Peloponnese
You don’t have to travel far to find the magic of the Mediterranean. Leave Athens behind and head west—you’ll stumble upon ancient seaside villages in the Peloponnese like Epidaurus. Or try going southeast toward Sounion, where you can spend the night right under the Temple of Poseidon. Don’t skip Monemvasia. This medieval town, carved straight into the rock, is one of the most romantic places in Greece. Seriously, it’s unforgettable.
Argo-Saronic Islands
Just a short sail from Athens, the Argo-Saronic Islands are perfect for an easy escape. This little cluster—Spetses, Poros, Aegina, Hydra, and Agistri—each has its own personality. Poros is all pine trees and charm, tucked right next to the Peloponnese. Hydra’s a classic: no cars, gorgeous harbor, neoclassical mansions, and more cozy cafes than you’ll know what to do with. Spetses is just as beautiful, with tree-lined beaches and secret coves waiting to be found.
Crete
Crete is the biggest Greek island and a fantastic spot for a sailing adventure. You’ll find fewer boats here than in the Cyclades or Sporades, so it feels a bit more laid-back. The beaches are stunning, and history is everywhere—you’re walking in the footsteps of the ancient Minoans. Don’t skip Knossos, where King Minos supposedly ruled. If you can, avoid the heavy winds in July and August. May, June, September, and October are the sweet spot.
Thassos
If you’re already sailing around Halkidiki, swing by the peaceful island of Thassos. You might spot dolphins near Panagia, a protected marine area, or check out the wild rock formations around Giola. Take a dip at Aliki, then head to Archodissa—a tiny local tavern—for grilled lamb and homemade stuffed vegetables (gemista). Cruise north to Paradise Beach, and finally, drop anchor for the night in the small harbor of Thassos town.
Sporades
The Sporades are made up of four main islands: Alonissos, Skopelos, Skyros, and Skiathos. Skiathos gets most of the attention, but if you’re after something wilder, Alonissos is much less developed and has a protected marine park—perfect for spotting wildlife. Skopelos comes with its own Byzantine castle, while Skyros is the place for empty beaches and quiet coves far from the crowds.
Dodecanese Islands
Give yourself at least a week to sail the Dodecanese. Start with Rhodes—its old town is a UNESCO site for good reason—then head to Tilos and wind-swept Karpathos. Or take a detour to Kos, where Venetian castles and flashy resorts mix with quiet corners. Don’t miss the almost-deserted islet of Levitha, and make time for Lakki Town on Leros, famous for its Greek-Italian cuisine.
Ionian Islands
Zakynthos sparkles among the Ionian Islands. Slip into the Blue Caves or land on Navagio beach—you can only get there by boat. Sail north to Kefalonia and take your time; you’ll want at least two days here. After that, hop over to friendly Ithaca and its little neighboring islands, then west to Lefkada. Wrap up your journey in Corfu, and don’t forget to make a stop in Paxi and Antipaxi for their dreamy beaches and hidden coves.
Cyclades Islands
For those classic Greek views—white houses, blue domes, endless sea—the Cyclades are calling. Party all night in Mykonos, soak up the sunsets in Santorini, or get away from it all on wild Koufonisia. History lovers will want to see Delos, believed to be Apollo’s birthplace. Amorgos is a dream for hikers, with trails that look out over the Aegean. There are 39 islands in the Cyclades—you won’t see them all in one trip, but you can cross off quite a few.
