Romance & Ruins: Greece 8-Day Itinerary

A 8 day trip to Greece 
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Inspiring sunsets, sandy beaches, and ancient love stories will combine for the ultimate romantic tour of Greece with all of the island splendor and legendary luxuries you could wish for. Whether embracing the passion of a spirited getaway or in the wild throes of a honeymoon, your romantic Greece tour will celebrate love and adventure, enchantment and charm in Athens, Hydra, Chios, and Lesbos. The islands of Greece have captured the hearts of travelers for thousands of years inspiring poets and playwrights, as well acting as the mythological homes of heroes and gods. Embrace the notion of romance and intimate with opulent accommodations during your Greek getaway.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Athens, Acropolis, Hydra, Chios, Mestá, Nea Moni Monastery, Pyrgi, Olympi, Lesbos, Molyvos, Skala Eresou, Ayvalik

Departure Dates 

Dates are flexible and customizable for private departures.


Detailed Itinerary 

Day 1: Athens – A Romantic Introduction to Greece’s Capital

Your private transfer will meet you at Athens Airport upon your arrival and lead you to your accommodations near the heart of the city. As you drive, you will see how the modern city of Athens remains the symbol of Western Civilization and is still wrapped around the summit of the Acropolis. Ancient Greek temples and Roman theaters decorate the slopes and crown the hilltop with architecture that dates back more than 3,000 years. The gilded mosaics of Byzantine frescoes add an extra layer of luster to the city within the beautiful churches that are scattered between neoclassical structures, antique shops, and contemporary homes.

Settle into your hotel, and then stave off any jet lag as you venture to the top of the famous hill with your guide to see the incredible Acropolis with your own eyes. The Olive Tree of the Pandroseion rises out of the ground between the Erectheion and the Old Temple of Athena Polias. The structure was named after the daughter of the first king of Athens and celebrated the myth of Athena having presented the sacred tree to the city after her victory of Poseidon during their competition for the city. The quiet allure of the tree against the backdrop of the elegant Doric columns and lavish Caryatids of the Erechtheion highlight the beauty of Athens, the importance of Greece, and the wonder of preserved legend.

After visiting the temples, continue to the prominent rocky outcropping along the Acropolis known as the Areopagus. The bare white marble reflects the shifting color of the sky at dusk making and offers a sensational view of the sunset for the perfect romantic introduction to Athens. It will likely be an early night, so your guide will ensure that you have recommendations for restaurants before leaving the two of you to enjoy your first night in Greece.

What’s Included: airport transfer, accommodation

Day 2: Athens – Enjoy a Full Day on the Gorgeous Island of Hydra

In the morning, the romance of Athens will continue with your private escort to the port of Piraeus, the largest seaport in Greece, where you will board the ferry bound for the island of Hydra. The tranquil and surprising beauty of the island emanates from the unspoiled scenery emanating from the esplanade along Hydra Town. Cobblestone streets wrap around the slopes of the surrounding hills resembling a natural amphitheater enclosing traditional stone mansions and classic Greek taverns. Instead of motor vehicles, the island continues to utilize donkeys and water taxis to traverse the slopes or travel around the shoreline. Boats wade in the marina with classic fishing vessels shining with bright colors.

The bastions of a medieval castle run along the western edges of town and bring charm to the streets, the architecture, and the squares. Boutique shops reflect the artistry of the locals displaying magnificent jewelry, stunning pottery, and unique embroidery. The scent of almond cake, a local specialty known as amygdalotá, lingers in the air beneath the sea breeze. The peaceful complex of monasteries along the harbor includes Kimisis Tis Theotokou Cathedral, which was built in the seventeenth century with a marble bell tower. The interior hosts an Ecclesiastical Museum showcasing an assortment of religious icons and vestments, as well as images of holy gospels. Hydra is an island on which wandering the streets is as memorable as any historical landmark, especially if preferring the view from the 19th-century Monastery of Agia Efpraxia, located 1,640 feet above sea level overlooking Hyrda Town and the Aegean Sea. The afternoon and evening are yours to enjoy, with free time to explore before a wonderful dinner and return to your accommodations.

What’s Included: accommodation, tour, breakfast

Day 3: Chios – Fly to Chios and Indulge in the Beauty of Mestá at your Leisure

In the morning, the aroma of freshly brewed Greek coffee fills the dining room of your hotel. Your private transfer will greet you in the lobby and escort you to the airport for your short flight to the island of Chios, where serene landscape, fascinating mythology, and a welcoming ambiance await your arrival. Chios is located 192 miles east of Athens and boasts a unique, spirited atmosphere deriving from the enchanting village and ancestral mansions of former shipping magnates. The landscape contains elegant crags in the north and citrus groves around the center of the island. The famous mastic tree grows only on the south of the island, whose bark produces an elegant and easy herbaceous flavor.

Arrive in the town of Mestá for your first introduction to the island where the romantic character rises from the castle-like village that dates back to the Byzantine era. The walls look like a fortress stringing alongside the cobbled streets beneath the layered houses. Castle towers and church doorways weave between the tightly-knitted houses that connect by the rooftops allowing visitors and locals to walk the whole of the town without ever touching the streets. However, the winding lanes offer a loving, fairytale ambiance leading to the central square where you can enjoy the only open area of the castle complex amid the semi-sweet aroma of mastic.

What’s Included: airport transfer, accommodation, breakfast

Day 4: Chios – Discover the Secluded Caves and Remarkable History of Chios

The Aegean Sea shimmers with turquoise, azure, and cobalt hues brushing against the white pebbles of Yossonas beach along the Bay of Nágos. The sea breeze carries through the streets accompanied by the anise aroma emanating from the scattered ouzerie across the island. Venture out into the passionate wonders of Chios at your own pace to view the Cave of Sykia Olymbi along the southern coast of the island. The natural elements have shaped the rocks inside the cave to resemble fascinating formations like cactus, jellyfish, and a pipe organ, as well as at smooth icicle-like formations dangling from the roof.

Before visiting the villages of the northern island, you can spend time at a mastic farm to learn more about the low bush with outstretched branches particular to the island. The bent trunk provides a distinct ominous character to the bush related to the pistachio tree. Farmers harvest the resin on the bark by making small incisions causing the tree to drip a gentle, fragrant tear exclusive to Chios. Residents on the island have harvested the resin since the first century AD with many locals believing the traditions have therapeutic properties. The herbaceous aroma gives way to a sweet flavor similar to a subtle combination of cinnamon and juniper.

What’s Included: accommodation, tour, breakfast

Day 5: Lesbos – Venture to the Distant and Tranquil Island of Lesbos

Your private transfer will greet you at your hotel after breakfast and escort you to the airport for your short flight to the renowned, yet often overlooked, island of Lesbos. The rich culture, splendid beaches, fantastic cuisine, and captivating history offer samplings of the best of Greece. Whether following the footsteps of the Greek poet Sappho the Nobel Prize poet Elytis, or the painter Theophilos, Lesbos welcomes you with a tapestry of the desert-like plains, the forested mountains, dense olive groves, and the peaceful sandy beaches.

Your romance continues as you explore the capital, Mytilini Town. The settlement is one of the oldest in all of Greece dating back to the eleventh century BC. The neighborhoods overtake the seven hills with traditional houses blending the history of the town with Byzantine temples, ancient monuments, and neoclassical mansions. Pleasant cafes fill the air with the aroma of grilling octopus and clams cooked in lemon. The medieval castle of Mytilene spans 60 acres and was built over the foundations of the first castle on the island dating back to the sixth century AD. The magnificent structure resembles the storybooks sparking a deeper romantic ambiance on the island between the stone tower decorated the Gattilusi coats of arms and the dramatic Ottoman gate. The archways along the edge of the hill provide an exotic view of the Aegean Sea, and it is all yours to take in together.

What’s Included: transfer, accommodation, breakfast

Day 6: Lesbos – Indulge in Romance of Lesbos with an Exploratory Tour

After breakfast, you can venture to the Molyvos Castle standing atop a hill overlooking the pine trees. The epic fortress dominates the region physically and historically as one of the best-preserved castles in the Eastern Mediterranean. The castle was built in the 13th century but has undergone renovations by the Genoese and the Turks over the centuries. Strong walls, coasts of arms, and other distinctive elements of the building process provide a specific perspective of the castle, its design, and its differences such as the forceful wood door with metallic tables.

The fascinating Petrified Forest has turned the former lively trees into stone fossilizing the leaves and wood by replacing the organic elements with minerals like quartz while retaining the same shape. The rich volcanic soil of the island has encouraged the petrification of the forest as well as its preservation as early as 20 million years ago. The collection of four archeological sites leads you to Plaka Park, home to the largest petrified tree in the world. The protected area encompasses over 15 acres of cinnamon, oak, pine, and cypress trees offering more information on the history of the island’s ecosystem, the greater biology of the Mediterranean, and the laurel tree’s 45-foot diameter trunk.

What’s Included: accommodation, tour, breakfast

Day 7: Lesbos – Experience the Splendor of Lesbos at your Preferred Pace

The day is yours to indulge in the splendors of Lesbos. After breakfast, you can take to the golden sands of Petra Beach and bask in the sunlight washing over the turquoise water or hide in the shade of a colorful umbrella cast over a row of lounge chairs. Dip into the refreshing heat of the ancient hot springs of Eftalou whose waters reach temperatures of 115 degrees Fahrenheit. Birdwatchers set out into the landscape to spot of the 325 species nesting on the island, and the romantic ambiance of Agiassos village derives from the verdant slopes of Mount Olymbos and endless views of the sea. For a unique adventure to your romantic getaway in Greece, you take a boat ride into Turkey at Ayvalik for a treat on the Aegean.

Wandering the waterfront and through the winding cobbled lanes reveals stone houses alight with colorful shutters and elaborate mosques converted from Greek Orthodox curses. Colorful fishing boats wade in the marina in view of graceful old mansions while the traditional bazaar of the city stems from the Persian marketing customs dating back as early as 3,000 BC. Local men sip black tea from clear glasses as they watch passersby wander through the marketplace. Fruits, watches, carpets, and lamps become staples of the labyrinthine shops as you explore the depths of the bazaar.

What’s Included: accommodation, breakfast

Day 8: Lesbos – Return to Athens and Depart for Home

The architecture of the Ipsilou monastery looks like a lavish castle in the mountainous village of Andissa. The foundations of the church date back to the 9th century with the gold-plated gospels and crossed adorned with rubies and pearls emphasizing the historical importance of the religious site, the grandeur of the Byzantine era, and the importance of heritage on the island. After breakfast and one last outing, your private transfer will greet you at your hotel and escort you to Mytilene International Airport for your flight to Athens, where you continue home.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.