The Greek Isles are peak Eurosummer. Though we've spent time in the islands each summer since moving to Europe, we decided to take ten days in August to revisit some of our favorite spots with Erin's brother Mason and his friend Pete, welcoming them to Europe on their semester abroad.
Part One: London to Santorini
We started our adventure with a few days in London on business. Since Mason and Pete hadn't visited before, we embarked on an extended walking tour, stopping at Borough Market for famous cheese toasties at Kappacasein, walking through the Tate Modern, past Shakespeare's globe and browsing vintage shoppes in Soho.
Our flight to Santorini was scheduled to leave at 6:35 am, and we were not confident that Mase and Pete would wake up for our driver pickup at 3:15 am. Luckily, they'd had a pub and hotel bar night and were still awake from the night before, so we scooped them up and headed out of London. After a quick stop at the airport lounge for breakfast, we hopped on the EasyJet flight and landed in Santorini by lunchtime. Our Airbnb host picked us up and helped us rent ATVs, our rides for the next few days, and we picked up some cheap gyros for lunch, which we enjoyed on the deck of our classic concrete cave house.
Since we've visited Santorini before, we decided to spend or days on the water and hit a few favorite spots:
Boat Day with Sunset Oia:
Taking a catamaran along the coast and around the caldera is the best way to experience Santorini. Recommended to upgrade to the more expensive trips for more space and fewer passengers. We started this day with snorkeling and cliff jumping at various spots around the island, enjoyed a delicious Greek lunch on board, and watched the sunset (drinks included) from the boat.
Hike Fira to Oia:
This hike is no joke (took us 4 sweaty hours) but the changing views, landscapes and endless photo opportunities are totally worth it. We recommend hiking from Fira to Oia. Stop near the donkey ride spot at a little cliff-side cafe selling fresh orange juice and homemade walnut cake.
Follow the path past the restaurants around the corner to the swimming area. Be careful laying out, as the boulders lining the cliff up to Oia have been known to fall down. Even so, super fun to swim out to the tiny island with a church on it for some epic cliff jumping. Dave and Mase were awarded beers from a passing yacht from their acrobatics
Ruins dating from the 16th century BC on the far end of the island - everything is located under a tented ceiling, so you're shielded from the sun. For anyone into history, this is a must.
Great stop to visit after Akrotiri - pebble beach with clear, deep water and various heights of cliff jumping at one end. Grab groceries in the little town alongside the beach and have a picnic.
Fun ATV ride down a twisty road from Oia, sunset views, short hike to the beach below and delicious vegetarian Greek mezes (tapas)
Off the beaten tourist path local spot for home cooked food - stuffed tomatoes, grape leaves, tatziki, roasted meats, all super fresh and cheap
If you are sick of simple Greek breakfasts (as Mase and Pete were), American-style pancakes with Caldera views await.
In Oia with caldera views - delicious Greek mezes with a central location along Oia's famous walking streets
Santorini is a place that has to be seen, but because so many cruise ships visit, there are too many tourists. We recommend spending a couple of days and then moving on to a less populated island with more freedom to explore.
Part 2: Santorini to Milos
Due to its now Instagram-famous Sarakiniko Beach, Milos is gaining prominence on the Greek Isles list, but it is thankfully still a breath of fresh air after the seemingly endless tourists in Santorini. We took a ferry from Santorini and arrived in Milos a couple of hours later. Once again, we went with an Airbnb in Plaka, the classic, whitewashed old town with views across the island out to sea.
The Milos Adventures full day boat trip (itinerary Route 2 along Milos and Poliegos) is my favorite boat day in all of Europe. This was our second time doing it, and the color of the water in Poliegos is still stunning - the water is so neon turquoise that it burns your eyes. With a trip to old pirate hideout Kleftiko with just us and a few super yachts, this trip, with lunch on board and drinks included, is a must do in Milos before anything else. The open seas can get a little rough, so be prepared to get wet.
Famous on Instagram but still not super crowded, especially if you hike away from the entrance, past the tiny swimming beach over to the coves and cliffs. All heights of cliff jumping, moon-like surroundings and former mining caves to explore. Mase and Dave put on a flip show, recruiting a few brave tourists to join them. Worth the trip to Milos alone.
Shimmy down through a steep sandy canal with a rope and climb down a steep ladder to reach a cove of crystal turquoise water, with caves on both sides to explore.
Sulphur Mines Thiorichio:
The perfect Bond movie villain's lair. Only accessible in a 4X4 or by those ignoring the advice of their ATV rental company. Abandoned sulfur mines and housing for workers. Interesting to hike around and explore, plus a nice beach with sulphur hot springs.
The Bonfires of Old Man August:
If you happen to visit on the last day of summer, you can take part in the local bonfire jumping ceremony.
A super fun and picturesque ride down to the little town of Mandrakia. While you wait for your table, you can view the octupus catch of the day drying in the sun or take a dip. Part restaurant, part cat sanctuary, kittens will sleep alongside you as you enjoy fresh seafood and Greek classics.
A more modern take on Greek food, with all of the vegetables grown in the restaurant's garden. The zucchini blossoms are so good - filled with flavorful rice and herbs.
In Plaka, fresh and modern takes on Greek cuisine. Plaka is the best town to walk around in and has good shopping. Feels like quintessentially Greek island vibes.
Just as you exit the port down and head toward Plaka, next to the market is a bakery with everything you could need or want for a picnic - famous Milos watermelon pie (which tastes like watermelon flavored cornbread with a little gelatin but is somehow tasty), fresh baked pizza breads, cookies, cold drinks and ice cream pops
Part 3: Milos to Athens
Sad to be leaving Milos, we hopped on a big ferry and headed to Athens (definitely recommend taking the larger ships for longer journeys in Greece, unless you have a very strong stomach). We checked into our Airbnb near the Acropolis.
Since it was our first time in Athens, we hit all of the major sites like the Parthenon, Temple of Hephaestus and the Erechtheion. Our biggest advice: hit the Acropolis early, just as it opens. On our first try, we went an hour after opening and were swarmed by tour buses. We tried again the following day and had the epic ruins and views across Athens all to ourselves for a short time.
In the US especially, the media paints Greece as a place with economic and political concerns. While that may be true, Greece is the perfect place for a summer vacation - the people are friendly, the food is fresh and delicious, and the weather and seas are perfect for adventure, cliff jumping, snorkeling, or chilling on the beach. We would recommend Greece to anyone.
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