From Naxos to Mykonos, Greece’s many islands are temping to cover all in one trip, but the best way to enjoy them is by choosing 3 to 5 at a time to fully relax and enjoy what each island has to offer. Here’s your guide to the best Greek island-hopping trip:
If you’ve arrived in Athens the night before, take a day to soak up some of the city’s most important sites, including the Acropolis and Parthenon, a quick walk through Anafiotika, and a glass of wine from one of the city’s many delicious wine bars.
Take the earliest possible ferry from Piraeus port (southwest of central Athens; easily accessed via metro from Athens, but arrive early to avoid missing your boat!). You’ll arrive a few hours later in fertile Naxos, the largest of the Cycladic islands. Visit the Temple of Apollo and go have lunch at Yema Agapis. Spend an hour or two walking around Hora and up in the Kastro. Eat dinner at Axiotissa Taverna, the best restaurant on an island full of amazing food.
Get the blood pumping with an early morning hike through Mt. Zas’ loop from Arai Spring. The first half is well-marked; beyond the cave you’ll just follow the beaten foot path. Then, drive over to the cozy seaside village of Moutsouna for a grilled fish lunch, before heading down to Psili Ammos for a relaxing afternoon by the sea.
Devote a day to exploring the mountainous interior of the island, where charming traditional villages dot the landscape and the view. As you drive up increasingly winding road, the scenery becomes more and more breathtaking. A good trip is to go from Sangri to Halki (you must try the custard pie from To Spitiko Galaktobouriko) to Apiranthos, before stopping in Koronos for a very late lunch at Matina & Stavros’ Taverna. Consult the map beforehand; the most circuitous route is often the safest and best paved road to travel.
Naxos to Mykonos
Spend the morning relaxing on Alyko Beach and exploring the many coves and abandoned hotel covered in artistic graffiti. In the late afternoon, take the fast boat to Mykonos, where you can catch the sunset at the aptly named 180 Degrees Sunset Bar in Hora. Hunker down in your hotel; Mykonos is going to get you good tomorrow.
Day Trip to Delos Archaeological Site
Take the 9am boat to Delos and spend your allotted four hours wandering around this amazing piece of living history. On your return, head directly for Super Paradise Beach and spend the afternoon sipping champagne and dancing with beautiful people. Cap off the evening with some debauchery at Jackie O.
You’ve probably felt better, huh? Take a leisurely car drive through the island’s interior roads, and head to one of the more secluded beaches, such as Agios Sostis on the northern coast, where you can enjoy a delicious meal at the seaside taverna. Before sunset, head to Scorpios for a cocktail, and then let the night take you…
Head out of Mykonos to Anafi (the easiest way is to take a boat through Santorini; the whole journey takes 5 hours). It would defeat the whole purpose of Anafi if I were to give you an itinerary. Instead, spend your days lounging around the beach, occasionally walking the trails. If you see only one beach, make it Megalos Roukounas. If you do nothing else, you’ve done it correctly.
Anafi to Athens
Take the ferry back to Athens (8 hours) feeling relaxed and completely rejuvenated.