Whether you're windsurfing, hiking, or sea kayaking, this nine-day itinerary will take you to some of the highlights of Athens and the islands. Start off high atop the Acropolis, then set sail for bustling Naxos, one of the largest islands in the Cyclades, where you can take advantage of one of the best windsurfing spots in the region. Then head to Santorini to sea kayak and hike around the island's famed caldera.

Highlights

  • Hear and tour the mythology of the ancient Acropolis
  • Windsurf on Naxos at one of the world's best spots for the sport
  • Kayak and hike on the iconic shores of Santorini

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Guided Acropolis Visit Athens
Day 3 Ferry to Naxos Naxos
Day 4 Windsurfing or Paddleboarding in Naxos Naxos
Day 5 Naxos to Santorini Santorini
Day 6 Sea Kayaking in Santorini Santorini
Day 7 Caldera Day Hike Santorini
Day 8 Return to Athens & Free Evening Athens
Day 9 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: 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 4: Windsurfing or Paddleboarding in Naxos

The area is also popular with kitesurfers
The area is also popular with kitesurfers

You have two ways to get in the water today in Naxos.

Your first choice is a windsurfing at Laguna Beach Park. Classes are available for all levels, with consistent breezes to help you stay upright and warm waters to catch you if you don't quite make it. If you prefer something a little more serene, opt for a stand-up paddleboard to peacefully paddle to your heart's content.

Stick around to relax on the beach or take a bike ride into the afternoon. If you'd prefer a break from the sea, head inland to visit Koronos village. Located in a valley filled with vineyards, this mountain village is an ideal spot to linger over a taverna table in the central square.

Day 5: 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 6: Sea Kayaking in Santorini

Your vessel awaits
Your vessel awaits

This morning, you'll take a post-breakfast 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 to see your fellow sea creatures. 

Once you've returned to your hotel, rest in the free afternoon before dinner. For those who still have energy, visit the Archaeological Museum for a glimpse into the island's past, or stroll through the streets to scout for perfect souvenirs.

Day 7: 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 8: 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 9: 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.