Greece: Island Discovery

Terms & Conditions

Trip Date
Price from
Single Supplement
Number of Days
Highlights & Inclusions
  • Tour the Acropolis of Athens with an Insider Expert
  • Hike the rim of the Santorini caldera 
  • Watch the world-famous Oia sunsets 
  • 8 breakfasts, 1 dinner
  • 2 nights: Hotel Fresh, Athens
  • 2 nights: Hotel Hermes; Syros 
  • 2 nights: Hotel Princess of Naxos, Naxos
  • 2 nights: Pelican Hotel, Santorini

Alternate hotels may be used. 


Ancient history and endless sunsets

Nestled between the waters of the Aegean and Ionian seas, Greece’s captivating history and scenic beauty make it a perfect pathway to personal discovery. Beginning in the capital of Athens, we’ll journey out to the magnificent islands — exploring crescent-shaped Santorini, the beaches of Syros, and the archaeological treasures of Naxos.

Day 1: Athens
Kalimera! Welcome to Greece. Meet your Local Leader and fellow travelers at a welcome meeting.

Day 2: Athens
Today visit one of the most recognizable sights in Athens: the Acropolis. Our Insider Expert leads the way as we learn more about ancient Greek civilization and culture. The remainder of the day is unscripted. (b, d)

Day 3: Athens > Syros
Cruising the glistening blue waters of Greece, we ferry toward Syros — a hidden gem of the Islands where Greek tradition and western influence exist harmoniously. (b)

Day 4: Syros
We wander this morning through the fortress-like town of Ana Syros — with its cathedral dedicated to Saint George and amazing views of the Aegean Sea. Meander up the stairs to the top of the hill — passing through narrow streets with traditional whitewashed houses — before reaching breathtaking views of the island. (b)

Day 5: Syros > Naxos
We ferry this morning toward Naxos, the largest and most fertile of the Cyclades islands. Look for the famous Naxos Eye jewelry — a stone that was created by the combination of sea and sun and is now a symbol of the island. Embark on a walk with your Local Leader and visit the Temple of Apollo, known as Portara or Palatia. (b)

Day 6: Naxos
Today we traverse inland and walk from the mining town of Apiranthos, up to the island's second-highest peak — before following old mule paths down to the picturesque villages of Moni (and further to Halki). After, we visit the local distillery which produces Kitron, a liqueur made from local citrus trees. The afternoon is yours. (b)

Day 7: Naxos > Santorini
Our last stop is the island of Santorini, known for iconic blue-domed buildings clinging to its cliff face. Here, you can choose your own adventure: discover the hilltop ruins of Ancient Thera and its prehistoric museum or check out the restaurants and shops in the island’s capital, Thera. (b)

Day 8: Santorini
In 1500 B.C., a volcanic eruption sank the center of Santorini, forming the awe-inspiring caldera. Today, take an excursion along the crater rim or spend the day on a boat sailing the caldera. This evening dine with friendly locals in neighborhood pubs and cafés. (b)

Day 9: Santorini
Our Grecian adventure ends today. (b)