The Jewels of the Cycladic Islands of Greece

from $6,995.00 CAD per person based on double occupancy May 27 - Jun 09 , 2026 14 Days Tour

The Jewels of the Cycladic Islands of Greece

Join us for a curated journey through the heart of the Cyclades, where ancient history, island charm, and authentic Greek hospitality come together in perfect harmony. This 14-day adventure blends iconic landmarks with hidden gems, offering a rich tapestry of experiences across Athens, Santorini, Paros, Syros, and Tinos.

We begin in Athens, where a welcome dinner sets the tone for the days ahead. After a leisurely morning, we fly to Santorini and check into our hotel with sweeping Caldera views. A full-day tour the next day reveals the island’s volcanic past at Akrotiri, paired with wine tasting and a delicious lunch.

From Santorini, we ferry to Paros, a tranquil island known for its blend of traditional villages, coastal beauty, and artistic heritage. Our full-day sightseeing tour takes us through the island’s most captivating areas such as Parikia, Naoussa,, Lefkes, Pyrgos .  This day offers a rich blend of history, artistry, and local flavor. The following day is free to enjoy Paros at your own pace — whether you choose to unwind by the sea, revisit favorite spots, or simply take in the Cycladic serenity.

Next, we arrive in Syros, the cultural capital of the Cyclades. Over four nights, we delve into its neoclassical elegance of the Capital Hermoupolis. We also explore Ano Syros’ medieval charm, sample local delicacies like loukoumi and spoon sweets, A visit to a local winery rounds out our time with a tasting lunch and free afternoon.

We ferry to our last Cycladic Jewel: Tinos  An island of spiritual significance and artistic heritage. We visit the famed Church of the Virgin Mary, the marble village of Pyrgos, and the surreal landscape of Volax. Along the way, we enjoy local cuisine, coastal beauty, and the island’s rich cultural traditions.

Our journey concludes with a return to Athens via Piraeus, where a farewell dinner offers a final taste of Greece’s warmth and flavor. The next morning, we say goodbye — carrying with us the rhythm, stories, and spirit of the Cyclades.

Itinerary

1
May 27

Athens

Arrival at Athens International Airport. After clearing customs formalities transfer from the airport to the  Amalia Hotel. This evening a special welcome to Athen’s dinner is planned at a local restaurant. (D)

2
May 28

Athens – Santorini

Breakfast at the hotel. Morning free at leisure. Check out of our hotel and transfer from the hotel to the Athens Airport for flight to Santorini. Upon arrival in Santorini meet and assist at the airport and transfer to the Iliovassilema Hotel. Junior Suite with Caldera View. Breakfast included.

3
May 29

Santorini

Breakfast at our hotel this morning. After breakfast, our adventure begins in Firostefani, the elevated "crown of Fira," offering breathtaking views of the capital and the caldera. A visit to the famous Blue Domed Church, an iconic landmark gracing countless postcard, sets the perfect tone for the day.

We then journey to Oia, undoubtedly the most celebrated village in Santorini. Nestled into volcanic cliffs, its whitewashed houses, blue-domed churches, and picturesque alleyways create an unrivaled setting—especially at sunset, when the sky ignites in brilliant hues.

Our next stop is Pyrgos Village, a hidden gem that offers panoramic views and an enchanting blend of Cycladic charm and Venetian history. With its traditional houses, winding paths, and the Venetian castle, Pyrgos encapsulates Santorini’s rich heritage.

Moving on to Emporio, Santorini’s largest settlement, we wander its medieval streets and explore Emporio Kastelli, the island’s best-preserved castle, surrounded by traditional houses and historic churches.  Lunch today will be at a local taverna at Perissa Beach.

Diving deeper into Santorini’s ancient past, we visit the Akrotiri Archaeological Site, one of the most significant prehistoric settlements in the Aegean. Preserved beneath volcanic ash, this site offers fascinating insights into an advanced civilization frozen in time.

To conclude this enriching experience, we visit Venetsanos Winery, where tradition meets exceptional craftsmanship. Here, we discover Santorini’s celebrated wine culture and savor the island’s renowned volcanic vintages—a perfect toast to an unforgettable day. (B,L)

4
May 30

Santorini – Paros

Breakfast at the hotel.  After breakfast, we will be met at our hotel and transfer from the hotel to the port of Santorini. High speed ferry from Santorini to the island of Paros.  Upon arrival on Paros, we will be met and transferred to the Contaratos Beach Hotel for a 3-night stay.  Superior room with Sea View. (B)

5
May 31

Paros

Embark on an unforgettable journey through the most renowned destinations of Paros, starting from your designated area of residence, accompanied by our professional English-speaking guide. Travel comfortably in an air-conditioned minibus as we set off for Parikia, where you will explore the enchanting old town.

Our first stop is Panagia Ekatontapyliani, home to the Byzantine Museum and the Ancient Baptistery—one of Greece’s most significant early Christian monuments. Dating back to the 4th century, the baptistery on the south side of the complex is regarded as the best-preserved in the entire Orthodox East.

Leaving Parikia, we proceed to the Port of Pounta, where we board a ferry bound for the captivating island of Antiparos. After a short 10-minute crossing, we arrive in Antiparos, where we stroll through the vibrant marketplace, connecting the port to the island’s central square and Venetian Castle.

Next, we venture to the Cave of Antiparos, an ancient site used for pottery and the worship of Artemis. This remarkable natural refuge houses Europe’s oldest stalactite, while the temple of Ai Giannis Spiliotis stands proudly at its entrance. Inside the cave, you can still see the signature of King Otto of Greece, marking his historic visit.

Following our exploration, we head to the popular Soros Beach, where you can unwind and enjoy a refreshing swim while admiring breathtaking views of the Salt Lake of Paros.

Returning to Paros, we make our way to Lefkes, passing by the island’s ancient marble quarries, once a vital source of wealth. These quarries produced the famous Parian marble, highly prized in antiquity. Lefkes, the island’s first capital, is one of its most picturesque mountain villages.

Our journey continues to Naoussa, where we visit Agios Nikolaos and the scenic natural harbor, home to the Venetian Fortress. Strolling through Naoussa’s charming marketplace and cobbled streets, you will experience the authentic beauty of this remarkable village.

We conclude our excursion and return to your accommodation having explored the historical and cultural treasures of Paros and Antiparos.

6
Jun 01

Paros

Breakfast at the hotel.  Today is a free day to relax and enjoy Paros at your own pace. (B)

7
Jun 02

Paros – Syros

Breakfast at the hotel.  After breakfast, we will be met at our hotel and transfer from the hotel to the port of Paros.  High speed ferry tickets from Paros to the island of Syros.  Upon arrival on Syros we will be met and transferred to the Syrou Melathron Hotel.  Sea view rooms for 4 nights.   Breakfast included.  (B)

8
Jun 03

Syros

Our adventure begins at the majestic Cathedral of St. Nicholas, the patron saint of Hermoupolis. Nestled in the prestigious Vaporia district, this architectural marvel boasts lavish interiors and breathtaking design. Surrounded by grand high-ceiling mansions that appear to float above the sea, the cathedral is a stunning introduction to Syros’ timeless charm.

Next, we step into the cultural heart of the island at the iconic Apollon Theater. Built in 1864 by renowned Italian architect Pietro Sampo, this masterpiece draws inspiration from Italian gems like the Scala di Milano. Today, it continues to host vibrant cultural events, celebrating the island’s artistic spirit.

From there, we enter a remarkable Neoclassical mansion, a living testament to Syros’ aristocratic past. As we step inside, we are enveloped in an atmosphere of elegance—the walls adorned with scenic paintings, the ceilings graced with intricate plasterwork, each room whispering tales of refinement and grandeur.

Our journey then leads us to Miaoulis Square, the historic heart of Hermoupolis. This picturesque square is a breathtaking blend of 19th-century architectural marvels. Here, we visit the Town Hall, a striking creation by famed architect Ernst Ziller. Built in 1898, this masterpiece seamlessly combines Tuscan, Ionic, and Corinthian styles, crowned by a majestic 15.5-meter-high princely staircase.

Leaving the town center, we ascend to the medieval settlement of Ano Syros, perched atop the hill overlooking Hermoupolis. As we step into its historic streets, we explore notable landmarks, including the Cathedral of St. George, the island's Catholic cathedral, the Catholic Monastery of Capuchins, and the church of St. John, which dates back to 1635. Wandering through the charming center of the settlement, known as Piatsa, we discover quaint shops and the Museum of Markos Vamvakaris, a tribute to one of Greece’s most influential rebetiko musicians.

Finally, we embark on a scenic bus tour through Syros’ Neoclassical villages, where historic mansions reveal captivating stories of aristocratic life. Each stop on this unforgettable journey paints a vivid portrait of Syros’ deep-rooted elegance, tradition, and timeless beauty.  Upon arrival back in Ermoupolis we will enjoy another delicious lunch at a lovely Greek Taverna. (B,L)

9
Jun 04

Syros

Step into the heart of Syros at Syros Market, where tradition meets modern convenience. The owner’s passion for Greek flavors has led to a curated selection of authentic products from across Greece. With decades of experience in tastings and culinary exploration, he has crafted a delicatessen that showcases the finest traditional Greek ingredients and gourmet delights. Since 1993, his mission has been to revive classic flavors from the Cyclades and Syros, preserving Greece’s rich gastronomic heritage.

Next, indulge in Syros' beloved Loukoumi, the island’s signature sweet treat. Made with water, starch, and sugar, this confection owes its uniquely exquisite taste to Syros' pure, mineral-rich water. Loukoumi is more than just a dessert—it’s a symbol of history and culture. In the workshop, you’ll uncover its storied past and masterful craftsmanship, while sampling an array of delightful flavors that highlight this timeless tradition.

Then, we journey to Episkopio, known as “The resort of sovereigns.” Once the first metropolis of Syros, this picturesque hilltop was home to grand villas built by aristocrats. Here, you’ll receive a warm welcome into a local family home, where history comes alive through elegant furniture, treasured photographs, and evocative paintings. As you soak in the ambiance, Mrs. Peggy will treat you to homemade lingonberry and bitter almond liqueur, a unique “underwater” sweet (vanilla in cool water), and a frappe spoon dessert, a cherished recipe passed down from her grandmother—who came to Syros as a refugee. Savor spoon sweets infused with grape and rose, a taste of generations past.

Our final stop is a local winery, where age-old traditions blend seamlessly with innovative winemaking techniques. As you explore the vineyard, you’ll be surrounded by lentisks, osiers, thymes, and sages, all contributing to the complexity of Syros' renowned wines.

A knowledgeable member of the winery team will guide you through the winemaking process, unlocking the secrets behind the island’s celebrated rosé and white wines—each sip revealing a beautifully layered, fruit-forward elegance.  After our visit to the local winery it is time for an included leisurely tasting lunch menu at a local taverna.  The afternoon is free at leisure. (B,L)

10
Jun 05

Syros

Breakfast at the hotel today.  Today is a free day to relax and enjoy Syros at your own pace today. (B)

11
Jun 06

Syros – Tinos

Breakfast at the hotel.  After breakfast transfer from the hotel to the Syros port.  High speed ferry tickets from Syros to Tinos.  Upon arrival on Tinos meet at the port and transfer to the hotel.

12
Jun 07

Tinos

Breakfast at the hotel. After breakfast we depart on a full day’s tour of Tinos. Today we will be visiting the most beautiful sights of the island, such as picturesque villages, beautiful beaches, restaurants, museums, archeological sites and many more.  

The trip starts at Chora of Tinos where you visit the famous church of Virgin Mary (Panaghia). The most well-known church in Greece, which thousands of people visit from all over Greece every year. Then, you visit the traditional village of Kardiani, one of the most beautiful villages of Tinos, because of its 180-degree view of the Archipelago and its impressive architecture.

We continue your trip to Pyrgos village. A village built of marble, famous for its marble sculptures and also the birthplace of the famous marble sculptor Yiannoulis Halepas. You wander in the narrow village alleys and have a break for dessert or coffee at its famous square. Afterwards, you visit the Marble Museum, to learn about the history of Tinian marble.

Following that, you visit Kolymbithra beach. One of the most beautiful beaches on Tinos.  Next, you visit a traditional nearby village for lunch break at a traditional tavern.

Last but not least, you visit Volax, a quite exceptional village, built among world-unique large spherical rocks, the origin of which remains a mystery. (B,L)

13
Jun 08

Tinos – Piraeus

Breakfast at the hotel.  After breakfast, we will be transferred to the Tinos port for high speed ferry journey to the port of Athens; Piraeus. Upon arrival, we will be transferred to our hotel.   Farewell dinner this evening at local restaurant. (B,D)

14
Jun 09

Athens – Home

Breakfast at the hotel. After breakfast, we check out of our hotel and say goodbye to Greece. Transfer from the hotel to the Athens International Airport. (B)

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