See the lesser-known side of the Cyclades on this 16-day  island itinerary. After sampling the street foods of Athens, you'll ferry off to the Cycladic islands that deserve just as much of the spotlight as their more-famous siblings. Tour the mansions of the Cycladic capital on Syros, explore the Tinos marble scene, bike the beaches of Naxos, and see the villages and vineyards of Ios before your return to Athens, accompanied by the sweeping of the Aegean Sea.

Highlights

  • Pay tribute at the Panagia Evangelistria pilgrimage church
  • Sample the culinary specialties of Naxos
  • Sip wine on the hills of Sikinos
  • Watch the sunset over the Temple of Poseidon

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Athens Food Tour Athens
Day 3 Day Trip to Mycenae and Nafplio Athens
Day 4 Travel to Syros Syros
Day 5 Syros Mansions Driving Tour Syros
Day 6 Ferry to Tinos Tinos
Day 7 Follow the Marble Route Tinos
Day 8 Tinian Culinary Workshop Tinos
Day 9 Ferry to Naxos Naxos
Day 10 Naxos Food Panorama Naxos
Day 11 Naxos Bike Tour Naxos
Day 12 Ferry to Ios Ios
Day 13 Ios Village Tour Ios
Day 14 Sikinos Island Tour & Wine Tasting Ios
Day 15 Return to Athens, Sunset at Cape Sounion Athens
Day 16 Depart Athens  

Detailed Itinerary

Day 1: Arrive in Athens

Monastiraki Square and the Acropolis
Monastiraki Square and the Acropolis

Welcome to Greece! You'll begin your trip in Athens, home to both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

  • Check out the views of the can't-miss Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki flea market. 

Spend your evening exploring the up-and-coming Pangrati neighborhood or amid the nightlife and mezze of the Psyrri district.

Day 2: Athens Food Tour

Vendors in the market
Vendors in the market

Meet your guide in Syntagma Square to start sampling the best of what the city's street food stalls have to offer. You'll learn about the Mediterranean diet and its potential benefits while strolling the city streets in neighborhoods you may not have discovered yet and exploring bustling open-air markets.

Say good morning with Greek coffee at one of the city's landmark coffee houses, then pick up some street snacks to sample on the go. Venture into the aromatic Varvakios Market, the largest and most popular fish, meat, and vegetable market in the city, and explore the city's main spice street. Sample olive oils, honey, cheeses from around the country, cured meats, olives, and more. Everything from baklava to souvlaki is available to appeal to even the pickiest eaters.

If you haven't had your fill of adventuring during the afternoon, spend your evening in the Koukaki neighborhood. This area's off-the-beaten-path wine bars will introduce you to a wide selection of Greek wines amid friendly crowds, or if you're with the whole family a selection of great local restaurants await.

Day 3: Day Trip to Mycenae and Nafplio

The Lion Gate
The Lion Gate

Start the day early with a full day trip back to a true classic. You may recognize Mycenae from its role in Homer's Iliad: It was home to the famous Helen, whose Mycenean husband King Agamemnon led his people to war when she left him for Paris of Troy. See its Cyclopean walls, whose construction method is still a mystery. They got their name due in part to the belief that only the mythical Cyclops would have been strong enough to lift their boulders.

You'll pass through the Lion Gate to enter the ruins of the city, wandering past the tombs of Aegisthus and Clytaemnestra and the Treasury of Atreus.

You'll go on to Nafplio, one of the prettiest seaport towns in the Peloponnese peninsula and once believed to have been founded by the son of Poseidon. The town was the first capital of the new Greek state after the war of independence in the 1800s. Take a stroll through the old town, where you'll pass statues honoring significant figures from Nafplio's history, Ottoman fountains, and Venetian architecture along the winding streets, topped off by the Bourtzi Castle in the middle of the harbor. Don't miss the climb up 1,000 steps to see the view from the Palamidi Castle before you're transferred back to Athens in the evening.

Day 4: Travel to Syros

Homes on the coast
Homes on the coast

Start your morning by heading to Syros, home to the capital of the Cyclades. You'll be greeted by the domes of the Greek Orthodox and Catholic churches atop the hills of Ano Syros and Ermoupoli, churches that join together for yearly Easter celebrations.

Follow the cobblestone streets through the squares and past architectural features like the Ermoupoli City Hall designed by Ernst Ziller, also responsible for many of the mansions and national buildings in Athens. Visit the Vaporia neighborhood, home to the mansions of 1800s sea captains, or the medieval hilltop settlement of Ano Syros for expansive sea views. The yearly music festival attracts visitors from around the country to the Apollon theater, built in 1864 as a replica of La Scala in Milan.

Day 5: Syros Mansions Driving Tour

One of the mansions along your route
One of the mansions along your route

Tour the villages of Syros with their many stately homes on today's private driving tour. You'll head to a slew of towns to see some of their architectural attractions, starting in Poseidonia at the old town hall, once a villa and garden now turned exhibition hall.

See the grand homes of ship captains and owners in Episkopio, then the smaller everyday homes and churches along with the scenic pine forest surrounding quaint Chroussa.

Make your way to Kini or San Michali before the sunset to enjoy dinner and the seaside sunset views.

Day 6: Ferry to Tinos

Panagia Evangelistria church
Panagia Evangelistria church

Take an early ferry to Tinos, one of the most overlooked islands of the Cyclades. Tinos has remained under the radar for many years, overshadowed by its celebrity neighbor of Mykonos and seen mainly as a religious destination. Those who continue to believe that, however, are missing out on an island with fascinating history and culture, winding streets, great outdoor activities, and glittering beaches.

The imposing Panagia Evangelistria should not be overlooked, as Tinos is also known as the island of the Virgin Mary. Its icon is believed to have healing powers, and the annual August pilgrimage is a key part of the island's identity as churchgoers crawl on their knees toward the temple as a sign of piety.

If pilgrimage isn't quite your scene, there are also nearly 80 windmills to be explored, Venetian ruins, hiking at Exomvourgo mountain, and beaches for any moods. Try the island's craft beer from Nissos brewery or sample the cheeses at the shop belonging to the Cheese Cooperative of Tinos. Keep an eye out for the many painted dovecotes around the island as well, small white pigeon homes dotting the countryside of which there are nearly 1,000.

Day 7: Follow the Marble Route

Marble in the wild
Marble in the wild

Tinos is known for its marble crafting, and you'll see why as you follow this route from raw materials to artists' workshops.

Start at the Museum of Marble Arts. In its halls, you'll learn how Tinian craftsmen start with slabs of stone and craft them into artful statues and other works from fountains and altarpieces to tower bells, palaces, and stadiums. See that work in practice as you walk through the cemetery of Pyrgos, also an open-air sculpture museum, on your way to Pyrgos Square. Take a break in the square for some coffee or ouzo along with an afternoon snack or sweet. 

Your next stop is the home of sculptor Yannoulis Chalepas and the Museum of Tinian Artists. You'll make your way through the workshops of the village, where you can meet a sculptor who will introduce you to the raw marble along with their tools and tricks of the trade. 

Cap it off with a swim at Agia Thalassa beach and dinner in the fishing village of Panormos.

Day 8: Tinian Culinary Workshop

Just-picked produce
Enjoy the greenery

Visit an aromatic garden and harvest fresh ingredients as part of this culinary experience. You'll learn the stories of some Greek recipes, then cook them yourself with expert instruction. Enjoy the fruits of your labor al fresco, as you consume your creations under the trees and arched alleyways accompanied with local wines and the scent of the herb garden.

Spend your evening in the main Tinos town and take advantage of the many cafes and tavernas along the seaside or in the interior. Complete your island culinary education with louza, a cured pork that's been refined by Tinians over years of practice, and rich volaki cheese balls and kariki cheese aged within pumpkin skins, similar to a stilton or roquefort. See if the menus offer fourtalia, a fresh Cycladic dish similar to an omelette made with fresh local eggs, sausage, and potatoes, or dishes made out of the signature Tinian artichokes. Complement them with a glass of crisp, light Tinian wine or Nissos beer brewed right on the island.

Day 9: Ferry to Naxos

Looking back from the Portara
Looking back from the Portara

Time to ferry over to bustling Naxos after breakfast. With an active main town where you can shop and admire the Venetian architecture, a historic Kastro (castle) area, and expansive beaches, the island offers opportunities for both laidback relaxation, as well as water or land activities. The rest of the day is yours to unwind as you choose. Try out some of these options:

  • Hike up to the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods, and the highest point in the Cyclades.
  • Head inland to the town of Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon. Stop at the kitron distillery to sample the local liqueur and learn about its distillation process over the years.
  • Visit the Temple of Demeter at Sangri on your way. Multiple deities of fertility were worshipped here, particularly the goddess Demeter. The temple was constructed in 530 BC, during the tyranny of Lygdamis, and represents a precursor of classical Athenian architecture. 
  • Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BCE but was never finished, but the still-standing entranceway has become one of the hallmarks of the island. You can find it on the islet of Palatia, just over a causeway from the heart of Naxos Town (Chora).

For dinner, wander up the hill through the streets of the Kastro neighborhood to pick out your favorite of the area's tavernas, where you can sample the island's fresh produce in its best forms.

Day 10: Naxos Food Panorama

Winding traditional streets
Winding traditional streets

Taste some of the trademarks of the island known for having some of the best local produce in the Cyclades.  Your guide will take you around the island to towns like Kindaros, Kaloxylos, Chalki, and the marble town of Apeiranthos, as well as the main Naxos town.

You'll meet with local producers to sample and even create some of the island's better-known dishes, such as loukoumades fried donuts, keftedes meatballs with tzatziki sauce and Naxian cheeses, and a cheese or olive pie picnic with coffee, juice, bread, fruit, and yogurt. You'll also sample the local kitron liqueur at a distillery before you top off the afternoon with a tour of the Venetian castle in the main town.

Spend your evening wandering the streets of town in search of your perfect aperitif spot. Or, put your new food-spotting skills to use in the tavernas.

Day 11: Naxos Bike Tour

Cycle by the sea
Cycle by the sea

Discover Naxos's hidden spots on today's two-wheeled tour. You'll bike with an expert guide through the villages and attractions on the west side of the island. The western coast is also home to some of the island's best-known beaches, including Agios Prokopios, Agia Anna, Plaka, Orkos, and Mikri Vigla. 

On your way back, you'll see the villages of Vivlos, Agios Arsenios, and Glinado. The beginner-friendly route covers roughly 12 miles (20 km) and will take you about 2.5 hours. 

Spend the rest of your day exploring the main Naxos Chora, especially the Kastro district. Wind up the narrow streets to the Venetian Castle in the center of town, stopping at the neighboring Catholic church, Ursuline school, and Archaeological Museum along the way. Even the houses are part of the experience, once home to the descendants of Duke Venetians.

Day 12: Ferry to Ios

The port at Ios
The port at Ios

Your next island awaits after breakfast! Ferry over to Ios, where lazy afternoons on the beach ease into a booming nighttime scene, with nightlife venues to suit your every possible interest. 

Mylopotas beach is the most popular choice for daytime, with its proximity to town and plentiful facilities. If you're in search of solitude, head out to the farther Manganari beach, a secluded, shallow bay known as one of the most scenic beaches on the island with its dark golden sands. 

In the evenings, don't miss Far Out Village at the far end of Mylopotas, a four-part beach club, campground, hotel, and spa, and one of the biggest hotspots on the island. It's the perfect place to meet some new friends and see where the evening goes.

Day 13: Ios Village Tour

Church perspective
Church perspective

Take a morning tour through the villages of Ios with this guided experience. You'll see the hidden treasures of the island while meeting fellow travelers and hearing the stories of your expert guide. Potential stops include the Archaeological Museum, home to Cycladic figurines and artifacts from the prehistoric settlement of Skarkos, or the island's Orthodox and Roman Catholic churches.

The tour ends with plenty of time to explore on your own in the afternoon. Wind your way through the back alleys of the main town to find the Panagia Gremiotissa church dedicated to the island's patron saint. This petite building can be seen from nearly everywhere on the island, which means you'll get excellent views of the town below and the option to continue further up the hill if you're feeling especially athletic.

Day 14: Sikinos Island Tour & Wine Tasting

Ceramics to spare
Ceramics to spare

Take a morning day trip to neighboring Sikinos island, whose quiet, undeveloped hills will provide the perfect break from lively Ios. Your fully guided tour will included all of the island highlights of culture, history, and scenery. Check out the Monastery of Episkopi with a scenic hike up from the main town, central Folklore Museum, and top it off with a toast from a local winery. The island was once named the "Isle of Wine," after all.

Once you return to Ios, head back to Mylopotas beach to cool off with an afternoon swim in its deep water and stick around for a sundowner at one of its beach bars. Or, try the quieter Kalamos or Magganari beach.

Day 15: Return to Athens, Sunset at Cape Sounion

Temple of Poseidon
Temple of Poseidon

Return to Athens in the morning.

In the afternoon, you'll be transferred down to the Athenian Riviera, full of both history and stunning island views. Your adventure will take you along the coast to visit the Temple of Poseidon, while being provided with historical background on the way. The views overlook the Saronic Gulf, with one of the best sunset views Greece has to offer. Sip a complimentary beverage and take in the sunset while you listen to music and immortalize the moment with a Polaroid-style photo.

You'll be transferred back to your lodging in the evening just in time for a late (Greek-style) dinner. Or, if you're not ready to call it a night, you can request a drop-off at some of the most popular beach bars to dance until the sun comes up.

Day 16: Depart Athens

Wave to the city
Wave to the city

Time to say farewell to Greece. Enjoy your final Athenian breakfast before your transfer to the airport.

Map

Map of Relaxing Secret Cyclades - 16 Days
Map of Relaxing Secret Cyclades - 16 Days