Planning a Trip to Greece: Our Itinerary

Academy of Athens

We were very lucky to visit Greece in August/September 2021 for 3.5 weeks! In our years of traveling, this is the most time we have ever spent in one country and we left Greece feeling like there was still so much to see and explore. In this post, we share details about our itinerary and tips to help you plan your trip.

Our Itinerary:

  1. Mykonos: 3 nights
    1. Stayed at Aegon Mykonos
    1. Rented a car through Budget
  • Odos Araxame in Ano Mera: Max enjoying our first dinner!
  • The narrow roads of Mykonos!
  • Mikonos Brewing: beer tasting
  • Vioma Organic Farm and Vineyard: Jason at lunch and yes they serve beer here!
  • Aerial view of Mykonos Town
  1. Corfu: 4 nights
    1. Stayed at Domes Miramare
    1. Rented a car through Europcar
  • Old Town Corfu
  • Jason with the car in the hills of Corfu
  • Domes Miramare Corfu Resort: Max on her way to breakfast
  • Domes Miramare Corfu Resort: Olive trees at sunrise
  • Pesce Bar: Grilled sardines and salad
  1. Athens: 3 nights
    1. Stayed at Moniseur Didot
    1. Took public transit
  • View of Athens from Lycabettus Hill
  • Our room at Monsieur Didot, a small boutique hotel in Kolonaki
  • Walking in Athens
  • Monsieur Didot Room 6 - The ode to the light: bedroom
  1. Crete: 11 nights
    1. Stayed in Chania: The Theodore Boutique Hotel and Domes Zeen
    1. Stayed in Agios Nikolaos: The Island Concept
    1. Rented a car from Hertz at Chania Airport and returned it at Heraklion Airport
  • Crete's famous pink sand beach, Elafonissi
  • Chania's Venetian Harbour
  • Max floating in the sea at sunrise
  • Manousakis: wine tasting with rusks, olive oil and sea salt
  • Mastrapas: raki
  1. Santorini: 3 nights
    1. Stayed at SantAnna Suites
    1. Took the bus and walked
  • Our private pool at SantAnna Suites
  • Pickled fish at Melitini in Oia
  • Wine tasting at Vassaltis Vineyards

Lessons Learned:

  • When to go: Spending time in Greece in the summer is the best time to be there but next time we go, we will plan to be there after September 15th and before the end of October. Mid-August to Mid-September is the busiest time; things get less busy when school starts. You can go before August too but the ocean is much warmer later in the season.
  • Mykonos: Mykonos is known as a party place but we were able to escape that and enjoyed our visit. Not sure if we would go back as there are lots of other places to visit in Greece but it was an easy first stop for us to relax and acclimate to Greece as we were jetlagged.
  • Santorini: We would have enjoyed Santorini more if it has been the first or second stop on our trip. We came, we saw, and we thought it was beautiful but we will not return as there are other places in Greece we want to visit. Mass tourism in Santorini is a real downer.
  • Athens: We felt that 3 nights and 2.5 days in Athens was enough for us but we did miss out on visiting some of the wineries just outside the city. After spending time in Mykonos and Corfu, we were over out jetlagged and ready to explore Athens from early in the morning to late at night even if it was very hot. Next time, we will plan for about the same amount of time and stay at a different hotel in another part of the city.
  • Crete: Crete was by far our favorite and we left with lots of unfinished business. It was very expensive to rent a car but we were able to do so much on our schedule and it was easy to drive here. Next time, we would consider staying in the south to explore that part of the island.
  • Corfu: We would most definitely return to Corfu as we ran out of time to do everything on our list. Due to the weather, it was not possible for us to spend time at night in the old town as planned. Corfu offers a good mix of culture and beaches and is less crowded.
  • Flights: We booked all our flights on Aegean and recommend booking “Flex” if you are traveling with carry-on and need flexibility. The “Flex” fare is usually about 10 euros more and ensures you can travel with a carry-on and personal item, free standard seat selection, and you can change your flights without paying a 40 euros booking fee. We chose to fly Aegean because we could also access their lounges when in Athens with Star Alliance Gold status. Overall, the flights were good; cabins clean, small snack and water provided but the bus gates were a pain.
  • Cash vs Credit Card: We used our credit card more than we expected but always had cash on hand. We exchanged some money in Canada prior to leaving when the exchange rate was decent. We also had no issues using Europbank as Canadians: decent exchange rate and no high service fees. We also avoided accepted the Dynamic Currency Conversion (DCC) which is a rip-off. Make sure to say “no” twice going through the prompts. I.e. we took out 300 euros and it cost 483 euros. Anything above 1.5 is a good deal for Canadians!
  • Driving: Overall, we found driving to be easy enough. It was the best way for us to explore on our time since we didn’t feel like doing group tours. Some of the drives were a little more challenging than others due to the narrow roads on cliffs and through villages but totally doable. We also found it easy to get around using Google Maps on our phone.
  • SIM Card: We purchased a SIM card on Amazon prior to departure and installed on arrival. It was super easy and much cheaper than the $10 a day international package offered by the cell phone company.


Greece really does live up to its hype; the beaches are stunning, the people are friendly and welcoming, the architecture and historical sites are awe-inducing, the food is delicious, the wine is underrated, and “filotima” really is a thing. We really enjoyed planning this trip and learned so much to help us plan our next trip to Greece!

Have you visited Greece? Are you planning a trip to Greece this summer? Do you have any questions?

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