Cultural Cyclades - 13 Days

Day 1: Arrive in Athens

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 to Mykonos

You'll start your tour of the Cyclades on Mykonos, one of the larger islands in this chain. Known for its glitzy restaurants and nightlife, art scene, and jet set crowds (it was recently home to a Gucci pop-up boutique), Mykonos will throw you headfirst into your island adventure.

Your first day's itinerary is up to you. You'll receive a personalized list of tips for exploration, but some highlights include:

• If you need to get your toes in the sand immediately, head to remote Agios Sostis beach to find your own isolated paradise.
• For a more active experience, Ftelia Beach is known for its excellent windsurfing.
• Take a short ferry over to the archaeological site at Delos for a day-trip. This entire island is full of ancient ruins and is one of the most important in the country for its history as both a sanctuary and the mythological birthplace of Apollo and Artemis.
• Stroll through Little Venice, an 18th-century neighborhood where colorful former captains' mansions and seaside restaurants seem to sprout straight from the sea. It's also right next to the island's famous hillside windmills for great photo ops.

Day 3: Explore Authentic Mykonos

Today, you'll sneak away from the cosmopolitan side of this island to discover Mykonos' authentic heart, touring charming villages, little harbors, and remote beaches with your expert guide. You'll start with a panoramic viewpoint of Mykonos Town to capture the perfect 360 shot. Head to the port of Agios Ioannis, a protected harbor where fishing boats now launch. Hear the stories of its namesake saint, including a church dedicated to him and the cell he was held in that are now home to an annual festival. 

Next, you'll go through the island's agricultural and livestock country, past cultivated fields and animals grazing. At Ano Mera village, you'll explore a farm with its superintendent and even have the opportunity to help out with some farm work or say hi to the animals. You'll also sample a light snack lunch with products grown right there in the fields. After lunch, the colorful village square awaits, including a monastery tour and stroll through the open-air market.

From there, the shores of Kalo Livadi, Kalafati, and Aghia Anna all await your camera lens as you pass them on your way to learn about the island's history at the site of former mines. The now-abandoned structures used to mine lignite from the island's soil. Wrap your tour up on the picturesque narrow streets of Mau, home to the Mykonos dam.

The evening is yours to spend as you will, whether you want to relax by the sea, wind away the hours with a sundowner in Little Venice, or dance the night away on the boardwalk of Paradise Beach.

Day 4: Day Trip to Delos

Travel back in time after breakfast with a morning boat ride out to the archaeological site at Delos. You'll board a small boat at the old port to cruise for 45 minutes out to one of ancient Greece's most sacred sites. This small island was the center of the Cyclades during the Classical era and the birthplace of twin deities Apollo and Artemis. Pilgrims from around the region were attracted to the mystical site and helped it evolve into one of the largest trade centers of the Mediterranean.

Your guided tour will wind you through the foundations of former traders' mansions, temples, and landmarks such as the Terrace of the Lions. Don't skip the island museum, where many of the smaller artifacts and frescoes have been moved to protect them from the elements.

You'll return to Mykonos in time to catch up on your shopping in your the afternoon as you explore some of the best boutiques in the Aegean, or check out the weathered Faros Armenistis lighthouse perched high above the Aegean on the island's northwestern tip, with views across to the neighboring island of Tinos.

Day 5: Ferry to Naxos

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 6: Ancient Naxos Hike

After breakfast, head to the village of Myli, where you'll pick up an old footpath that leads to the island's ancient aqueduct. Hike up to the nearby quarry, where you'll find two large kouros, unfinished statues of ancient Greek gods, lying on the ground. Originally intended to hold up a temple roof, these giant statues were abandoned by their ancient sculptors when they discovered faults in the marble, but they're no less impressive for that today.

Pass the statues along with olive groves, orchards, and a shady riverside. You'll visit the Catholic church of Theoskepasti, also known as Agios Mamas, the island's oldest chapel, along with Episkopi, the summer residence of the Catholic archbishop, on this 2.5-hour guided hike.

Stop in Mesi Potamia on your way back to town to take a break at a taverna under the trees on the river bank. Spend your afternoon exploring the town along with its neighboring riverside settlements at Ano Potamia and Kato Potamia, connected by a walking path, or return to town for a well-deserved beach break.

Day 7: Cooking Class on Naxos

Take a leisurely morning after breakfast, adding more shopping or time in the sun to your itinerary. At your choice of time in the afternoon, you'll head to Kaloxylos village to learn how to prepare a typical Greek meal in a local home. Join in the village life, with a menu that you can help determine based on your personal preferences, season, and what's growing in the village garden. 

At sunset, head to the Portara if you haven't yet. The unfinished entrance to the Temple of Apollo on an islet outside of town is one of the island's best views as the sun goes down.

Day 8: Naxos to 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 9: Ios Village Tour

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 10: Ios to Santorini

After breakfast at your hotel, you'll get an early ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. Upon arrival, you'll take in the island's central caldera—the site of one of the largest volcanic eruptions in history—rising above you. 

The island's volcanic history has led to the formation of some of the more unique beaches in the Greek islands, along with the dramatic cliff views on the island's caldera side. Spend your day relaxing at the beach or catching some exercise—and even more views—from one of Santorini’s more than 12 scenic walking routes, ranging from between two to eight miles each.  At dinner, sample the island's signature cherry tomatoes and white eggplants as guest stars in seafood dishes or the main event.

Day 11: Santorini Tour & Wine Tasting

The morning is yours to spend as you will, whether that's browsing the boutiques of Fira or getting beachside. Don't wear yourself out too soon, though, as in the afternoon you'll take a guided tour that will show you a side of Santorini that most travelers don't see.

You'll check out hidden gems in Oia, the furthest town along the rim of the caldera. Oia's arty streets are the quintessential Santorini scene. Later, you'll take a trip up to the highest peak on the island. Bring your camera for the 360 views at the top, as well as the many stops on your way down. You'll also see medieval villages at Megalochori and Pyrgos and the Blue Dome in Firostefani before your voyage ends with a wine tasting to sample varietals dating back centuries, complete with epic caldera views as the sun goes down.

In the evening, return to Oia to wander the alleys and linger in the town's tavernas into the evening and experience a calmer vibe after the sunset crowds subside. When searching for your dinner, seek out tomato keftedes, deep-fried tomato balls that encapsulate the essence of the Mediterranean diet, and the Santorini specialty spelt pie.

Day 12: Discover Prehistoric Akrotiri

Take a guided tour of one of the Aegean's most significant prehistoric settlements. You'll head to the excavated city at Akrotiri, hidden away at the southern tip of Santorini on the slopes of the caldera. These ruins were once the site of one of the Bronze Age’s most advanced settlements, which prospered for centuries before being buried by a volcanic eruption in the mid-second millennium BC. You'll have the morning to explore its well-preserved (thanks to the volcanic eruption) streets alongside a local guide who will share its stories.

On your way back, stop to see the three bells of Fira. The trio of bells atop this blue-domed church is pictured on many of the postcards you'll find on the island, it's your turn to take a photo of your own

Unwind on the beach with the remainder of your afternoon. The black sands of Perissa and Kamari are always popular, but the colorful Red or White beach are also well worth seeing. Or seek out some solitude within the cliffs at Koloumbos on the island's northern tip.

Day 13: Santorini to Athens and Depart

It's time to say farewell to Greece! Savor one more breakfast in Santorini before your transfer to the airport or your ferry to begin your journey home.