This exciting two-week itinerary through Greece has something for everyone: ancient history, cultural experiences, outdoor adventure, world-class beaches, and gourmet food and drink. Spend the first few days sightseeing in Athens, learning about Greek antiquity at the Acropolis and the Acropolis Museum. Then you'll head to Mykonos for relaxing beach time and a half-day cruise around nearby islands. Catch the ferry to Santorini next, exploring traditional villages and sampling locally crafted spirits — and soaking up views of truly spectacular sunsets, of course. Wrap up the trip on Crete, where you'll tour the Cave of Zeus and marvel at dramatic scenery on the drive to the legendary Elafonissi Beach, famed for its pink sands and clear blue waters.


  • Discover classical antiquities at the Acropolis and the Acropolis Museum
  • Cruise from Mykonos to Delos and Rinia on a traditional boat
  • Sample local spirits, including ouzo, during a guided tasting
  • Explore quiet villages on the island of Santorini
  • Relax on gorgeous Elafonissi Beach, famed for its turquoise waters 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens & Sightsee Athens
Day 2 Boat to Agistri, Moni & Aegina Athens
Day 3 Visit the Acropolis Athens
Day 4 Transfer to Mykonos Mykonos
Day 5 Go on a Cruise to Delos & Rinia Mykonos
Day 6 Relax in Santorini Santorini
Day 7 Tour the Traditional Villages of Santorini Santorini
Day 8 Taste Local Spirits  Santorini
Day 9 Travel to Heraklion Heraklion
Day 10 Visit the Cave of Zeus & Attend a Wine Tasting Heraklion
Day 11 Get Off the Beaten Path in East Crete  Heraklion
Day 12 Go on a Self-guided Tour of Chania Chania
Day 13 Chill Out on Elafonissi Beach  Chania
Day 14 Depart Chania - End of Trip  

Detailed Itinerary

Day 1: Arrive in Athens & Sightsee

Monastiraki Square and Sunset over Plaka
Monastiraki Square in Athens
Welcome to Greece! Your private driver will be waiting at the airport to transfer you to your hotel in Athens. In the afternoon, get out for some sightseeing. Those interested in history and mythology might choose to visit the National Archaeological Museum, the Museum of the Ancient Agora, or the Archaeological Museum of Kerameikos. View fine art at Benaki Museum, the Museum of Modern Art, or the National Gallery. You could also go off the beaten path at the Museum of Cycladic Art, where you can buy truly unique souvenirs, or the Museum of Ancient Greek Technology. You'll overnight in the city. 

Day 2: Boat to Agistri, Moni & Aegina

Full Day Boat Tour Unique Sailing Experience to Agistri Moni Aegina
Snorkeling off the boat
Set sail for the Saronic IslandsAgistri, Moni, and Aegina — aboard a spacious Greek sailboat. Find your favorite spot on deck to soak up the Mediterranean sun while island-hopping! From ancient temples and wild peacocks to pristine beaches and an optional bike ride, there’s something for everyone at each stop along the way. Swim and snorkel right off the boat, then indulge in a delicious Greek lunch served on the boat.

Day 3: Visit the Acropolis

The Parthenon at the Athenian Acropolis
Today you'll visit the Acropolis, taking in views of the world-famous Parthenon. This temple, dedicated to the goddess Athena, has enchanted visitors since its construction was completed in 438 BCE. Afterward, the tour continues at the Panathenaic Stadium, the marble stadium where the modern Olympic Games were first held in 1896. Then you'll visit the Acropolis Museum, built to house every artifact found around the ancient citadel, from the Greek Bronze Age to Roman and Byzantine Greece. The tour finishes at the Athens Central Food Market (Varvakios Agora), where you'll sample regional delicacies made by Greek cheese-makers, pastry chefs, and food vendors of all kinds. The evening is free to relax or explore the city.

Day 4: Transfer to Mykonos

Little Venice in Mykonos
Colorful beachfront houses in Mykonos
Catch a ferry to Mykonos this morning and enjoy a free afternoon on the beautiful island! If you want to get your toes in the sand immediately, head to Agios Sostis beach to find your own quiet paradise. For a more active experience, Ftelia Beach is known for excellent windsurfing. Later, stroll through Little Venice, an 18th-century neighborhood where colorful former captains' mansions and seaside restaurants are lined up along the seafront. 
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Day 5: Go on a Cruise to Delos & Rinia

Half Day Cruise with traditional motor sailing boat from Mykonos to Delos and Rinia
Sailing from Mykonos to Delos and Rinia
Today, you'll go on a half-day cruise on a traditional sailboat. The first stop is Delos. You'll go for a walk through the old town and visit the island's main archaeological site. As mythology has it, this is the birthplace of Apollo (god of light and the sun) and Artemis (goddess of the hunt). The second stop is Rinia Island and a break on the beach at Skinos Bay, known for its clear azure waters. You'll head back to Mykonos later in the day. 

Day 6: Relax in Santorini

Sunset in Santorini
Sunset in Santorini
It's time to say goodbye to Mykonos! Your driver will take you to the port, where you'll board a boat for the next island, Santorini. On 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 most 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 strolling on one of Santorini’s scenic walking routes. For dinner, sample the island's signature cherry tomatoes and white eggplant, typically served as side dishes with fresh seafood. 

Day 7: Tour the Traditional Villages of Santorini

Tables overlooking the water in Imerovigli

In the morning, visit Prophet Elias Monastery, the highest spot on the island. Walk around Megalochori, one of the most picturesque villages on the island. You'll also go on a walking tour of the village of Emporio. Take a break for lunch before heading to Red Beach, one of the most scenic and interesting beaches on Santorini. In the afternoon, you'll have the chance to sample wines at a local winery nearby. At sunset, catch the views of the Blue Dome Church at Firostefani and the spectacular landscape below.

Day 8: Taste Local Spirits 

Boats off the coast of Santorini

Explore the southeastern part of the island today, starting with a visit to the village of Kamari. Stop into Panagia Episkopi, the oldest Byzantine church on the island. Relax on the beach after lunch, then head to Canava Ouzo for a guided tasting of locally produced spirits, including ouzo.  

Day 9: Travel to Heraklion

Heraklion harbor
Heraklion's harbor
Bid farewell to Santorini and get ready for another fascinating island — Crete! Take the ferry to the port of Heraklion. In the afternoon, you'll visit Heraklion's Archaeological Museum, with one of the largest collections of Minoan artifacts in the world. This is an excellent crash course to prepare you for the site you'll visit tomorrow — the 3500-year-old Palace of Knossos, a sprawling maze of royal chambers, grand staircases, storerooms, and workshops. This evocative Bronze Age site is believed to be Europe's oldest city. Have a relaxing meal in a beachfront restaurant before tomorrow's excursion.

Day 10: Visit the Cave of Zeus & Attend a Wine Tasting

The Palace at Knossos
The day starts with a guided tour of the Palace at Knossos. Next, you will journey to the mountainous East Crete and the Dikti Mountains with your guide. You will visit ancient Cretan villages, engage with locals, and take in views of the region's stunning landscapes. Break for coffee under an ancient tree in the traditional village of Krasi before touring the Cave of Zeus. On the trip back, you will visit a family-owned traditional ceramic workshop and a Byzantine monastery. Finish the day with a meal in an authentic Cretan tavern.

Day 11: Get Off the Beaten Path in East Crete 

Cave of Zeus & Knossos Palace with Local Food & Wine Tasting
Outdoor café seating in East Crete
After breakfast, begin a memorable journey deeper into the heart of East Crete. The first stop will be in an ancient Cretan village, an authentic center of weaving that's famous for its textile shops. The next village over is famous for its traditional cafés and abundant fruits. It's a cozy spot to enjoy a coffee served with ripe local fruits. You will also have the opportunity to visit the historic Church of Panagia Kera. The tour continues in one of the most beautiful wild gorges of East Crete, where you'll go hiking with your guide, spotting wildflowers, waterfalls, wild goats, and Cretan Golden eagles along the way. Finish the day relaxing on a beach by the Libyan Sea, an area known for its emerald blue waters and craggy coastline.

Day 12: Go on a Self-guided Tour of Chania

Chania's Old Town Harbor
The harbor in Chania's Old Town
Chania is the second-largest city in Crete and one of the most scenic spots on the island. Discover this former Venetian city today, including its charming 14th-century harbor, narrow streets with winding alleys, and colorful architecture influenced by past Ottoman and Egyptian eras. While you're exploring the area, don't miss the elevated neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli — great for panoramic harbor views, Cretan taverns, and architectural history. You can see the ruins of the Minoan city of Kydonia and high walls of former Venetian moats integrated into the city. Other highlights include the Municipal Market of Chania, the neighboring Municipal Garden, and the Botanical Parks and Gardens of Crete. Finish the day with sunset drinks on the rooftop at one of Chania's bars overlooking the town and harbor below.

Day 13: Chill Out on Elafonissi Beach 

A trail along Crete's coast
On the way to one of the most amazing pink sand beaches of the world — Elafonissi Beach — enjoy the beauty of Western Crete, with its dramatic panoramas, deep gorges, and sea caves. Before reaching Elafonissi, stop at the Monastery of Panagia Chrisoskalitissa (Our Lady of the Golden Step), a hilltop Orthodox monastery with a stunning view of the Libyan Sea. When you finally arrive at Elafonissi, you will notice how the lagoon blends together with waters from the Mediterranean and the Libyan Sea. Relax on pale pink sands, swim in shallow, clear waters, and finish the excursion with a seafood dinner in a locally run restaurant. 

Day 14: Depart Chania - End of Trip

Photo taken by Victoria P
An idyllic beach on Crete
The trip comes to an end today. You'll head to the airport to catch a flight out. Safe travels!

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