Christos Stergiou's 16-day Greece Itinerary

View of Acropolis, Athens, Greece
Photo: Poike/Getty Images

Christos Stergiou is a member of Travel + Leisure’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. Below is an example of the type of itineraries he creates. To work with Christos, you can contact him directly at

Days 1-3: Athens

Fly into Athens, the capital city of Greece and one of the oldest cities of Europe. Although its history dates back to Neolithic times, it’s Athens’ classical history that has so distinctly influenced modern thought; democracy, philosophy, art, architecture, and literature are just a few things that have marked Western civilization. As you wander the streets of modern Athens, you will encounter visitors from all over the world who have come not only to pay their respects to Athens of the Golden Age, but also to experience the incredible energy of this extraordinary contemporary city. Athens was and continues to be one of the most multi-dimensional cities in the world.


Grand Bretagne

Potential Activities

A guided visit to Delphi: Surrounded by the beautiful forests of Mount Parnassus, Delphi is one of the most famous and significant remains of the ancient Greece. According to Greek mythology, the god Zeus sent two eagles flying from east and west in search of his ‘Grandmother Earth’ (or Gaia in Greek), and the birds met here. The exact location became a spiritual center that was also known as ‘the navel of the earth.’ Today a UNESCO World Heritage Site, Delphi was most famous for being a sanctuary of the Delphic Oracle, which was consulted on important decisions throughout the ancient classical world. Your TrueTrips guide will walk you through this extraordinary archaeological site and bring the captivating myths and legends of ancient Greece to life.

A city highlights tour: Delve into both ancient and modern Greek life as your TrueTrips guide brings the city of Athens to life. Walk up the historic steps of the Acropolis that stands proudly above the city and then drive by the Parliament Building, the Monument of the Unknown Soldier, the Columns of Olympian Zeus, and the Presidential Mansion. Your TrueTrips guide will give you a glimpse into Athens’ history while illustrating how it evolved into the fascinating city it is today. You will also visit the stunning Acropolis Museum. With an exhibition space of over 14,000 sq. meters, the museum is home to some of the world’s most stunning and valuable artifacts of classical history.

Days 4-7: Patmos

Fly to Kos, and transfer to Patmos via ferry. Located in the Dodecanese group of islands of the Aegean, Patmos is considered by many to be the secret gem of the region. Sheltered from the modern developments of mass tourism, Patmos has maintained its traditional island architecture and atmosphere. Its main town is an UNESCO World Heritage Site, while the entire island offers truly beautiful village settlements, scenic beaches, elegant restaurants and traditional tavernas.


Petra Hotel & Suites

Potential Activities

Boating in the Aegean Sea: Famed as the hidden gem of the Aegean, Patmos and its surrounding small islands have been a secret paradise to which the Greek and international elite go to escape. Board a traditional Greek boat for a day-cruise to a series of pristine isles, all with crystal-clear waters and virtually deserted shores. Together with your captain, discover beautiful landscapes and relish in the tranquility of this incredible natural setting. Be sure to bring along your swimming gear and enjoy a refreshing swim in the incredible blue sea! After a perfect day of swimming and exploration, anchor at the small island of Marathi and enjoy a late lunch at the local seafood taverna that is among the very best in Greece.

A tour of Hora, the Cave of the Apocalypse & the Monastery of St. John: Built in 1088 AD by Saint Christodoulos, Patmos’ historic monastery houses an impressive exhibition of ecclesiastical embroideries, pendants, ceremonial artifacts, rare manuscripts, and beautiful icons. Get a glimpse of the capital town of Patmos, called Hora, a UNESCO World Heritage Site and one of the best preserved medieval settlements in the Aegean, before you make your way to the Cave of the Apocalypse where Saint John the Theologian is said to have written his Gospel and the Book of Revelation.

Dining at Pandelis Marathi: Set on the beautiful and tiny island of Marathi, where time has stopped, this is a traditional family run restaurant offering authentic and simple Greek flavors. Fresh fish, cooked specialties, a variety of meze and homemade dessert make for an incomparable lunch right by the sea.

Days 8-11: Santorini

Fly to Santorini. World-renowned for its incredible views, romantic sunsets and unique, volcanic natural environment, Santorini is arguably the most striking of the Greek islands. One of the premier luxury destinations internationally, Santorini’s traditional Cycladic homes and colorful cliffs enchant each and every visitor of this island. Its dramatic red and black sand beaches, narrow white-washed alleys, exquisite traditional and international cuisine, as well as its agricultural and wine-making tradition, all combine to make Santorini a truly spectacular island.


Canaves Oia Suites

Potential Activities

A private wine tour: Discover the secrets of local wine-making and learn why Santorini produces some of the world’s most distinctive wines despite its dry and seemingly infertile terrain. Visit three family estate wineries and enjoy a unique wine- tasting where you will sample several local wines. Under the guidance of the sommelier, you will enjoy a wine presentation paired with Cycladic cheese and local delicacies. Learn about the unique viniculture and the indigenous grape varieties and end your experience with a scenic tour around the island of Santorini.

Cultural immersion and an off-the-beaten-path walking tour: This walking experience won’t take you to all of the island’s famed highlights - it will take you completely off-the-grid to its well-kept secrets and unknown (really raw and local) corners. Walk alongside beautiful mansions, explore quaint rural houses and discover the charm of Santorini’s abandoned neighborhoods. Meet locals still living in the countryside - learn about professions and crafts that no longer exist - visit a traditional winery to taste local volcanic wines, a unique microbrewery for a fresh beer tasting experience, or stop-in for a bite at one of the island’s best family-run tavernas. One thing is for sure, your cultural immersion in to Santorini’s local life will be something you savor for a lifetime. This walking experience was first developed by TrueTrips to be featured in a New York Times article.

Days 12-15: Porto Heli

Transfer to Porto Heli. Located in southern Greece along the coast of the Aegean Sea, Porto Heli is a small settlement that has gained the likes of many travelers in recent years. Filled with traditional homes, narrow streets, and a port filled with yachts and fishing boats, this seaside town seems much like any other in Greece, but its beautiful sandy beaches and world-class luxury resorts have put Porto Heli in a class of its own.



Potential Activities

A tour of Epidaurus Theater, Mycenae & Nafplio: Drive along the beautiful Saronic Gulf to the atmospheric hilltop ruins of ancient Mycenae. Today a UNESCO World Heritage Site, Mycenae was once a major center of Greek civilization and a military stronghold that dominated much of southern Greece. Continue with one of the greatest monuments of Greek Antiquity, the famous Theater of Epidaurus. With a capacity of almost 14,000 spectators, the magnificent theater combines perfect acoustics with elegance and symmetrical proportions. Your journey will then take you towards the eastern Peloponnese to discover Nafplio, one of the most romantic destinations in Greece. The first capital of the newly born Greek state between 1823 and 1834, Nafplio has a combination of medieval and neoclassic characteristics. It is a lively and charming seaside town that will surely enchant you.

Day 16: Athens

Depart from Athens International Airport.

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