Greece does not need convincing anyone it belongs on a bucket list, and honestly, that is what makes planning a trip there so overwhelming. Do you spend the whole time on the mainland chasing three thousand years of history, or fly straight to Santorini and never leave the caldera view? [The honest answer, we think, is both, done properly, with someone else handling the ferries.]
Greece tours from Canada mean long flights, a country that rewards slow travel, and an itinerary that has to balance ancient ruins against island time without shortchanging either. We built ours around exactly that balance. If you are weighing whether Greece and the Cyclades belong on your list this year, here is what an Approach Tours trip actually looks like, what it costs, and how we plan around the parts that catch first-time visitors off guard.
Key Takeaways
- Greece is a country worth a real itinerary, not a highlight reel. Our Iconic Greece & the Cyclades Tour is 15 days, all-inclusive, and moves through Athens, Meteora, Delphi, Kefalonia, Ancient Olympia, the Argolis Peninsula, Santorini and Naxos. See our full Greece experience.
- Mainland and islands, in one trip. Most Greece itineraries pick a lane. Ours does both: a week of mainland history followed by island time in Santorini and Naxos, connected by ferry and one short flight.
- Every departure is capped at 30 travellers, all-inclusive from flights out of Canada to gratuities on the ground, with a Group Guru at your side the entire way.
- This is rated High difficulty, and we say so plainly. Cobblestones, some early ferry mornings and a full mainland-to-island itinerary make this a trip built for travellers who want the real thing and can keep pace with it.
- Not sure which Greece trip fits your style? Our Greece tour package guide walks through how to pick.
Why Greece rewards a guide who knows it
Everyone pictures the Acropolis first, understandably. But some of the more memorable stops on this trip happen four hours north of Athens, at Meteora, where six monasteries still sit perched on top of sandstone pillars that rise straight out of the Thessalian plain.
Here is the part most visitors never get told, and it is worth knowing before you go. The monks did not build up there for the view. Byzantine monks fleeing Ottoman raids in the 14th century chose these rock towers specifically because they were nearly impossible to reach, and for centuries the only way up was a net and a rope pulled by hand, or a ladder that could be hauled up behind you the moment danger arrived. [Imagine being the new arrival and having to trust that rope.] Concrete steps replaced most of that only in the 1920s.
That is the kind of context a good guide hands you standing at the base looking straight up, not read off a plaque you skim once and forget by lunch. It is also, honestly, why we think a small group with a dedicated Group Guru beats touring Greece on your own. You could see the monasteries without that story. You would not feel the same about the climb.
What a typical Greece itinerary covers
Our Iconic Greece & the Cyclades Tour runs 15 days and does not rush the country. The rough shape of it, without pretending to cover every stop:
Athens first. You will land, meet your Group Guru and the rest of your small group, settle in, and set out on foot to discover the city before a welcome cocktail kicks off your journey into Greek gastronomy. The next day is dedicated entirely to Athens: the Parthenon, the Erechtheion, the Propylaea, the Acropolis Museum, and a panoramic tour past the Panathenaic Stadium and Hadrian’s Arch.
From Athens, the route heads north to Meteora (stopping at Thermopylae along the way to see the statue of Leonidas), then south again to Delphi, home of the Oracle and, according to Greek myth, the exact centre of the earth. A scenic drive along the Corinthian gulf and a ferry ride lead to Kefalonia, where two full days go to exploring Argostoli, the Melissani Caves and the postcard village of Fiscardo.
From Kefalonia, a ferry back to the Peloponnese brings you to Ancient Olympia, birthplace of the Olympic games, and on to the Argolis Peninsula for an olive oil tasting and a visit to the acoustically famous theatre at Epidaurus. A short flight from Athens then swaps ruins for islands: Santorini for two days of Akrotiri, Fira and Oia, then a ferry to laid-back Naxos before the trip loops back to Athens for a folkloric farewell dinner in Plaka.
Costs, timing and getting there from Canada
The Iconic Greece & the Cyclades Tour runs $11,295 CAD per person in double occupancy for 15 days, all-inclusive, from your flights out of Canada right through to gratuities on the ground. A single supplement applies at $2,500 (add $200 for Fall 2027 departures), and if you would rather arrange your own flights, a land-only option saves $1,275. Deposits work the same as every Approach Tours departure: $500 per person to book, $1,000 per person 45 days later, and the balance due 90 days before departure.
Wondering when to actually go? We have a full seasonal breakdown for Greece that walks through spring versus fall departures and everything in between, worth a read before you pick a date.
Radically All-Inclusive, applied to Greece specifically
“All-inclusive” gets used loosely by a lot of operators. For us it means every flight, every ferry, the vast majority of meals (38 of them on this trip, including a folkloric dinner and an olive oil tasting), and a Coach and local guides that take you between every stop without a single logistics decision landing on your plate. You will not be sorting out inter-island ferry tickets from a Naxos dock at 6am or trying to book a domestic flight to Santorini on your own. Your Group Guru handles it, and handles the small stuff too: the reservation nobody remembered to make, the traveller who needs a slower pace on a cobblestone morning, the details that add up to a trip that actually feels like a vacation rather than a project.
Built for Travellers 55 and Up: difficulty, honestly addressed
We rate this itinerary High difficulty, and we are not going to soften that. Between the Acropolis, Meteora’s stairs, cobblestone lanes on three different islands and a genuinely full 15-day pace, this trip asks something of you physically. So here is the thing: we would rather tell you that upfront than have you find out on day four.
It still rewards the effort. The pacing gives you a full free day in Naxos specifically to recover before the final push home, and your Group Guru is there for the early ferry mornings and the uneven ancient stone, not just the highlight-reel days. Our physical requirements FAQ covers what to expect in more detail, and our guide to Greek islands for senior travellers is worth a read if pacing is your main concern.
How to choose the right Greece tour
A few things worth checking before you book with anyone, us included: does the itinerary actually connect the mainland to the islands, or does it just pick one and call it Greece? Is the group size genuinely small, or is “small group” doing a lot of marketing work for what turns out to be forty-plus people crowding onto a single ferry? And does the operator handle the inter-island ferry and flight logistics for you, given how easily a missed connection can unravel a Greek itinerary?
We think our answer to all three holds up. Thirty travellers maximum, a route that treats the mainland and the Cyclades as one trip instead of two, and a Group Guru who has done this exact route before and knows which ferry to build slack around.
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Frequently Asked Questions
How long is the Approach Tours Greece itinerary?
Fifteen days, all-inclusive, covering Athens, Meteora, Delphi, Kefalonia, Ancient Olympia, the Argolis Peninsula, Santorini and Naxos.
How much does a Greece tour from Canada cost?
Our Iconic Greece & the Cyclades Tour is $11,295 CAD per person in double occupancy, with a $2,500 single supplement and a $1,275 discount for travellers arranging their own flights.
Is Greece difficult for travellers with mobility concerns?
We rate this itinerary High difficulty because of cobblestone streets, ancient sites with uneven stone, and some early ferry mornings, and we would rather tell you that upfront. The pace still builds in a full free day on Naxos, and our Group Guru paces the group throughout, but it is worth an honest conversation with us before booking if mobility is a concern. Our physical requirements FAQ is a good place to start.
What is the best time of year to visit Greece?
It depends on what you want from the trip. Our seasonal guide to Greece breaks down spring versus fall departures in detail.
Does the tour include both the mainland and the islands?
Yes. This is one of the few Approach Tours itineraries that treats Greece as a single trip rather than choosing mainland history or island time. A week on the mainland leads into island stops in Santorini and Naxos before the trip loops back to Athens.
