Travel across the Peloponnesian peninsula and dive into Greek history with this 14-day itinerary. After a brief stay in Athens, go down to the sea to visit Nafplio, Ancient Olympia, and Delphi. Set sail for the quintessential Greek island of Santorini to end your journey on its stunning caldera.


  • Appreciate the timeless magnificence of the Acropolis 
  • See where Helen of Troy lived at Mycenae
  • Follow in the footsteps of ancient athletes in Olympia
  • Climb to the clifftop monasteries of Meteora
  • Admire Santorini's volcanic landscape from a sea kayak 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Acropolis Guided Tour & Acropolis Museum  Athens
Day 3 Athens Food Tour  Athens
Day 4 Nafplio  Nafplio
Day 5 Explore Ancient Olympia  Olympia
Day 6 Travel to Delphi  Delphi
Day 7 Travel to Meteora  Kalabaka
Day 8 Meteora - Return to Athens Vouliagmeni
Day 9 Ferry to Santorini Santorini
Day 10 Beach Day in Santorini Santorini
Day 11 Sea Kayaking in Santorini  Santorini
Day 12 Guided Hike along Santorini's Caldera Santorini
Day 13 Santorini Biking Tour  Santorini
Day 14 Fly back to Athens & connect with your international flight  

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.

Have dinner with a view of the romantic moonlit Parthenon.

Day 2: 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 3: Athens Food Tour 

Olives for sale at Athen's markets.
Olives for sale at Athen's markets

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.

Say good morning with Greek coffee at one of the city's landmark coffee houses, then pick up some street snacks to sample on the go. Venture into the aromatic 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: Nafplio 

The Fortress of Palamidi
The Fortress of Palamidi

Today, explore the Argolis region and the remains of the ancient city of Mycenae — a major center of Greek civilization from 1600 BCE to 1100 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.E. structure

Later in the day, continue your historic tour with a visit to the first capital of modern Greece, Nafplio, to see its Venetian Palamidi fortress and the fortified islet of Bourtzi.

Day 5: Explore Ancient Olympia 

The fire is lit in Ancient Olympia and travels to the Beijing Olympic Games
The fire is lit in Ancient Olympia and travels to the Beijing Olympic Games

Spend the day exploring ancient Olympia, the birthplace of the Olympic Games and Zeus' sacred land. Your guide will meet you in the morning to give you plenty of time to see all the sights at the archaeology site. And there's a lot to cover—it's one of the largest sites in the country, surrounded by wild olives and plane trees.

This place is connected to many gods and myths. There are different versions of how the Olympic Games got their start. According to one version, Olympia was where Zeus struggled with his father Cronus, finally beating him and seizing the throne. As a memory of his victory, Zeus organized the games.

Once you arrive, 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 ancient stadium once used by the ancient world's best athletes.

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Day 6: 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), you'll have the option of taking a guided or self-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. 

After you have explored the sites of Delphi, return to your accommodation to relax and have lunch. In the evening take a stroll around town to find a quiet cafe for a relaxed evening meal. 

Day 7: Travel to Meteora 

The Monastery on a clifftop
The Clifftop Monastery

Start your day with a 3-hour drive 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 that overlook the surrounding landscape. These religious buildings sit atop rock formations that are more than 60 million years old. You'll tread the same paths that monks used for hundreds of years to reach these holy places, perched close to 1,000 feet 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. 

Despite their seemingly precarious location, they are still inhabited and used by monks and nuns today. Thanks to its incredible history, the area has been named a UNESCO World Heritage site and is one of the largest pilgrimage sites in Greece.

You'll meet your guide for a three-hour tour to see all six of the monasteries, with visits inside one or two of them for a glimpse of what the ninth-century monastic life may have been like. 

Day 8: Meteora - Return to Athens

Monastries on the clifftop
Monastries on the clifftop

Spend a bit of time this morning exploring more of the incredible cliff-side monasteries of Meteora on your own. Enjoy a final lunch in the shadow of the dramatic rocks before returning to Athens and checking in your hotel in Vouliagmeni — the Athenian Riviera's premier beach town.

Day 9: Ferry to Santorini

Sunset in Oia
Sunset in Oia

Catch a ferry from Athens 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: Beach Day in Santorini

Pink Beach in Santorini
Pink Beach in Santorini


Thanks to its volcanic activity, Santorini is famous for having beaches with a multitude of different colors. Instead of the regular golden or white sand beaches which you may find anywhere else in the world, Santorini amazes with its own palette of colored beaches. Pick one to relax for the day, or try to visit them all! 

  • Kamari Beach: The most upscale and touristy of the beach towns, with plenty of family-friendly options.
  • Perissa and Perivolos Beach: Essentially one very long beach that caters to the backpacker crowd and party scene (beach style, not clubs) but still has a wide range of accommodations and restaurants.
  • Red Beach: The pebbly sand here is red and the backdrop is stunning.
  • Monolithos Beach: The nicest sand and the most family-friendly beach on Santorini. It's quiet, with a small collection of hotels and restaurants.

Day 11: Sea Kayaking in Santorini 

Sea Kayaking in the Aegean Sea
Sea Kayaking in the Aegean Sea

After breakfast, you'll transfer to the island's southern coast for a new perspective on Santorini. Hop in a sea kayak to enjoy spectacular rock formations, crystal waters, and beaches on the island's frequently overlooked southern side. The tour will last about 3 hours, with a stop for snorkeling in the warm water. 

Once you've returned to your hotel in Fira, enjoy a free afternoon to rest and relax before dinner. If you still have the energy to explore more of Fira, visit the Archaeological Museum for a glimpse into the island's past, or stroll through the streets to scout for perfect souvenirs. In the evening, don't forget to enjoy your final sunset in Greece. Santorini is the perfect island for a mesmerizing sunset!

Day 12: Guided Hike along Santorini's Caldera

Hiking the Caldera
Hiking the Caldera

The best way to enjoy the famous views of Santorini is to walk along its breathtaking caldera. We can thank one of the world's largest volcanic eruptions for creating the caldera, which is mostly submerged below the blue-hued Aegean Sea.

Your guide will start with a popular route out of Fira, then you'll ditch the crowds and enjoy some secret spots with incredible views. All the local guides are passionate about showing off their homes and love to bring guests to the hidden and more authentic side of the island. 

Before returning to Fira for the evening, you'll join your guide for an optional picnic overlooking the caldera and the infinity of the Aegean Sea.

Day 13: Santorini Biking Tour 

Bike & Caldera
Bike & Caldera

Discover even more of Santorini on two wheels with today's bike tour. You'll explore traditional villages, medieval castles, and scenic landscapes, along with the classic caldera views. Refuel with a Greek coffee or juice at a local kafeneio. 

The tour takes roughly three hours, including stops, and bicycles and equipment are provided. You'll explore the southern part of the island, starting from the black sand beaches of Perivolos. Cycle along an ancient trail loop, passing stops like Perissa and Vlychada beaches and the villages of Emporio and Megalochori before returning to Perissa.

Spend your afternoon lounging by the sea at one of Santorini's many colorful beaches.

Day 14: Fly back to Athens & connect with your international flight

Wave to the Acropolis
Wave to the Acropolis

Time to say farewell to Greece. Catch the early morning flight back to Athens airport to connect with your international flight.