Spend 21 days in Greece with this unique itinerary that balances history, relaxation, and culture. Start in Crete, Greece's largest island with the oldest civilization. Explore the Venetian town of Chania and the massive Samaria gorge, and Crete's capital — Heraklion. Catch a ferry to Naxos where you'll learn how to cook Greek food and relax on an idyllic beach. Finish your trip in laid-back Santorini for an immersion into Greek winemaking.


  • Discover the natural wonders of Chania
  • Experience the ancient Minoan palace of Knossos
  • Explore Santorini and Naxos, a lesser-known gem of the Cyclades islands
  • Drive through the winding back roads in the Peloponnese
  • Climb to the clifftop monasteries of Meteora

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Chania Chania
Day 2 Explore the Old Town of Chania  Chania
Day 3 Explore Nature in Chania  Chania
Day 4 Knossos Palace Guided Tour & Museum/ Drive to Heraklion Heraklion
Day 5 Ferry to Naxos Naxos
Day 6 Beach Day in Naxos Naxos
Day 7 Cooking Class in Naxos Naxos
Day 8 Naxos Villages Tour: Apiranthos and Filoti Naxos
Day 9 Ferry to Santorini Santorini
Day 10 Santorini Food Tour  Santorini
Day 11 Visit Santorini's Wineries  Santorini
Day 12 Fly to Athens, Sunset at the Temple of Poseidon Athens
Days 13-14 Nafplio Nafplio
Day 15 Travel to Olympia  Olympia
Day 16 Travel to Delphi  Delphi
Day 17 Travel to Meteora  Kalabaka
Day 18 Hike Around the Monasteries of Meteora  Kalabaka
Day 19 Return to Athens  Athens
Day 20 Acropolis Guided Tour & Acropolis Museum  Athens
Day 21 Departure  

Detailed Itinerary

Day 1: Arrive in Chania

Chania's Old Town Harbor
Chania's Old Town Harbor

Today you will fly (via the Athens airport) to the enchanting Venetian town of Chania. Upon arrival in Chania, a city (and region) on the northwest coast, you'll be transferred to your hotel to rest.

Chania will be the main base of your travels during your trip. It's the second-largest city in Crete and one of the most scenic, although Crete's other towns offer stiff competition for that title. Life in this former Venetian city revolves around its 14th-century harbor, narrow streets, winding alleys, and colorful architecture that is influenced by the city's past Ottoman and Egyptian eras.

Depending on what time you arrive, take some time to wander around town or head to the water at one of the western region's 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 2: Explore the Old Town of Chania 

Houses in Old town of Chania
Houses in Old town of Chania

Today, you'll explore the streets, 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 and the Cretan mythology and traditions, and mingle with locals as you find the best local cafes. 

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 the high walls of former Venetian moats, which are now integrated into the city.

When hunger strikes, visit the Municipal Market of Chania and the 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 3: Explore Nature in Chania

Olive groves
Olive groves

Take a free day to spend as you wish. You may have already seen the Samaria Gorge, but there's even more natural beauty around Chania waiting to be discovered.

If you'd like something organized, head to the bright tropical gardens and the shade of avocado trees at the Botanical Park and Gardens of Crete. The trail will lead you under citrus trees and other Mediterranean flora, with lessons about the different climates around the island and the produce that grows there (which you can also sample in the onsite restaurant). 

The Vouves region to the west is home to olive oil production, complete with a museum and one of the oldest olive trees in existence. Also to the west are the beaches of Falassarna and Elafonissi, with gorges and waterfalls along the route. 

For a day on the water, visit Kournas Lake, which is fed by two natural springs. This shallow freshwater lake is the ideal place to experience the natural life on the island. The nearby town of Argyroupoli makes for a great food stop, with lunch options next to its many springs and small waterfalls.

Day 4: Knossos Palace Guided Tour & Museum/ Drive to Heraklion

Knossos Palace
Knossos Palace

Today after breakfast, take a tour of the magnificent Palace of Knossos.  Knossos flourished for approximately two thousand years. It had large palace buildings, extensive workshop installations, luxurious rock-cut caves, and tholos tombs. As a major center of trade and the economy, Knossos maintained ties with the majority of cities in the Eastern Mediterranean. 

After Knossos, continue driving eastwards towards Heraklion. Heraklion is a bustling, lively city, and with any luck, you'll stumble upon one of its many festivals in its streets as you arrive in the capital of Crete.

Take some time to walk around the old city's medieval streets, where the architecture reflects the island's Venetian past. The neighborhood's surrounding walls were built by the island's Arab population and later reinforced by the Venetians in the fifteenth century. There were originally seven bastions, but only one is left standing today: the Martinengo bastion. It's now home to the tomb of the renowned writer Nikos Kazantzakis, best known for his works including Zorba the Greek and The Last Temptation of Christ. 

Day 5: Ferry to Naxos

the Portara
The Portara

Time to ferry over to relaxed 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 relaxations, 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: Beach Day in Naxos

Alyko Beach
Alyko Beach

What's a trip to the islands without a day on the beach? With smaller crowds than its Cycladic neighbors, Naxos makes it easy to find your own slice of paradise, whether you want privacy or a more lively scene. Terminology tip: If a beach is described as "organized," that generally means it has sunbeds and umbrellas available to rent and plentiful restaurants.

Agios Georgios is the closest to the main town and is generally filled with families enjoying the shallow waters. Neighbors Agia Anna and Agios Prokopios also have plenty of amenities on their sweeping sands, with enough shoreline that you'll be able to stake out a spot but sufficient tavernas to keep you fed.

The more isolated beaches of the southwest coast — including Plaka, Mikri Vigla, and cedar-lined Aliko — are some of the best on the island. They're farther out from the main town, and your travel will be rewarded with quieter sands and scenic surroundings.

Day 7: Cooking Class in Naxos

Grandma prepares a meal
Grandma Prepares a Meal

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.

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Day 8: Naxos Villages Tour: Apiranthos and Filoti 

Meandering steps in Apiranthos village
Meandering steps in Apiranthos village

Today you'll explore two of the villages that surround inland Naxos. Leave the crowded beaches and streets behind as you head out into the countryside to explore the first village — Filoti

Economically and culturally vibrant, the village of Filoti is the largest of all Naxian villages. Set amphitheatrically on the slopes of two hills at the foot of Mount Zas, it is virtually surrounded by impressive summits which leave two openings, one headed west to Tragea, the other south to the local livestock farms. 

Filoti’s liveliness and cultural richness are evident upon entry to the village. It is well-known for the excellent quality of its livestock products, such as lamb and goat’s meat and a variety of cheese products, while a woman’s cooperative is reputed for the sweet preserves it produces and sells. Sample the region's best culinary products for lunch at a quiet al-fresco cafe.

From here, continue to your second stop of the day — the village of Apiranthos. Venetian towers, old two-story houses, marble-paved alleys, picturesque squares, and the poetic disposition of Apiranthians combine to create a rare atmosphere in the Cycladic islands.

Its inhabitants are considered to have largely come from other areas (e.g. Crete, Asia Minor) and Apiranthos’ local language idiom, morals, and customs are quite distinct from other Naxian villages. This small but particularly energetic community has developed while keeping its local customs largely unaltered, and its history is depicted in several of the town's museums. 

Day 9: Ferry to Santorini

Sunset in Oia
Sunset in Oia

Catch a ferry to Santorini and enjoy your dramatic first glimpse of the island's iconic cliffside architecture. Watch for your first views of Santorini's central caldera—the site of one of the largest volcanic eruptions in history—rising in a crescent. After you've settled into your hotel, spend some time wandering the streets of Fira, or head to the beach.

In the afternoon, spend some time exploring Santorini's lesser-known sites. Stroll through famous Oia or explore the nearby medieval villages at Megalochori and Pyrgos, which feel a world away from the touristy towns along the caldera rim. For a relaxing culinary afternoon, stop for some wine tasting at the caldera's edge to sample varietals dating back centuries as you watch the sun sink into the Aegean Sea.

In the evening, head back to Oia, passing the Blue Dome of Firostefani on the way. The furthest town along the rim of the caldera, Oia's arty streets are the most famous spot for sunset views, and evenings, after the crowds have left, are one of the best times to wander the alleys and linger in the town's tavernas. When searching for your dinner, seek out tomato keftedes, deep-fried tomato balls, and the Santorini specialty of spelt pie.

Day 10: Santorini Food Tour 

Eating like a local in Santorini
Eating like a local in Santorini

Go beyond the caldera to see another side of Santorini on today's tour. You'll start by following an expert guide to the stone streets of Megalochori, where you'll see how the island's full-time residents live. Then head to a small family-owned winery, using centuries of tradition to cultivate vines in the volcanic soil, where you'll taste three different ancient varietals along with local snacks.

The produce grown on Santorini is known for its waterless farming methods that help enhance the flavor of specialties like tomatoes, yellow beans, eggplants, and capers. Your next stop will feature a cooking demonstration using ingredients from an anhydrous farm surrounded by caves and pumice stone canyons.

End your day with a glass of wine and sunset views over the caldera at a winery built into the island cliffs.

Day 11: Visit Santorini's Wineries 

Hard Working Hands

Raise your glasses to a day in the islands with a vineyard tour. You'll visit three of the island's ancient wineries, where you'll learn about some of the award-winning volcanic vintages of Santorini. With twelve varietals, all accompanied by local cheese and other snacks, the history of the island will be right at the tip of your tongue. 

Don't miss a dramatic Santorini sunset. You can visit the smaller town of Firostefani or stay on the other side of the caldera rim out in Oia. The furthest town along the rim of the caldera, Oia's arty streets are the perfect spot for sunset views, although you won't be alone. 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.

Day 12: Fly Back to Athens, Sunset at the Temple of Poseidon

Sunset falls on the Temple of Poseidon
Sunset falls on the Temple of Poseidon

Return to Athens in the morning. After you've settled back into the city, 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.

Days 13-14: Nafplio 

The Fortress of Palamidi
The Fortress of Palamidi

Spend the day exploring the Argolis region and the remains of the ancient city of Mycenae — a major center of Greek civilization from 1,600 BCE to 1,100 BCE.

Visit the archaeological site, home to the kingdom of mythical Agamemnon. You will see the Cyclopean Walls, the Lion’s Gate, the Royal Tombs, including Agamemnon Clytemnestra's, and the Treasury of Atreus — a magnificent 14th-century B.C. structure

Later in the day visit the first capital of modern Greece, Nafplio, to see its Venetian Palamidi fortress and the fortified islet of Bourtzi.

Day 15: Travel to Olympia

Ancient columns stand in Olympia
Ancient columns stand in Olympia

Start your morning with a 5-hour drive to Olympia.

One of the most significant archaeological sites in Greece, the ancient stadium was where the most important competitions took place. Pass under the arched entrance and you’re in a place with a significant history and influence.
The stadium you see today was built around the same time as the temple of Zeus, in the 5th century BC.

The hippodrome for chariot races lays to the south of the stadium. Still standing are ruins left from a later age, like the ones the Roman emperor Nero had constructed as a private residence when he attended the races. Don’t forget to explore the other ruins — the Temple of Hera, the oldest and best-preserved temple at Olympia, the Bouleuterion, the Prytaneion, the Gymnasium, the Palaestra (Pheidias’ workshop), the Leonidaion, the Philippeion, the Echo Colonnade, the pedestal of Paionios’s Nike and the Nymphaion. Each one has a special aura and its own story.

Day 16: Travel to Delphi 

Temple of Athena
Temple of Athena

Today, you'll seek out the oracle during a trip to the ruins of Delphi, once home to priestesses of Apollo who Ancient Greeks believed could predict the future. After being transferred from your hotel to Delphi (about 2.5 hours from the city), explore this sprawling archaeological site. You'll see sites such as the Treasury of the Athenians, the Temple of Apollo, and the expansive theater.

Explore the ruins or venture up an ancient footpath once used by worshippers of the god Pan, who started from the temples of Delphi and proceeded to Corycean Grotto for their religious rites, surrounded by the valley of olive trees and views of the Corinthian Gulf and peaks of the Peloponnese on your way. 

After you have explored the sites of Delphi, return to your accommodation to relax and have lunch. In the evening take a leisurely stroll around town to find a cafe to linger at into the night. 

Day 17: Travel to Meteora 

The Monastery on a clifftop
The Monastery on a Clifftop

Head across the Central Greece countryside to visit the famous monasteries of Meteora. These clifftop monasteries, including Megalo Meteoron and Agios Stefanos, sit perched atop high rock formations but are still inhabited and used by monks and nuns today. The area has been named a UNESCO World Heritage site and is one of the largest pilgrimage sites in Greece.

Day 18: Hike Around the Monasteries of Meteora

Sunset falls on the monsteries of Meteora
Sunset falls on the monasteries of Meteora

Discover some of the six cliffside monasteries in Meteora that remain open to the public: Varlaam, Great Meteoron, Aghios Stefanos, Rousanou (renowned for a marvelous depiction of the Second Coming), Holy Trinity (featuring an old church dating back to 1475), and Aghios Nikolaos Anapausas (adorned with very significant post-Byzantine murals). 

Tread the same paths that monks used for hundreds of years to reach these holy places, climbing almost 1000 feet (300 m.) in the air above the canyons of the Pindos range. Before the paths were constructed, the monastery residents used nets and rope ladders to hoist goods (and sometimes their fellow clergy) to the clifftops. You'll experience both living history and panoramic views as you explore.

Day 19: Return to Athens

View of the city's rooftops

Today you will return to Athens for a day of exploration and shopping. Take a guided biking trip or stroll around the narrow streets of the 'Plaka' area. Other options include the National Archaeology Museum, the ancient marketplace of Agora, the Byzantium Museum, the frescoed Church of the Holy Apostles with its Ashlar exterior, and the Panathenaic Stadium. See the changing of the guard at Syntagma Square and shop for souvenirs in the  as a fitting end to your stay in Athens.

Another area to spend the day is the Athenian Riviera, starting from Faliro and ending at Cape Sounio where the Temple of Poseidon is located. In between, you will find amazing beaches, scenic coastal towns as well as the unique Lake of Vouliagmeni, famous for its surreal landscape and therapeutic mineral waters which remain at a steady 71.6 degrees F (22 degrees Celcius) all year round.

Day 20: Acropolis Guided Tour & Acropolis Museum

The Parthenon
The Parthenon

Today, delve into Athens' centuries of history. Experience the ancient stories surrounding you on a guided mythology tour. Meet your archaeologist guide at Syntagma square, then head to landmarks around the city, including the Acropolis and the Herodion Theater. Hear stories about Zeus, Athena, Poseidon, Dionysus, and more, all adding resonance to the archaeological ruins you'll visit on this four-hour tour.

Later, take another guided tour at the Acropolis Museum. Named one of the 10-best museums in the world by National Geographic, this modern museum houses a multitude of artifacts removed from the hill of the Acropolis for safekeeping. You'll learn all about ancient religious practices and daily life. From the museum cafe, there are great views of the former hilltop home of the museum's collection.

Day 21: Departure

Aegean Flight Departing
Wave goodbye to Greece

Transfer to the airport for your connecting flight home.