Gems of the Mediterranean: 14-Day Italy and Greece Tour

If you're considering a trip to Greece, look no further than Zicasso. Our travel expert planned an unforgettable journey for our family; Athens, Mykonos, and Santorini, and every detail was executed with care, expertise, and passion. 

From the moment we arrived in Athens, we were immersed in the country’s warm hospitality. Our agent made sure we had the perfect balance of sightseeing and relaxation. The historical sites in Athens, like the Acropolis and the ancient Agora, were must-sees.

Mykonos is vibrant yet relaxed. The beaches were beautiful. Every meal on this trip was a highlight. Fresh seafood, local cheeses, olive oil, and delicious pastries—each bite told a story of Greece’s deep culinary heritage.

In Santorini, we were captivated by the island’s charm—whitewashed buildings, breathtaking sunsets, and the deep blue Aegean Sea. We visited traditional villages, giving us a glimpse into the rich cultural traditions that are still very much alive.

Throughout the trip, what stood out most—beyond the stunning landscapes and ancient history—was the friendliness of the Greek people. Their warmth and pride in their culture made every moment feel welcoming and genuine.

Our agent didn’t just plan a vacation—he created an experience rooted in history, tradition, and hospitality. I can’t recommend him and Zicasso highly enough.

We had a wonderful time in Greece. We spent 10 days there and went to Athens, Mykonos, and Santorini. The accommodations were great and the planned excursions were fantastic. The weather was perfect.

Zicasso’s travel company was awesome. Our agent did a great job planning our trip experiences. The execution of all the private drivers and excursions was perfect. The trip planner tool was great to use, as we referenced it every day. The hotels, in-region airlines, and ferry reservations and tickets were all perfectly planned and delivered. Our many scheduled drivers were all on time and courteous. Our drivers were great drivers and scholars. They provided awesome restaurant and pub recommendations. 

We absolutely loved Santorini and the two excursions on that island. Both definitely exceeded our expectations. Our only excursion not rated five stars was the Jeep tour on Mykonos. Four of us were crammed into a closed, small Jeep and driven around the island with only a few stops. We were not taken to a top spot we heard about, which was the windmills and little Venice.  We rate that excursion zero stars for those reasons. 

All four trip participants agreed this was one of their best-ever vacations. We highly recommend this travel company for a great Greek vacation!

Zicasso's travel specialist went above and beyond to curate a fantastic, scenic, exciting, and restful vacation for us and was sure to provide us the best possible accommodations at each destination (Athens, Mykonos, Santorini). We didn't have to worry about one single detail for the entire trip as all of our transport was covered, we had a local contact in each location, and all hotels were pre-paid and perfect. We loved every single second of the trip and would absolutely recommend our specialist for anyone seeking a wonderful visit to Greece!

Our trip to Greece was everything we had hoped for and more. Each day was filled with experiencing the culture, the history, and the amazing atmosphere of Athens and the islands of Mykonos and Santorini. It was all made possible by our amazing "travel fairy," Zicasso's travel designer! At every turn, we were taken care of, which made our trip the best it could be. We couldn't have done it without her. She and her team were there for us no matter what, big questions/issues and small.

For over a year, I planned this Greek getaway. This was going to happen, Kimbal and I on a Greek adventure for 14 days. On his first international flight, I just wanted him to be comfortable.  I am interested in learning about ancient artifacts and civilizations. I will take you on our journey…

San Diego to Munich and Munich to Athens. We arrived in Athens! Our driver pulled up in his Mercedes wearing a white shirt and black suit. Wow, this felt like royal treatment. He took us along the beautiful shores of the coastline that runs all the way from Athens down to Cape Sounion. He showed us a lagoon which people swear is healing. Next time, we will have to take a dip. We saw the Temple of Poseidon, a fifth-century archaeological site overlooking the Saronic Gulf and its islands – where the horizon meets the Aegean Sea, and where stories and legends unveil about the ship of King Menelaus, who stopped briefly at Sounio on his way back from Troy; or about the unfortunate King Aegeus, who drowned himself at that spot and the Aegean Sea got named after him; or about the people who built a temple using local marble to honor the god of the sea and safeguard the profits from the neighboring Lavrio mines.  

The next day, we would meet our first archeologist guide. She was about the same age as our daughter, Alexandria. We enjoyed her infectious enthusiasm for sharing some of the most important contributions of Ancient Greece to world culture: the amazing monument of the Acropolis and the timeless notion of democracy. We visited the Acropolis, the Doric gateway to the Acropolis, dating to 420 BC, and the spectacular Parthenon, the temple dedicated to Athena, goddess of wisdom and protector of Athens, that has become the most famous architectural embodiment of classical Greece. She talked about the Parthenon sculptures taken in the 1800s by Lord Elgin. Today, they reside in the British Museum in London. Greece wants them back and I am optimistic they will be returned one day. We saw Propylaia, the Temple of Athena Nike, and the Temple of Erechtheion. We learned about the historical personalities and facts that led to the birth of democracy in Athens, its key values and principles, the purposes it served, as well as why it was considered a radical political system at the time. During our tour, we also had the chance to learn about the similarities and differences between ancient and contemporary democracy.  

Kimbal and I wandered around the neighborhood of Plaka. This is a very populated area; there were so many active small businesses.  We saw no unoccupied storefronts. The nightlife was bustling. 

We would be meeting with the car rental agent at our hotel; Kimbal gets to drive in Greece, in Athens, where 3.1 million people live. Yikes. Oh geez, this was going to be interesting. We would be going to Crete and this would allow us to move around at our own pace. We stopped at Mer des Oliviers de Delphes to indulge at an olive oil producer and relax with the dazzling view of the ancient olive grove, Chrisso village, and the Gulf of Corinth, which unfolded beneath our eyes. We got a traditional lunch experience. The host introduced us to the history of their family, who, for five generations, has produced olive oil, while we tasted the fruits of their labors: the extra-virgin olive oil, the olives, and the tapenade derived from the local olive tree variety called "Amfissis".  

Next, we headed toward the Delphi Archaeological Museum. We were warned the archaeological site involves quite a steep uphill climb. Lesson learned; your eyes and legs and hips don’t always agree.  

Our next guide oozed with excitement about what she was to share with us – the Pythia, the mythical oracle of Ancient Greece that was consulted in all major decisions regarding the future of the Empire. With the dramatic landscape of Mount Parnassos as our backdrop, we explored the most sacred place in ancient Greek civilization, walking amongst stunning ruins and learning all about the secrets of the old Greek prophecies. Delphi, according to legend, is the center of Earth, with Zeus, father of the gods, sending two eagles to find it. Delphi also acts as a symbol of unity for the Hellenic world and is home to numerous renowned monuments, such as the Temple of Apollo, the Athenian Treasury, and further up, the well-preserved theater, with its beautiful view back down over the complex. Our guide shared insight into Delphi's religious and political significance in ancient Greece. After roaming the ruins, we walked up to the highest point of the archaeological complex for a stunning view of the Corinthian Gulf across olive grove-carpeted slopes. Next, we visited the Delphi Museum, where we looked at the bronze statue of the Charioteer of Delphi, the haunting Sphinx of Naxos, and what might be the very first recorded notation of a melody. At that moment, I thought of Alexandria and Ryan, and how they would love visiting and learning all this history of Greece! I wished all four of them were with us, enjoying this adventure. Another time! 

The next day, we were moving on to Galaxidi. The hotel was an old mansion, converted into a boutique hotel. The owner made the most delicious homemade breakfast, freshly prepared every day! The courtyard was surrounded by pink bougainvillea; absolutely charming. The next day, we drove from Galaxidi to Olympia and enjoyed the views of the Gulf of Corinth coastline. I thought of Heather as we crossed the Rio-Antirrio Bridge, one of the longest fully suspended bridges. Nafpaktos is a beautiful seaside town featuring an old port (where the Battle of Lepanto took place in 1571 CE) and a hilltop castle. The battle's victory launched Greece into the world's spotlight, as the people of Nafpaktos helped push back the Ottoman Empire of Turkey.  We passed through more olive groves than we have ever seen in our lives. After finally arriving in Olympia, we checked into our hotel. This hotel was built on the top of Drouvas Hill in Ancient Olympia, at the foot of which lies the sacred Altis, which encompasses the most eminent and significant buildings and monuments, as well as the ancient stadium of Olympia, where the Olympic Games were held. Visitors can admire a valley of outstanding beauty spreading between two rivers, the Alpheus and the Cladeus.  

Next we would visit Ancient Olympia with our guide. She took us on a trip to explore the ruins of Ancient Olympia, where the Olympics first started in 776 BCE. A fascinating fact: all Olympians competed nude. No women were allowed to watch the Olympics. Once a “copter” mom, disguised as a trainer, snuck into the Olympics to watch her son compete. When he won, they somehow noticed she was a woman and, from that point forward, all trainers also had to be nude. We explored the massive temple of Zeus, the Temple of Hera, in the ruins of which the Olympic Torch is still lit to this day, and the archeological museum of Olympia, containing many amazing artifacts found at the site. The Olympic torch is still lit in the same stadium where the Olympics first started. The Greeks have female dancers and one lead actress for the ceremony.  We also got to see the site's highlight, the ancient stadium and athletic training facilities where athletes competed and trained in the original Olympic Games over 3,000 years ago.  

Next up was a drive from Olympia to Kalamata and West Mani. Sound familiar? Yep, olives, olives, and more olives. We enjoyed a scenic drive from Olympia to Kalamata. We headed southeast through the rural countryside toward the Gulf of Kyparissia coastline. Kimbal drove from Olympia to Kalamata and West Mani. We were excited to see Nestor’s Palace. Our guide showed us the beauty and history of Nestor’s Palace, the best-preserved Mycenaean palace.  As an influential site in Mycenaean times, Homer described the palace in The Odyssey and The Iliad as Nestor's kingdom. I just happen to be reading The Odyssey. Nestor was a wise man from whom everyone requested advice before making serious decisions. Our guide spoke about this impressive site. Its primary structure sits within a larger, late-Helladic era. Then she took us to Niokastro (the New Castle), also known by its Venetian name, Navarino. It received the honorary name of Pylos in 1833 due to lack of evidence about the location of the Ancient Kingdom of Nestor.  We walked through the well-preserved walls of this 16th-century Ottoman castle, later reinforced by the Venetians and French. We admired the blend of architectural styles reflecting its rich history.  

Next, we checked into a boutique hotel located in the center of Kalamata. We were ready for the private Ancient Messene tour with our guide. This tour took us back in time to the fourth century BCE. We got to learn all about the ancient history and culture of the Messenians. The perimeter walls were erected in the third century BCE; the walls contain a massive Arcadian gate and eight surviving towers. Before its excavation, the area was nothing more than a field of green. Archaeologists have only unearthed a third of the site. We saw the gymnasium, theater, the Temple of Zeus, and more. Next up was the Kalamata olive grove tour and meal. We visited an olive grove with perennial olive trees; a beautiful, peaceful landscape, and we learned about the cultivation and harvest of the olive trees. We had the chance to taste fruits directly from the garden. In the heart of the Androussa village, we met family owners of an olive oil mill, where a demonstration of the extraction of the olive oil took place, as well as a tasting workshop with the different varieties and qualities of extra-virgin olive oils. We completed our tour with a food pairing with extra-virgin olive oil and a light meal with Greek traditional mezedes (similar to tapas). Our guide was the wife and owner of the olive grove, and a certified olive oil taster. We learned most of the olive oil that Italy produces is exported, so they buy their olive oil from Greece. I understood that to be a friendly rivalry over which country has the best extra-virgin olive oil. Customers of the town pay them with olive oil for processing their olives. It is more important to them to employ people of the town than to make more money automating the labeling and bottling process. She had two gentlemen handling that part of the process.  Customers would watch as their olives were converted to extra-virgin olive oil.  The facility would stop for five minutes between each customer to show their olives were not getting mixed with the olives of others. The Greeks take pride in their olives.  

Next, we left the beautiful castle of Androussa, driving toward Nafplio, the first capital of Greece.  We were told we could park in front of the hotel to drop off our luggage and then park in the lot by the oceanfront. Our GPS kept telling us we were two minutes from our hotel. We drove around the adorable town of Nafplio at least five times. We drove on sidewalks thinking we were just on a narrow road. Everyone was so kind. Finally, Kimbal parked and we got out and asked someone where the hotel was. Well, it was nestled quietly in a corner of the town. Our hotel was a neoclassical building of the 19th century. It had excellent architecture and unique and thoughtful interior design, with a beautiful and welcoming entrance. It was situated in the heart of the historic town of Nafplio on Syntagma Square, just a few steps from the picturesque port.  We met with our guide and our tour began with a beautiful panoramic view of the city. We discovered the streets and monuments of Nafplio, the first capital of modern Greece and one of the country's most charming cities. We strolled through the colorful lanes and alleyways, and noticed a mix of Venetian, Ottoman, and Greek architecture. We started our tour from Acronafplia, from where we enjoyed the incredible views over the red rooftops and out into the sea. From here, we saw the Bourtzi Fort on a small island in the middle of the harbor and we continued to the old town itself. Then, we walked through the Gate of the Land, which was once part of the city's original walls. We visited the Vouleftikon building, the very first Greek Parliament, and Constitution Square, also known as Syntagma Square, the main square in Nafplio. Other tour highlights included the seafront, and the town hall, a beautiful neoclassical building. Next on our agenda was the tour of the Acropolis of Mycenae. With our guide, we were ready to visit the impressive Mycenae site, a massive monument built before 1100 BCE. If you are a fan of Homer's The Iliad, you may recognize the name. Mycenae's King Agamemnon led the Greek armies to the War of Troy on behalf of his brother Menelaus to bring back his beautiful wife, Helen. We visited the Treasury of Atreus, where you'll find the Tholos Tomb, assumed to belong to King Agamemnon. We stepped through the Lion Gate and visited the ruins of the palace and the castle. Along the perimeter, look up and admire the Cyclopean walls surrounding the triangular-shaped Acropolis. Their size indicates quite a historic feat for ancient times. Our guide had a baggie with dog treats that he gave the regular dog, which sleeps in the monument. Everywhere we went, we would see a dog or a cat. We marveled at the spectacular views from the top of the hill and headed to the Archeological Museum of Mycenae to explore the various artifacts revealing the Mycenae civilization's everyday life. You'll quickly understand why it was called "rich in gold" and learn about the city's olive oil production from the Bronze Age. Next, we headed to Pataia Epidavros Beach to meet our guide and get in our kayak. We would sea kayak above sunken Epidaurus at Gialasi Beach. This felt like we had reserved a private beach just for us. The water was so calm, the tide never changes. We snorkeled above the sunken remains of an ancient city! We paddled over the ruins of Epidaurus, which was built in 1200 BCE. You may know it better as Argolida’s Lost Atlantis. We saw an entire metropolis preserved under the sea. We had a homemade picnic made by the owner’s mom and grilled by his father; stuffed tomato for Kimbal and stuffed bell pepper for me; such a delicious lunch.  We continued snorkeling, held a Greek sea urchin, and saw an Indian sea urchin. We enjoyed swimming in such calm water among the fish.  

Next for us was meeting back with our guide for a tour of Epidaurus. He told us the remarkable ruins at this site are known as the world's starting point of medical healing. With this tour, you will have the chance to discover everything about their history and significance. The site includes several major monuments, making it perfect for a little exploration. We visited iconic buildings like the Temple of Asklepios, the Temple of Artemis, the Tholos, the Ceremonial Hall, the Stadium, the Greek Baths, and the Stoa. We learned about how the site functioned in terms of medicine and why it is compared to a hospital or "holistic therapeutic center." Next, we visited the Ancient Theater of Epidaurus, known for its perfect acoustics. This is the best-preserved theater of its time in ancient Greece. I thought of Uncle Mike; he was quite a Shakespearean actor. I could picture him performing here like he did in the playhouse in Escondido. The Greeks performed many plays here, not only during celebrations and events, but also as an important part of the sanctuary's healing program. As we stood in the center of the Theater, I could only think of our daughter, Alexandria, and how beautiful it would be to hear her sing here. It reminded me of the acoustics in the center of the Integratron in Landers, CA. The only difference, this theater was open-air, while the Integratron was a closed dome. As our guide stood in the center of the Theater, he spoke using his diaphragm and the sound carried throughout. He said they do not need microphones here.

Next, Kimbal was to drive from Nafplio to Athens airport and return our car rental. While driving, we started from that which connects the Gulf of Corinth with the Saronic Gulf and the Aegean, and it is the second-most important place to visit in Greece after the Parthenon. Our one-hour flight heading to Heraklion was the most efficient way of getting to Crete! Our driver took us to our hotel in Archanes Village in Crete, where Greek tradition, combined with modern comfort, comes to life. Crete is the largest island in Greece and having a car rental is the best and most cost-efficient way to explore it. I remember Kimbal said, ”I could imagine Fred Flintstone living in a place like this.” This had the steepest driveway. Of course, we parked our car at the bottom and then had to hike to our room. We enjoyed an authentic Cretan dinner.  

The next day, we were heading to the Minoan mythology tour with Knossos Palace. We met our tour guide, an archeologist, at the central square of Archanes. We followed her for an innovative introduction to the Minoan civilization in the mythical landscape of ancient Knossos. We explored the legendary past of Knossos and its palace, center of the greatest and most famous city of Crete. We got acquainted with fabulous mythical scenery, the landscape around the town, and palace of Knossos, learned about the control of space and time in Eastern cultures, and explored moments of worship of Bronze Age Crete. Knossos was the largest and most ancient city of Minoan Crete. Its king, Minos, son of Zeus and the oriental princess Europe, holds a prominent place in the mythical past of Crete. According to the oldest sources, every nine years, the legendary king ascended the sacred mountain of his territory, where he received the divine laws in order to renew his term. We toured around an important Minoan sanctuary and after that enjoyed a meal in a local tavern, following the ancient Cretan diet. Our guide asked me which was my favorite goddess. I had to think about it, then responded, Athena, courage and law and justice. I thought of my friend Sue; sounds right. After the meal, we headed to the archaeological site for a guided visit. In a Venetian building, the Palazzo d’ Ittar, within a total area of 460 square meters, we had the unique opportunity to get to know a relatively unknown aspect of Ancient Greek culture through the exhibition, "Ancient Greece - the Origins of Technologies,” which includes approximately 80 selected exhibits, from the robot-servant and the "cinema" of Philon to the automatic theater of Heron, and from the Hydraulic Clock of Ktesibios to the Antikythera Mechanism. It was the Antikythera that brought me here, the first computer found in a shipwreck, dating back to 200 BCE. The exhibits were fully functional and accompanied by rich audiovisual material. The explanatory information, the analytical designs, the images, the videos, the animations, and the references of the bibliography provide a complete experience of a visit.  

The next day, we took a speed ferry and arrived in Imerovigli, Santorini. We checked into our hotel, with 27 steps down a steep stairway to our room. We just relaxed in our hot tub, stared at the most beautiful view in the world, and rested. After hiking so much, we thought of our friends Tim and Irene and, of course, Jim and Diana. They are all avid hikers and would have done just fine on this adventure. Kimbal and I were feeling it! There's nothing like a Santorini sunset, as the island's viewpoints are some of the Cyclades' best. 

The next day, we headed to the historical Santorini tour with Akrotiri. We also visited the Museum of Prehistoric Thera in Fira (where amazing murals are kept). It was very interesting to learn about the Aegean Sea's most significant prehistoric settlements. This archaeological site features an ancient city preserved by volcanic ash for thousands of years. We visited one of the two most important museums, offering various prehistoric and perfectly preserved artifacts.  We walked through the city's remarkably preserved ruins and learned why this site played such an essential economic role. Stroll amongst the ancient walls of the houses and hear stories about how its inhabitants lived. For example, each time the volcano erupted, they took their ships out to sea, only to return and rebuild their settlement from scratch! A fascinating fact about this site is that no DNA has been discovered yet. Our guide took us through different artifacts, spanning thousands of years, from both Akrotiri and Ancient Thera, including entirely preserved murals.   When done, our driver dropped us off in Oia. Kimbal and I decided to explore on foot and discover its curious side streets, unique shops, and dreamy terraces. You will have the chance to gaze at the pearly-white buildings stoically perched on the cliff side, as well as its infamous blue domes.  

The time to return home has arrived; three flights in one day – Santorini to Athens, Athens to Montreal, and Montreal to San Diego. I am so happy that I got to share this adventure with Kimbal. He is the hardest-working man on this planet and I was so happy we burned this into our hearts forever! I will never forget walking in Athens and we both see a McDonald’s. Two Big Macs in Greece made my man smile! 

Zicasso’s company is the best travel organizer I have ever dealt with. Everything was perfect!  Thank you to our travel specialist and the support team for always being available!!!