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The Cycladic Islands

Naxos and Santorini
Naxos and Santorini

Immersed in the unspoiled beauty of the minor Greek islands, you'll encounter a slower pace of life and a restorative week where you'll learn to live like the Greeks who never seem to grow old and who always have time for a conversation.

A Greek Island Escape

This eight-day journey explores the art of uncomplicated living through contrast and intention. Shaped by the island's understanding that slowing down does not mean doing less, but seeing more clearly, this retreat steps away from the pace of modern life in favor of an older, more attentive way of traveling. You will spend time on Naxos and Santorini—two islands with very different relationships to time, visibility, and change—each revealing a distinct face of the Cyclades.

On Naxos, daily life still moves with the land, the seasons, and the sea. On Santorini, you will look beyond the spectacle to the deeper layers of history, labor, and endurance beneath its famous surface. Through visits with weavers, cooking alongside farmers, sailing on traditional fishing boats, learning herbal remedies, and sharing music and dance with locals, you’ll encounter island life as it is lived rather than displayed. This journey invites you to step away from a fast-paced, digital world where everything looks the same. Instead, you’ll experience the handmade, walk through monasteries, rest on open shores, share local wine, and meet people who value resilience, interdependence, and generosity—those who know that the most precious things are not what we acquire, but what we share.

DAY 1
Welcome to the Greek Isles

Your journey will unfold from the serene island of Naxos, the most fertile place in the Cyclades. Its beach and mountain scenery are shaped by centuries of sea, sun, and marble quarries, and its proud independence is still felt today in the joy of its people. You may hear the locals say "Kalos Irthate", or “welcome,” as you arrive in the port and glimpse the Temple of Apollo glittering over the water. As the poet Sappho aptly put it: “love for the sun has a share in brilliance and beauty.”

Upon arrival you’ll be free to settle into your sea-view hotel or explore before 4:00 pm, when you'll meet your Alithea guide and Naxos local for an orientation to the week of discovery, movement, whole foods, and in-person connection. This evening we'll dine overlooking the Aegean while enjoying the Greek tradition of philoxenia (Φιλοξενία): the love of travelers that turns visitors into honored guests, and strangers into friends.

DAY 2
Mountain Villages and Postcards from the Past

After an energizing Pilates session overlooking the Aegean followed by breakfast in your hotel, you'll journey to the center of the island for your first full day dedicated to Naxian life. You’ll be introduced to the agriculture and seasonal festivals that defined Greek communities as you visit the ancient temple of Demeter, and you’ll begin to see how the story of Greece illustrates the development of humanity’s fellowship with nature, the divine, and one another. 

Your next stop, the neoclassical village of Chalki (known for its citrus groves and jewelry galleries), will usher you through winding cobblestone streets and give time for encounters with a traditional weaver, a dedicated honey farmer, and a visit to the local church with breath-taking frescoes. You'll feel the love of the craft shared by each of these artisans, and see the important role Greek religion and nature played in maintaining the bonds between generations.

After lunch in Chalki and an opportunity to try the Naxian classic dessert, galaktoboureko, you'll take a stroll through some of the oldest olive trees in the world before returning to your hotel for a free evening or a swim in the sea.

DAY 3
Mediterranean Cooking and Lessons of Farm Life

After breakfast and Pilates this morning, you'll return to where the rhythms of Island life are still deeply connected to the land and sky. Strikingly similar to the days when Homer's Odyssey was the talk of the towns and goats roamed the hillsides freely, this world of Mountain views and sustainable nourishment will be spent soaking up the culture of hospitality while your host, a local goat farmer, introduces his farm and explains the making of cheese.

After your introduction to the farm, the rest of your morning will be dedicated to learning a few Mediterranean recipes with ingredients grown from the surrounding gardens followed by enjoying the lunch that you have prepared together.

This evening you’ll have time for another Pilates session or a free night to explore or relax.

DAY 4
Five Millennia and the Capital of the Bronze Age Seas

This morning after poolside Pilates and breakfast together, we'll embark on a walking tour through the labyrinthine streets Chora, or Naxos Town. These winding white washed passageways offer surprises at every corner, and stories from times gone by. Continuously inhabited for more than five thousand years, Naxos was the capital of the Aegean in Bronze Age times. Today, whether strolling through the medieval town or old market, walking the beaches marked by shells and pottery, or ascending to the temple of Apollo, you’ll share in an immersive journey through the architecture, stories, and spirit that makes Naxos unique among the Greek Isles.

After a free afternoon for shopping, lunch, and beach hopping, we will regroup in the evening.

DAY 5
Sailing the Cyclades

This morning after Pilates and breakfast, you'll hop on a private boat and glide at the speed of the wind along Greece’s most beautiful cliffs and beaches. Sailing the waters where the earliest Greek sailors developed the art of navigation, come ready for a day of sun, swimming, exploring coves reachable only by boat, and chatting with your local Greek captain—perhaps even taking a turn at the helm yourself and experiencing the sea as a horizon of curiosity connecting one world to another. 

In the early evening, you'll return to the island for a free evening to explore the nightlife and warmly lit city streets alive with music and the aromas of Naxian cuisine. 

DAY 6
Santorini: Beautiful Sunsets Over the Caldera

After a free morning, we’ll arrive in Santorini. Famous for its beauty even in ancient times, the Phoenicians who settled here in the thirteenth century B.C. called the island Kallisti, ‘the most beautiful’. Created by the volcanic craters that gave way to its existence, the Caldera of Santorini is unique in the Aegean. 

Time-permitting,  we’ll explore the archeological site or the museum of Akrotiri. Like a Greek Pompeii, this city was destroyed when the volcano erupted in the sixteenth century B.C. and is a window in time to observe the daily lives of bronze-age Greeks.

For lunch this afternoon we’ll enjoy a tasting of its world-famous wines paired with a light Greek lunch that create a sommelier’s journey through the ages.

And after checking into our hotel in the late afternoon, we’ll be free for the evening to stroll through Oia and conclude with a spectacular view of the sunset over the Caldera.

DAY 7
Sailing the Caldera

After breakfast in our hotel, we'll be free this morning to hike the path towards Fira or to relax and explore the cobbled streets and classic views of Oia.

We will regroup in the early afternoon and head to the port to embark on a spectacular sailboat cruise around the island. During our last evening together we'll sail through the caldera and have dinner on board while observing the sunset and sea of the Greek mariners.

Walking: moderate

DAY 8
Farewell Santorini

Breakfast is included this day but there are no planned activities. Catch a boat to Crete, Folegandros and other easily reachable Greek islands or head to the airport to connect to your next destination or to fly home. Your Alithea guide will be available to help with travel plans throughout breakfast.

OVERVIEW

7 Nights / 8 Days

5 Nights
Naxos
2 Nights
Santorini
Naxos
Santorini
5 Nights
2 Nights
i
Full Trip Details

What people say

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Trip FRAMEWORK

TRAVEL DATES
Sept. 26 - Oct. 3, 2026
overview
PRICE
$6,500
per person
GROUP
14
travelers max.
INCLUSIONS
MEALS
All breakfasts and seven additional meals
ACCOMMODATION
Seven days accommodation in Lianos Village Hotel
ACTIVITIES
Daily Pilates sessions, sailing day-trip, Temple of Demeter, Naxos Chora Museum, cooking lesson, day-trip to Paros and Anti-paros, Naxos Villages tour, Naxos Hidden Landscapes tour, and Naxian wine tasting.
TRANSPORTATION
All transportation throughout the trip
GUIDE
Your friendly Alithea guide throughout the trip
EXCLUSIONS
INSURANCE
Travel insurance for peace of mind
INTERNATIONAL FLIGHTS
International flights are not included. Travelers will arrive independently and join the group at the destination.
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Lianos Village | Naxos

Our home in Naxos is Lianos Village, a peaceful hillside property overlooking the turquoise waters of Agios Prokopios Beach. The whitewashed architecture, soft blue details, and expansive sea views create an atmosphere that immediately invites you to settle in.

Rooms are light filled and designed in classic Cycladic style with private balconies or terraces, comfortable bedding, modern baths, and thoughtful touches throughout. Mornings begin with a generous Greek breakfast, and afternoons invite you to lounge by the pool or stroll to the beach just minutes away.

Strogili Traditional Houses Santorini

Perched along the cliffs of Oia, Strogili Traditional Houses offers breathtaking caldera views and the iconic beauty Santorini is known for. Built into the volcanic rock in traditional cave house style, the property feels intimate, elegant, and quietly luxurious.

Each suite features curved white interiors, private terraces overlooking the sea, and modern comforts for a restorative stay. Many accommodations include outdoor seating or hot tubs, perfect for sunset moments with a glass of wine.

Lianos Village | Naxos

Our home in Naxos is Lianos Village, a peaceful hillside property overlooking the turquoise waters of Agios Prokopios Beach. The whitewashed architecture, soft blue details, and expansive sea views create an atmosphere that immediately invites you to settle in.

Rooms are light filled and designed in classic Cycladic style with private balconies or terraces, comfortable bedding, modern baths, and thoughtful touches throughout. Mornings begin with a generous Greek breakfast, and afternoons invite you to lounge by the pool or stroll to the beach just minutes away.

READ MORE

Strogili Traditional Houses Santorini

Perched along the cliffs of Oia, Strogili Traditional Houses offers breathtaking caldera views and the iconic beauty Santorini is known for. Built into the volcanic rock in traditional cave house style, the property feels intimate, elegant, and quietly luxurious.

Each suite features curved white interiors, private terraces overlooking the sea, and modern comforts for a restorative stay. Many accommodations include outdoor seating or hot tubs, perfect for sunset moments with a glass of wine.

READ MORE
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A Christian Classical Approach to Travel
Travel encourages a living experience of art, history, and ideas that transforms the classroom into an immersive experience of truth, beauty, and goodness. Museums, meals, archeological sites, and foreign languages are not merely artifacts that help students consider the world, they cultivate a love of wonder, moral imagination, and a rich understanding of the truth. More than a student trip, travel is an invitation to become a lifelong practitioner of the loves that shape the soul.
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Rather than treating churches and monasteries as defunct historical monuments, Alithea and Oakdale Academy invite students to approach them as places of prayer and worship

FAQ

For further questions don't hesitate to reach out to us directly.

explore@alitheatravel.com
How active is the retreat?

The week includes light to moderate activity such as walking through villages, boat outings, and island transfers. Movement sessions are optional and designed to feel enjoyable and accessible rather than intense.

Do I need a roommate?

Not at all. We offer both single occupancy rooms and shared double accommodations. If you’d like to bring a friend and share a room, that’s wonderful, but many women attend on their own and quickly connect with the group.

What airport should I fly into?

You will fly into Naxos Island National Airport (JNX). Most international travelers will first arrive in Athens (ATH)and then take a short connecting flight to Naxos, which takes about 40 minutes. After you register, we will provide detailed travel guidance, recommended flight windows, and step by step instructions to make planning your journey easy and stress free.

Is a visa required to enter Europe?

Yes. Starting in late 2026, U.S. citizens will be required to obtain an ETIAS travel authorization before entering Europe. ETIAS is a simple online application, with responses typically issued within 96 hours. Once approved, it is electronically linked to your passport.

ETIAS is not yet in operation, but it is expected to be introduced soon. We kindly ask travelers to check whether ETIAS is required for their travel dates and to complete the application if necessary.


To apply, please visit: https://travel-europe.europa.eu/etias

What is the cancellation policy?

Your deposit is fully refundable for 30 days. Consider purchasing trip insurance that provides cancellation for any reason if you'd like to have complete flexibility.

Do I need travel insurance?

Yes. We strongly recommend purchasing travel insurance to protect your investment in the event of unexpected changes to your travel plans.

Can dietary restrictions be accommodated?

Yes. We are happy to accommodate dietary preferences and restrictions, including vegetarian, vegan, and gluten free options whenever possible.