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Image by Jonathan Gallegos
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Greece in September is IT. Warm weather, sunshine, Athen’s history, the famous sunsets of Santorini, and the sandy beaches of Paros are the perfect combination for the trip of a lifetime.


This trip begins in Athens where we’ll have a happy hour overlooking the Acropolis and visit the temples dedicated to ancient Greek gods and goddesses. From the start, the food will be delicious, and you HAVE to try a gyro stuffed with french fries and allll the tzatziki.


Next, the group will take a ferry over to the first island of the trip: Paros. Paros is a combination of authentic towns, trendy nightlife, and the best beaches. When we visit this island, we always meet locals who chose this island to vacation at in their home country. We’ll embark on a boat day together with drinks, a homemade Greek lunch, swimming in the turquoise water, and island hopping around Antiparos.


Our next destination is the iconic Santorini, which we will reach by another ferry. This island, which was created by a volcanic eruption in 1620 BC has the most breathtaking views at every turn. The volcanic beaches, lunar landscapes, white buildings with blue domes carved into the cliffside, hot springs, and restaurants overlooking the water are the perfect way to finish off a week in Greece.

On this trip, you can jump off a boat into the crystal clear Aegean Sea, sip a glass of wine overlooking Santorini’s caldera cliffs, and ride ATVs across Paros to discover traditional villages with their white buildings contrasting with the blue skies and sea. It’s time to adventure!


Stay tuned for 2024 dates and updates.


  • 7 nights in accommodations

    • All rooms are private rooms with ensuite bathrooms in hotels. There will be 2-3 travelers from the TWC group per room. Please reach out to to get a quote for a single occupancy upgrade.

  • 7 meals

  • Transportation from Athens to Paros and Paros to Santorini

    • Enjoy beautiful ferry rides to the islands.

  • Airport transfer service on arrival in Athens and departure in Santorini

  • Several fun excursions

    • See the full itinerary below for specific details on included excursions. 
    • Most notably, a tour of the Acropolis, a catamaran around Paros, Antiparos, and another island, and a winery tour and tasting in Santorini.
  • A group leader for the duration of the trip

  • Individual TWC Traveler Account and access to a private Facebook group for the trip

    • Each TWC Traveler will be given access to their own account where they will find a trip-specific packing list, options to contact their trip consultants with any questions, a link to a private Facebook group, and more information. 

  • TWC trip consultants leading up to and during the trip for travel advice and to answer any questions

    *Note that your international flights to Athens and from Santorini are not included. However, we have free information on how to find the best flights, and we work with travelers to help find available deals.

There is a 3% fee for paying with credit card.


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Day Zero

Flight to Athens

Relax on your overseas flight.

The flight will most likely be an overnight flight due to the time change from the Americas, so get some sleep and watch some movies.

Day One

Arrival in Athens

​Arrive in historic Athens! TWC will provide several airport transfers to the accommodation. Your TWC group leader will greet you upon arrival and introduce you to the group!

In the evening, you can join a happy hour with the group overlooking the Parthenon. Our groups get close quickly, so say hi to your new travel buddies.


In your free time, explore the recommendations given to you by TWC. This includes trying the Greek "fast food" gyros and exploring the Plaka neighborhood with its cobblestone pedestrian-only streets, sidewalk cafes covered in flowers, shops of all kinds, and ruins intertwined with the modern city. If you're feeling adventurous, walk into a traditional Greek restaurant, called a taverna, and try ouzo, a traditional liquor.

Day Two

Acropolis of Athens and the Parthenon

After an included breakfast, join an included tour of the most famous landmark in Athens. The Acropolis is a rocky plateau that the Parthenon and other monuments rest on, including the Temple of Athena Nike and the Propylaea. The Parthenon is one of the most recognizable buildings in the world and was built to honor the Greek goddess Athena Parthenos, the patron of Athens. 

After the tour, you can head to any of the world-famous museums, see where the first Olympic games were held, or hit the picturesque streets for shopping and amazing food.

Day Three

Athens to Paros

It's time to head to the islands! Take a ferry ride with ocean views to Paros, where the locals vacation. We'll check into our accommodation and have the rest of the day to explore! What's on the agenda? Your options are spending time at any of the golden beaches on the island or renting an ATV to explore the island in detail. 

Day Four

Boat Day in Paros and Antiparos

Boat day! Today the group will spend a day sailing from Paros to the beautiful surrounding Cyclades Islands. Stop at secret beaches, swim, snorkel, and sunbathe. What could be better? After a swim in the turquoise-colored waters, you’ll be served a lunch prepared by the crew. Throughout the day, you'll try local delicacies with Greek wine.

Day Five

Paros to Santorini and Sunset in Oia

Mamma Mia, we're getting on a ferry to Santorini! 

After checking into our accommodation, the group will head to the most famous spot to watch the sunset on the entire island, Oia. Oia is on the north side of the island and features the traditional white buildings that Greece is famous for on the side of Santorini's volcanic cliffs. 

To end off the night, are you looking for nightlife, some gelato, or both?

Day Six

Wine Tasting 

After a morning exploring Fira, Santorini's capital, the group will spend the afternoon at an included wine tasting with one of the most unreal views in the world. The winery is family owned. A tour of how the wine is produced and a tasting is included.


For those who don't want to try the wine, a non-alcoholic drink and snack will be provided instead. Trust me, the views are worth it regardless!

Day Seven

Free Day in Santorini

Perfect day to sign up for one of the many activities in and around Santorini!

You can take a pirate boat to explore the small islands near Santorini. Soak in hot springs, walk up to an active crater, and swim in the sea.

Calling all hikers! You can hike 6 miles from Fira to Imerovigli to Oia. The entire way consists of ocean panorama views, small villages, and viewpoints. Catch one last sunset and then take the bus or a taxi back.

Blow up your Instagram feed after even a short walk around the village of Oia. 

Taxi, bus, or rent an ATV to visit one of Santorini's interesting beaches. There are red, black, white, and rock beaches around the island. 

Day Eight

Flight Home

Grab one last breakfast and take in the caldera views.

Transportation to the airport in Santorini is included. 


Think back on all of the special moments from the trip. It's about time to plan the next one!

Image by Philip Jahn
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