Girls Trip to Greece? We said yes !
- Maureen
- Jun 19
- 4 min read
Updated: Jun 27
In 2019 my three sisters and I took a trip to Greece with our Mom, something she had always wanted to do. We organized a two week self guided ferry hoping tour of the Cyclades islands. The hardest part was choosing which which islands!
Here is our itinerary:
✈️ Athens, 3 nights (⛴️ day trip to Hydra)
⛴️ Naxos, 5 nights
⛴️ Santorini, 2 nights
⛴️ Milos, 4 nights (✈️ Athens ✈️ Home)
The Cyclades are a group of stunning Greek islands in the deep blue Aegean Sea. They are famous for whitewashed buildings, blue-domed churches, and vibrant culture. You can’t go wrong with any of the Islands. Each has scenic beauty, crystal-clear waters, rich history, amazing local cuisine and charming villages.
We started our Greek adventure in Athens, where our Airbnb had an amazing rooftop terrace with a view of the Acropolis. We spent our first day visiting the ancient ruins and the bustling pedestrian streets of the Plaka at the foot of the Acropolis. We shopped, had a lunch at sidewalk café and soaked up the sites and sounds around the winding stone streets, colourful shops and bright blooming bougainvillea. Be sure to save some space in your luggage as this is a great place to pick up leather sandals, hand made jewelry and cotton hammam beach towels.
The next day we took a day trip to Hydra (pronounced EE-drah). A charming island within easy reach of Athens (1h 20 min ferry ride). My mom is a huge fan of Leonard Cohen and he had a vacation home here. There are no cars in Hydra, the main transport are water taxis and donkeys. We walked the town, had a nice lunch on an outdoor patio, and then continued our walk along the coast finally settling in at a picture perfect beach club along the way. We headed back to Athens just before dinner.
Next up was Naxos, the largest island in the Cyclades. Known for its sandy beaches and authentic white washed villages, here we had a lovely Airbnb right on the coast in Naxos Town (aka Chora). We had an amazing view of the Portara a mythological ancient ruin that is a giant marble doorway to the unfinished Temple of Apollo. This monument is simply stunning at sunset. People make there way out to catch the show each evening. The pace in Naxos is easy. We loved meandering through the charming villages, stopping in at waterfront cafés, enjoying typical Greek fare and relaxing on the beach.
Our next stop was iconic Santorini, known for its breathtaking cliff top views of the sea, the cobblestone streets, the domed churches and postcard perfect villages perched atop of the cliffs formed by a volcanic eruption thousands of years ago.
Here our VRBO accommodation was in beautiful Fira along a cobblestone pathway and nestled into the cliff side. It offered stunning views of the caldera, the crescent shaped crater filled with deep blue water.
On our first day here we walked around Fira stopping in its quaint shops, and having lunch at an outdoor café. We loved lounging in an infinity pool at a neighbouring hotel that had a beautiful view on the caldera.
On our second day we escaped the heat by taking a fun catamaran tour around the coast of Fira and capped off our day by taking a taxi over to the Oia to visit this gorgeous village, have dinner and soak up its legendary sunset views.
A couple of things to consider when visiting Santorini:
It is one of the most visited islands in Greece, departing from the ferry terminal can take quite a bit of time as there a long taxis and buses lines to pick up people and take them to their destinations.
You may need to walk a fair distance with luggage in tow to reach your accommodation as many accommodations are located in spots where there is no car access. If that is an issue for you, plan ahead with your accommodation to pick up your luggage, if possible, or pack light!
Depending on when you go it is likely to be quite hot. If possible get an accommodation with a pool so you can cool off, as getting down to the sea takes a cable car ride or a 20-30 minute walk down nearly 600 steps.
Our final island hop brought us to Milos. A hidden gem and a nice quiet spot to counterbalance busy Santorini. We had an Airbnb on the outskirts of the port town of Adamas (also known as Adamantas). We chose it for its proximity to a beach with crystal clear waters. With over 70 beaches, Milos is haven for beach lovers. The highlight of our time here was a private kayak tour starting at Fyriplaka beach and taking us along the volcanic coastline with stunning moonlike rocks and sculpted cliffs, secluded coves and turquoise waters.
We flew out of Milos to Athens for our final flight home.
A couple of additional notes:
Accomodations: Since we were a group of five, vacation rentals were the best option for us on this trip. They provide multiple rooms, a kitchen for flexible eating schedules and common living spaces to comfortably kick back and enjoy each others company. We found some great accomdations for each of our locations (see links within the paragraphs above).
Ferries: We used ferryhopper.com for our inter island travel. If you are concerned about motion sickness while ferry hopping through Greece try these motion sickness patches. I did not have any issues on the ferries, but my sister is very sensitive to motion and she swears by these patches, she uses them in cars, buses, ferries and cruises and it has made travel easy for her.
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