Greece: Island Discovery

Terms & Conditions

Trip Date
Price from
Number of Days
Highlights & Inclusions
  • Tour the Acropolis of Athens with an Insider Expert
  • Visit the Temple of Apollo on Naxos Island
  • Explore the fortress-like towns on the island of Syros 
  • Hike the rim of the Santorini caldera 
  • Watch the world-famous Oia sunsets 
  • 8 breakfasts, 1 dinner
  • 2 nights: Hermes Hotel, Athens
  • 2 nights: Diogenis Hotel; Syros 
  • 2 nights: Hotel Princess of Naxos, Naxos
  • 2 nights: Costa Marina Hotel, Santorini

Alternate hotels may be used. 


Nestled between the Aegean and Ionian Sea, Greece’s ancient ruins, fascinating history and scenic beaches 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, lively Syros and the archaeological treasures of Naxos. 

Day 1: Athens

Kalimera! Welcome to Greece. After meeting your Local Leader and fellow travelers at a welcome meeting, the evening is yours to personalize. Perhaps head out for some gyros with your new adventure companions or stroll the world-famous neighborhood of Plaka.

Day 2: Athens

Today visit one of the most recognizable sights in Athens: the Acropolis. Our Insider Expert leads the way through these magnificent ruins as we learn more about ancient Greek civilization and culture. The remainder of the day will be unscripted, so you can make your own discoveries. In the evening head to a local taverna and try some of the typical Greek delicacies — a local meze accompanied by ouzo and wine. (b, d) 

Day 3: Athens > Syros

Cruising the glistening blue waters of Greece, we’ll ferry toward Syros – a hidden gem of the Islands. This island is where Greek tradition and western influence exist harmoniously and provide a connection to ‘real’ Greece. Upon arrival, enjoy time unscripted to explore. (b)

Day 4: Syros 

We’ll wander this morning through the fortress-like town of Ana Syros (Upper Syros) with its cathedral dedicated to St. 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. This afternoon and evening are yours to visit handmade-souvenir shops and keep your ear open for traditional music floating out of family-run tavernas. (b)

Day 5: Syros > Naxos

We’ll ferry this morning toward Naxos; the largest and most fertile of the Cyclades islands, Byzantine churches and medieval towers dot the landscape here. 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’ll 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’ll visit the local distillery which produces Kitron, a liqueur made from local citrus trees. The afternoon is yours to relax and soak in the stunning scenery. (b)

Day 7: Naxos  > Santorini

Our last stop on our Greek adventure is the southern island of Santorini. Renowned for its spectacular natural beauty, Santorini is the home of the iconic image of the Greek islands — blue-domed buildings clinging to the cliff face with sparkling water in the background. There are so many options to help craft the story of your adventure: Discover the hilltop ruins of Ancient Thira and its fascinating Prehistoric Museum, or check out the range of restaurants and shops in the island's capital, Thira. Maybe one of Santorini's volcanic beaches is calling you, or an island winery beckons. Either way, be sure to try some of the island’s delicious food grown from the nutrient-filled volcanic soil — which makes the ingredients burst with flavor. (b)

Day 8: Santorini

In 1500 B.C., a volcanic eruption sank the center of Santorini, forming one of the most significant geological formations on the planet — the awe-inspiring caldera. Today it’s your choice! Take an excursion along the crater rim; starting in Thira town and walking through little villages all the way to Oia. Or, if you prefer to relax, spend the day on a boat sailing the caldera. On the last evening of our adventure, rub shoulders with friendly locals in neighborhood pubs and cafés, as we witness a magnificent Santorini sunset. (b)

Day 9: Santorini 

Our Grecian adventure ends today. (b)