As our ship approaches the massive, semi-circular rim of Santoríni’s volcanic crater, the chalk-white buildings clinging to the island’s edge come into clearer view. Small sailboats rest in the channels between nearby islets—dark, rocky reminders of what remains from one of the most powerful volcanic eruptions in human history.
The Celestyal Olympia eases to a stop while tender boats ferry passengers to shore. Once ashore, a bus winds up the steep hillside and takes us to Oia, the postcard-perfect village at the island’s northern tip. Famous for its blue-domed churches and spectacular caldera sunsets, Oia draws visitors from around the world. As the sun sinks, casting orange and pink across the layered cliffs, the island’s appeal is unmistakable.
Blue-domed church in the island’s village of Oia © Mikael Damkier | Dreamstime.com
Santoríni is arguably the best-known of Greece’s roughly 100 permanently inhabited islands scattered across the Aegean and Ionian seas. These islands sit at the crossroads of millennia of history—Romans, Byzantines, Ottomans and others have all left their mark. That deep past sits alongside modern restaurants, luxury hotels, boutique shops and marinas filled with yachts.
Signs of Greece’s recent economic struggles are more evident in Athens than on the islands, which often feel removed from the capital’s unrest. Despite the country’s long recession following 2008, many islands remain well set up for tourism, welcoming millions of visitors each year and offering services geared to short stays.
Cruising remains a popular and efficient way to visit multiple islands. Most sailings run from April through October, with July to September being busiest. Cruise offerings vary from large lines such as Holland America and Princess Cruises to smaller yacht companies like Setsail and Tasemaro Sailing. You’ll find everything from ships carrying over a thousand passengers to intimate yachts visiting lesser-known harbors.
The islands are grouped by region: the Cyclades in the central Aegean and the Dodecanese in the southeast, near Turkey, are among the most visited. Typical itineraries highlight Santoríni and Mykonos, two standout jewels of the Cyclades.
In Santoríni, most visitors flock to Oia for its views, but the island also preserves important history at sites like Akrotiri, a Minoan city buried under volcanic ash. Nearby Sikinos offers a quieter, more traditional island experience, where commercial tourism has made less of an imprint. Explore Kastro, sample local wines at the Manalis Wine Factory, and visit the dramatic beach at Agios Nikolaos for a fuller sense of the island.
Mykonos has a glamorous reputation and a thriving nightlife scene, but it also has quieter charms. Little Venice, where colorful buildings meet the water, is a must-see. Wander the narrow alleys of Hora, the island’s port and capital, relax at a seaside bar, or find a more secluded beach when you need a break from the crowds.
Naxos, the largest of the Cyclades, balances a lively town center with sandy beaches, mountain villages and notable archaeological sites. The Vallindras Distillery welcomes visitors for tours and tastings, and the Melanes Valley houses impressive ancient kouroi—large carved stone figures that recall the island’s long past.
The Dodecanese archipelago feels more remote; traveling there from Piraeus takes you across much of the Aegean. These islands are layered with history—Byzantine churches, Ottoman architecture and Italian influences sit alongside traces of Ancient Greece.
Tourists on the cobbled streets of Rhodes © Rangpl | Dreamstime.com
Rhodes, the largest Dodecanese island, offers a mix of attractions. Many cruise passengers disembark near Rhodes’ Old Town, a medieval walled city where cobbled streets wind past shops, cafés and restaurants. The town is built around a Byzantine fortress and has far more to explore than one day allows. On the east coast, the white houses of Lindos cling to cliffs above an ancient Acropolis, reachable via a scenic climb through town.
Kos features one of the region’s richest clusters of ruins, including the Asklepion—an ancient healing sanctuary associated with Hippocrates—and the Castle of the Knights. Charming mountain villages such as Zipari, Asfendiou, Zia and Pyli invite visitors to discover quieter, traditional island life between archaeological sites and coastal beaches.
Samos stakes its claim in both myth and philosophy: it’s associated with Hera and was the birthplace of thinkers such as Epicurus and Pythagoras. Key sights include the Heraion sanctuary and the remarkable Evpalinos Tunnel, an ancient engineering feat excavated in 524 B.C. The Samos Wine Museum provides guided tours and tastings for visitors interested in the island’s viticultural traditions.
Patmos is smaller and more contemplative, known primarily for the Cave of the Apocalypse, where Saint John is said to have received the visions described in the Book of Revelation. Pilgrims and tourists alike can visit the cave and tour the nearby Monastery of Saint John the Theologian.
Crete, Greece’s largest island, remains a major draw for its Minoan heritage and the Palace of Knossos, a centerpiece of Bronze Age civilization dating back to around 1900 B.C. Heraklion, the island’s bustling capital, is home to the Archaeological Museum, which houses an outstanding collection of Minoan artifacts and is well worth a visit.
Greece Info to Go
Most cruises begin and end in Athens’ port of Piraeus, so it’s convenient to fly into Athens International Airport. Direct flights connect Athens with cities such as New York and Philadelphia, or you can transfer through many European hubs. Ground transportation between the airport and Piraeus includes taxis and a range of private shuttle services, making transfers simple for cruise passengers.
Where to Stay in Greece
Kivotos Luxury Boutique Hotel A beachfront, art-oriented property offering extensive amenities including a spa, hammam and a private yacht available for guest charters. Ornos Bay, Mykonos — premium price point.
Lindos Blu Luxury Hotel & Suites A contemporary hotel that steps down a hillside with panoramic sea views, attentive service and close proximity to historic sites. Lindos, Rhodes — premium price point.
Mystique, a Luxury Collection Hotel An adults-only, cliff-edge retreat with sea-facing terraces and an infinity pool; mountain bikes are available but the views may keep you on-site. Oia, Santoríni — high to very high price range.
Restaurants in Greece
1800 Located in Oia, this standout restaurant operates in a former sea captain’s mansion overlooking the caldera. It serves contemporary Greek cuisine with a view that complements the meal. Oia, Santoríni — upscale pricing.
M-eating A creative take on Greek cooking in Mykonos, known for dishes like the Mykonian honey pie. Comfortable yet refined, it’s a popular choice in town. 10 Kalogera St., Mykonos — upscale pricing.
Marco Polo Café One of Rhodes’ top fine-dining options with a strong seafood focus and excellent desserts. Enjoy meals in a charming courtyard and pair dishes with selections from an extensive wine list. 42 Agíou Fanuríu St., Old Town, Rhodes — moderate pricing.