Athens has been drawing travellers for three thousand years, and it's easy to see why. The Acropolis rising above the city at sunrise. The hum of a kafeneion in a back-street neighbourhood. The moment a ferry pulls away from Piraeus and the open Aegean unfolds ahead of you. Whether you're dreaming of a self-guided island hop, a scenic self-drive through Crete's wild interior, or a flexible adventure where you choose the islands yourself, our Athens and More Your Way packages give you Greece on your own terms — with return flights from Canada already included.

The Freedom to Choose

What makes this collection different is flexibility. Several packages let you select which islands you visit, tailoring the experience to your travel style. Beach lover? Choose Milos. Nightlife seeker? Pick Mykonos or Ios. Romance on the agenda? Santorini is waiting. Independent traveller? Rent a car and explore Crete at your own wheel. There's no one-size-fits-all Greece here — just options.

Your Packages:

Hermes — Choose Your Greek Island Adventure

Athens · Choose 2 from: Mykonos, Naxos, Santorini

The most compact of the Choose Your Adventure packages, Hermes is designed for those who want Athens plus two beloved islands without overextending the trip. Begin in Athens, where you'll have a full day to explore the Acropolis, the new Acropolis Museum, the Panathenaic Stadium and the buzzing neighbourhood of Monastiraki. Then board a ferry and spend three nights on each of your two chosen islands — lively Mykonos with its windmills, charming alleyways and legendary nightlife; fertile, green Naxos with its fantastic hiking trails, traditional villages and long sandy beaches; or iconic Santorini, where the cliffside village of Oia offers what many consider the most beautiful sunset view on earth. The journey ends back in Athens. Perfect for a first-time Greek island experience, and easy to personalise around your priorities.

Andromeda Island Hopping

Athens · Choose 2 from: Mykonos, Santorini, Naxos, Paros

Named for the mythological heroine of the Aegean, the Andromeda package keeps things beautifully focused. You'll spend your first and last days embracing Athens — its history, its architecture, its magnificent ancient ruins — before escaping to two islands of your own choosing. Mykonos for glamour and beach clubs; Santorini for volcanic drama and caldera views; Naxos for authentic villages and the Aegean's finest beaches; or Paros for whitewashed charm, turquoise coves and that rare balance of lively and laid-back. All transfers, breakfast daily and high-speed ferry connections are included. A great first island-hopping experience, priced for two and designed for freedom.

Athena — Choose Your Greek Island Adventure

Athens · Choose 2 from: Mykonos, Ios, Milos, Santorini · Crete

One of the most satisfying packages in the collection, Athena gives you the best of both worlds: a curated mix of the Cyclades and a proper stay on Crete. After two days in Athens taking in the capital's ancient wonders, you'll ferry to your first chosen island for three nights — whether that's cosmopolitan Mykonos, beach-and-party Ios, the dramatic volcanic landscapes of Milos, or breathtaking Santorini. Then move on to your second chosen island for another three nights before heading to Crete, Greece's largest and most diverse island, for a final few days. Crete alone rewards an entire holiday: stunning beaches, the Palace of Knossos, the Samaria Gorge, charming Chania Old Town and a food culture that rivals anywhere in the country. A truly rounded Greece experience.

Pegasus Island Hopping 

Athens · Multi-island, including Crete

The Pegasus 10-night package expands the island-hopping formula for those who want more time in the Aegean. Beginning in Athens, the itinerary moves through a sequence of Cycladic islands by high-speed ferry before including a flight to Crete for the final leg — meaning you arrive in Greece's most storied island rested and ready, rather than ferry-weary. Breakfast is included throughout, all airport and port transfers are arranged, and the pace is designed to give you genuine time on each stop rather than rushing through. For the specific island sequence and current availability, check the Transat website directly — departure days and gateway cities vary.

Colossus — Choose Your Greek Island Adventure

Athens · Choose 2 from: Mykonos, Paros, Naxos, Ios · Crete · Rhodes

The grandest of the Choose Your Adventure packages, Colossus earns its name. Starting in Athens, you'll choose two islands from a strong Cycladic lineup — lively Mykonos, charming Paros, authentic Naxos, or party-loving Ios — spending two nights on each before sailing to Crete. After soaking up the island's wild natural beauty, historic sites and exceptional cuisine, the journey continues to Rhodes for the finale. Rhodes is one of Greece's great surprises: a medieval walled Old Town that's a UNESCO World Heritage Site, spectacular beaches along the coast, and the archaeological remains of one of antiquity's wonders, the Colossus itself. A flight brings you back to Athens for your return home. Fourteen days, five destinations, and a Greece you won't forget.

Perseus Island Hopping 

Athens · Multi-island, including Crete and Rhodes

Perseus is Transat's most expansive Greek island-hopping itinerary, combining the Cyclades with both Crete and Rhodes — connected by air transfers so you spend your time exploring rather than sailing long distances. Like its mythological namesake who journeyed across the Greek world, this package takes you through some of Greece's most distinct landscapes: the sparkling Aegean, the mountain villages of Crete, and the medieval grandeur of Rhodes. Breakfast and all transfers are included throughout. Visit the Transat website for current island sequences, departure dates from Montreal and Toronto, and pricing.

Cretan Odyssey Self Drive

Athens · Chania · Rethymnon · Agios Nikolaos · Ierapetra · Heraklion

Not every Greece adventure involves a ferry. The Cretan Odyssey Self Drive is for those who prefer to chart their own course on land — and Crete is the perfect canvas for it. After arriving in Athens, you'll fly to Crete and collect your rental car, then spend nearly two weeks discovering the island at your own pace across six distinct stops. Chania, with its Venetian harbour and labyrinthine old town, is one of the most beautiful cities in Greece. Rethymnon blends Venetian and Ottoman architecture along a stunning crescent beach. Agios Nikolaos sits beside a mysterious lake connected to the sea. Ierapetra, Europe's southernmost city, boasts long beaches and exceptional Cretan cuisine. Finally, Heraklion — home to the Palace of Knossos and one of Greece's great archaeological museums — closes the loop before your flight home. A self-guided, road-trip adventure through an island that deserves far more than a stopover.

Planning Your Trip

All packages include return flights from Canada with Air Canada or Air Transat, daily breakfast, and transfers between airports, ports and hotels. The best time to visit is May through September, with late May, June and September offering warm, swimmable weather with fewer crowds than peak July and August. Most packages depart from Montreal and Toronto; check individual listings for gateway cities and departure days. Not sure which package is right for you? Call us at 1-800-665-4981 and speak to one of our agents that has been to Athens and the Greek islands.