisors through its travel agent program.

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Honest answers

What does a trip to Greece cost?

There is no single figure, because the trip can be built so many ways. Cost is driven mainly by when you travel — high summer on the most requested islands is the most expensive window — by your cabin or room class, and by how much private touring and inter-island travel is included. Your advisor will quote a real number for the exact itinerary you choose, rather than an estimate built on someone else's trip.

Is a cruise or a land stay the better value?

Neither is automatically better value; they buy different things. A small-ship sailing bundles your room, transport between islands, and often excursions into one arrangement, while a land-based trip gives you longer on each island and more choice of hotel, at the cost of arranging each move yourself. Your advisor can price both shapes of the same journey so you can compare them honestly.

How far ahead should we book?

Earlier is generally better for Greece, particularly for summer. The most requested island hotels and the best-located ship cabins are finite, and booking early widens your choice of both — which usually matters more to the final cost than any single line item. Shoulder-season travel, in May or September, is the other reliable lever.