Taste of the Cyclades and Crete - 14 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 Mykonos, Traditional Dinner and Optional Cooking Class

You've got two options for your early day today. Independent types can continue their island explorations on their own or head to a beach to lounge. Stroll through the cosmopolitan streets, scoping out the boutiques that draw the island's stylish crowd season after season.

If you'd prefer a more guided experience, opt for a cooking class to learn about Greek cooking techniques and ingredients. You'll master strategic deployment of olive oil, fresh produce, seafood, and more with your master instructor.

Either way, as the sun begins to set, you'll sit down to a traditional dinner, either cooked by you or your fellow travelers. You'll be welcomed into a local Mykonian household for the meal, where you'll experience the traditional Greek way of life, culture, and cooking. Hear all about their stories of the island's culture and history as well as their own family history, over authentic dishes and free-flowing local wine (for the older crowd).

Day 4: 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 5: 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 6: Beach Day on Naxos

Naxos has numerous spectacular beach options. Since the island is less famous than nearby Mykonos and Santorini, it is easy to find your own private slice of paradise. Some of the best beaches are located along the southwest coast of the island, from Plaka down through Mikri Vigra and Aliko.

Day 7: Naxos to Santorini & Caldera Hike

Today you can linger over breakfast and take a swim or stroll in the Naxos port until an early afternoon ferry takes you to Santorini, star of the Cyclades. Nothing says "welcome to the islands" like the views of Santorini's iconic cubic architecture and central caldera—the site of one of the largest volcanic eruptions in history—rising above you. 

Transfer from the port to your hotel and get settled in. Once you're set, you'll depart for one of the best walks on the island. Circle the caldera from Fira to Oia, taking in the picture-perfect surroundings. As the furthest town along the rim of the caldera, Oia's arty streets are the perfect spot for sunset views. Stake out your viewing platform over the panorama, then stick around to wander the alleys and linger in the town's tavernas into the evening.

Hiking time: 4 hours with stops
Hiking distance: 7 miles (11 km)

Day 8: 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 9: Santorini Catamaran Cruise

Enjoy a leisurely morning breakfast with time to stroll through town and scope out the small shops and boutiques. Head over to Fira, the capital of the island, which offers plenty to explore. History buffs will be delighted by proximity to the Archaeological Museum of Santorini, the Museum of Prehistoric Thera, the Folklore Museum of Emmanuel Lignos, and the church of Hypapante.

As the late afternoon unfolds, you'll head toward Vlychada Port to board your semi-private catamaran cruise around the island. Your first stop will be at the Red Beach to swim and sun, followed by a second stop at the White Beach to take in all the distinctive-colored sands of Santorini.

Barbecue will be served onboard while you sail past landmarks at Aspronisi, the Ancient Lighthouse, Indian Rock, and the prehistoric city at Akrotiri, hidden away at the southern tip of Santorini. These ruins are the site of some of the Bronze Age’s most advanced settlements, which prospered for centuries before being destroyed by a great volcanic eruption in the mid-second millennium BC. Top it off with a jump into the hot springs at Nea Kameni, where the mineral-rich volcanic waters are believed to have therapeutic properties.

Day 10: Santorini to Chania

After some final free time in Santorini, your journey will take you by ferry to Crete, the largest and most populous of the 230 inhabited Greek islands. Upon arrival in Heraklion port, you'll be transferred to Chania, a city (and region) on the northwest coast, and get settled into your hotel as you get ready to explore this stunning island, equipped with tips from your local specialist. 

Chania itself will be the main base of your operations during your trip. It's the second largest city in Crete and one of the most scenic spots on an island with stiff competition for that title. Life in this former Venetian city revolves around its charming 14th-century harbor, narrow streets with winding alleys, and colorful architecture influenced by past Ottoman and Egyptian eras.

Depending on what time you arrive, wander around town or head for one of the western region's spectacular beaches such as Falassarna and Elafonissi. There are also plenty of deserted coves and quiet bays to enjoy total privacy. 

For dinner, wander around Chania's harbor and check out a slew of waterfront restaurants with a sunset view.

Day 11: Old Town of Chania Tour

Today, you'll experience the streets, buildings, high spots, neighborhoods, and monuments that only locals know with a guided tour. Walk the stone paths where the Venetians, the Ottomans, and older generations of Cretans used to live and work, admiring the flower-decorated neighborhoods. You'll learn about Cretan history, the Cretan mythology and traditions, meet the locals, and eat like the locals.

Visit the neighborhoods of Topanas, Splantzia, Kolombo and Kasteli, along with high spots to admire the panoramic view of the harbor, as well as traditional Cretan taverns and magnificent buildings. You'll also see the ruins of the great Minoan city of Kydonia and high walls of former Venetian moats now integrated into the city.

When hunger strikes, visit the Municipal Market of Chania and neighboring Municipal Garden to enjoy a coffee amid the shade of the trees or garden clocktower. Then, top it off with a sunset drink on the rooftop at trendy Pallas.

Day 12: Botanical Park Tour & Tasting

Today, you'll surround yourself with the bright tropical gardens and the shade of avocado trees at the Botanical Park and Gardens of Crete. Your trail will lead you under citrus trees and other Mediterranean flora. Learn about the different climates around the island and the produce that grows there before you enjoy a lunch in a restaurant overlooking the sweeping garden view. 

Spend the evening enjoying your return to Chania town. Head to Kikbar, located in the former 16th century Monastery of Karolos. This converted building is now home to an art gallery, theater space, and swoon-worthy open air bar.

Day 13: Gramvousa and Balos Beaches

Spend your day on the pink sands of some of the most beautiful beaches in the world. You'll be transported to Balos and Gramvousa beaches, where crystal-clear turquoise waters are home to stellar swimming, sunshine, and protected animal and plant species. If you're lucky, you may even spot a Mediterranean seal. 

In Gramvousa, you can also choose to hike up to a former Venetian castle or a shipwreck along the beach. Nearby Balos is a shallow, more protected lagoon, home to placid waters.

After you've sunned and swum to your heart's content, return to Chania for your final night on the town. Visit the graves of the Eleftherios Venizelos family, one of Greece's most notable political figures, for spectacular panoramic views.

Day 14: Chania to Athens and Depart

It's time to say farewell to Crete with one final breakfast in Chania. Take a sunrise stroll along the harbor or perhaps indulge in one more scoop of graviera cheese before you're transferred to the airport or ferry to return to Athens in time for your departure.

If you have 2 more days to spend, consider the 16-day version of this itinerary. You'll experience many of the aforementioned highlights, along with stops on Paros and Ios, an excursion to the Samaria Gorge, and more.