Greek Islands
Explore the best of the Greek islands.
Between the thoughtful history, immersive landscapes—and a lot of time on your feet—it’s going to be unforgettable.
Together, we’ll hike through towering gorges, trace ancient paths across sun-drenched islands, swim in hidden coves, and explore ruins that inspired myth and legend. You’ll cover miles—up to 10 a day—on foot, over tough terrain, with a small group of fellow adventurers (max 30 people) who are just as eager to push boundaries and soak in the magic of the Mediterranean.
This isn’t your average Greek getaway and we can’t wait to share it with you.
Reserve your spot with a non-refundable $500 deposit. The balance is split into four payments, with the final payment due three months before the tour start date. Please view our Booking Terms & Refund Policy.
12-DAY
TOUR
June 18-30, 2026
$2,250 / person
$650 Single Room Supplement
Book travel to arrive in Chania, Crete (CHQ) and depart from Athens, Greece (ATH).
12-Day Tour Itinerary
This itinerary is a sample and small items may be changed or rearranged to capitalize on additional opportunities and build the best adventure possible.
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Day 1
Chania
Arrive in Chania, where Venetian charm meets stunning natural beauty. Stroll through the old town’s maze of streets, enjoy the vibrant harbor, and take in the towering White Mountains. Your afternoon is all about getting to know the town with an audio-guided walking tour before savoring a delicious Cretan dinner, full of local flavors.
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Day 2
Chania
Ease into the day with a relaxed morning, completing your walking tour. Then, it’s time to visit Elafonisi, the world-renowned pink sand beach. Enjoy the sun and sea as you reflect on the fact that the apostle Paul once passed this very spot on his fateful journey. Tomorrow, we’ll trade the beach for a hike!
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Day 3
Chania
Rise early for an adventurous hike through the Samaria Gorge, one of Europe’s deepest canyons. The 10-mile journey takes us from the Omalos Plateau to the seaside village of Agia Roumeli. Towering canyon walls and wild landscapes make this a day to remember, before we return to Chania by ferry.
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Day 4
Chania
Today, we dive into a day full of swimming and optional hikes to take in some incredible views. Whether you’re relaxing on the beach or climbing a nearby trail, it’s a chance to appreciate Crete’s stunning beauty and unwind from the previous days’ adventures.
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Day 5
Chania
It’s your free day to explore Chania. Wander the charming old town, shop for souvenirs, or visit the Maritime Museum to learn about Crete’s rich seafaring history. For those who want more adventure, an optional excursion to the stunning Seitan Limania Beach awaits.
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Day 6
Heraklion
A two-hour drive brings us to Knossos, the ancient Minoan palace that once boasted running water and sewers. Step into the world of Theseus and the Minotaur and marvel at the advancements of an ancient civilization. Tonight, we’ll stay in Heraklion, Crete’s bustling capital.
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Day 7
Amorgos
Catch an early ferry to the quiet island of Amorgos, stopping for a scenic lunch in Santorini along the way. The dramatic caldera views will leave you breathless, but save your energy for the beauty of Amorgos, which we’ll explore after arriving in the afternoon.
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Day 8
Amorgos
Today’s hike takes us across Amorgos’ rugged terrain, with views that are truly million-dollar. Along the way, we’ll visit the Hozoviotissa Monastery, perched on a cliff high above the Aegean Sea. After a long hike, cool off with a refreshing dip in the crystal-clear waters.
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Day 9
Naxos
Start your day with a swim at Ayia Anna beach, where the water is the clearest we’ve seen. After snorkeling or taking some postcard-perfect photos, enjoy a lunch in Katopola before catching a ferry to Naxos, where high mountain villages and beautiful beaches await.
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Day 10
Naxos
Today, we explore Naxos' ancient paths. You'll become beguiled as you hike from Melanes to Milli to Ano Potami, passing the mysterious 2,500-year-old Kouros statues. After a village lunch, get your adrenaline going with some cliff jumping at one of Greece's top spots, choosing a height that suits your comfort level.
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Day 11
Naxos
We tackle the highest peak in the Cyclades today, where Greek mythology says Zeus was born. The 4-mile hike is short but features a significant elevation gain, making the panoramic views from the top all the more rewarding. Afterward, relax on a Naxos beach or explore the lively streets of town.
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Day 12
Athens
Our final morning begins with a short hike to Apano Castro, where you’ll explore the ancient Venetian citadel with spectacular views of the sea. Then, we visit the Temple of Demeter, a fascinating blend of ancient Greek and Christian history. In the afternoon, we head back to Athens for one last meal together.
What to expect
This is a group adventure right from the beginning and from the moment you sign up, we will make sure you feel prepared, excited, and supported. You'll hear history where it actually happened, gain confidence as a traveler, and experience the kind of camaraderie that only comes from shared adventure.
Before departure:
Group calls: You’ll be invited to two group calls where you can ask questions, meet fellow travelers, and get a feel for what’s ahead.
Packing lists & recommended reading: To help you prepare, we’ll send a packing list and recommended reading list ahead of time—so when you step off the plane, you're ready to immerse yourself in the journey.
While traveling:
Arrival: When you arrive, we’ll be there to greet you at the airport and take you to our hotel to drop your bags—no stress, no guesswork. You’ll receive a detailed itinerary booklet, and everything you need to start exploring immediately.
Balance of structure & freedom: Each day begins with breakfast at your hotel before setting out on that day's adventure. Expect a mix of guided walking tours that bring history to life and free time to explore at your own pace. Lunchtime? We’ll point you to the best local spots. When it’s time to meet for an afternoon activity, a quick WhatsApp notification will keep you on track.* Evenings are for sharing stories and enjoying great meals together. As we walk to dinner as a group, you'll find yourself laughing over the day’s experiences and forming friendships that will last long after the trip ends. Before bed, you'll receive a message with any updates for the next day’s itinerary.
*We use a WhatsApp group to communicate with everyone in-country and alert you to potential schedule changes. You will be required to use this platform during our trip. A key benefit of using WhatsApp is that it doesn’t require cell service to function—as long as you have a data package, you will be able to stay in contact with everyone. This can be a significant cost savings if you opt for purchasing an eSIM card for the country.
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You can expect 3-star accommodations in central, walkable locations with lots to see and do right outside the hotel door. Rooms will be comfortable but not luxurious. You’ll want to be prepared to climb stairs because many of the prime-location hotels that we stay in do not have elevators.
Rooming assignments: Our tour is priced to fill rooms, so if you’re joining us as a solo traveler you will be paired up with a roommate unless you purchase a single room upgrade at the time of booking.
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Breakfast and most dinners are included in your trip fee (see list of inclusions below for more details). Each morning you’ll eat breakfast in the hotel and each evening our group will gather for dinner together in delicious local restaurants. You will be responsible for your own lunch, but we will always be happy to make recommendations.
Vegetarian options are always available. Other special diet requests should be made at the time of booking. While we will make every effort to accommodate you, we cannot guarantee options for all dietary needs in every location.
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Once you’ve signed up for a trip we will send you a packing list. We always plan an opportunity to do laundry approximately halfway through the trip and most pack in carry-on sized luggage.
While not required, packing in a carry-on can avoid logistics nightmares if an airline looses your luggage and they are easier to carry up hotel stairs!
What’s included—and what’s not
We want you to feel confident about what’s covered in your trip cost and what extra expenses to plan for. By covering the essentials and giving you flexibility in other areas, we ensure a balance of structure and freedom—so you get the most out of your trip. Here’s a breakdown of what’s included in your tour fee and what you’ll need to budget for separately:
Included
✔️ Airport Transfers – From the moment you arrive, we’ve got you covered. We’ll pick you up at the airport and ensure a smooth transfer to your hotel. At the end of our journey, we’ll get you back to the airport for your flight home. Please be prepared to provide your flight information so we can coordinate your pickup.
✔️ Lodging – You’ll stay in well-located accommodations chosen for their character, convenience, and welcoming atmosphere. They will be comfortable, but not luxurious. Be prepared to climb stairs as many hotels in Europe do not have elevators.
✔️ All Major Ground Transportation – Whether it’s ferries, buses, or private coaches, all necessary transportation between tour destinations is arranged for you. On this trip, this includes airfare from Naxos to Athens.
✔️ Breakfast & Most Dinners – Start each day with breakfast at the hotel, fueling up for a full day of exploration. In the evening, we’ll enjoy a group dinner, featuring local flavors and great conversation. Exception: Of the 12-days we spend on the Greek islands, there will be 3 evenings when we do not eat together and you will have the opportunity to explore the local cuisine on your own.
✔️ All Site Entrance Fees – No surprise costs at the door. Your entry to historical sites, museums, and major attractions is covered, so you can focus on the experience.
✔️ Experienced Tour Coordinator – Your dedicated coordinator ensures everything runs smoothly, answers your questions, and helps create a seamless, stress-free travel experience.
Not Included
❌ Airfare & Baggage Fees – You’ll book your own flights to and from the tour destination. Be sure to check your airline’s baggage policies and budget accordingly.
❌ Lunches – Midday meals are on your own, giving you the flexibility to explore local cafés, grab a quick bite, or indulge in something special that catches your eye.
❌ Passport Application Fees – Your passport must have at least 6 months of validity past the end of this tour. If you need a new passport or renewal, be sure to take care of this in advance. Please be prepared to provide us a photo of your passport.
❌ Bottled Drinking Water – You’ll want to stay hydrated while exploring on your feet all day in the summer heat! Tap water is safe to drink, so consider bringing a reusable bottle to keep with you.
❌ Gratuities – Tips for local guides, bus drivers, and hotel staff are not included.
❌ Travel Insurance – Deposits are non-refundable. For peace of mind, each participant is highly encouraged to protect their travel investment by purchasing CFAR (Cancel For Any Reason) insurance immediately after booking your trip.