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Island Hopping
Greece
Sept. 24 - Oct. 1 , 2026
Pre-Trip: Crete
Post-Trip: Delphi & Meteora
A Jo Ann Taylor Signature Adventure
Culture | Cuisine | Connection | Discovery
Island Hopping Greece
8-Days/7-Nights Signature Walking Adventure
From Athens To Tinos To Naxos
Sept. 24 - Oct. 1, 2026
Journey to the Heart of the Cyclades
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Welcome to Greece—where mythology meets mountain paths, and sun-bleached islands float in the bluest seas you’ve ever seen. From the historic streets of Athens to the whitewashed villages of Tinos and the fertile, trail-laced hills of Naxos, this Walking Connection Signature Adventure is designed for travelers who want more than a snapshot. You’re not just visiting—you’re stepping into the rhythm of local life.
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This trip is a curated blend of iconic landmarks, timeless culture, and island living. We walk village to village, dine in private homes, cook with local farmers, and set sail across the Aegean. It’s the kind of journey where you’ll share stories over wood-fired meals, sip wine in seaside tavernas, and feel the warmth of the Cycladic sun as it lights the ancient trails beneath your feet.
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INSPIRATION
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Athens: Marvel at the Acropolis and explore the ancient Plaka neighborhood before we head island-bound.
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Tinos: Discover a wonderland of 40+ marble-carved villages perched on hillsides and cliffs, many connected by winding trails.
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Naxos: Walk through fertile valleys and remote villages; explore ruins, groves, and Venetian heritage; and end your journey sailing the sea.
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Culinary Adventures: Learn to cook authentic Cycladic dishes with fresh, local ingredients—served with a side of laughter, storytelling, and ouzo.
Come Island Hop Greece With Us!
Hosted by Walking Connection Founders,
Jo Ann & Gene Taylor
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Adventure to Athens, Tinos & Naxos - 8-Days/7-Nights
Sept. 24 - Oct.1, 2026
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Pre-trip: Crete - 3-Days/2-Nights
Post-trip: (Hosted) - Delphi & Meterora | (Independent) - Santorini & Mykonos
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Priced from:
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$6498 per person, double occupancy. (Limited Single Occ. is available).
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$1500 Deposit Due with Registration.
Pre- and post-trip extension Prices to be determined by the number of guests participating. To be confirmed with guest registration
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​Highlights and Inclusions:
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​A unique itinerary created by Jo Ann Taylor & our team in Greece.
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Hosted by WC owners, Gene & Jo Ann Taylor.
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Professional English-speaking Interpretive resident guides.
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8-Days/7-Nights as indicated by the final itinerary.
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All tour transfers and meals as indicated in the final itinerary.
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Entry into all site visits as indicated in the final itinerary.
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Detailed Know Before You Go information.
Payments, Cancellation Policy, Trip Minimums, Trip Grading for Walks, and recommended footwear and gear are linked below. Click "Get Details."
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Every detail reflects the heart of Greek hospitality, carefully curated by Jo Ann Taylor to create an experience that’s authentic, immersive, and true to place—without compromise.
A Signature Adventure
This isn’t a cruise stop or a checklist tour. It’s the Walking Connection—on foot, with purpose and presence.
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We believe the best way to understand a place is to walk it—step by step, with time to pause, reflect, and connect. On this journey, Jo Ann and Gene invite you to experience Greece the way they do: with open hearts, curious minds, and a deep appreciation for the stories that shape people and place.
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Together, we’ll wander through marble villages, sip coffee with locals, and sail between islands under wide Aegean skies. Every detail of your trip is meticulously curated to ensure a seamless and enriching experience. All you need to do is breathe it in, walk it out, and let the spirit of Greece move you.
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Athens to Tinos to Naxos
Athens doesn’t just tell the story of Western civilization—it is the story. From our base in the heart of the city, we walk the Plaka and ascend the Acropolis with a guide who brings history to life. Later, we’ll toast to what’s ahead with a welcome dinner in a traditional taverna.
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A walking dreamscape of villages carved into stone and tradition. This is Tinos! We’ll hike from the surreal boulder-strewn village of Volax to the sea-facing town of Tinos. Along the way, we’ll share a slow-cooked meal at the home of a beloved local host and climb trails that lead to marble artisan workshops and cliffside chapels.
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The largest of the Cycladic islands, Naxos is all contrasts: wild mountains, fertile farmland, ancient ruins, and relaxed coastal towns. Here, we’ll cook a farm-to-table meal with a local family, hike past kouroi (ancient statues), and wander through the Venetian quarter. We end our adventure aboard a private catamaran, exploring the hidden coves and clear waters of the Cyclades.
ITINERARY
Day 1 – Arrival in Athens
Welcome gathering and walk through the Plaka district, followed by dinner at a local taverna.
Overnight: Athens
Day 2 – Athens & Ferry to Tinos
Guided visit to the Acropolis, then ferry to Tinos.
Overnight: Tinos
Day 3 – Volax to Tinos Town Hike & Local Dinner
Walk through boulder fields and medieval ruins, ending with a shared home-cooked meal at Mrs. Nikoleta’s.
Overnight: Tinos
Day 4 – Marble Village Loop Hike
Walk from Panormos to Pyrgos, visit the Museum of Marble Crafts, explore local workshops, and lunch by the sea.
Overnight: Tinos
Day 5 – Ferry to Naxos & Cooking Class
Ferry to Naxos. After a relaxing arrival, take part in a traditional Naxian cooking class at a local farm.
Overnight: Naxos
Day 6 – Melanes to Chalki Hike & Venetian Quarter
Hike past ancient kouroi and olive groves to the village of Chalki. In the evening, explore the Venetian quarter.
Overnight: Naxos
Day 7 – Catamaran Sailing
Full-day sailing adventure to hidden beaches and coves. Swim, snorkel, and celebrate with a farewell dinner.
Overnight: Naxos
Day 8 – Farewell or Extend Your Journey
Morning at leisure. Depart for home or continue your adventure with us to the Island of Crete.
