We rendezvous in Athens (sounds like the beginning of a spy thriller, haha). Meet our guide for orientation and head to lunch at a bustling Athenian taverna. From there we transfer to the port where we board a ferry for the start of our island-hopping adventure. Arrive on Paros and check into our hotel in Naoussa, the island’s most picturesque town. Naoussa is built amphitheatrically around a tiny port packed with colorful traditional fishing boats and ringed with seaside cafes. Lunch included.
Ferry: 4 hours
Pinch-me moment: When you first lay eyes on our first destination: the sun-kissed Greek island village of Naoussa.
You know the Venus de Milo, the famous ancient sculpture thought to depict the Greek goddess of love and beauty? It’s carved of marble from this island. And how appropriate. Paros is drop-dead gorgeous. We begin the day with baklava and good, strong Greek coffee. A leisurely start gives you time to check out Lefkes, a traditional village garlanded with meandering stone walls and spritzed with lemon trees and bright pink bougainvillea. Then we set out on the ancient Byzantine Trail, walking a marble stone road laid in Christian Roman times. Soak up the blue vistas and the scent of thyme and wild sage. Wind through the white village of Prodromos. End at the sea in Piso Livadi. Choose from many tavernas and beach cafes for a light bite or more traditional Greek lunch. Enjoy beach time and cool off with a swim, stand-up paddleboarding or kite surfing. Late afternoon, we return to Naoussa to enjoy an evening together amidst twinkling village lights and the creaking of fishing boats rocking in the harbor. Breakfast and dinner included.
Hiking: 4.7 miles; Elevation gain/loss: 243’/-919’
Note: Cost of optional beach activities not included.
Pinch-me moment: Walking a thousand-year-old stone road through timeless countryside.
How many shades of blue are there, really? Prepare to find out. Setting out from the village of Aliki, we board a traditional fishing boat and cast off for an island-hopping adventure. Imposing cave-riddled cliffs rise around us, guarding remote islets and storied Antiparos, an island crowned with a Venetian castle. Leap from the boat to wild swim in the crystal-blue waters of Panteronissia, sometimes called the Blue Lagoon. Cliff-jump at Mastichari Cave if you dare. Enjoy a floating picnic lunch on the boat. Walk the white sands of Despotiko Beach, where the remains of an ancient Greek sanctuary continue to yield archaeological insights. Take one last dip in the warm waters in a breathtaking hidden bay. Back in Naoussa, choose from lots of tasty options for dinner. Our guides are happy to recommend their favorites, of course. Breakfast and lunch included.
Swimming, beach time, and boat time: 7 hours
Pinch-me moment: Strolling near the ruins of an ancient Apollonian temple and hestiaron (ritual banquet hall) to the sound of lapping surf.
Pack your camera, open your eyes and experience the Greek Isles from a local perspective. Today, you wander Amorgos, an island brimming with visual treasures, with plentiful free time to follow your own bliss. The classic French film The Big Blue was filmed on this jewel of the Cyclades. Little-known compared to its larger neighbors, Amorgos is as authentic as it gets, with whitewashed villages and shepherds tending their flocks, plus a layered history that includes periods of occupation by pirates, rule by the Venetians and conquest by the Ottoman admiral Barbarossa. We settle into our hotel overlooking Aegiali Bay and then you’re free to roam. Our guides can help you choose from the abundant options. Relax in the hills with walking paths and amazing views of the Aegean. Venture to the Hellenistic-period Tower of Agia Triada. Take a lesson in pottery, traditional dance or Greek cooking. Go scuba diving. Hike with our guide. Go stand up paddle boarding. Go on an “Herbs of Amorgos” tour with a local herbalist. Wander the village and valley, camera in hand, on a DIY photo safari. Climb the steps of Ano Potamos for a jaw-dropping sunset. Breakfast included.
Ferry: 2 to 4 hours; Activity: optional activities; cost not included and paid on site.
Pinch-me moment: Discovering the hiking trails here are called blue paths because it is possible to see the sea at every turn.
Our destination this morning is the Monastery of Hozoviotissa. From Amorgos’ interior and the settlement of Asfontilitis, we hike a meandering trail into an almost surreal scene: a gleaming white 11th-century monastery built into a sheer cliff hanging high above the sea. The monastery is home to a revered icon of the Virgin Mary, brought over from Palestine long ago. Next, we continue our hike to Chora, a village set high above the Aegean. Its landmarks bear witness to its deep history: windmills, Byzantine churches, a 13th-century castle built by Venetian brothers. Back at the hotel, we take the afternoon to chill on the beach, explore, enjoy quiet time away from the group (we’ve got your back, introverts), or partake in the many activities mentioned on Day 4. In the evening, we meet up with our guide and fellow adventurers for a multicourse Greek dinner. Breakfast and dinner included.
Hiking: 5.5 miles; Elevation gain/loss: 939’/830’; Activity: optional activities; cost not included and paid on site.
Pinch-me moment: Toss-up between the dreamlike monastery by the sea and the epic multicourse Greek feast.
Ever met a supermodel? Santorini is the Greek Isles equivalent. A quick ferry ride delivers us there today. Marvel at the sight of multicolored cliffs rising up from a craggy volcanic caldera. Beneath the island’s beauty lies a tumultuous natural history; here, around 1600 BC, a volcanic eruption wiped out an entire civilization. We check into our hotel just steps away from the famous black-sand Kamari Beach before heading to the caldera side of the island. Our destination: the photogenic village of Oia. (You’ll recognize it. Guaranteed.) We take some leisurely time exploring its narrow cobblestone streets and discovering why it’s one of the most visually popular destinations in Greece. Then we hike the volcano. Specifically, on paths of black lava rock along the edge of the caldera, high above the sea. The blue endlessness of the views inspire and exhilarate us. We end in Fira to savor our last sunset together over a traditional Greek meal in a restaurant overlooking the caldera. Tonight, we can hang out at a beach bar and toast to new friends, happy memories, and the immortal beauty of the Greek Isles. Breakfast and dinner included.
Hiking: 6.6 miles; elevation gain 1800’/loss 1100’; ferry: 1 hour
Pinch-me moment: Taking in the iconic vision of Santorini’s bell towers outlined against the shockingly blue Aegean.
Sleep in if you choose, or rise early to catch the legendary Santorini sunrise. Our odyssey concludes after breakfast. You'll then depart Greece (transferring on your own to the Santorini airport or ferry terminal) or stay a bit longer to explore on your own. For those with late afternoon flights or ferries, or who are extending their stay independently, our guide can hook you up with the best guided sea kayaking excursion on the spectacular south coast. Breakfast included.
Optional guided sea kayaking excursion: 3 hours; not included in trip and subject to availability.
Pinch-me moment: Not to state the obvious but the sunrise on Santorini. (Or sleeping in and waking up to Greek Isles sunshine.)