Greece Mainland Tour and Sailing Cruise

Experience the best of Greece in a journey that blends ancient history with island serenity. Begin in Athens, exploring iconic landmarks like the Acropolis. Continue to Corinth, Delphi, and the breathtaking monasteries of Meteora. Then set sail on a week-long private catamaran cruise through the Cyclades Islands, visiting Santorini, Mykonos, and quieter gems like Syros, Kea, and Kythnos. Enjoy sunsets, crystal waters, and charming villages on this unforgettable land-and-sea adventure.

​​​

ITINERARY:​​

​

Day 1: May 25th - Arrival at Athens Airport

​

We will arrive at Athens International Airport, stepping off the plane with a sense of quiet anticipation for the days ahead. The warmth of the Greek sun will greet us even before we leave the terminal. Our transfer will already be waiting, and we will be driven through the bustling capital—past hills crowned with white buildings and olive trees, glimpses of the Acropolis rising in the distance—until we reach our hotel.

​

Soon we will find ourselves in the comfort of our rooms, where we will have a few hours to rest. Some may choose to walk through the nearby streets, perhaps stopping at a shaded café for a first taste of Greek coffee. Others will simply relax, letting the long journey settle behind them.

​

As evening falls, we will gather for our first group dinner. The meal will be generous and unhurried, paired with local wines and flavors that will give us a first glimpse into the richness of Greek cuisine. Everyone will have an opportunity to be formally introduced before retreating for some much deserved rest.

​

Day 2: May 26th - Athens City Tour

 

Our Athens city tour will begin with a visit to the Acropolis, where we’ll explore its iconic monuments—the Parthenon, Erechtheion, Temple of Athena Nike, and the Propylaea. From the hilltop, panoramic views stretch over the Odeon of Herodus Atticus, the Theatre of Dionysus, and the Areopagus. We’ll continue to the Temple of Olympian Zeus, Hadrian’s Arch, and the Panathenaic Stadium, where the first modern Olympics were held in 1896.

​

We’ll witness the changing of the guard at the Presidential Palacebefore driving past Athens’ cultural landmarks, including the Parliament, Constitution Square, and the neoclassical Athens Trilogy. A scenic stop at Lycabettus Hill will offer sweeping views of the city.

​

Later, we’ll stroll through Plaka and the Flea Market for local delicacies and shopping. If time allows, we may also visit the Ancient Agora, the Roman Forum, and Socrates’ Prison. The day will conclude with a visit to either the New Acropolis Museum or the National Archaeological Museum—both offering a perfect ending to our exploration of this timeless city. (B)

​

​

Day 3: May 27th - Argolis Day Trip: Corinth, Nafplion, & Mycenae 

​

We will depart from Athens and follow the scenic coastal road to the Corinth Canal—a remarkable 6-kilometer waterway that connects the Aegean and Ionian Seas, separating the Peloponnese from mainland Greece. After a brief stop to admire the canal, we will continue through traditional villages to reach Ancient Corinth. There, we will visit the Agora, the 6th-century BC Temple of Apollo, and the museum featuring mosaic floors, Corinthian pottery, terra cotta sphinxes, statues, and the Roman head of Tyche. We will also see the podium where St. Paul was judged.

​

Our journey will then take us to Mycenae, where we will explore the famous Cyclopean Walls, the Lion Gate, and the Treasury of Atreus—believed to be the tomb of Agamemnon. We will pass through Argos and arrive in Nafplion, the first capital of modern Greece. Here, we will admire the Venetian fortress of Palamidi and the small islet of Bourtzi, with time for a relaxed lunch.

​

In the afternoon, we will visit the ancient theater of Epidaurus, known worldwide for its superb acoustics. Our return journey will follow the beautiful coastal road along the Saronic Gulf, and we will arrive back in Athens in the evening, having experienced a full day of Greece’s historical and cultural treasures. (B)

​​

Day 4: May 28th - Delphi Tour and Meteora Sunset

 

We will depart early from Athens, following the national road past Thiva, Levadia, and the village of Distomo, eventually arriving at the picturesque ski town of Arachova—famous for its mountain charm and traditional architecture.

 

Our journey will continue to Delphi, once considered the center of the ancient world. We will explore the archaeological site, home to the famous Oracle, the Temple of Apollo, and the ancient stadium. A visit to the museum will reveal treasures from the site, including the renowned Charioteer of Delphi.

 

Later, we will enjoy lunch at a traditional taverna in the modern village of Delphi before heading north, crossing Mount Parnassosand passing through charming Greek villages and the regional capital of Lamia. We will arrive by evening in the scenic village of Kastraki, nestled beneath the cliffs of Meteora, where we will spend the night. (B)

 

Day 5: May 29th - Meteora "Hanging Monastery" Tours

 

The morning will begin with visits to the Meteora Monasteries, a UNESCO World Heritage site and one of the most spectacular locations in Greece. Perched atop towering rock pillars, these monasteries offer both spiritual richness and breathtaking views. We will visit at least 2–3, if not more, of the monasteries depending on opening hours, with highlights including the Holy Monastery of Great Meteoron and the Monastery of Varlaam. If accessible, we may also explore St. Stephen’s Monastery or the more remote Holy Trinity Monastery, known for its dramatic location.

 

At the end of the day, we will enjoy the epic sunset overlooking the monasteries before retiring back to our hotel for rest. (B)

​

THE CRUISE 

 

Day 6: May 30th - Depart Athens to Sounion to Kea

 

Early in the morning, our arranged transport will depart Meteora to return us to Athens for our cruise. During our drive back, we will pause at the historic battlefield of Thermopylae, where King Leonidas and his 300 Spartans made their legendary stand. We will then continue straight to the Agios Kosmas marina, the departure point of many motor yacht charters. We will be greeted by the crew and will depart for Sounion. There will be a lot of space in the bay. With some time before lunch, the braver among us will be taken to shore for a quick walk up to the Temple of Poseidon, while the rest will just relax on the yacht’s sundeck. Lunch will be served, and we will depart in the direction of Kea shortly after.

 

Kea will offer us a wealth of history, both ancient and modern. Being close to the mainland and the first Cycladic island, Kea will have strategic importance. Notably, the Britannic (Titanic’s sister ship) will have been sunk off Kea, on its way to pick up wounded Allied soldiers, and its wreck will still lie there. We will choose a quiet little bay, away from many other boats, and will have dinner. If we are not too tired, we will have the opportunity to discover the area of Ay Nikolaos – a city with tavernas – that evening. (B, D)

 

Day 7: May 31st - Kea to Syros

 

After lunch, we will depart from Kea. We will have decided against visiting Ermoupolis, the capital of the Cyclades, as we are already accustomed to large urban environments and much of the historical character of the city will no longer be present. Instead, the captain will select a tranquil bay where we will spend the day. We will finalize our overnight location and will eventually settle in Finikas, a well-sheltered bay on the northwestern side of the island.

 

We will have the opportunity to venture out to explore the surrounding area. The island of Syros will appear largely barren. We will learn that it had been under Venetian rule throughout much of the Middle Ages before being succeeded by the French. (B, L)

​

Day 8: June 1st - Syros to Delos to Mykonos

 

The next three days are really why we decided to charter a private cruise through the Cyclades.

 

We will leave early for Delos. Delos used to be the most important island in the Cyclades, and the weight of that history is everywhere. At every turn, we will find remnants of what once was—fragments of temples, streets, mosaics. You start to picture the ancient city as it once stood, sprawling across the island.

 

The Cyclades—Kukloi, meaning “rings”—were formed around this very island, Delos. It was the last safe anchorage between Europe and Asia, sheltered by Mykonos to the east, Rheneia to the west, and Tinos to the north. The harbor itself stretches half a mile into the sea. Delos was both a commercial hub and a sacred place, its significance peaking around 500 BC. It was considered so holy that no births or deaths were allowed to occur here—expectant mothers were ferried to Rheneia. Eventually, the island’s prominence faded as power shifted to Rome, and in 80 BC it was sacked. Still, even today, it’s not hard to imagine the grandeur it once held.

 

We will be able to roam freely; Delos isn’t too crowded. We will walk among the five lions guarding the sacred lake, pass the Temple of Apollo, the remains of the ancient theatre, and see what’s left of the harbor. It feels like time stands still here.

 

From Delos, we will sail toward Mykonos, aiming to catch the sunset. We reach Little Venice just in time, find a waterfront spot, and maybe order coffee as waves lap just a few feet from our table. There’s music everywhere in Mykonos— the group will have the chance to experience the legendary Mykonos nightlife, while the rest of us start wondering what a “realistic” departure time might look like the following morning. (B, L) 

 

Day 9: June 2nd - Mykonos to Naxos to Santorini

 

We will set sail early in order to have time to explore Naxos and still make it to Santorini in time for sunset. The charm and timelessness of Naxos are immediately apparent—even from the marina, which is conveniently located right beside the Old Town and the iconic Temple of Apollo.

 

There are surprisingly few tourists; it feels as though Naxos has, for the moment, been spared the wave of mass tourism. We will step ashore and make our way directly to the Temple, taking photos in front of the Portara—a monumental marble doorway that truly looks like it was meant for the gods. Most of us then will wander into the labyrinth of narrow streets that lead up to the Venetian castle. Though little of the fortress remains, we’re quickly captivated by the intimate white-and-blue alleyways, each corner offering another picturesque scene. After a late lunch in town, we return to the marina and continue our journey southward.

 

As the yacht approaches Santorini, we leave the comfort of the aft deck to witness the approaching island. The volcanic origins of the place are unmistakable—even its silhouette sets it apart from the other Greek islands we’ve visited. Passing along the caldera’s edge, we’re reminded that this entire island is the remnant of a massive volcano.

 

We will dock at the old port and head into town for a wonderful dinner. (B)

​

Day 10: June 3rd - Free Day in Santorini/Scuba Diving

 

We will awaken to a quiet morning in Santorini, with no fixed schedule—just a free day to follow whatever pace the island sets for us. The light will be soft at first, spilling gently over the caldera and painting the whitewashed terraces in gold. After a leisurely breakfast on deck, some of us will decide to head toward Oia.

 

Upon arrival, we will stroll through Oia’s iconic alleyways, where blue-domed churches and charming boutiques will line narrow stone paths. 

 

For those drawn to the sea, a different kind of adventure may await. If arranged in advance, a scuba diving excursion will take part of the group into Santorini’s underwater world. The volcanic seabed will reveal lava formations, submerged cliffs, and perhaps remnants of an ancient caldera rim. The water will be startlingly clear, and the feeling of descending into the depths of a sleeping volcano will leave a lasting impression. 

 

Later in the afternoon, we will reunite—whether from the village or from the dive—and return to the yacht for a few quiet hours on the sundeck. The sun will begin its descent, and once again we will find ourselves captivated by Santorini’s famed twilight. We will choose to dine on shore and enjoy the island one last time. It will truly be a day without urgency, a rare luxury in itself. (B)



Day 11: June 4th - Santorini to Sifnos

 

Anchored within the flooded caldera of Thira, we will find ourselves near Tholos Naftilos in the morning. We will make our way to the hot springs of Nea Kameni, located on the island’s western side. We will eventually opt to take the RIB and head inland to explore the heart of the volcanic island. Steam will rise from fissures in the earth, a quiet reminder that this volcano remains very much alive. It will be a surreal moment—standing in the center of an active volcano, in what some believe to be the very site of Atlantis.

 

Following lunch, we will continue to the sulfurous springs, their shores painted with vivid hues of red and yellow stone. The warm waters will be soothing, and drinks delivered by RIB will offer a perfect moment of indulgence. We will coat ourselves in the volcanic mud—especially entertaining for the children. 

 

Eventually, we will need to begin our journey back toward Athens, having reached the farthest point of our yacht charter. Passing by Ios, we will hear that this island is believed to be the final resting place of Homer. Legend has it that the blind poet, unable to complete his journey from Samos to Athens, was cast into the sea, only for his body to wash ashore here. The Tomb of Homer will remain unseen this time, as we will have devoted more than our share of time to the wonders of Mykonos, Naxos, and Santorini. Still, it would have been meaningful to connect it with the memory of visiting the Prison of Socrates in Athens.

 

We will arrive at Kamares Beach in Sifnos but ultimately choose a more peaceful anchorage for the night. (B, L)

​

Day 12: June 5th - Sifnos to Kithnos to Athens

 

It will be the final full day of our Greek sailing journey. Our plan will be to reach Kythnos by lunchtime. We will arrive at Kolona Beach, a breathtaking sandbar that connects Loukas Island to Kythnos. Most of the water toys will be brought out as we spend a leisurely afternoon between the sea, the yacht’s sundeck, and the soft sands of the beach. After the exhilarating days spent exploring Delos, Mykonos, Naxos, and Santorini, this slower pace will be much needed. 

 

The hours in Kythnos will pass more quickly than expected, and soon it will be time to set off to ensure we arrive in Athens before sunset. We will pass by Cape Sounion once more, offering a quiet nod to the Temple of Poseidon silhouetted against the sky, and continue along the Peloponnesian coast.

 

Eventually, we will return to Agios Kosmas marina, where a splendid farewell dinner will bring our charter to a perfect close. (B, L)

 

Day 13: June 6th - Return to Athens; Depart for Home or Turkey Extension

 

The final morning will begin with a generous breakfast on board. We will feel a sense of reluctance as we prepare to say goodbye to the crew, who will have been exceptional throughout the journey. Their warmth, professionalism, and care will leave a lasting impression.

 

As we sip our final coffees, the cars will arrive to take us to the airport to either return to the United States or adventure on to Istanbu. (B)

​

Turkey Extension: Istanbul​

​

Day 13: June 7th - Arrive in Istanbul

 

This morning, we will bid farewell to Greece and continue our journey as we board a flight from Athens to Istanbul, the city where East meets West. Upon arrival at Istanbul Airport, we will be warmly greeted by our local hosts and transferred comfortably to our centrally located hotel.

 

After check-in, you will have time to relax and settle into your new surroundings. Whether you choose to unwind or take a short stroll around the neighborhood, the rest of the day is yours to enjoy at leisure.

 

The evening will offer a perfect opportunity to gather as a group for a welcome dinner, where we’ll share impressions from the journey so far and set the tone for our discovery of Istanbul—a city layered with history, culture, and vibrant energy. (B)

 

Day 14: June 8th - Istanbul Day Tour 1: Palaces, Markets & the Bosphorus

 

We will begin our day with a visit to Dolmabahçe Palace, an opulent symbol of the Ottoman Empire's later period, located on the European shores of the Bosphorus. With its grand halls, crystal chandeliers, and blend of Ottoman and European styles, Dolmabahçe offers a striking introduction to Istanbul’s imperial legacy.

 

From there, we will continue to the lively Spice Market, one of the city’s oldest covered bazaars, where vibrant stalls overflow with fragrant herbs, Turkish delights, dried fruits, and local specialties. It’s the perfect place to enjoy the colorful energy of Istanbul’s trade culture and perhaps pick up a few flavorful souvenirs.

 

Next, we will embark on a Bosphorus cruise, gliding between Europe and Asia along the strait that defines Istanbul. Along the way, we will see historic waterfront mansions, Ottoman-era palaces, and grand mosques—all set against the dramatic silhouette of the city.

After the cruise, we will head to the heart of modern Istanbul: Taksim Square. From here, we will stroll down Istiklal Street, a vibrant pedestrian avenue filled with boutiques, cafes, galleries, and street performers.

 

We will make a stop at the atmospheric Çiçek Pasajı (Flower Passage), once a flower market, now home to charming meyhanes (taverns), where you may choose to enjoy a traditional Turkish lunch or meze.

This day will offer a perfect blend of royal splendor, local culture, and modern city life—all within the unique East-meets-West atmosphere that defines Istanbul. (B)

 

Day 15: June 9th - Istanbul Day Tour 2: Sultanahmet Classics (Duration: 6–8 hours, mostly walking)

 

Our journey through the heart of historic Istanbul will begin at the majestic Hagia Sophia, a marvel of Byzantine architecture that has served as a cathedral, mosque, and now a museum. Inside, we will admire its soaring dome, ancient mosaics, and the layered history that shaped the city across centuries.

 

Just steps away, we will continue to the Blue Mosque, known for its cascading domes and six elegant minarets. Its interior, lined with over 20,000 Iznik tiles in shades of blue, offers a peaceful contrast to the bustling square outside.

 

From there, we will walk to the Hippodrome, once the social and sporting center of Constantinople. Here, we will see historic monuments such as the Egyptian Obelisk, Serpent Column, and the German Fountain—each echoing stories of imperial grandeur.



Next, we descend into the mysterious Underground Cistern, also known as the Basilica Cistern. This atmospheric space, supported by 336 columns and home to the enigmatic Medusa heads, offers a cool and haunting glimpse into the city’s ancient water system.

We’ll then explore the Topkapi Palace Museum, focusing on its highlights: the opulent courtyards, imperial treasures, and sacred relics of the Ottoman Sultans who ruled for centuries from this iconic hilltop residence.

 

The tour will conclude at the legendary Grand Bazaar, one of the largest and oldest covered markets in the world. With over 4,000 shops under its vaulted ceilings, it’s the perfect place to wander, sip tea, and perhaps bargain for a keepsake of your journey.

This walking tour offers a vivid immersion into the spiritual, political, and commercial life of Istanbul—then and now. (B)

 

Day 16: June 10th - Return to Athens and Depart for Home

 

Our journey comes full circle as we prepare for our return. After breakfast, we will check out of our hotel and transfer to Istanbul Airport for our flight back to Athens. Upon arrival in Athens, you will be check in for your international departure home.

 

As we part ways, we carry with us unforgettable memories of Aegean islands, ancient wonders, and vibrant cities. This has been more than a trip—it has been a shared experience of culture, history, and connection. (B)

​