Mainland & Island Hopping Greece Adventure Tour

A 14 day trip to Greece 
5 out of 5 stars
4 reviews

From the cradle of Western civilization to island hopping across the Aegean, welcome to two weeks of chic cafes, charming villages, lively heritage, and magnificent old ruins. Mix the classical past with the relaxed coastal present, then travel into time-warped settings, where you live out mythical tales. Handcrafted to incorporate a complete variety of Greek highlights, this is the very best of the mainland and island Greece in two weeks.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Athens, Acropolis, Erechtheion, Odeon of Herodes Atticus, Temple of Olympian Zeus, Beule Gate, Acropolis Museum, Parthenon, Theater of Dionysus, Plaka, Anafiotika, Monastiraki, Ancient Agora, Temple of Athena Nike, National Archeological Museum, Athinas Street, Peloponnese, Corinth, Roman Odeum, Temple of Apollo, Mycenae, Mycenae Archaeology Museum, Epidaurus, Epidaurus Theater, Nafplio, Palamidi Fortress, Psaromachalas, Kalambaka, Meteora, Santorini, Fira, Oia, Imerovigli, Firostefani, Fira, Red Beach, Kamari, Perissa, Pyrgos, Thirassia, Akrotiri, Koufonisia, Chorta, Mykonos, Hora (Mykonos Town), Panagia Paraportiani, Little Venice, Delos

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Athens – Keeping it Local in Plaka

Local tavernas entice you with aromas and clinking plates while artisanal shops engage through splashes of color and antiques. Decadent buildings juxtapose with 3,000-year-old relics showing their age. You will be in Plaka, a bustling local neighborhood beneath the glowing Acropolis. Time has moved slowly here, and it may seem that you are still in the 17th or 18th century, especially when you get lost in a whitewashed maze. In some ways, Plaka looks as you might imagine a blue and white Greek island village, however, it has a gritty local edge that most visitors find to be utterly charming. Your guide will meet you at the airport for your short transfer to your boutique hotel in Plaka. After a brief orientation, tour, you will have a free evening to make up your own impressions.

What’s Included: airport transfer, accommodation

Day 2: Athens – The Ancient Acropolis and More

Ruins dot the path skywards, as the remains of temples and markets spread across the hill. You will walk slowly, rising towards the Corinthian columns of the Acropolis, where the Parthenon is just one of the legendary sights. From this enormous hilltop citadel, it feels as if you have reached the center of the old world, with such detail and beauty inscribed in the remains. Stories emanate from every wall as sculptures watch you through impassive eyes. Polished marble remains occupy the Acropolis Museum while tales of Apollo and Athena Nike find you at every turn. There is nowhere in the world like the Acropolis hill and a full day is dedicated to this and the Ancient Agora, giving you a good sense of Western civilization’s cradle.

What’s Included: accommodation, tour, breakfast

Day 3: Athens – Lesser Known Athens Highlights and Heritage

On your third day in Athens, and will move beyond the world-famous central sites, piecing together other histories that shaped the world. Walk into a part of Plaka that is completely hidden and not signposted, enjoying a medieval village experience in the city. Wander across the marble of the first modern Olympic stadium, Panathenaic still feeling like 1896. See a part of Athens that still seems to be an old-world fishing village, and then rise up Lycabettus Hill for a fabulous sunset over the Attica Peninsula. You will be back in Plaka as it starts getting lively just after dusk, with iron lanterns illuminating squares and colorful cafes beckoning you onto their terraces.

What’s Included: accommodation, tour, breakfast

Day 4: Corinth to Mycenae to Nafplio – Legendary History On Route to the Coast

The region of Peloponnese is where legends were made. Cross the water, and you will be immediately in Corinth, a destination that really suggests its age, the crumbling ruins overtaken by moss and green. Here you can walk across sunbaked remains and get a feel for the ancient vernacular. Nearby Mycenae was the epicenter of Mycenaean civilization some 3,500 years ago, the fortified citadel suggesting the dawn of Western history – when walking around you can imagine why it was so revered by the poet Homer. Continue to Nafplio, your overnight base, where the streets have a Venetian flair while hiding an ancient Greek legacy. You will see its sights properly tomorrow – for now, just find a little restaurant in the old town or on the coast, and watch rural Greece come to life.

What’s Included: accommodation, tour, breakfast

Day 5: Nafplio – Exploring Psaromachalas Fishing Village and Epidaurus Theater

Peloponnese is where the Greeks go on vacation, and while the main attraction is the relaxed atmosphere, one day of sights can cover 4,000 years of history. In Nafplio you take an exclusive look into the ongoing excavations of a Mycenaean archaeological site, beneath a fort citadel that had its heyday 2,500 years ago. Wander up the steps to a Venetian fortress, and then explore other beautiful architecture this republic left behind. Spend the afternoon in the fishing village of Psaromachalas, which can feel like it comes from anywhere from the eighth to 18th centuries. Then end your day in the grandest Greek theater of them all, Epidaurus. It is magnificent to behold, and that is before you sit down and watch a theatrical performance unfold. Constructed more than two millennia ago, the theater is a hub for modern drama, creating a link between classical and modern eras.

What’s Included: accommodation, tour, breakfast

Day 6: Nafplio to Meteora – More Venetian Charm and Mountaintop Monasteries

Take a final stroll around Nafplio this morning before leaving Peloponnese for a dramatic mountain scene. Dozens of wind-shaped mountain pinnacles fill a valley, shaped like tree vines stretching skywards. Monasteries are perched on their tiny peaks, sanctified spaces that feel like islands in the sky. It is a scene so dramatic that it has been featured in much popular fiction – Game of Thrones, Tomb Raider, Indiana Jones – yet the simple sanctified monasteries come with a serenity that’s often unexpected. It is both quiet and beautiful up here, perfect for taking a break from the world. Six monasteries can be reached by road, and the guide takes you to at least two of these. But save your energy for one that’s only accessible on foot, a thin, spindly monastery cone with views to stay with you for eternity.

What’s Included: accommodation, tour, breakfast

Day 7: Meteora to Athens to Oia (Santorini) – A World-Famous Sunset and Setting

From Meteora, it is a four-hour drive back to Athens and a late-morning flight to Santorini, the most picture-perfect of the Greek islands. You will be staying in Oia, a blue and white village that has become one of the world’s most famous sunset spots. Your hotel has an infinity pool for watching the sun’s show without any crowds. And once the sunset seekers have left, Oia proves to be a traditional village with all the Santorini favorites. Think small tavernas serving seafood and local wine, blue church domes and bells that echo softly, steep mazy streets where getting lost is part of the experience, and Cycladic houses with window shutters painted the same blue as the Aegean.

What’s Included: accommodation, tour, breakfast

Day 8: Oia – Vineyards and Villages

With your private guide, you will spend today on the Santorini mainland, uncovering treasures found beyond the coast. In the cooler morning hours, you can take a short hike towards Fira, along the cliffs that look out towards a volcano. In Akrotiri, you will find what remains of a thriving Minoan city, one that is slowly being excavated from volcanic ash. On a rugged mountain slope, you walk through the vines and go tasting at a winery, following the wine with a sumptuous organic lunch. There will be plenty of time to visit two more Santorini villages later in the afternoon, each with their own little highlights. Then you will be back in Oia by evening, witnessing how the whitewashed town changes color with the setting sun.

What’s Included: accommodation, tour, breakfast

Day 9: Oia – Catamaran Cruising and Coastal Highlights

Wake up late and take a dip in the pool, and take your time over breakfast. Inhale the salty breeze and slowly get yourself ready for another day on the Greek islands. This island hopping section of the tour is intended to be laid-back and languid, so you will not worry about setting your alarm. After a relaxed morning, you can spend the afternoon and evening cruising, a private catamaran taking you along the Santorini coastline. Stop at volcanic hot springs and dive into the healing water, visit a cave and uninhabited island or go swimming in a remote place of Aegean turquoise. Drift off on the deck and watch the sunset as you cruise back towards the coast and a final evening in Oia.

What’s Included: accommodation, tour, breakfast

Days 10 – 11: Koufonisia – Off the Beaten Track Beach Indulgence

Santorini and Mykonos are the popular favorites as Greek islands with a plush feel and real sense of indulgence. While traditional, they are never that quiet, especially during the summer. Koufonisia is very much like a Greek island used to be, some 60 years ago. There are barely 500 inhabitants and just a handful of hotels. The coastline is remote and rugged, dotted with small beaches that are devoid of sun-loungers. This island provides a detox from everything, as there is not much to do bar beach hopping and laying back in the sun, but this one highlight is why Koufonisia is such a wonderful island to visit.

Travel here by boat and settle into two days of coastal indulgence. You will be staying in Chora, the fishing village and port, a simple Cycladic maze of streets where you will struggle to find souvenir shops or international restaurants. It is authentic Greek life here, which is relatively simple but all the more charming for it. Expect great local seafood, lazy hours on the terraces, and walking to beaches where there are not any people. In short, expect a Greek island that has yet to be uncovered by the rest of the world.

What’s Included: accommodation, tour, breakfast

Day 12: Hora (Mykonos) – Chic Mazy Wonder of the Cycladic Island

The vibe changes drastically when you travel to Mykonos, the most popularized of all the Greek islands. It will be a lively place to finish with chic cafes are tucked into the whitewashed villages, and colorful balconies gaze over the water. You will be staying on the quieter end of Hora, away from the bustle of Matoyianni Street. Here you can still find beautiful local alleys and the tradition that made Mykonos famous in the first place. Take a walk to the Kato Milli Windmills and relax in Little Venice, two destinations that are easy to visit without a guide.

What’s Included: accommodation, tour, breakfast

Day 13: Hora – Discovering the Wonder and Mystique of Delos

You will need a guide for Delos, as this nearby island was the mythical birthplace of Apollo and flourished as the major Greek trading center for a couple of centuries. The island is dotted with lion statues, local houses, Doric temples, vast remains still under excavation, and memoirs to various Greek gods. The area is now the most important archaeological site in Greece, work still ongoing to bring up an island that really shaped world history. There are sculpted guardians, great slabs of marble, and towns that tumble down the hillsides as if waiting to be populated once more. Visiting Delos is the highlight of staying on Mykonos and provides a big change from the island’s popularity. But the two experiences go hand in hand, a day of mystique before an evening of chic.

What’s Included: accommodation, tour, breakfast

Day 14: Hora – Departure

After two weeks in Greece, you will depart from Mykonos Airport with a quick domestic flight back to Athens then your international departure.

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.