Our journey through Athens and the Greek Islands is a celebration of history, culture, and the timeless beauty of the Aegean. We begin in Athens, the birthplace of Western civilization, where ancient temples rise above a vibrant modern city. As we wander the cobblestone lanes of Plaka and stand before the mighty Acropolis, we feel the enduring spirit of the Greek gods and philosophers who shaped the world’s earliest ideas of art, democracy, and beauty.
From Athens, we ferry to the Cyclades Islands, where island life moves to a gentler rhythm. On Tinos, we discover a world of whitewashed villages, terraced hillsides, and age-old craftsmanship. Our days blend gentle hikes through marble-sculpted landscapes with intimate encounters—like cooking alongside a local host in her home or sharing lunch in a seaside taverna. Each step reveals another layer of Cycladic tradition, from the intricate dovecotes to the artistry that has defined this island for centuries.
Our adventure continues on to Naxos and Santorini, where mythology and natural splendor intertwine. We follow ancient trails past olive groves and up to the summit of Mount Zeus, where legend says the king of gods was born. On Santorini, we trace the dramatic rim of the caldera, kayak along volcanic cliffs, and toast the sunset over the shimmering sea. Throughout our journey, the spirit of Greece shines through—in the warmth of its people, the richness of its flavors, and the timeless landscapes that remind us what it means to travel deeply and with wonder.
Welcome to Athens
Often referred to as the cradle of Western civilization, Athens has been continually occupied by people for the last 7,000 years. One can hardly move without bumping into an ancient ruin or building, which evokes imagery of the Greek gods and the wisdom of philosophers.
In the afternoon, we meet at our hotel for an introductory talk, followed with a walk around Plaka, the oldest neighborhood of Athens. As evening falls, we have our first dinner together in a traditional Greek restaurant, getting to know one another in eager anticipation of our adventure ahead.
Athens Gate HotelAthens, Greece
The Athens Gate Hotel is a 4-star hotel located in the historic heart of the city. It is situated directly opposite the Temple of Olympian Zeus and Hadrian’s Arch. The hotel is known for its rooftop restaurant and bar, which offers panoramic views of the city, including the iconic Acropolis.
Acropolis and Ferry to Tinos
No matter how many photographs we've seen, nothing prepares us the moment we witness the Acropolis in person, still standing proudly after thousands of years. Alongside our specialized guide, we journey back in time and reflect on the splendor, power, and enduring legacy of this remarkable city.
In the afternoon, we drive to the port of Rafina and take the ferry to Tinos. Here, fascination lies in the island's more than forty beautifully preserved villages, its intricate dovecotes, stone huts and the terraced hillsides shaped by hand over generations.
Porto RaphaelTinos, Greece
Porto Raphael, located in one of the most beautiful areas of Tinos, will inspire you with its spectacular view of Mykonos and Delos. On the restaurant and cafe verandas you can enjoy traditional island food and relax while gazing at the Aegean Sea.
Volax to Tinos & Cooking Class
We begin our day in the surreal village of Volax, where whitewashed cottages sit among enormous round boulders scattered like dice by the gods. The origins of these formations remain a mystery volcanic to some, cosmic to others—while philosopher Cornelius Castoriadis once declared that Tinos was “not made by human hand.”
From Volax, we hike toward the dramatic rock of Exombourgo, crowned by a medieval castle, before descending into Tinos town for lunch and some time to relax at the hotel.
In the afternoon, we visit Mrs. Nikoleta, who welcomes us into her home for a hands-on cooking class. With her guidance, we prepare traditional Cycladic dishes using local herbs, fresh vegetables, and treasured family recipes.
Panormos Port to Pyrgos Village
We begin today’s hike in Panormos, a quiet fishing village once central to Tinos’s marble trade. Our scenic trail leads uphill to Pyrgos—the island’s renowned marble village, where doorways, fountains, and even bus stops are adorned with intricate carvings. The legacy of generations of Tinian sculptors lives on in every corner.
In Pyrgos, we visit the Museum of Marble Crafts, take a break beneath the shaded plane tree in the main square, and enjoy some free time to explore the alleys and nearby workshops. From there, we follow a loop trail that descends past windmills, dovecotes, and quiet chapels back toward Panormos, where we enjoy lunch by the sea—with time for a swim if anyone wishes.
We return to the hotel by late afternoon, and the evening is free for dinner on your own.
Ferry to Naxos and Hike to Chalki
As our ferry arcs towards Naxos, we catch our first glimpse of the Portara—a marble gateway standing proudly on a headland, the last remnant of a temple once dedicated to Apollo. It's a striking welcome, and just the beginning of our adventure here.
After settling into our hotel and enjoying a light lunch, we head out for our hike, starting at the site where two “small” Kouroi—unfinished statues abandoned in the marble quarries over 2,600 years ago—still lie in quiet repose. Our trail leads us towards the Upper Castle, a former Venetian stronghold, passing olive groves scented with thyme, oregano, and sage. We end the day in the elegant village of Chalki, once the commercial center of the island and still home to neoclassical mansions and citrus-scented courtyards, where we enjoy dinner together.
Porto NaxosNaxos, Greece
Located just minutes from the heart of Naxos Old Town and the sandy beach of Agios Georgios, the renovated and inviting Porto Naxos offers contemporary designed rooms, blended with superior comforts and the magical breeze of the Aegean. Enjoy the outdoor pool and on-site restaurant, Thyme & Olive, serving authentic Greek cuisine.
Mount Zeus
Naxos is home to the highest mountain in the Cyclades—Mount Zeus—and the hike to its summit is perhaps the most epic in the region. In ancient times, locals believed the cave on its northwest flank was the birthplace of the god Zeus himself, and climbing it, you may well feel that mythology and landscape are one and the same.
After our hike, we head to Apeiranthos for lunch—a stunning mountain village of marble alleys and stone-built houses that seems to grow organically from the mountainside.
The afternoon is free to relax with a swim at the beautiful sandy beach in front of our hotel or explore the charming streets of Naxos town. In the early evening, we take a guided walk through the Venetian quarter, uncovering its hidden corners and layered history. Afterwards, enjoy free time for dinner and a sunset stroll by the iconic Portara.
Santorini and Oia Village
This morning we ferry to Santorini, crossing the deep blue Aegean as the island’s striking cliffs rise into view—layered in volcanic tones and topped with whitewashed villages that seem to defy gravity. After settling into our hotel, we set out on one of the island’s most scenic walks: the caldera-edge trail from Imerovigli to Oia.
Following the rim of the volcanic crescent, our path offers breathtaking views of the caldera, tiny chapels perched on cliffs, and the ever-changing colors of sea and sky. Our hike concludes in Oia, a postcard-perfect village known for its narrow marble alleys and blue-domed churches. Explore town at your leisure before dinner on our own.
Aperonto SuitesSantorini, Greece
Facing the infinite blue of the Aegean and the beautiful rural landscape of Santorini, the brand new Aperanto Suites are tucked away in a peaceful neighborhood near Oia—one of the most picture-perfect towns on the island. The suites boast large and bright spaces throughout, complemented by delicious breakfast options, and an ample pool area and sun-terrace.
Akrotiri & Kayak the Coast
Today, we visit Akrotiri, Santorini's principal archaeological treasure. This ancient coastal settlement, established around the third millennium BCE, grew into a prosperous city thanks to its strategic location on the trade route between Europe and the Middle East. Its life was abruptly ended in the late 17th century BCE by a volcanic eruption that buried the entire island in ash. Like Pompeii, the thick ash preserved the buildings and their contents, making Akrotiri one of the most important archaeological sites in the Aegean.
Afterward, change into your swimwear for a scenic sea kayaking adventure along Santorini's stunning coastline. We paddle past red cliffs, secluded pebble beaches, and crystal-clear waters, experiencing the island from a unique perspective. The afternoon is yours to relax or explore at your own pace, before gathering for our farewell dinner in Fira with breathtaking views of the Caldera at sunset.
Departure
Our journey in Greece concludes after breakfast with independent departures to the airport or onward travels.
Please note that this is a typical itinerary, and actual activities may vary due to weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these or the order visited should the need arise.
9 Days
Sep 15-23, 2026
$6,595 Per Person
First two reserved:$700
Additional:$1,200
See single supplement policy below.
SINGLE SUPPLEMENT: Accommodations are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability.
Single Supplement for Scheduled Group Departures. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement. This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Free or reduced single supplements are not combinable with other offers or promotions.
If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and request a roommate but one is not available, you will receive a $500 reduction from the standard single supplement (unless otherwise noted in the detailed itinerary for your specific trip).
Single Supplement for Custom Tours. Custom Tour prices are generally based on two or more participants; therefore, single supplements for “solo” Custom Tours will vary and are available upon request.
Boundless Journeys' trips are designed for active individuals who have a spirit of adventure and a positive attitude. Greece: Athens to the Aegean Islands is rated 3, moderate, on a scale of 1-5 (with 5 being the most strenuous). It features walks of varying lengths and easy-to-moderate difficulty that average 3-5 hours per day. Walks on this tour will be on varying terrain, including cobblestone streets in and around villages and some dirt roads and rocky trails. Walks are broken up by rest, cultural activities, and meals. Please refer to the detailed itinerary for descriptions of the activities on each day of the trip.
Santorini, Greece
Temperatures in Greece in September during the day typically fall between the mid-70's and mid to upper-80's °F. In the evenings, conditions remain mild with lows in the low to mid-60s°F. Humidity levels drop compared to the summer months, particularly on the islands where gentle breezes offer added comfort. The skies stay mostly clear with abundant sunshine, and rainfall remains minimal throughout this period. The sea temperature is still warm and pleasant, ranging from around 73 to 77 °F.
As September progresses, temperatures start to cool down slightly compared to the summer months. However, it remains warm and comfortable, especially during the daytime.
Athens
High: 83 Low: 68
Cyclades Islands
High: 79 Low: 66
Most Convenient AirportArrival: Athens International Airport Eleftherios Venizelos (ATH).Departure: Santorini Airport (JTR), also known as Thira National Airport.
Arrival RecommendationAlthough it may be possible to arrive to Athens on the morning that your Boundless Journeys trip begins, we recommend arriving at least one day ahead to allow for any travel delays and to recover from the effects of jet lag.
Meeting Time and PlaceYour guide(s) will meet you at 6:30 p.m. in the lobby of the Athens Gate Hotel on Day 1 of your trip.
Departure Time and PlaceYour Boundless Journeys experience will end after breakfast on Day 9, September 23rd. You may opt to extend your stay in Santorini, continue on to other Greek Islands, or return to Athens.
The cuisine of Athens and the Greek Islands is a vibrant reflection of the Mediterranean way of life—fresh, flavorful, and deeply connected to the land and sea. In Athens, traditional Greek cooking meets modern creativity, with chefs reimagining classic dishes in lively tavernas and sleek urban eateries. You'll find beloved staples such as grilled lamb, moussaka, and spanakopita, as well as meze—small shared plates of olives, tzatziki, dolmades, and fried zucchini. Local markets overflow with ripe tomatoes, fragrant herbs, and golden olive oil, while café culture thrives with thick Greek coffee and syrupy sweets like baklava and loukoumades.
Across the Greek Islands, cuisine takes on a more regional and rustic flair, shaped by local ingredients and island traditions. Freshly caught seafood is the star of many meals—think grilled octopus, red mullet, and lobster pasta—served simply with lemon and herbs. Each island adds its own signature: Santorini's cherry tomatoes and fava purée, Naxos's rich cheeses and potatoes, Tinos's artisanal sausages and capers. Meals are often shared outdoors, accompanied by local wines, creating an atmosphere that is as much about connection and celebration as it is about food.
With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work—the mark of a truly great leader—our guides make magical things happen and add a dimension to your trip that you could not experience on your own. Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.
Our journey through Athens and the Greek Islands is a celebration of history, culture, and the timeless beauty of the Aegean. We begin in Athens, the birthplace of Western civilization, where ancient temples rise above a vibrant modern city. As...
Walking, hiking, and kayaking, 3-5 hours per day, moderate, with one day of kayaking.
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