Summary
A Classic Crowd Pleaser, Arranged by Petros G. Zissimos of Hellenic Holidays
Days 1–3
This quintessential itinerary includes visits to some of Greece’s most iconic destinations, Zissimos notes, adding that “it’s our most popular trip for 2023 so far.” Touch down in Athens, where you can hit highlights such as the Acropolis and Areopagus with a guide, then explore neighborhoods like Kolonaki and Plaka on your own. Zissimos recommends staying two nights at the well-situated Electra Metropolis before heading off to the Cycladic island of Mílos, which is accessible either by air (45 minutes) or by ferry (from three hours).
Days 4–6
“Mílos has dozens of beaches to visit, with different combinations of sand, stone, and shells,” Zissimos states, emphasizing his preference for Sarakiniko. Moreover, he recommends a sailing excursion to Kleftiko, where volcanic rock formations make for spectacular photographs, and an afternoon in Adamantas, where tavernas line the waterfront. The seaside Melian Boutique Hotel & Spa, on the northeastern tip of the island, is a top recommendation.
Days 7–9
It’s essential to set aside a morning for the four-hour ferry ride to Naxos, which offers a mixture of archeological sites and contemporary adventures. “There’s a beach for everything here,” Zissimos notes. For instance, Agios Georgios is famed for windsurfing, while Mikri Vigla is ideal for kitesurfing. Zissimos can also organize guided visits to the Temple of Demeter and the Portara, a 2,500-year-old marble gate that stands at the entrance to Naxos Harbor. His preferred lodging includes Villa Marandi Suites, known for its ocean-view rooms.
Days 10–14
After breakfast, catch a high-speed ferry (90 minutes) to Santorini, then check in to the cliff-top Grace Hotel, Auberge Resorts Collection. Spend the next day enjoying a sailing excursion, complete with snorkeling stops. Furthermore, Zissimos can arrange wine tastings and recommend hikes, such as the coastal path from Fira to nearby Imerovigli, which offers spectacular views of the caldera. Don’t forget to leave time for a sunset dinner in the bustling village of Oia. After exploring Santorini, travelers can ferry or fly back to Athens for the journey home.
Something Less Expected, Planned by Christos Stergiou of TrueTrips
Days 1–3
The capital is a must-see, Stergiou asserts, “because its classical history has so distinctly influenced modern thought.” He suggests a guided tour that takes in both the ancient and contemporary sites, visiting the Acropolis Museum and the Temple of Olympian Zeus, as well as landmarks around central Syntagma Square, including the Greek Parliament. Conveniently, his hotel pick, Hotel Grande Bretagne, a Luxury Collection Hotel, is located on the same square. “It’s the grande dame of Athenian hotels,” Stergiou mentions.
Days 4–7
From Athens, travel to Patmos, “an island that exudes a unique aura thanks to its seemingly untouched natural beauty,” Stergiou says, emphasizing that it’s a Christian pilgrimage site, believed to be the location where the Book of Revelation was written. His favorites include the village of Chora, a UNESCO World Heritage site and “one of the best-preserved medieval settlements in the Aegean.” Stergiou can also arrange private boat excursions for sightseeing, swimming off uncrowded beaches, and dining in local family-run restaurants. His go-to hotel is the Petra, a family-run establishment since 1989, now part of Small Luxury Hotels of the World.
Days 8–10
After a late checkout, hop aboard the overnight ferry from Patmos back to Athens — in a private cabin, of course. In the morning, it’s an easy one-hour flight to Páros, an island Stergiou describes as “up-and-coming, or maybe already there.” Make your way with a guide to the island’s north and the Environmental and Cultural Park of Páros. The area “is filled with fascinating attractions, including the old shipyard and the Monastery of Agios Ioannis Detis, built right above the sea.” Check in at Cosme, a Luxury Collection Resort, where Stergiou enjoys the Aether suites, with their sea views. Spend the rest of your time either lounging on Páros’s sandy beaches or making day trips to nearby islands like Antiparos, before taking the ferry (from 90 minutes) over to Santorini.
Days 11–14
“It’s not exactly under the radar,” Stergiou remarks regarding Santorini, “but with the right guides, you can still tap into the more traditional side of the island.” He recommends spending one day exploring Assyrtiko vineyards, such as Domaine Sigalas; he also suggests a guided walk through Oia, the picturesque yet popular village that still conceals a few lesser-known corners. As for accommodations, the Canaves Oia Epitome strikes the right balance between proximity to the island’s best restaurants and seclusion — particularly if you’re staying in a one-bedroom pool villa. Stergiou suggests ending your journey with one last night back at the Grande Bretagne before your return flight home.
Off the Tourist Trail, Recommended by Mina Agnos of Travelive
Days 1–2
Start in Athens, Agnos suggests, “but unless you’ve never visited the Acropolis, I’d recommend a tour of the stunning archaeological site of Cape Sounion, south of the city, where there are breathtaking sunsets.” Spend another day on a guided tour of the city’s cafés and ouzeri, casual bars that serve anise-flavored spirits alongside platters of meze. Agnos highly recommends the centrally located and recently opened hotel Xenodocheio Milos, from the group behind the esteemed Estiatorio Milos restaurants.
Days 3–5
Your next stop is Sérifos, “a Cycladic island that boasts some of the most stunning beaches in Greece, including sandy Psili Ammos, often listed among Europe’s finest.” Agnos mentions. More rugged and less commercial than nearby spots like Mílos, it’s nevertheless easily reachable by ferry (from two hours). Agnos suggests taking time to explore the island’s mythological sites, such as the ancient construction known as the Throne of the Cyclops, then spend time swimming or hiking. She recommends staying at the Hotel Rizes, which overlooks the port.
Days 6–9
From there, continue by ferry (from 6 1/2 hours) to Naxos, a beachy island that is also a favorite of Zissimos. Agnos recommends exploring the island’s many hikes (such as a half-day round-trip from the village of Chalki) and can also arrange cooking or pottery classes. Accommodation options include the hilltop 18 Grapes, which has two pools and sea views, or Naxian on the Beach, which features ten seafront suites.
Days 10–13
From Naxos, it’s a convenient ferry trip (from 90 minutes) west to Sífnos, a lesser-visited Cycladic island gaining a reputation for its culinary scene. “It’s renowned in Greece for offering some of the country’s finest dining experiences,” Agnos elaborates, noting that it is the birthplace of distinctive dishes like revithada, a chickpea stew, and mastelo, red-wine-braised lamb. The island also has various hiking trails, ranging from easy three-mile loops to more challenging nine-mile hikes. Agnos recommends a stay at Elies Resorts, situated on Vathi Beach.
A version of this story first appeared in the February 2023 issue of GoTravelDaily under the headline “The Best of Greece, Three Ways.”
