The warmth of the Mediterranean sun on your skin, the soft murmur of waves, and the sight of whitewashed houses perched along rugged coastlines, spilling down toward the sparkling Aegean. This is Greece, as you’ve always imagined, brought to life on our journey to the enchanting islands of Naxos and Paros. Unlike the bustling shores of Santorini and Mykonos, these islands offer a peaceful charm, treasured by travelers who crave Greece’s magic without the crowds. Here, you’ll find serene beauty, endless blue skies, and moments like pure poetry. Our adventure begins in Athens, where ancient myths and modern spirit unite. Standing before the iconic Acropolis, you’ll feel the echoes of centuries past. In the nearby Acropolis Museum, you’ll walk among treasures that tell stories of gods and heroes. And then, we’ll dive into Plaka’s narrow streets, each turn revealing charming boutiques and hidden tavernas serving up flavors that will make you fall in love with Greek cuisine from the very first bite. Then we’re off to Naxos, where golden beaches stretch as far as the eye can see, and the rhythm of island life invites you to slow down and savor every moment. Imagine strolling through its cobbled streets, discovering family-run cafés, and feeling the island’s warm embrace. After Naxos, we sail to Paros, where vibrant energy meets timeless beauty. From elegant boutiques to lively tavernas, Paros has a contagious joy in the air. Swim in turquoise waters, explore secluded coves, and watch as the sun sets over the horizon, painting everything in hues of gold and pink. Late September and early October offer Greece at its finest, with gentle breezes, warm seas, and golden sunsets that linger in the sky. This journey celebrates history, relaxation, and adventure—a symphony of sights, sounds, and flavors that will stay with you long after you return home. The dream is waiting… are you ready to dive in?
Here's a day-by-day itinerary of the trip.
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The centrally located Electra Metropolis is applauded by many for its easy access to shopping, restaurants, and attractions.
Situated on the beach in Naxos, Nissaki Beach Hotel will be our home away from home while we are in Naxos.
Achieving the ideal fusion of style and comfort, the Cove Paros is a boutique hotel characterized by clean architectural lines, earthy materials, and meticulous attention to detail, all basking under the warmth of the Aegean sun.
We're not quite ready to publish this trip, but you can reserve your spot with a FULLY-REFUNDABLE deposit of $250.
FROM$250
Jewels of the Cyclades
Naxos and Paros stand out as quintessential Greek island destinations. Naxos boasts sandy beaches, ancient ruins like the Portara gate, and a charming old town adorned with Cycladic architecture and quaint churches. Meanwhile, Paros offers a tranquil escape with its picturesque white-washed villages, vibrant bougainvillea, and secluded chapels. These islands invite you to indulge in local cuisine, explore historical treasures, and immerse yourself in their rich cultural heritage amidst stunning Aegean landscapes.
Lodging at unique hotels
All entry fee and tickets listed in the itinerary
All transportation during the trip (except where indicated)
All meals (except where indicated) including beer or wine with dinner
In country flights
Expert guides, guided tours, and trip leaders
Wine tastings listed in the itinerary
Spa treatment in Naxos
Luxury Boat Cruise
Visit to the Acropolis Museum
Walking food tour of Central Athens
Guided walking tour of Naxos
Traditional Greek BBQ on the beach
Roundtrip airfare to Athens.
All personal souvenir purchases
Travel and Medical Insurance (required)
Additional wine, beer, or spirits beyond what is offered at meals.
Fly into the Athens International Airport.
The trip officially starts on the afternoon of September 29th, but if you are traveling overnight to get to Greece, consider arriving a day early so you have time to rest, relax and adjust to the local time zone. You can purchase the option to arrive early in the Add-ons section of this page.
About 6-8 weeks before the trip starts, we'll organize a Zoom video call to discuss all the details of the trip and give you a packing list. Here is a great website that we love that will help you with packing and travel trips.
Highs of 72 degrees and lows of 69, late September and early October on these two islands is idyllic and still warm enough to swim. Athens temperatures are virtually the same however at times it can get a bit chilly at night so bring a light jacket or sweater.
Beginning in Q4 2026, travelers from visa-exempt countries—including the U.S., Canada, and Australia—will need an ETIAS permit to visit most of Europe. No action is needed just yet. As we get closer to the launch date, likely several months in advance, we’ll share all the details on how to apply. Feel free to reach out with any questions!