Get acquainted with some Greek highlights both large and small on this 15-day itinerary. Start off in Athens atop the Acropolis and wheeling through the city streets. Then sail down to the Cyclades, starting with sun, sailing, and snacking on Naxos and following it up with exploration of both the history and landscape of Santorini before you return to Athens.

Highlights

  • Hear and tour the mythology of the ancient Acropolis
  • Sample the culinary specialties of Naxos's agricultural scene
  • Sun and swim on sparkling island beaches
  • Hike along the scenery and architecture of Santorini's iconic caldera

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Guided Acropolis Visit Athens
Day 3 Good Morning Athens Bike Ride Athens
Day 4 Ferry to Naxos Naxos
Day 5 Beach Day on Naxos Naxos
Day 6 Small Cyclades Day Sail Naxos
Day 7 Inland Naxos Food Tour Naxos
Day 8 Explore Apeiranthos Village Naxos
Day 9 Naxos to Santorini Santorini
Day 10 Relax in Kamari Coastal Village Santorini
Day 11 Caldera Day Hike Santorini
Day 12 Discover Prehistoric Akrotiri Santorini
Day 13 Santorini Wine Tasting Tour 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: Guided Acropolis Visit

Caryatid Porch of the Erechtheion
Caryatid Porch of the Erechtheion

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: Good Morning Athens Bike Ride

Get around on your new wheels
Get around on your new wheels

Say kalimera with a good morning bike ride around the city. You'll wheel past many of the highlights of the city over the course of 3.5 hours, complete with a coffee break at a cafe. Your guide will tell you about all the spots you pass, such as the Panathenaic Stadium, National Gardens, the Agora, Keramikos, and of course the Acropolis, along with insider tips on the best spots to eat and drink in Athens and plenty of breaks to take in the views.

Put those tips into practice by spending the rest of your day in the posh Plaka district, also known as the neighborhood of the gods. One of the city's oldest neighborhoods, the area features neoclassical architecture in both its homes and shops. When hunger strikes, find a spot at one of the outdoor tables lining the streets. Diners feast on Greek favorites such as the classic horiatiki salad, souvlaki, lamb dishes, and more. Go mezze-style to try them all.

For photography enthusiasts (or those who prefer to sleep late), it is also possible to take the bike ride in the late afternoon rather than the morning, when the soft light is great for pictures.

Day 4: Ferry to Naxos

Hiking the Portara in Naxos
Hiking the Portara in Naxos

Time to ferry over to bustling 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, 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 5: Beach Day on Naxos

Aliko Beach on Naxos
Aliko Beach on Naxos

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 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 6: Small Cyclades Day Sail

Get onboard
Get onboard

Sail out on a catamaran to the "Small Cyclades." This less-traveled chain include six main islands and their many smaller companions. Your particular destination will depend on the winds as you sail around the various unspoiled islands.

The full-day cruise takes you out away from the hustle and bustle to enjoy the still-pristine nature of the islands, listening to the waves and chorus of cicadas as you visit traditional settlements, relax on the beaches, and take leisurely hikes along old paths and goat tracks.

Day 7: Inland Naxos Food Tour

The power of cheese
The power of cheese

As the largest island in the Cyclades, Naxos is home to a wide range of agriculture in addition to its tourist industry. Livestock live alongside the western farms, home to the famous Naxian potatoes, and mountainous areas full of olive groves provide the staples of Greek cooking.

Travel into the Naxos mainland to experience the agriculture and food scene the island is known for. Over the course of this 4-5 hour tour, you'll visit a local farm, family-owned cheese production workshop and winemaker, lush farmland, and a distillery that produces the local kitron liqueur.

Day 8: Explore Apeiranthos Village

Aerial view over Naxos
Aerial view over Naxos

Today, you'll have an opportunity to travel to the village of Apeiranthos. This fantastical spot is situated at the foot of the Fanari Mountain, the island's third-highest peak. Also known as the Marble Village, its winding streets and traditional architecture have been nearly untouched since the days of the Venetians, as has its language. The local dialect is believed to contain both ancient Greek and Byzantine elements.

Most of the village can only be accessed on foot. Have a coffee on the pedestrian-only main street and soak in a slower pace of life, and get lost in the village's winding pathways that crawl up and down the mountainside. Don't miss a visit to the nearby Agia Kyriaki church, located within hiking distance beyond the village. This former Byzantine church is best known for the remnants of its historic murals.

If you're looking for a break from Greek food in the evening, the seasonal Picasso Mexican restaurant on Plaka beach has been drawing loyal visitors to its fresh fajitas and margaritas for more than 20 summers.

Day 9: Naxos to Santorini

Caldera-side lights
Caldera-side lights

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 10: Relax in Kamari Coastal Village

Go poolside or seaside
Go poolside or seaside

After yesterday's activities, take a day to just relax in your temporary neighborhood. The cosmopolitan Kamari beach area is worth savoring, not just sleeping in. The peak of Mesa Vouna, which you spotted previously from Perissa beach, also overlooks this long stretch of black sand, running into crystal blue waters. A stone promenade runs the length of the crescent-shaped bay and is closed to traffic during the summer, making it ideal for a casual stroll.

Wander past a wide spread of cafes, bars, shops, and even supermarkets to complement your sun session, or just recline on a sun lounger and order drinks. As the sun goes down, the beach swings into nightlife mode just waiting for you to dance until dawn. Romantics, on the other hand, can skip the party crowds and take an evening stroll.

Day 11: 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 12: Discover Prehistoric Akrotiri

Explore the wonders of Akrotiri
Explore the wonders of Akrotiri

Take a guided tour of one of the Aegean's most significant prehistoric settlements. You'll head to the excavated city at Akrotiri, hidden away at the southern tip of Santorini on the slopes of the caldera. These ruins were once the site of one of the Bronze Age’s most advanced settlements, which prospered for centuries before being buried by a volcanic eruption in the mid-second millennium BC. You'll have the morning to explore its well-preserved (thanks to the volcanic eruption) streets alongside a local guide who will share its stories.

The Museum of Prehistoric Thera Museum and Archaeological Museum of Thera complement your visit, with findings including murals preserved from Akrotiri and the settlement of ancient Thera once found on the eastern part of the island. 

On your way back, stop to see the three bells of Fira. The trio of bells atop this blue-domed church is pictured on many of the postcards you'll find on the island, and now it's your turn to take a photo of your own

Unwind on the beach with the remainder of your afternoon. The black sands of Perissa and Kamari are always popular, but the colorful Red or White beach are also well worth seeing. Or seek out some solitude within the cliffs at Koloumbos on the island's northern tip.

Day 13: 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 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 to the Acropolis

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