Spend 15 full days discovering some of Greece's most iconic sites on this itinerary.  Divide your time between three different spots, starting with a few days to discover what modern Athens has offer from the top of the Acropolis down to the street food stalls. Then sail down to Mykonos for both inland village tours and leisurely beach time to see every angle of the island, and follow it up with the white cliffs and colorful beaches of Santorini as you sip their ancient wines and sail through the classic caldera.

Highlights

  • Hear and tour the mythology of the ancient Acropolis
  • Sample local specialties on an Athenian food tour
  • Cruise around the luxury beaches of Mykonos
  • Hike and sail the classic volcanic caldera of Santorini
  • Sip volcanic varietals in Santorini's ancient wineries

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Explore Athens & the Acropolis Athens
Day 3 Free Day in Athens Athens
Day 4 Athens Food Tour Athens
Day 5 Athens to Mykonos Mykonos
Day 6 Explore Authentic Mykonos Mykonos
Day 7 Mykonos Beach Day Mykonos
Day 8 Mykonos Day Cruise Mykonos
Day 9 Agios Sostis Beach Mykonos
Day 10 Mykonos to Santorini Santorini
Day 11 Santorini Wine Tasting Tour Santorini
Day 12 Caldera Day Hike Santorini
Day 13 Santorini Sail Santorini
Day 14 Return to Athens & Free Evening Athens
Day 15 Depart Athens  

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: Explore Athens & the Acropolis

The Panathenaic Stadium
The Panathenaic Stadium

Today's full day tour brings you up to the mighty Acropolis and more. You'll start at the white marble Panathenaic Stadium, home to the first Olympic games in 1896 as well as previous tributes to Athena. Continue past Zappeion, the Temple of Olympian Zeus, and the Athens Trilogy, which includes the University of Athens, the Academy of Athens, and the National Library.

Eventually, you'll reach the top of the Acropolis hill, where you'll follow your expert guide through the ruins of the iconic 5th-century BC complex overlooking the city and hear 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.

Continue with a walk past Herodion and the Dionysus Theater to the 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. Don't miss the Caryatids or the Parthenon Hall, with its impressive metopes, pediments and frieze. Complete your visit with a stop in its cafe for either lunch or a relaxed snack and coffee.

Day 3: Free Day in Athens

Frying loukoumades
Frying loukoumades

Start your day by picking up a koulourithe popular Athenian street sesame bread rings, or sweet loukoumades donuts with Greek coffee. You have plenty of time during the day to seek out the city's culinary highlights, including souvlaki in the Monastiraki neighborhood or neo-tavernas on Aiolou Street.

Visit a new neighborhood in the afternoon with a trip to Kerameikos, home to the ancient city cemetery. Wander through the graves and look for the carvings depicting portraits and everyday scenes to envision what life and death were like in the ancient world. Pass through the Sacred Gate, where pilgrims from Eleusis used to pass on their way to the Eleusinian ritual, or the Dipylon Gate, which used to be the starting point of the Panathenaic Procession. The neighborhood isn't all history, though—it's now home to some of the city's most interesting restaurants, ranging from two-Michelin-star Funky Gourmet to Ta Kanaria cafe, which is also home to a street theater company, to one of the city's only Thai restaurants. 

If you're more in the mood for museums, scope out some of the many around Athens. The city has a whole slew to be explored, depending on what specialty speaks to you.

For more history and mythology:

  • Acropolis Museum
  • National Archaeological Museum
  • Museum of the Ancient Agora
  • Archaeological Museum of Kerameikos

Find some fine arts at:

  • Benaki Museum
  • Museum of Modern Art
  • National Gallery

Go off the beaten path at:

  • Museum of Cycladic Art, where you can also buy some truly unique souvenirs
  • The digital interactive museum at the Platonic Academy, next to the site where the actual Academy stood
  • Museum of Ancient Greek Technology in the center of Athens, featuring a working model of the Antikythera mechanism (which can roughly be described as the first analog computer). It was used to predict astronomical positions and eclipses years in advance.

Day 4: Athens Food Tour

Olives for sale
Olives for sale

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 5: Athens to Mykonos

Bright balconies of Little Venice
Bright balconies of Little Venice

You'll start your time in the islands on Mykonos, one of the most famous islands in the Cyclades 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.
  • 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 6: 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 degree shot. Then, head to the port of Agios Ioannis, a protected harbor where fishing boats now launch. Hear the stories of its namesake saint, including a church dedicated to him and the cell he was held in that are now home to an annual festival. 

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. You'll also sample a light lunch with products grown right there in the fields. 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 7: Mykonos Beach Day

Join the lines
Join the lines

Spend a relaxing day filled with sea and sun! Choose from one of Mykonos's many lovely beaches, such as:

  • Agios Sostis, full of island residents and travelers who prefer tranquility to amenities, with just sand and a nearby taverna.
  • Fokos, a quiet beach on the northeastern end of the island, with no distractions but a single taverna serving up local favorites and organic white wine produced on the island.
  • Elia, considered one of Mykonos's most beautiful beaches. This beach has one of the longest stretches of sand on the island and plenty of sunbeds and umbrellas to keep you fed and serviced.
  • Kalo Livadi, a petite pebbled beach on eastern Mykonos. This is one of the best spots for swimming, with plenty of people enjoying the beach along with you.
  • Platis Gialos, a popular beach lined with hotels and restaurants with music drifting out of their patios.
  • Kalafatis, a quiet beach ideal for family relaxation.
  • Ftelia on the northern side of the island, known for windsurfing and sailing when the winds are blowing and tavernas along the bay.

Day 8: Mykonos Day Cruise

Your potential vessel
Your potential vessel

You have two seafaring options to choose from for today's excursion.

Your first option is a private yacht cruise around the secluded bays of Mykonos, along with a stop at the uninhabited island of Rineia. In addition to the natural attractions, your boat will come equipped with snorkeling gear, floating mats, and fishing equipment, and you can even add a jet ski if you so choose.

Option two is a group experience on a glass-bottomed boat. Mingle with fellow travelers as you enjoy a barbecue meal and soft drinks while enjoying views of the Aegean horizon.

Day 9: Agios Sostis Beach

Hop in
Hop in

Trek out to one of the island's remote beaches at Agios Sostis today. Located on the northern side of the island, the beach is named for a nearby church overlooking the bay and remains one of the last bastions against Mykonos's organized sunbed beaches. Though it does get busy during the high season, this uncultivated stretch of sand provides quiet seashore devoid of beach chairs or umbrellas—just you and your towel and whatever else you choose to bring with you.

Day 10: Mykonos to Santorini

Santorini's caldera
Santorini's caldera

After breakfast at your hotel, you'll get an early ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. Upon 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 more 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 catching some exercise—and even more views—from one of Santorini’s more than 12 scenic walking routes, ranging from between two to eight miles each.  At dinner, sample the island's signature cherry tomatoes and white eggplants as guest stars in seafood dishes or the main event.

Day 11: Santorini Wine Tasting Tour

Vineyard hills
Vineyard hills

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: Caldera Day Hike

Trailside views
Trailside views

You'll really get those postcard views with today's hike. Lace up your sneakers and depart for one of the best walks on the island. 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 13: Santorini Sail

Red Beach, Santorini
Red Beach, Santorini

Today takes you on a 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 and make sure you've gotten plenty of beach time.

After your second swim, barbecue will be served onboard while you sail past landmarks at Aspronisi, the Ancient LighthouseIndian 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 by dropping anchor at a spot below the cliffs of Oia to watch the sunset from the water, with just you and your shipmates away from the crowds.

Day 14: Return to Athens & Free Evening

National Archaeological Museum
National Archaeological Museum

Return to Athens after your final breakfast. Once you've returned, use your afternoon to scope out some of the museums you may have missed earlier in your trip. The city has a whole slew to be explored, depending on what specialty speaks to you.

For more history and mythology:

  • Acropolis Museum
  • National Archaeological Museum
  • Museum of the Ancient Agora
  • Archaeological Museum of Kerameikos

Find some fine arts at:

  • Benaki Museum
  • Museum of Modern Art
  • National Gallery

Go off the beaten path at:

  • Museum of Cycladic Art, where you can also buy some truly unique souvenirs
  • The digital interactive museum at the Platonic Academy, next to the site where the actual Academy stood
  • Museum of Ancient Greek Technology in the center of Athens, featuring a working model of the Antikythera mechanism, the first analog computer 

Museum tickets and guided tours can be arranged upon request.

Day 15: Depart Athens

Wave farewell to your new friends
Wave farewell to your new friends

Time to say farewell to Greece. Enjoy your final Athenian breakfast and sneak in some last-minute exploring before your transfer to the airport.