Some destinations live up to the myth. Greece is one of them. The ancient marble of the Acropolis glowing gold in the late afternoon light. The impossible blue of the Aegean seen from a Santorini clifftop. A whitewashed lane in Mykonos that opens suddenly onto a view of the sea. A quiet beach on Milos that looks like it was painted rather than formed by geology. Greece has been drawing travellers for centuries, and it keeps delivering — because the reality is just as beautiful as the idea.

Our packages to Athens, Santorini, Mykonos and the broader Cyclades combine the best of Greece's ancient history with its island life, offering routes for every kind of traveller — from those seeking an unhurried self-guided escape to those ready for a fully curated luxury experience. Flights from Canada and all transfers are included, so the only thing left to do is show up and let Greece do the rest.

When to Go:

Greece has a long, generous travel season, and the Athens–Cyclades route rewards visits across much of it.

• May and June are many experienced travellers' favourite months. Temperatures reach a comfortable 22–28°C, the sea is warming up nicely for swimming, wildflowers are still blooming on the hillsides, and the islands feel like themselves rather than like a crowd management exercise. Ferry services are in full swing, restaurants are open, and you'll find that iconic spots — the Oia sunset terrace, the windmills of Mykonos, the caldera path between Fira and Oia — are actually enjoyable to linger at.
• July and August are peak season in every sense. Temperatures climb to 30–35°C across the Cyclades, the beaches are at their most electric, and the nightlife on Mykonos and Santorini reaches full intensity. This is Greece at its most vibrant — and its most crowded. Book well in advance, and budget for peak pricing. The meltemi, a dry northern wind that sweeps the Aegean in mid-summer, keeps the heat bearable on the islands and makes sailing days particularly exhilarating.
• September and early October offer what many consider the best conditions of all. The sea has reached its warmest temperatures of the year (25–26°C), the crowds have thinned, prices drop from their peak, and the light takes on a golden quality that makes the whitewashed villages of the Cyclades look like they've been lit for a film. Locals return to their islands and restaurants, and Greece settles into a more relaxed, authentic version of itself.

Must-See Sights:

Athens

No trip to Greece begins without the Acropolis, and with good reason — standing beneath the Parthenon is one of those rare travel experiences that genuinely matches the expectation. Pair it with the Acropolis Museum directly below, which houses the sculptures and friezes that bring the ancient city to life with remarkable clarity. Beyond the ancient sites, the Plaka neighbourhood is perfect for wandering: narrow streets, Byzantine churches, open-air markets and terrace cafés with Acropolis views. The National Archaeological Museum, a short taxi ride from the centre, contains the finest collection of ancient Greek artefacts in the world. And for a day trip, the Temple of Poseidon at Cape Sounion — a 70km coastal drive south — offers one of the most dramatic ancient settings imaginable, perched on a cliff above the sea.

Mykonos

Start in the Chora, the island's main town: a labyrinth of whitewashed alleys, bougainvillea and blue-domed chapels that manages to be both impossibly photogenic and genuinely lived-in. Little Venice — where the buildings extend directly over the water — is the place to be at sunset, ideally with a drink in hand. The iconic windmills just above the town are best visited in the early morning before the crowds. For a day trip that adds real depth to the island experience, the short ferry to Delos is unmissable: this tiny uninhabited island was one of the ancient world's most sacred sites, the mythological birthplace of Apollo, and an extraordinary open-air museum of temples, mosaics and ancient streets.

Santorini

The caldera is the centrepiece — a vast flooded volcanic crater ringed by sheer cliff-face villages that seem to defy gravity. Oia is the most celebrated of these villages, famous for its sunsets and its marble-paved lanes lined with boutiques and galleries; arrive early morning to appreciate it without the crowds. The hike along the caldera rim from Fira to Oia takes three to four hours and delivers some of the best sustained views in Greece. A sailing cruise around the volcanic islands — with stops at the hot springs, the Red Beach and the White Beach — is the highlight many travellers name as their single best day in the country. Don't miss Akrotiri, the Bronze Age settlement buried by the volcanic eruption that created the caldera: it's one of the most significant and evocative archaeological sites in the Aegean.

Paros

Quieter and more genuinely local than its famous neighbours, Paros rewards the traveller who goes looking. The harbour town of Parikia has a beautiful old quarter with a Byzantine cathedral built from the marble the island has been quarrying since antiquity. Naoussa, on the north coast, is one of the prettiest villages in the Cyclades — a small fishing port lined with tavernas where the evenings stretch long and easy. The beaches here are some of the best in the Aegean: Kolymbithres, with its sculpted granite rocks, is unlike any other beach in Greece. A short ferry from Parikia reaches the sister island of Antiparos, with its sea caves and relaxed, almost deserted beaches.

Sifnos

Off the main tourist trail and proud of it, Sifnos is the Cyclades' culinary island — its food culture is so celebrated that it has produced some of Greece's most famous chefs. The villages are traditional and beautiful, with Kastro — a medieval clifftop settlement above the sea — being one of the most atmospheric spots in the entire archipelago. There are over 100km of marked hiking trails crossing the island, and the beaches, particularly around Platis Gialos, are quiet and genuinely lovely. Sifnos pairs wonderfully with Milos, just a short ferry ride away.

Milos

Milos is the dramatic one — a volcanic island with a coastline so varied and strange that it feels like a different country every few kilometres. The famous beach at Sarakiniko, where white pumice rock has been sculpted by wind and sea into lunar formations, is one of the most photographed spots in Greece. Boat trips are the best way to explore the coastline: sea caves, hidden coves and the colourful fishing village of Klima, where the boathouses are painted in vivid reds and yellows, appear one after another. Inland, the village of Plaka sits high above the island with sweeping views, and the ancient catacombs — among the most important early Christian sites in Greece — are a surprising and fascinating discovery.

Crete

Greece's largest island is the one that rewards the most time. Chania's Venetian harbour, with its lighthouse and maze of stone lanes behind it, is one of the most beautiful old towns in the Mediterranean. The Palace of Knossos — the great Minoan site just outside Heraklion — is among the most significant archaeological sites in Europe, the kernel of a civilization that predates classical Greece by a thousand years. The Samaria Gorge, descending 16km through the White Mountains to the Libyan Sea, is one of Europe's great hikes. And Crete's beaches — particularly on the south coast — are some of the most beautiful and least crowded in the country.

Mainland highlights: Delphi and Meteora

For packages that venture beyond the islands, two mainland sites stand above the rest. Delphi, two and a half hours northwest of Athens, was the spiritual centre of the ancient world — the sanctuary where the Oracle spoke and leaders from across the Greek world came to seek guidance. The setting, on the slopes of Mount Parnassus above the Gulf of Corinth, is stunning. Meteora, in central Greece, is unlike anything else: medieval monasteries perched atop impossibly steep rock formations, accessible by staircases carved into the stone, above a valley of extraordinary beauty.

Your Packages:

Charming Cyclades | Athens · Sifnos · Milos · Santorini · Mykonos

The most distinctive route in the collection, the Charming Cyclades ventures beyond the famous stops to include two islands that most travellers haven't yet discovered — and that regulars consider among the best in Greece. After immersing yourself in Athens, you'll island-hop to Sifnos, the Cyclades' celebrated culinary island with its traditional villages and hilltop kastro, before continuing to Milos, whose extraordinary volcanic coastline and lunar beaches make it one of the Aegean's most visually dramatic destinations. From there, the route joins the classic Greek journey: the iconic caldera views and cliff-face villages of Santorini, then lively, beautiful Mykonos to close. Fourteen days, five destinations, and a Greece that goes well beyond the postcard. Lots of free time at every stop means the pace is genuinely yours to set.

Island Delights | Athens · Mykonos · Santorini · Crete

For those who want Greece's greatest island experiences without leaving anything out, Island Delights delivers. Thirteen days cover the full sweep: Athens for history and culture, Mykonos for nightlife and island charm, Santorini for the most dramatic views in the Aegean, and Crete — the island that takes a lifetime to fully know — for a finale that combines ancient sites, stunning beaches and exceptional local food. Ancient monuments, picture-perfect seaside villages and long afternoons on the beach are all part of the journey. The route balances famous highlights with genuine relaxation, and the pace gives you enough time at each stop to discover something beyond the obvious.

Island Discovery (3- and 4-star hotels) | Athens · Mykonos · Paros · Santorini

The Island Discovery package adds Paros to the classic Athens–Mykonos–Santorini route, and it's a meaningful addition. Where Mykonos buzzes and Santorini dazzles, Paros offers something quieter and more genuinely local — charming fishing villages, some of the Cyclades' finest beaches, and an easy, unhurried pace that makes it a favourite among travellers who've been to Greece before and know what they're really looking for. Twelve days take you through the fascinating history, vibrant culture and distinctive character of all four destinations, with three- and four-star accommodations, all flights and transfers included, and ample time to explore historical monuments, fishing villages and beautiful beaches at your own pace.

Island Discovery Premium (5-star hotels) | Athens · Mykonos · Paros · Santorini

The same beautifully crafted route as Island Discovery — Athens, Mykonos, Paros and Santorini over 12 days — elevated throughout with five-star accommodations at every stop. In Santorini, that means a caldera-view hotel in Oia or Fira. In Mykonos, a boutique property in the Chora or above the sea. In Athens and Paros, carefully selected hotels that place you at the centre of everything without sacrificing comfort. Premium accommodations change the texture of a trip — when the room itself is a destination, you slow down, stay longer over breakfast, and return in the afternoon rather than pushing through. Everything else remains: flights from Canada, all transfers, and the same generous time at each stop to explore Greece at your own pace.

Islands and Legends Tour | Athens · Mainland Greece · Multiple islands

Greece is a country built on stories, and this is the package for travellers who want to understand them. The Islands and Legends Tour combines the iconic island stops with some of Greece's most remarkable mainland sites — including the monasteries of Meteora, balanced atop their extraordinary rock formations in central Greece, and the ancient kingdom of Mycenae and Agamemnon in the Peloponnese, where the Bronze Age world of Homer's epics is not mythology but archaeology. Between these mainland discoveries, the tour moves to the islands, where the fun-filled Aegean experience of beaches, ferries and seafront tavernas provides a vivid counterpoint to the weight of history encountered on the mainland. This is the itinerary for the curious traveller — the one who wants Greece to mean something, not just look beautiful.

So many inclusions

All packages include return flights from Canada, accommodation throughout, and all land and ferry transfers between destinations. Breakfast is included daily on most packages. You arrive in Athens and everything else is arranged — the only planning left to do is how you want to spend each day.

For current departure dates, gateway cities, pricing and availability, contact us at 1-800-665-4981 or visit our booking pages for each package.