Famous for their beautiful beaches, the Cyclades Islands aren't just for lounging. Hike, bike, and sail around whitewashed fishing villages and over rocky landscapes on this 12-day active tour. Start off in Paros with a cooking class and scenic horseback ride before cycling in Naxos and a sunset hike in Santorini. You'll explore more of the Aegean Sea before bidding farewell to Greece with a well-deserved wine toast.


  • Learn to make a traditional Greek meal using local olive oil, seafood, and more
  • Take a scenic half-day hike from Lefkes through the interior of Paros island
  • Sail around Santorini, making a stop to relax in the hot springs at Nea Kameni
  • Enjoy a native varietal wine tasting at the Santo Wines Oenotourism Center

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Athens to Paros Paros
Day 3 Cooking Class & Horseback Riding Paros
Day 4 Hiking in Paros Paros
Day 5 Paros to Naxos Naxos
Day 6 Naxos Hike & Cultural Tour Naxos
Day 7 Cycling Tour Naxos
Day 8 Naxos to Santorini & Caldera Hike Santorini
Day 9 Sea Kayaking in Santorini Santorini
Day 10 Santorini Sailing Tour Santorini
Day 11 Wine Tasting and Return to Athens Athens
Day 12 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: Athens to Paros

Kolymbithres beachgoers
Kolymbithres beachgoers

You'll start your island adventure in Paros, one of the quiet gems of the Cyclades. You can arrive either via plane to the island's small airport or by ferry, with schedules varying by season. Either way, you'll be met with a transfer to your hotel.

Depending on when you arrive, you'll have the afternoon to explore on your own. Hit the sea air and golden sands of popular Kolymbithres beach if you need to feel the sand under your toes as soon as possible. The beach umbrellas are accented by towering granite rocks, resembling natural sculptures. Enjoy the sea breeze or take a coastal walk past the area's attractions. You'll spot ancient chapels, flowering vines, and rustic farmhouses on your way to the hillside ruins of the Mycenean Acropolis, dating back to the 13th century BC, and the Monastery of St. John.

Day 3: Cooking Class & Horseback Riding

Learn time-tested cooking techniques
Learn time-tested cooking techniques

Start your day in a delicious way with a four-hour cooking class led by an expert chef. You'll learn about traditional cooking methods and recipes from both Greek tradition and the island of Paros. Master the strategic deployment of olive oil, fresh produce, seafood, and more, culminating in a feast of your own making. 

After you've had your fill, transfer to a riding center to meet some of the island's four-legged residents. A two-hour horseback tour will take you through hidden spots on the island not accessible by the main roads as you take in the surrounding scenery.

Day 4: Hiking in Paros

Streets of Lefkes
Streets of Lefkes

Load up on breakfast today, as you'll depart for the village of Lefkes for a scenic half-day hike through the interior of Paros island. 

The trail route passes the classic whitewashed churches of Agios Ioannis (St. John) and Agios Georgios (St. George) sitting snugly on their hillsides, alongside the small settlements at Aneratza and Kamari. Your trail eventually leads to Alyki beach, where you can wash off the dust of the trail with a dip in the clear waters of the Aegean. Refuel with lunch in a seaside taverna.

Return to your hotel to freshen up before heading to the chic port town of Naoussa. This picturesque fishing village, complete with boats bobbing offshore, is home to a myriad of tiny shops, cafes, and bars and clubs that attract guests to its cobblestone streets all season long.

Hiking time: 5 hours with stops
Hiking distance: 9 miles (15 km)

Day 5: Paros to Naxos

Naxos port
Naxos port

Spend one more morning in Paros, complete with breakfast and sightseeing in Paroikia. Stroll through the island's main town, including the traditional and contemporary designs at Yria Ceramics and the famous Byzantine church of Ekantotapiliani. Also known as the Church of 100 Doors, it's worth a stop to see one of the best-preserved Christian churches in Greece.

You'll hop on the ferry to Naxos and be transferred to your hotel, with time to explore the island in the evening. 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.

Don't miss the Portara, the entrance to the former Temple of Apollo. Construction on the temple began in the 6th century BC but was never finished. 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).

If you prefer something a bit more pastoral, Naxos is also known for its rich agricultural industry. Pay a visit to a cheese-producing facility or a local distillery to sample the famous local kitron liqueur. 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 6: Naxos Hike & Cultural Tour


After breakfast, you'll head to the Kouros statues to start your day's hiking in the shadow of these large sculptures. Originally set to hold up a temple roof, these giant statues of young men were abandoned by their ancient sculptors when they discovered faults in the marble, but they're no less impressive for them today.

Follow the path to picturesque Ano Potamia village, where you'll cool off with a dip in the village spring. Continue on to Apana Kastro (the Upper Castle district) to take in panoramic views of Naxos town, port, and the surrounding villages. 

Keep going via the village of Tsikalaria to Halki, a town at the center of the island. You'll visit the Valindras distillery, where they produce kitron, the local citrus liqueur. Have a taste—you've earned. it.

Hiking time: 4 hours (including stops for rest and lunch)

Day 7: Cycling Tour

Naxos trails
Mountain trails in Naxos

Today, you'll take to the side streets and secret paths of Naxos on two wheels. The adventure bikes over small tracks through farmland and the surrounding rich vegetation, taking in mountain views and some of the best coasts in the Cyclades. 

The small stony roads lead you to the white sands and blue waters of Mikri Vigla beach. Stop for a swim and snack or drink (or both!) before you hop back on the bike to return to base, via the beach.

Biking time: 4-5 hours

Day 8: Naxos to Santorini & Caldera Hike

Today you can linger over breakfast and take a swim or stroll in the Naxos port until an early afternoon ferry takes you to Santorini, star of the Cyclades. Nothing says "welcome to the islands" like the views of Santorini's iconic cubic architecture and central caldera—the site of one of the largest volcanic eruptions in history—rising above you. 

Transfer from the port to your hotel and get settled in. Once you're set, you'll depart for one of the best walks on the island. Circle the caldera from Fira to Oia, taking in the picture-perfect surroundings. As the furthest town along the rim of the caldera, Oia's arty streets are the perfect spot for sunset views. 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.

Hiking time: 4 hours with stops
Hiking distance: 7 miles (11 km)

Day 9: Sea Kayaking in Santorini

Wind along the cliffs
Paddle along the cliffs

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 10: Santorini Sailing Tour

Hot springs at Nea Kameni
Hot springs at Nea Kameni

Get back into the water this morning, though, this time, you get to be the passenger. Your full-day sailing tour covers all the coastal hotspots, beginning at Vlihada Marina. Start by passing the ancient city of Akrotiri, a Bronze Age Minoan settlement destroyed by the great volcanic eruption, then onward to the famous Red and White beaches—named due to their colorful sands. Breeze around Indian Head Mountain and the Venetian Lighthouse to enter the caldera, where you'll find private bays for swimming and snorkeling.

Hop in the hot springs at Nea Kameni, which are high in sulfur and renowned for their potential therapeutic benefits. After emerging back to dry land, you'll be served a barbecue lunch in a secluded bay. Continue past the volcanic islands in the caldera, including the white island of Aspronisi, on your return to port. 

Cap off your stay with a farewell dinner overlooking the caldera as the cliffside buildings sparkle around you.

Day 11: Wine Tasting and Return to Athens

Get one more glimpse over the caldera
Get one more glimpse over the caldera

Don't be too quick to depart! Take the morning to enjoy breakfast or wander around and shop for souvenirs. You can also sample some of the fruits of the island with a wine tasting at the Santo Wines Oenotourism Center. Toast to your travels (and travel partners!) with a wine tasting while savoring your last views of the volcano.

Later in the day, take a ferry or quick flight back to Athens.

Day 12: Depart Athens

Wave to the city
Wave to the city

Time to say farewell to Greece. Enjoy your final Athenian breakfast before your transfer to the airport.


Map of Active Cyclades Adventure - 12 Days
Map of Active Cyclades Adventure - 12 Days