Discover Athens, Delphi, and the best of the Greek islands during this fun 14-day itinerary. Visit major archeological sites, sample volcanic vintages at wine tastings on Santorini, visit an organic farm on Mykonos, sail the Athenian Riviera, and much more.

Highlights

  • Visit the Acropolis, the Monastiraki flea market,  and more in Athens
  • Tour the Treasury of the Athenians and more on a Delphi day trip
  • Hike around Santorini's caldera from Fira to Oia
  • Hop between the most popular beaches in Greece on a Mykonos cruise
  • Taste at ancient wineries and learn about Santorini's volcanic vintages

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Guided Acropolis Visit Athens
Day 3 Athens Food Tour Athens
Day 4 Olympia Archaeological Site to Nafpaktos Nafpaktos
Day 5 Visit Delphi, Return to Athens Athens
Day 6 Visit Cape Sounio and the Temple of Poseidon Athens
Day 7 Athens to Mykonos Mykonos
Day 8 Day Trip to Delos Mykonos
Day 9 Explore Authentic Mykonos Mykonos
Day 10 Ferry to Naxos Naxos
Day 11 Ancient Naxos Hike Naxos
Day 12 Santorini Hidden Gems Tour & Wine Tasting Santorini
Day 13 Caldera Day Hike Santorini
Day 14 Santorini to Athens and Depart  

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: Guided Acropolis Visit

Today you'll get to experience the mighty Acropolis—ruins of the iconic 5th-century BCE complex located on the rocky hilltop overlooking the city. Take a guided tour of the entire settlement with an English-speaking professional guide who will share the stories of the country's most famous monument. In addition to the iconic Parthenon, dedicated to the city's patron goddess Athena, you'll view and learn about the Propylaea, the Temple of Athena Nike, and the most sacred temple of Erechtheion, all located on the sacred rock of the Acropolis.

Complement your tour with a trip to the nearby modern Acropolis Museum. Many of the more delicate statues and other artifacts originally found at the Acropolis have been moved here, but you can imagine them in their previous home as you explore the exhibits. Complete your visit with a stop in its cafe for either lunch or a relaxed snack and coffee.

Stop to explore the Anafiotika neighborhood on the northeast side of the hill before you leave. The oldest neighborhood in the city, Anafiotika's classic white geometric architecture echoes the motifs of the Cyclades in this tranquil urban oasis.

Day 3: 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.

Venture into the 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 4: Olympia Archaeological Site to Nafpaktos

Fields of Olympia
Fields of Olympia

Explore the site of the first Olympic Games at the archaeological site of Olympia. There's plenty to cover—it's one of the largest sites in the country, surrounded by wild olives and plane trees. Your comprehensive guided tour will take you under the grand temple columns, past the Sanctuary of Olympian Zeus and through the onsite Archaeological Museum. 

There will also be free time after the tour to explore the site on your own. Scope out the treasuries, sacrificial altars, and stadium once used by the ancient world's best athletes. The natural landscape surrounding the site is also full of opportunities for a day hike if you'd like to put your muscles to use.

Once you've completed your explorations, head north over the Rio-Antirrio Bridge across the Gulf of Corinth—one of the world's longest multi-span cable-stayed bridges. You'll spend the night in Nafpaktos overlooking the waters of the gulf and the town's castle. Spend your evening exploring the town's charming streets.

Day 5: Visit Delphi, Return to Athens

The Treasury of the Athenians at Delphi
The Treasury of the Athenians at Delphi

Today, you'll seek out the oracle during a day trip to the ruins of Delphi, once home to priestesses of Apollo who Ancient Greeks believed could predict the future. Take a guided tour through this sprawling archaeological site, with stops such as the Treasury of the Athenians, the Temple of Apollo, and 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. 

Return to Athens in the evening and enjoy an al fresco dinner in a neighborhood you haven't yet visited.

Day 6: Visit Cape Sounio and the Temple of Poseidon

Quite the dramatic setting for the temple!
Quite the dramatic setting for the temple!

Take a leisurely morning with breakfast and the opportunity to explore the city on your own time, revisiting any favorite shops or undiscovered archaeological sites.

In the afternoon, you'll sail 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, providing you 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 7: Athens to Mykonos

Bright balconies of Little Venice
Bright balconies of Little Venice

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 8: Day Trip to Delos

Terrace of the Lions
Terrace of the Lions

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 9: Explore Authentic Mykonos

Colorful boats bobbing in Mykonos' Old Port
Colorful boats bobbing in Mykonos' Old Port

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. 

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. 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 10: Ferry to Naxos

Naxos
Naxos

Time to ferry to 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 and water activities. The rest of the day is yours to unwind as you choose. Try out some of these options:

  • Hike 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 Sangrion 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 11: Ancient Naxos Hike

Kouros in the shade
Kouros in the shade

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 12: Arrive in Santorini, Hidden Gems Tour & Wine Tasting

The approach to Oia
The approach to Oia

Welcome to Santorini! There's nothing like catching your first glimpse over the island's iconic cliffside architecture. Once settled, watch for your first views of Santorini's central caldera—the site of one of the largest volcanic eruptions in history—rising up in a crescent. 

Spend some time after you've settled in to wander the streets of Fira or get beachside. Don't wear yourself out too soon, though, as in the afternoon you'll take a guided tour which will show you a side of Santorini that most travelers don't see.

You'll start with a stroll through famous Oia, where your guide will point out hidden treasures, followed by a trip up to the highest peak on the island, with 360 degree views at the top for the perfect souvenir photo (or five). Then head on to the medieval villages at Megalochori and Pyrgos, which feel a world away from the touristy towns along the caldera rim. Finally, you'll stop for a wine tasting at the caldera's edge to sample varietals dating back centuries as you watch the sun sink into the Aegean.

In the evening, head back to Oia, passing the Blue Dome of Firostefani along your way. The furthest town along the rim of the caldera, Oia's arty streets are the most famous spot for sunset views, but the evening after the crowds have died down is 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 that encapsulate the essence of the Mediterranean diet, and the Santorini specialty spelt pie.

Day 13: Caldera Day Hike

Trailside views
Trailside views

You'll really get those postcard views with today's hike. Circle the caldera from Fira to Oia, taking in the picture-perfect surroundings. The full hike takes roughly five hours, but can be broken up with stops in the towns or tavernas along the way.

Start early if you'd like the trail to yourself or go out in the late afternoon to arrive in Oia just in time for the sunset views the town is known for, but try to avoid the heat of the midday sun. Stroll through Oia's alleyways and art galleries once you arrive, or head down into Ammoudi Harbor if you want seafood on the shore.

Day 14: Santorini to Athens and Depart

Santorini sunset
Santorini sunset

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.

Map

Map of Mainland Greek History & the Cyclades - 14 Days
Map of Mainland Greek History & the Cyclades - 14 Days