Discover the Cycladic Islands
It's hard to go wrong with the iconic Cycladic Islands: no matter which you choose, you’ll be accompanied by crystalline blue seas, winding stone streets, sunny beaches, and tavernas filled with all the ouzo you could ask for. And you'll certainly want to choose more than one. Ferries run regularly in the high season for easy inter-island transit, though schedules decrease from roughly September through June for the diminished crowds.
That said, don’t try to breeze through the whole chain at once; you should allot at least two to three nights per island, more if your schedule can manage it, to make sure you have time to truly enjoy what they have to offer. Each section below contains some itinerary inspiration to get you started.
Santorini: Caldera Sunsets and Colorful Beaches
When you think “Greek islands” and picture those cliffs lined with classic white buildings, you’re thinking of Santorini. As the other main star of the Cyclades, Santorini and its donkeys welcome thousands of visitors up the side of its almost excessively scenic volcanic caldera, the site of an ancient eruption felt all the way to China.
The main caldera-side towns of Fira, Firostefani, Imerovigli, and Oia all overlook this central basin, which you can also cruise through to visit hot springs and cross the small internal volcanic islands. The island’s most popular hike (though there are many trails crossing the island) runs from Fira to Oia through homes and hotel terraces along the cliffside, dropping you off in Oia hopefully just in time to battle the selfie-stick-wielding crowds searching for the perfect sunset shot.
On the slightly quieter opposite shore, towns like Perissa and Kamari offer beaches in hues ranging from white to red and pink to black. Or visit southern Akrotiri, once home to one of the most advanced settlements of the Bronze Age before it was buried by the volcano.
Interested in Santorini? Try these itineraries.
History and Culture in Athens and Santorini - 7 Days. Explore the island vineyards and Akrotiri archaeological site with this history tour.
Greek Panorama in Athens, Mainland Greece, The Cyclades, and Crete - 21 Days. See the spectrum of Greece on this itinerary including a Santorini island tour, wine tasting, and cruise through the caldera.
Relaxed Athens, Santorini, Naxos & Mykonos - 12 Days. Top off an island trip with a relaxed evening stroll followed by a catamaran cruise that takes you past Akrotiri and the other sights of the caldera, accompanied by onboard barbecue.
Mykonos: Glitter and Greek History
Glitzy Mykonos is the wealthy attention-seeking member of the Cycladic family, home to a jetsetting party scene that draws cosmopolitan crowds year after year, with prices to match. If you want to stroll the galleries and Gucci pop-ups by day and sip cocktails or dance on the beach by night, Mykonos is for you—assuming you’re willing to compete with the high season crowds.
Those who want to stop on the island without getting drawn into the scene can get lost in the bougainvillea-lined streets of the whitewashed main town or seek out one of the island’s 25 beaches, which range from party-hard Paradise Beach to naturist-friendly northern Panormos or active Platys Gialos. Stop for a sundowner in Little Venice, where 18th century sea captain’s mansions seem to rise out of the sea and you can seek out a photo op with one of the island’s famous resident pelicans or hilltop windmills.
If you’re more into Classics than Cartier, Mykonos is also the closest island to the archaeological site at Delos, one of ancient Greece’s most sacred sites. It’s a 45-minute ferry ride to the small island that was the center of the Cyclades during the Classical era as both one of the largest trade sites of the Mediterranean and the mythological birthplace of twin deities Apollo and Artemis.
Moved by Mykonos? Try these itineraries.
Cultural Cyclades - 12 Days. See some of the quieter side of Mykonos with an inland village tour and day trip to Delos.
Historic Athens, Mainland Greece, Cyclades and Crete - 13 Days. Explore the Classical era across the country, including two nights in Mykonos and a boat trip to Delos.
Family Adventures in Athens and the Cyclades - 10 Days. Bring your family to the islands and spend an afternoon on a Mykonian farm flowing into a home-cooked dinner.
Paros: Bustling Ports and Peaceful Beaches
Peaceful Paros lends itself best to long days in the sun and nights listening to bouzouki music in its seaside tavernas. You’ll find all the classic whitewashed architecture and winding town streets you expect of the Cyclades in the main town of Paroikia, along with the Panagia Ekatontapiliani church, also known as the Church of 100 Doors, one of the best-preserved Christian churches in Greece.
Sunbathe amid the towering sculpturesque rock formations of Kolymbithres beach or golden Molos or learn to kite- or windsurf off the winds of the strait. Head into the pirate den turned bustling marina of Naoussa to find your perfect evening adventure, whether it’s a relaxed dinner or bass-bumping bar.
If you need a break from the beach, you can venture up to the hillside ruins of the Mycenean Acropolis, dating back to the 13th century BC, and the neighboring Monastery of St. John for some inland history. Or head to the village of Lefkes and the Byzantine architecture of the Agia Triada church, located on what some consider one of the most beautiful squares in the Cyclades.
Ready to ferry to Paros? Try these itineraries.
Active Cyclades Adventure - 12 Days. Take a cooking class, horseback ride, and half-day interior hike on this physically engaging itinerary.
Off the Beaten Path in Paros & Naxos - 8 Days. Take advantage of a full four nights on Paros, with two days for Molos and Kolymbithres beaches and one to spend strolling the inland churches and Paroikia shops.
Naxos: Venetian Castles and Culinary Villages
One of the first things you’ll notice approaching Naxos is its famous Portara. The entrance to the never-finished Temple of Apollo sits on the Palatia islet just outside of Naxos town, marking a doorway into the sky. As the largest island in the Cyclades, Naxos merits a thorough exploration of its Venetian architecture, historic hillside Kastro district, beaches, and archaeological sites.
Learn to windsurf on the western beaches, then refuel with signature Naxian cheese and kitron liqueur along with its fresh produce in the many tavernas. Take a road trip around the island to sites like the Temple of Demeter at Sangri, ancient giant kouros statues of male youths, shady squares and kitron distilleries of Chalki, and marble village of Apeiranthos.
Is Naxos calling your name? Try these itineraries.
Cyclades & Peloponnese Culinary Heritage - 14 Days. Taste some of the benefits of Naxos's agriculture with a walk through the streets of the Kastro district on a castle food tour, then explore the marble streets of Apeiranthos.
Past and Present in Athens, Tinos, & Naxos - 7 Days. Travel on a food panorama around the island, sampling dishes from fried donuts to meatballs and olive pies, topped off with a taste of kitron.
Ios: Sleep on the Sands, Dance Under the Stars
With parties to compete with Mykonos and significantly lower prices, Ios is known for its intense nightlife. Mylopotas beach has become the unofficial center of the scene, boasting close proximity to the main town, long stretches of sand, and Far Out Village, a combination beach club, campground, and hotel.
You can dry out for a day by visiting what might be the poet Homer’s tomb or secluded Manganari beach. Boat and ATV tours run around and over the island, or take a ferry day trip to the quiet hills and wineries of neighboring Sikinos island.
Intrigued by Ios? Try these itineraries.
Active Cyclades: Tinos, Naxos & Ios - 13 Days. Canoe through Mylopotas Bay for a new perspective on the island.
Relaxing Secret Cyclades - 10 Days. Spend your island time in a more horizontal fashion, including a day trip to neighboring Sikinos for some leisurely touring and wine tasting.
Tinos: Pilgrims, Dovecotes, and Marble
Also known as the island of the Virgin Mary, petite Tinos’s primary visitors are the thousands of annual pilgrims to its Panagia Evangelistria church who crawl on their knees from the port toward the church icon in search of its healing powers. But it’s well worth a trip at any time, with nearly 80 windmills, Venetian ruins, hiking at Exomvourgo mountain, beaches, and even a craft brewery to be explored.
Tinos is also known for its marble crafting, and you can get a glimpse into the history of this most Greek of materials on its marble route from the Museum of Marble Arts through an open-air cemetery museum to the home-turned-museum of famous sculptor Yannoulis Chalepas. Keep an eye out for the many painted dovecotes (small white pigeon homes) dotting the countryside, of which there are nearly 1,000.
Packing your bags for Tinos? Try these itineraries.
Active Athens, Mainland Greece, Cyclades, and Crete. An active itinerary with three nights on Tinos that have you hiking through the lunar landscape of Volax and learning to surf or stand-up paddleboard on Kolymbithra beach.
Laid-Back Athens, Tinos, Mykonos, Santorini, and Crete. Walk the famed Marble Route on this relaxed two-week itinerary.
Syros: Sleepy Cycladic Capital
It may not have the name recognition of its more famous neighbors, but Syros is actually the administrative capital of the Cyclades. With the highest population of the islands and some of the lowest tourist crowds, Syros is a spot for those seeking a more everyday Greek island experience.
The island is mostly rural outside of the main town of Ermoupoli, whose Crayola-hued neoclassical buildings rise up amphitheatrically around the port. Look for the domes of the Greek Orthodox and Catholic churches atop their neighboring hills or visit the Apollon theater, built in 1864 as a replica of La Scala in Milan and host to an annual music festival that attracts visitors from around the country.
Hearing the siren song of Syros? Try this itinerary.
Relaxing Secret Cyclades - 15 Days. Sample some of the island chain's lesser-known highlights, including two nights on Syros and a drive through the island's historic mansions.