Greek Greats

19 Days

Slowly exploring Santorini, Milos, and Athens unveils a captivating journey through Greece’s enchanting landscapes, ancient history, and vibrant culture. Begin your odyssey in Santorini, where whitewashed buildings cascade down cliffs overlooking the Aegean Sea, offering stunning vistas and romantic sunsets. From there, journey to the lesser-known gem of Milos, with its rugged coastline, hidden beaches, and surreal rock formations sculpted by the sea. Finally, immerse yourself in the bustling streets of Athens, where ancient ruins like the Acropolis and Parthenon stand as testaments to the city’s rich heritage. Amidst the vibrant energy of modern-day Athens, discover traditional tavernas, lively markets, and the warm hospitality of the Greek people. This exploration promises a blend of breathtaking beauty, cultural immersion, and historical wonder, leaving you with cherished memories of Greece’s timeless allure.

Itinerary

Start your trip by flying into Santorini Airport.

Pick up your rental car at the airport.

Head to your accommodations to get settled in. There is no rush, as you are on Santorini for the week.

Around the corner is a beautiful little restaurant with fresh local dishes.

To keep today relaxing, you will explore one of the local villages. Depending on where you are located, this could be Immerovigli, Oia, Fira, or Pyrgos. Each of these places have incredible restaurants, cafes, shops, art galleries, and of course, views, to explore.

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts. We also like getting eggs with fresh feta! If you are looking to try many places, an abundance of quality bakeries exist here due to the many the island having so many towns.

Today will consist of exploring local towns then hiking the caldera.

Starting in Fira, you will explore the beautiful town then head on the path North to Imerovigli.

Imerovigli is another beautiful town to explore and just relax in, taking in the surroundings and the caldera. We can always arrange for taxis to pick you up to take you to the next town, as you will see later on, the entire hike from the starting town to ending town takes around 3 hours.

This is a great place to get lunch, because the hike can take a few hours.

After relaxing in Imerovigli, start your hike North to Oia, while hiking the caldera edge. The total hike takes about 3 hours, but that includes the time walking from Fira to Imerovigli.

Explore Oia including the many shops, art galleries, churches, and narrow alleyways.

For dinner, enjoy a delicious seafood restaurant in Ammoudi Bay.

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Megalochori is a great place to explore around to see different wineries, getting a different taste of what Santorini has to offer.

For lunch, head to Megalochori for a delicious meal focused on grilled meat such as souvlaki.

Meet at one of the local ports such as old port, Ammoudi, or Vlychada Beach to catch your catamaran to explore Santorini, that returns during sunset.

Your boat tour will stop at a few places to swim, including in the hot springs by the volcano, where the water can reach 95 °F (35 °C). You will also see Red Beach, White Beach, the Akrotiri Lighthouse, and Thirassia.

While the Catamaran Tour will have provided food and drinks, if you are like us, you aren’t passing up the chance at eating at another local taverna. Head to your accommodations for a bit to relax after the long day, and head out for a late relaxing dinner.

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Today you will be exploring Akrotiri and the Prehistoric Town of Akrotiri. To beat the crowds, head to the archaeological site first.

Just down the road from the archaeological site is Red Beach. Red Beach is worth a visit, but you will have seen this on your boat tour if you determine that the path is too rocky to get to from this side. You can drive up to Akrotiri, then down a path to the southwest to get to it, but the path is very steep. The cars can make it, but only do it if you are confident!

After the archaeological site, you are sure to be hungry, and lucky enough, there is a great restaurant just between the ruins and Red Beach. They grill the meat outside, so you are sure to notice it when walking by.

Go just Northeast of the town of Akrotiri to get to Paralia Gialos.

For a less busy atmosphere, visit Paralia Gialos, which is Northwest of Akrotiri. This beach is pebbly, but the lack of other people creates for a serene experience compared to the busier beaches on Santorini.

A great view of the sunset awaits at the Akrotiri Lighthouse.

For dinner, you will eat in the ruins of a Venetian Castle which has been turned into a beautiful restaurant serving local fish, meat, and vegetables. An unforgettable experience with a beautiful view of Santorini!

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Kamari Beach is a beautiful stony beach on the Eastern side of the island. Soak in the sun on sunbeds, relax at local cafes and bars.

When you want some food to go with your sun, head East of the airport to a beautiful restaurant along the water.

South of the restaurant a few minutes is a beautiful winery. (There is also a brewery West of Kamari, if you prefer trying the local beer.)

For dinner, head in town Kamari to a beautiful restaurant.

If you do not want to end your night after dinner, head to the Kamari Open Air Cinema to catch a movie. Movies are in English with Greek subtitles. Make sure to get there a bit early if you are very interested, as they do not take reservations.

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Soak up some sun at Vlychada Beach on a sunbed, with beautiful cliffs rising on either side.

Have lunch at a beautiful restaurant overlooking the marina, watching as boats and fishing trawlers head out to sea.

Head North to Megalochori to relax at a winery. Just North of town is a winery that has views of the caldera.

Go into Fira to a cafe to get a great view of the Caldera on your last day.

Let us know your favorite restaurant so far, and we will make reservations for that restaurant. As always, we are happy to choose for you as well.

Head to the local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Return your car to the port as you are continuing your travels via Ferry. You will be taking the slower ferry that also carries cars as the faster ferry can get a bit rough like a large jet ski.

As you arrive in the port, you will walk towards the town of Adamantas. Across the street from the port, you will pick up your rental vehicle, then you can head to your accommodations to get situated.

By the time you get situated, you probably will be hungry from your journey. Head to the port to eat to experience your first meal on the island, by the water.

Enjoy the shops around town, along with some sweets, or if you are tired, there is always time to live slow, and check it out tomorrow.

In the morning, head to a great bakery on the island. They have tons of different bakery items freshly made that day. They also have eggs and different breakfast items. We recommend the yogurt bowl, but it is big enough for ATLEAST two people easy! It wouldn’t be a bad choice to go here for breakfast every day, due to their vast array of items, but there are some other great spots as well. They also make sandwiches and other items, so it is more of a bakery with a deli.

After breakfast, head to Adamantas Beach which is located on the bay. This provides a great view of the geography of the island. This area also has some hot spring activity, so you with feel different currents of warm and cooler water at times.

If you are looking for a heavier lunch, head to a restaurant on the bay, close to Adamantas Beach. If you are looking for something lighter, you can get a gyro in town, or you can head to the bakery to get a sweet!

Return to the beach if you are looking to soak up the sun, or head to Milos’ Mining Museum to learn more history about the island.

Check out some of the shops in town, as well as a few interesting bars with great views.

Eat at a local favorite restaurant on the island, located in the bay. Note that you may have to wait a bit as they do not have reservations, and they are very popular, but rightfully so!

In the morning, head to our favorite bakery, or pick from our other list of recommended breakfast restaurants.

Head out to explore Plaka. The town is characterized by its narrow winding streets, traditional white-washed buildings, and charming squares.

Many restaurants exist in Plaka, but we have a favorite local one that provides a great deal of local fresh favorites.

Close to Plaka are the Milos Catacombs. It is a short tour, but it definitely is an interesting look into the history of the island.

Next to the catacombs, sits an ancient theater, that can be enjoyed from outside. Lucky guests may visit during a performance, but it is rare.

Below these sights, sits the beautiful town of Klima, known for the many-colored boat garages. You may visit here now, but you should also return for sunset, as it provides a beautiful view, as the sun descends below the horizon. Nearby is also

For dinner, you will head to the town of Triovasalos. This local filled town hosts a restaurant with many small plates and Greek favorites. The sun-dried octopus is fantastic.

In the morning, head to our favorite bakery, or pick from our other list of recommended breakfast restaurants. There is also a great bakery in Pollonia if you choose there.

Head to Pollonia to explore the small town and relax at the beach. Pollonia has a few restaurants, a cave wine bar, a beach, and some beautiful views. (For an incredible sunrise view, head to Pollonia beach before the sun comes up.)

Eat lunch in Pollonia on the water, taking in a view of the beautiful bay, full of small boats.

Head to Plathiena for a relaxing organized beach experience.

For dinner, eat in Mandrakia at a great restaurant on the water. During the day, you can see them drying some octopus in the sun. This makes the octopus a bit more chewy.

In the morning, head to our favorite bakery, or pick from our other list of recommended breakfast restaurants.

Head to Adamantas to catch your boat.

On this tour you will head to Sikia at the West of the island, working your way East to Kleftiko. Swim and relax in the beautiful blue waters. Lunch is included with the trip.

After your boat day, head to Trypiti for a great dinner, in a really nice open environment. They cook many dishes in a traditional wood fired oven. The dish they call chicken in paper is fantastic, with vegetables and a mustard sauce, cooked in the wood fire.

Lunch

In the morning, head to our favorite bakery, or pick from our other list of recommended breakfast restaurants.

Today is a full day at southern beaches including our favorite, Fryiplaka. It has become a bit more built up recently, but the colored pebbled, cliffs, and rock structures are just so interesting.

For lunch, you will head to a great local place near Golden Beach.

After lunch, switch beaches to another southern beach, as many have different colored rock formations, and different ones offer different amenities. Be sure to check our included beach guide for more info!

Drive back to the room to shower and relax a bit.

Head to dinner again in Triovasalos. This place is just so warm and local, you will definitely want to return.

In the morning, head to our favorite bakery, or pick from our other list of recommended breakfast restaurants.

You will be catching your ferry before arriving at the port in Piraeus.

Your taxi driver will be waiting at the port to take you to your accommodations.

After settling in, you are sure to be hungry, take a short walk to a cute little cafe to eat something fresh.

If you arrive later in the day, it would be best to save any ruins until the next day, and relax in the peaceful neighborhoods, enjoying the Acropolis.

Relax at a rooftop bar overlooking Monastiraki Square, taking in the acropolis and the square. One of a few incredible viewpoints.

Enjoy a bustling restaurant for dinner just a few blocks from Monastiraki. Hopefully you are hungry because some of their portions can be huge, but too much Greek food isn’t an issue!

Head to a local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts. We also like getting eggs with fresh feta!

The Acropolis is the first thing on our list on the first full day, and rightfully so! The admission actually covers a really large area just absolutely full of ruins leading up to the Acropolis, and back down the other side.

For more things to see, explore the area West/Southwest of the Acropolis, which has things like Socrates’ Prison, other ruins, and panoramic lookouts.

The Acropolis Museum will provide more insight to the things you have just seen, so make sure to check out this after you go through the Acropolis, or after grabbing lunch.

Eat lunch at a beautiful small bistro, just south of the Museum, whether you go before or after, it is in a convenient place to easily return to the Acropolis area.

Explore the Plaka neighborhood at the foot of the Acropolis, with small winding streets, family tavernas, interesting shops, and a random mix of ruins.

Enjoy dinner in Plaka in a great little taverna just off the beaten path.

Head to a local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Start the explorations for the day at the Ancient Agora. This complex of ruins holds many things to see and read about, but the main attraction being the Temple of Hephaestus, which is still incredibly preserved.

For lunch, there is a beautiful place in the middle of the hustle and bustle, serving homemade food.

Many shops and cafes exist in this area, leaving much to explore and great places to relax.

For dinner, head to a local restaurant, that is also a specialized deli. We love the charcuterie board, with many different specialty meats. (See gallery for picture)

After dinner, take a 10-15 minute walk through beautiful old streets to the rooftop theatre performance, with a view over some ruins and the Acropolis behind the stage.

Head to a local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Start the day with the Temple of Olympian Zeus, which also has the Temple of Apollo Delphinius, Temple of Kronos and Rhea, and Hadrian’s Gate very close by.

Get lunch in Koukaki, a 15 walk from the ruins. Koukaki is a beautiful little neighborhood with tons of restaurants, bars, cafes, etc. Geor. Olimpiou is a beautiful street lined with trees and many places to eat, with some different themed bars.

Spend the day relaxing in this charming area at our recommended places, or others, as there are many to choose from.

For dinner, head to a traditional taverna located just down the road from the main strip in Koukaki.

Head to a local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

Start the day by heading to the neighborhood of Kolonaki, but specifically the funicular, to take you up Mount Lycabettus. This will provide you with a beautiful view of the city to the sea.

Get lunch after exploring the neighborhood. There are many great options in this area including some great bars to relax at as well.

Catch a taxi from Kolonaki to the National Archaeological Museum, exploring the great history of Greece.

Just North of the museum is a beautiful park to explore and relax in, with greenery and statues to enjoy.

For dinner, head to a great restaurant just a few blocks East of the museum.

Get a taxi to your accommodation area and head to a bar to finish off the night.

Head to a local cafe or bakery for a great start to your day. For a traditional meal, enjoy local breads, fruits, pastries, and yogurts.

First off is Syntagma Square to see the Tomb of the Unknown Soldier and the changing of the guard. There are also many shops, cafes, etc around here.

Stop at Archaeological Site of the Lyceum of Aristotle. This set of ruins is not very populated and offers a more tranquil experience than some others.

A bit south of the Aristotle’s Lyceum is the Panathenaic Stadium, the stadium made of marble.

For lunch, you will have to walk a bit or get a taxi, as you will be in the middle of an area with more tourist restaurants.

Next, relax the National Gardens. This area spans 15.5 hectares and features lush vegetation, shaded pathways, ponds, and ancient ruins. The gardens are a great place to wind down on your last day.

For dinner, return to your accommodation area to have a delicious last dinner in Athens.

If you don’t want to say good night to Athens, head to Monastiraki for another rooftop bar experience.

Head to a local cafe or bakery for a great start to your day. Wake up early to savor these last hours in Athens, watching as the city comes to life.

If you have extra time and your flight doesn’t leave until late afternoon or evening, the National Gardens would be a great place to enjoy to wind down before a flight.

A car will pick you up to take you to the airport.

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