Greece Itinerary

14 Days in Greece ~ Athens & the Greek isles

October 2 – 16, 2015  (Completed)
May 19 – June 1, 2017 (Full)
October, 2019
(Booking open as of March 1, 2018)

Please contact Karen to be added to list

cycladic island

Daily Itinerary Description

Day 1:  “Καλωσόρισμα!”  Welcome to Greece, the cradle of Western civilization.  The tour begins at Athens International Airport, where a driver will meet you to take you directly to the beautiful Central Hotel Athens located in the heart of Plaka, the historic Old Town of Athens.  Settle in and relax in your comfortable and elegant room with beautiful views.  The afternoon is yours to rest and catch up on jet lag. Those arriving early in the day or want to hit the ground running may wish to visit the Ancient Agora, the National Archaeological Museum, or simply wander the streets of historic Plaka. Prior to dinner, indulge in a Greek cocktail (Ouzo for the brave!) while savoring breathtaking up-close views of the Acropolis and the city of Athens.  Delight in an authentic dinner that will tickle your taste buds in a place tucked away from the tourists. Overnight Athens (D)

Day 2:  Island of Santorini … the lost city of Atlantis?  Take a mid-morning 1.5-hour direct flight to the island of Santorini, a stunning island with its white villages clinging to volcanic cliffs above black sand beaches.  Colonized by the Minoans in 3000 BC, this volcanic island erupted around 1450 BC, forming Santorini’s crescent shape.  Inextricably bound to the legend of the lost civilization of Atlantis, this prize for several would-be conquerors refuses to succumb even to nature’s most ferocious powers.  With its unique blend of sulphur, salt and water, 120 miles southwest of mainland Greece, Santorini is the world’s largest inhabited caldera (a cauldron-like feature from the collapse of land following a volcanic eruption.)  Settle into your exquisite bed & breakfast, Le Petit Greek Hotel, in the town of Firá, the island’s capital, overlooking the Aegean Sea.  Your host Chef Thomas will show you to your luscious bedroom with striking views.  A native Greek, Thomas splits his time between Los Angeles and Santorini.  It is from dining at his Greek restaurant in Larchmont Village near Paramount Studios that we came to know of Thomas 20 years ago.  Enjoy a free afternoon to relax at your leisure.  Dine in the seaside village of Kamari. Overnight Santorini (B) 

Day 3:   Island capital of Firá, Excavations of Akrotíri.   Delight in a 2-hour privately guided walking tour of Firá with native guide Ioanna, including a tour of the Museum of Prehistoric Thira, a modern museum filled with impressive Bronze Age objects, fine frescoes, and other treasures from the buried town of Akrotíri.  Cycladic island culture, as well as ancient Minoan, is represented in the museum.  Following lunch, explore the mesmerizing ruins of a lost Minoan city at the Archaeological Site of Akrotíri during a 1.5-hour privately guided tour with Kostas. Similar to Pompeii, the settlement was preserved for posterity under the mantle of pumice and ash from the volcanic eruption, which destroyed the island almost 3,500 years ago, leaving the dramatic caldera that we see today.  The excavations at Akrotíri began in 1967 under the direction of Professor Spyridon Marinatos in hopes of verifying his theory that the eruption of the Thira volcano was responsible for the collapse of the Minoan civilization.  The excavations, which are still in progress today, have uncovered one of the most important prehistoric settlements of the Aegean. Interestingly, this “lost civilization” has been considered as a possible inspiration for Plato’s story of Atlantis.  Dine off-the-beaten-path in the village of Perissa, known for its striking black sand beach.  Overnight Santorini (B) 

Day 4:  Free day in Firá, Agriculture & Traditions of Santorini & Fine-Dining. Savor a free day to explore the town of Firá at your own pace and wander amid the white-washed alleys and houses.  The town is largely pedestrianized with winding cobbled alleys.  The most spectacular street, Agiou Miná, runs south along the edge of the caldera to the 18th-century church of Agios Minás ~ with its distinctive blue dome and white bell tower, it has become the symbol of Santorini.  Near our bed & breakfast, the pretty ochre chapel of Agios Stylianós, clinging to the edge of the cliff, is worth a stop.  Alternately, you may wish to opt for a boat excursion to visit the volcano. Of all the excursions offered by Dakoutro Bros J.V, I’ve been told the best is the 2-hour Volcano Trip; this tour departs from the port at 11:45am. Should you decide to take a boat excursion, be sure to read the useful information. This evening, learn about “Santorini of the Past” during a 1-hour guided visit to a folklore museum in the village of Pyrgos, followed by fine-dining at a restaurant specializing in Santorini and Cycladic cuisine prepared with local ingredients.  Pyrogos is one of the most beautiful and well-preserved villages of Santorini, built around a Venetian medieval castle, situated in one of the highest spots on the island, offering magnificent views.  You will be welcomed with a glass of local wine, followed by a visit to the quaint museum (“cultural village”) to learn of agricultural production in Santorini and traditional way of living on the island.  With more than 300 days of sunshine and its rich volcanic soil, the island yields an abundance of unusual indigenous herbs and vegetables ~ white eggplant, capers and caper leaves, fava (small yellow peas), exquisite baby tomatoes ~ all grown virtually without water.  It doesn’t take much to imagine the intensity of flavor from the local bounty.  Overnight Santorini (B, D)

Day 5:  Picturesque village of Oía.  Enjoy a leisurely outing to roam the island and visit the picturesque village of Oía, built on the steep slope of the northeastern edge of the caldera, considered by many to be the most beautiful village on Greece’s most romantic and dramatic island.  The old windmill and the ruined castle are among the high points to view, as is a simple stroll through the village.  Enjoy free time to wander the village on your own. We will meet in a special seaside taverna tucked down at the bottom of the cliff in a picturesque bay (have an adventure with a donkey ride back up to town!) Tonight, relish a private candlelit dinner on top of our terrace prepared by our host and esteemed Greek chef Thomas. Overnight Santorini (B, L, D)

Day 6:  Traditional Greek island of Sífnos.   Bid farewell to Santorini, and take a 3-hour comfortable ferry to island of Sífnos.  Have an early lunch on your own, or pack a picnic for the ferry. If Santorini is the starlet of Greek islands, Sífnos is the girl next door.  One of the quietest and least discovered islands of the Aegean, Sífnos is where time stops.  A small, hilly island popular with walkers and known for its pottery, poets, and chefs, Sífnos offers charming villages, terraced countryside dotted with ancient towers, Venetian dovecotes, and long sandy beaches.  In ancient times, Sífnos was renowned for its gold mines.  Legend has it that the islanders paid yearly homage to the Delphic sanctuary of Apollo with a solid gold egg.  One year they sent a gilded rock instead, incurring Apollo’s curse.  The gold mines were flooded, the island ruined, and from then on was known as sifnos, meaning empty.  Upon arrival at the Kamáres port, Stavros and Sarah will greet you, and take you to your private one-bedroom house with private veranda offering superb views.  Yours is one of five independent houses built in traditional Cycladic style charmingly nestled among olive terraces and gardens in a centrally located, yet quiet, spot near the village of Apollonia.  After settling in to your new lodging, stroll the town center to shop for basic necessities and food items for your house, if desired. Dine this evening in the heart of Apollonia to experience authentic, gourmet Greek food. Overnight Sífnos (B, D)

Day 7:  Ascension Day at Chrysopigi Monastery.  Take part in the biggest island festival of the year, Ascension Day at the island’s most theologically important and visually stunning monastery, indeed one of the most beautiful Orthodox churches found in the Cycladic islands.  Built in 1650 on a split rock, an islet accessible only by a single-arch bridge, the strikingly pure white monastery and church is set against the clear green waters of the Chrysopigi Bay.  Many pilgrims come to pay homage to Panagia Chrysopgi, the patron saint of Sifnos.

Day 8:  Guided outing with native Stavros, Explore Apollonia and Artemónas.  Enjoy a 4-hour private walking tour with our friends and hosts, Stavros and Sarah Kalogirou.  Stavros was born and raised on the island of Sifnos, and is happy to share its history and tradition with you from an insider’s perspective.  Sarah is from the United Kingdom; she came to the island years ago as a traveler, met Stavros, fell in love, and stayed. They are now raising a family and welcoming guests at their family-run hotels and guesthouses, as well as providing travel services to guests. Begin the outing on foot to visit the nearby church where they were married, and learn about wedding & marriage traditions on the island. Find out how the island came to have over 230 churches, and who maintains them.  Walk up to the neighboring twin village of Artemónas, the hometown of Stavros’ grandmother, with its quaint alleys and impressive Venetian houses sporting distinctive chimneys.  The 17th-century church, Agios Geórgios tou Aféndi, contains several fine icons from this period.  The church of Panagía Kónochi, with its cluster of domes, was built on the site of a temple of Artemis. Conclude the tour with a late lunch in the port town of Kamares, Stavros’ hometown, and a visit to the Kalogirou family church. Enjoy the remainder of the day on your own to explore our surroundings on foot. The picturesque capital town of Apollonia is named after the 7th-century BC Temple of Apollo, which once overlooked the town, but now is the site of the 18th-century church of the Panagía Ouranofóra. Apollonia is a Cycladic labyrinth of white-washed houses, cobbled alleys, flowers, churches with turquoise domes and beautiful bell towers all unfolding on the slopes of three hills in the center of the island.  Terrace dinner in Apollonia this evening. Overnight Sífnos (L, D)

Day 9: Greek Breakfast, Monastery Hike & Village of Kastro. Start the day with a traditional Greek breakfast in Karen’s apartment composed of freshly baked bread, butter, thick yogurt, local honey, Sífnos hard cheese, smoked sausage, olives, hard-boiled eggs, fresh fruit, almond pastries, sesame bars, coffee and herbal tea. Following breakfast, drive to nearby Kastro and hike the 1-mile seaside path to the striking Panagia Poulati Monastery, renowned for its beauty and the landscape surrounding it. Explore the village of Kastro, without a doubt the crown jewel of Sifnos.  Built on a hill on the island’s east coast, Kastro was the location of the ancient city of Sifnos, and was the capital until 1836.  Homes are built in a way that their external walls form the wall of the medieval fortification.  In its two- and three-story homes you will see ancient architectural members from buildings, inscriptions, grave steles, even parts of ancient sculptures.  Wander the striking village at your own pace for a glimpse of the glamour of ancient Sifnos in a place where time has stopped. The walk to the chapel of Epta Martyres (Seven Martyrs) is delightful, and the sea view from the tall cliff is astonishing.  Free afternoon to rest or explore at your leisure. Savor an early dinner at a family-owned taverna on the tiny harbor of Faros, a quaint seaside hamlet. Overnight Sífnos (B)

Day 10:  Seaside village of Vathy, Archaelogical Ancient Site of Agios Andreas, Sifnos Pottery & Eating with Locals. This morning, visit the beachside village of Vathy, considered by many to be the best beach on the island with its fine sand and beautifully enclosed horseshoe-shaped bay, which keeps the crystal clear water calm.  Wild thyme grows bountifully in the hilly landscape surrounding the bay, and we will probably cross paths with a goat or two along the way.  Bring your swimsuit & a towel, just in case you’re tempted to swim or wade in the irresistible water. Delight in lunch at a local taverna with your toes in the sand. Spend the afternoon with Greek-American Zefy, whose name, Zafira, means Safire in Greek. Begin our time with Zefy at the most significant archaeological site on the island, Agios Andreas, one of the best examples of Mycenaean fortifications in the Cyclades.  Positioned high on a hill above a cedar shrub forest, archaeologists have brought to light the impressive walls of a Mycenaean acropolis.  The picturesque church rises above the ruins and offers splendid views eastward to the Aegean Sea.  Meet Zefy’s parents and brother, a Greek family, to discover one of the most important traditions on the island. Originally from Sifnos, Costas, a 4th-generation potter, and his wife Nina, moved to America in the early 60s. They had two daughters, Zefy and her sister, and eventually returned to the island 30 years later with their son, Antonis, to continue the island traditions of stoneware, ceramics, and farming. Tour the family-owned pottery workshop, Sifnos Stoneware, for a personalized demonstration in ceramics. Visit Zefy’s homestead to witness & taste the local food that she and her husband, local Sifnian Franseco, produce on their land. Delight in an convivial evening, as we are welcomed into their home for an authentic meal that we may help prepare, including a taste of the local Sifnian Sunday specialty, chickpea stew, prepared in handcrafted clay flameware by Antonis.  Per tradition, large ceramic pots of chickpea stew prepared by local families are taken to various bakeries on the island every Saturday evening and cooked overnight in the wood-fired ovens.  Each family then collects their pot from the bakery on Sunday morning.  It is said this tradition came about because the bakery ovens are left empty Saturday evenings since fresh bread is not sold on Sundays.   Overnight Sífnos (D)

Day 11:  Heronissos, a fishing village at the edge of the world.  Pack up all belongings in preparation for our late afternoon departure by ferry to Athens. Drive to the northern tip of the island to savor lunch in the rugged fishing village of Heronissos.  Behold the wild, rocky landscape as we drive to the edge of the island to this remote coastal village with its small harbor of fishing boats and a long tradition in ceramics. Heronissos is the place to go for the best seafood on the island.  The restaurant sits on a picturesque jetty overlooking the tiny harbor, and is owned by a family of fishermen, who provide fresh catch of the day.  No need for a menu, simply pick the fish from the cooler.  Return to Apollonia to collect our bags, and take the 2½-hour evening ferry to Athens. Overnight Athens (L)

Day 12:  Culinary Secrets of Downtown Athens.  Relish a half-day tour uncovering and tasting some the city’s best hidden food treasures.  The bustling market streets beneath the shadow of the Acropolis are a lesser-known side of Athens.  Here, locals line up for a proper souvlaki done in the style of Northern Greece, older gentlemen sit down for a bowl of authentic Greek yogurt covered in honey and walnuts, the smell of fresh coffee wafts over neoclassical Kotzia Square, and a Cretan accent booms out of a humble kitchen that turns out the rustic, yet utterly delicious food of that Mediterranean island.  It is clear that in this part of town, life is lived by taste.  On this walk, you will explore the culinary backstreets and secrets of downtown Athens, in search of the soul of this historic, yet always vibrant city.  Visit an old-school dairy bar and a hidden gem specializing in loukoumades (homemade Greek doughnuts with honey & cinnamon).  Sample souvlaki and a kebab made according to a recipe brought to Athens by refugees from Constantinople. Brought to you by an Athens-based food writer and culinary enthusiast, this walk will explore the hidden seafood eateries of the stoa, the arcades that are among downtown Athens’ most unique architectural features.  There will be artisanal cheeses and honey, and even a few sips of homemade spirits, accompanied by an unforgettable taste in the center of the main fishmongers’ market.  As part of the color of this tour, we take a short ride on the metro. It is worth noting that the Metro Museum inside the Syntagma station houses interesting archaeological artifacts of the daily life of Ancient Athens that came to light during the construction of the metro. Free evening. Overnight Athens (B, L)

Day 13:  The Acropolis Museum, UNESCO World Heritage Acropolis Site & City of Athens Walking Tour.  This morning, enjoy a 2-hour privately guided visit to the Acropolis Museum, a beautiful modern structure of glass & steel, housing ancient artifacts from the Acropolis archaeological site. En route to the museum, behold the Monument of Lysicrates, the best-preserved choragic in Athens, and the St. Catherine’s Chapel, a small church with a beautiful sunken garden. Break for a light lunch in the swanky museum restaurant, offering stellar views of the Parthenon in the high city before embarking on a 3-hour privately guided walking tour to discover the most important landmarks and sights in the historical center of Athens. After having seen and learned about the artifacts in the museum, watch it come to life as you ascend the sacred hill to breathtaking views of the city unfolding beneath, and relish intriguing explanations of the glorious monuments that make up the Acropolis world heritage site ~ the Parthenon, the Erectheion, the Propylaia, the Nike Temple, the Agrippa Monument, as well as the outlying monuments such as Odeon of Herodes Atticus and the Observatory. The first stop on the way up is the Theatre of Dionysus, the vast, tiered open-air theatre dating from the 5th-century BC. Come back down to visit the Temple of Zeus and Hadrian’s Arch, followed by Zappeion, the Athens Academy of the Arts set within the National Gardens of Athens. Conclude with the House of the Greek Parliament. Relish a little downtime prior to a special Greek dinner in a private home in Athens. Experience Greek hospitality, and traditional recipes and ingredients, as your host prepares appetizers, salad, a main dish and dessert.  See how locals live and get to know an Athenian family. Overnight Athens (B, L, D)

Day 14:  Classical Greece at Delphi ~ the most famous Oracle of Antiquity, Center of the Universe. Enjoy a beautiful full-day private minivan excursion to the archaeological site of Delphi, spectacularly set against the craggy peak of Mount Parnassus, 115 miles northwest of Athens.  During the scenic journey, behold the countryside drive through the mountains and fertile valleys of olive groves and cotton fields of inland Greece.  Once at Delphi, your guide will share the history of this sacred site considered by ancient Greeks to be the center of the universe.  For more than 1,000 years Delphi was the site of the most important oracle of ancient Greece, believed to be the mouthpiece of Apollo himself.  On the seventh day of every month, a wise old Prythian priestess would go into a trance and utter her cryptic prophecies to the priests, who would redeliver them as enigmatic riddles that could be taken in many ways.  Lines would form days in advance with seekers of all kinds ~ peasants and world leaders alike ~ arriving from far and wide.  Today, Delphi still resonates with mystery.  Your guide will also explain monuments such as the Athenian Treasury, built to commemorate the Athenians’ victory at the Battle of Marathon in 490 BC, the Theatre, Navel of the Earth, Sacred Way, Temple of Apollo, and more.  We will touch on masterpieces of classical Greek art in the Delphi Museum, including the world-renowned bronze Charioteer, the Naxian Sphinx, and the Statue of Antinoos.  Free evening upon return to Athens. Overnight Athens (B) 

Day 15:  Farewell and Ευχαριστώ! (“Efharisto,” meaning “thank you.”)  Following breakfast, your pre-reserved taxi transports you to the Athens airport to catch either your international flight home. Tour concludes on Friday, June 2. Thank you for traveling with me, have a safe return! (B)

For more information, visit Greece trip details