Custom Greece Vacation: Santorini, Crete, Rhodes & Athens

Day 1: Greece Sky High

Discover the sensations of Greece before you even touch the marbled steps of The Acropolis. You sit within the anticipation, like Odysseus, ready for the oncoming journey, filled with excitement. The history of Athens and beauty of the islands have beckoned to you with the whisper of the gods. As the flight ascends you inch closer to the glorious history of the impetus of modern western philosophy; dream about the toga and scrolls, famous men proselytizing knowledge for the youth and one another. You can almost hear the calls of the city waiting for you.

Day 2: Athenian Beginnings

The odyssey begins with your arrival in Athens. Be picked up with a private transfer into the city and as you pass by the rolling hills of the outlands the pleasant aroma of reaching olive trees blankets the open space. The city center continues to bustle today as it did over 2,500 years ago, filled with people strolling along the Plaka, the pedestrian street filled with shops and restaurants. The buildings that line the narrow walkway have been occupied since Odysseus sailed the seas, filled with generations of family and Athenian history alike. Wander along the cobblestones, listen to the men tout their restaurants to passersby, enjoy a good look at the rising Acropolis and surround yourself with the mouthwatering honey soaked baklava that welcomes you to Greece.

What’s Included: accommodation, transfer, breakfast 

Day 3: Presenting Antiquity

Open the doors to your hotel and be greeted by a sea of history, some of which you might have strolled through previously, but today it is yours to experience. Be guided through the heart of Athens’s modern and not so modern history, where the journey of the past created the present. Begin your exploration standing beneath the expansive Parliament building originally built for King Otto I after he moved the capital to Athens in the late 19th century. The opulent façade with a neoclassical entrance and pink hue sits gracefully at the edge of the marbled walkway. The crowd grows larger, silently waiting for the changing of the guard. Every hour the guard shifts from their stoic expression to a masculine display of choreographed movements meant to help circulate the blood and pay homage to the Tomb of the Unknown Soldier chiseled into the marble base that holds up the palace.

Continue your journey into the depths of antiquity with the necessary visit to The Acropolis. Walk along the steps of the Plaka on the far side of the hill’s base, where the pillars and porticos of the temples shift in and out of view. The air is filled with blushing white-ridged pillars when you reach the entrance gate of the Propylaea. Walk through the gate and the plateau opens to you, chock full of legends, occupations, and ceaseless wonder. The Parthenon sits elegantly against the open blue sky, the centerpiece of millennia celebrating the gods. You may never want to blink worried that the moment you close your eyes it will be gone. Blink, wander, and hear about the Golden Age of Athens displayed in the pillars of the Parthenon.

What’s Included: accommodation, transfer, tour, breakfast 

Day 4: The Road to Rhodes

Your journey to Rhodes brings you face to face with the facets of history, from the mysteries of pre-Hellenistic society of the Dorians to the Ottoman Empire and the modern touch that the world often brings. The medieval town boasts the moats, walls, and towers of Europe with the elegant domes of the Moors. The fresh scent of the sea sits on the breeze, a constant reminder to look out into the horizon and notice the ceaseless splendor of the island and beyond. The bustling of fisherman rolls along the harbor, beneath the opulent facades of the New Town, mostly build by Mousseline during the occupation of Rhodes in in World War II.

Step into the Palace of the Grand Master of the Knights of Rhodes and step back into the history of the medieval stupor, within the fortifications that press against the shore. Built by the Knights of Rhodes in the 14th century, the fortress is in impeccable shape, with the main entrance as imposing and picturesque as any mainland European castle. Step into the vivid romantic ideal where the spice of history continues to drift through the halls, emanated from the walls themselves and from the vibrant frescos of Medusa, Thaliat the muse, and Byzantine mosaics that decorate the ground without pretention, complete with awe.   

What’s Included: accommodation, transfer, breakfast 

Day 5: In Step with Odysseus

The day is yours to explore and adventure as you please through the ceaseless, almost phantasmal, beauty of Rhodes. The Acropolis of Lindos sits atop the plateau that overlooks the town below and is set against the backdrop of the stupendous Aegean Sea. The ancient Doric temple was once draped at the peak of the rocky hill; however, now various temples and fortifications are sewn onto the tabletop. The serenity of The Acropolis gives you the sense you can hear the waves washing along the shore in the distance. The stoic columns stand poised in formation resisting the effects of time. Notice the five consecutive pillars standing before a magnificent staircase that lead to the stoa, a covered walkway or portico used by the public. Step in with history, in the footsteps of pilgrims and the shadows of gods while meandering through the open museum of Rhodes.  

What’s Included: accommodation, breakfast 

Day 6: Adventure to the Graces

There is always more to see on Rhodes but today you can venture to the nearby island of Symi, where mythology attributes the birthplace of the Charities. The Symian port looks a painting, with homes standing multi-storied and brightly colored against the craggy roll of the surrounding hills. Known as Gialós, the two and three-story traditional stone houses are painted in mostly indigo, ochre and terracotta, with red tiled roofs and charming balconies. The water verges on the unimaginable glimmer of blue as the houses look like you ventured into a fairytale. Take a moment to visit the island’s most famous landmark, the Monastery of the Archangel Michael Panormitis. Built in the early 18th century, the Monastery overlooks the bay bearing its name, where the rugged mountains and the luscious sea combine. Fresh grilled seafood tempts you with the herbaceous accompaniment of ouzo as the sky continues to wink at you with sincerity. 

What’s Included: accommodation, breakfast 

Day 7: The Lovely Lives of Cretans

Today the Odysseus-like adventure through the islands continues as you say farewell to the wonders of Rhodes and arrive in Heraklion on the island of Crete. The harbor stretches around the edges of the city where you can see the Venetian castle continuously standing guard over the raised city. Arrive at your hotel and let the majesty of the narrow, winding streets guide you along the afternoon. Away from the harbor, in the heart of the city center, remnants of fortified walls continue to angle the streets; however, the modern heart of Heraklion is a vibrant, cosmopolitan wonderland, with smatterings of Venetian walkways. The tiled paths off of the main walkway expand and contract at a whim. Coffee shops offer divine Greek coffee and candied cakes. Restaurants exude flavors and scents that beg to be devoured, whether sitting along the pathway or wrapped around the small park, just out of the main square. The bronze fountain trickles, people sit and watch passersby, and you are beginning to understand the lovely lives of Cretans. 

What’s Included: accommodation, transfer, breakfast 

Day 8: A Different Labyrinth to Discover

With so many labyrinthine streets to explore today you have the option of discovering the realm of the first and most famous labyrinth in mythology at the Minoan Knossos Palace, home to the infamous Minotaur. Step inside the grounds like Theseus, ready to climb inside of the maze and slay the monster. You may not find the remains of the mythologized labyrinth but the palace is as hypnotic and thought provoking as any tangle could be. The expanse of the palace is mystical, with servants’ quarters and storage units standing below the heights of the royals. Stone pots almost five-feet tall decorate entranceways and connote where roofs used to be. Frescos decorate the stone walls, from a bull charging over the mountains, to a griffin situated within the queen’s quarters, poised and elegant as a queen would ever be. Draped over the magnificence of the ruin’s vastness is the imagined lavishness of the Minoan palace. Although you may not find the maze, you have still found wonder.   

What’s Included: accommodation, breakfast 

Day 9: A Divine Taste of Crete

Today is your chance to get to know the majesty of Crete, whether by digging deeper into the hidden gems of Heraklion or wandering through the sensational Venetian towns of Chania and Rethymnon. If you feel like Odysseus and have a thirst for adventure, you could even take part in a traditional Cretan cooking class, where you will learn why all of Southern Greece knows that Crete boasts the best food.  Whether you choose to walk along the picture perfect harbor of Chania or dig into the home cooked meal that you have prepared yourself with the guidance of a proper Cretan, you will be surrounded by the luscious aroma of fresh, creamy cheese, vibrant red peppers, simmering eggplant, and delicious salty olives.

Chania is a quintessential representation of Venice’s influence on Crete, where the colorful buildings shine against the water’s reflection of the sun. Look into the harbor and notice the crystal clear water spotlighting the rocks below. Minnows search for thrown pieces of bread as old men with spectacular mustaches throw lines into the water. Garlic and Greek yogurt combine for the smooth combination of tzatziki. A gentle accordion plays in the distance. The sensation of Chania is not just on the mesmerizing harbor but behind the facades, where the pathways wind into the hillside, letting you get lost without ever needing to know where you are going. Restaurants place tables and chairs wherever they might fit, as people swarm around corners or sit and watch the crowds pass by. The essence of the city is a pleasant relaxed, with no reason to rush but every reason to enjoy. Vines crawl down the buildings. People sip on raki, an unsweetened aperitif made from grapes. The day passes with ease, giving you a taste of the spellbinding divine.

What’s Included: accommodation, breakfast 

Day 10: Somewhere Across the Sea

Somewhere across the Aegean Sea is the renowned island of Santorini. The Venetian castle stands proud against the backdrop of the city on the hillside while you board the hydrofoil and pull away from the harbor. Out the window is where the adventure continues. The city starts to fade; the water sparkles in various desirable shades of blue. If you could wrap the collection of colors up and take them with you it would be worth a try. The endless water begins to be littered with land. A mountainous crescent comes into view, the cliffs undulating from craggy terrain to vibrant white buildings. The classic architecture and postcard style homes of the Cyclades shines down on you with blue roofs, white walls, and a sense of comfort letting you know that you’ve arrived. 

What’s Included: accommodation, transfer, breakfast 

Day 11: The Attentive Nature of Island Life

Santorini can be called a charming island, from its delectable foods to its classically known architecture. Each town sits along the cliff giving optimal views of the sailboats, fishing boats, and pristine water below. The volcanic rock stands proud at the center of the caldera reminding everyone what power brought the allure of the island to life. Stroll along the marble streets of the capital of Fira, where the cable car can take you from the peak of the cliff to the harbor at the base below. You can travel by the well-known trail of donkey steps, riding along the rocky path on the back of the tamed animal. Each restaurant and café claims a view of the majesty of the island, brushed along the streets of the village or opening up to the vastness of what is beyond the cliffs, where the water sways, the boats glide, and the volcano quietly smolders.

The day is yours to adventure or luxuriate in the sensations of Santorini. Everyone says that the sunsets are not to be missed and what better way to see one than within the open expanse of the sea on a sunset cruise. Board the lavish catamaran with the water gently swelling below. The harbor is filled with various types of ships, from tiny fishing trawlers to affluent yachts. Journey around the crescent island, beneath the towering lighthouse, beside the oxidized cliffs of the Red Beach, and to the warm water of the hot springs. Jump into the royal blue water that surrounds the volcanic rock, where the pitch-black color of the earth is actually cooled lava from the most recent eruption in the 1950s. Enjoy the swim. Luxuriate in the ride. When the sun begins to set you can look out over the horizon and see the entire sky overtaken by the golden orange of the day.

What’s Included: accommodation, breakfast 

Day 12:  An Adventurer’s Respite

Your final day in Santorini will be spent however you desire, whether journeying to Kamari beach for a day of relaxation or discovering the secret riches of the hidden city of Akrotiri. The day could also bring you to the polished steps of Oia, pronounced “eeaah” and one of the four major towns on the island. The paths are paved with marble and extend to the edge of the island. The pristine white of the walkway reaches the colorful yellows and reds of certain homes that climb up and down the cliff; you can even see the actual postcard photo standing behind the blue domed roof of the church sunken beneath the main walkway. Oia is a classic gem where the tradition of the homes and the windmills that stand proud against the island’s edges remain in tact within the flickering jewelry and beckoning pastries of boutique shops. Who knew an adventure could be so simplistic?

What’s Included: accommodation, breakfast 

Day 13: When Odysseys End

Today you will depart Santorini leaving the world of the whitewashed buildings behind. Within the odyssey of your grand Greece getaway you have traveled through unspoiled waters, seen the megaliths of the cradle of western history, and explored the variety of cultures within each island. You have touched legends and stood atop myths, bringing antiquity to life where escapades abound. Every odyssey must come to an end but the majesty of Greece will always be ready to bring you another adventure.

What’s Included: transfer