
savoring the cyclades
13 days/12 nights: September 13-25, 2026
Detour with Randy
Nowhere pulls me in quite like the Cyclades, where time slows, and the Aegean glimmers with a quiet kind of magic. Naxos, the island of gods and farmers, balances myth with abundance—marble ruins rising over fertile valleys. Sifnos hums with the scent of simmering stews and the chatter of taverna tables, a place where food is history on a plate. And then there’s Milos, raw and restless, its volcanic bones shaping moonscapes and hidden coves. These islands don’t just ask for admiration—they demand that you sink in, stay awhile, and savor. And that’s just what we’ll do on this slow-food-detour!
highlights include
Savor the sugar-cube sweetness of white-washed Cycladic architecture
Relish the rich tradition of olive oil production on Naxos
Storm the labyrinthine streets of Kastro and admire elegant Artemonas
Engage in farm-to-table cooking in the culinary epicenter of Sifnos
Learn the ancient craft of Sifniot ceramics
Cruise the white rock moonscape of Milos' dramatic Kleftiko coastline
itinerary
“My purpose holds To sail beyond the sunset, and the baths Of all the western stars, until I die.”
Greece’s sun-drenched Cyclades are a stunning cluster of islands where whitewashed villages tumble into turquoise seas, golden beaches meet ancient ruins, and every meal celebrates fresh flavors and timeless traditions. Our journey takes us through the Aegean’s most vibrant, flavorful, and dramatic islands. Naxos, the largest of the Cyclades, beckons with its lush landscapes, where rolling hills of olive groves and ancient ruins blend seamlessly with pristine beaches. Sifnos, the "Island of Flavors," delights with its traditional recipes, farm-to-table dining, and photogenic villages that feel like a step back in time. Finally, Milos captivates with its volcanic beauty, from the lunar landscapes of Sarakiniko to the colorful fishing villages of Mandraika and Klima. Join us for a feast for the eyes, the palate, and the soul as we savor the best of the Cyclades!
Day 1: Welcome to naxos!
Sunday, September 13, 2026
Naxos is that stunning island that has it all: fertile valleys lined with vineyards, olive and citrus groves, rustic mountains dotted with charming villages, ancient temples, Venetian castles, and pristine beaches lapped with crystal-clear waters. It’s no wonder Dionysus, god of wine, made the island his home. We’ll follow suit and check into our beach-side hotel where we’ll meet for a welcome reception followed by an orientation of the Chora, finishing with sunset at the famous Portus (Gate) of Apollo, followed by a seafood dinner in a local taverna.
Hotel: Porto Naxos | Activity Level: Moderate | Meals: D
day 2: a taste of naxos
Monday, September 14, 2026
Today we waste no time savoring the flavors of Naxos on a half-day foodie tour of the Chora. We’ll explore the maze of Naxos’ Old Town, climb to the Venetian Castle for a snack inspired by Venetian influence, and enjoy stunning views of the Aegean. We’ll savor traditional Naxian dishes at a family-run tavern, refresh with farm-fresh ice cream, and taste the famous “Kitron” liqueur at one of the island’s oldest stores. Then, we’ll sample local cheeses and explore herbs and olives at a historic grocery store. To finish, we’ll visit a cozy wine bar for a guided tasting of exceptional Greek wines. The rest of the day is yours to rest, digest, and recharge.
Hotel: Porto Naxos | Activity Level: Strenuous | Meals: B, L
day 3: village naxos
Tuesday, September 15, 2026
Today we’ll embark on a full-day island tour with our knowledgeable local guide, immersing ourselves in the beauty and charm of Naxos. Our journey will take us through picturesque villages, where tradition and culture come alive. We’ll marvel at Mount Zas, the highest peak in the Cyclades and the legendary childhood home of Zeus. Along the way, we’ll visit an unfinished marble Kouros statue, reflect on the stunning Temple of Demeter, and enjoy breathtaking vistas. To cap off the day, we’ll savor an olive oil tasting paired with a delightful happy hour at a historic olive mill and museum.
Hotel: Porto Naxos | Activity Level: Moderate | Meals: B, Happy Hour
day 4: Naxos freestyle
Wednesday, September 16, 2026
Today is all about Naxos, and how you choose to experience it is entirely up to you. Lace up your hiking boots and tackle Mount Zas, the highest peak in the Cyclades, where mythology meets breathtaking views. Set sail around the island, discovering hidden coves and turquoise waters, or feel the thrill of the Aegean by trying your hand at windsurfing. If relaxation is the goal, unwind on one of Naxos’ many beaches, from secluded stretches of sand to lively shores lined with tavernas. However you spend the day, savor every moment—tomorrow, we set off for the charm of Sifnos.
Hotel: Porto Naxos | Activity Level: Your Choice | Meals: B
day 5: Sumptuous sifnos
Thursday, September 17, 2025
Today we ferry to the savory island of Sifnos, renowned for its high-quality ceramics and its richly flavored cuisine. Indeed, traditional Sifniot cooking is baked in the same terracotta casserole dishes that have been produced on the island for centuries. Recently, such dishes have helped propel the island to notoriety as one of the Mediterranean's most exciting emerging foodie scenes, including the “Nikolaos Tselementes” Food Festival honoring the legacy of one of Greece’s most renowned chefs. With luck, we’ll coincide with the festival, which takes place in September and is a must-visit for food lovers and culture enthusiasts alike.
Hotel: Petali Village Hotel | Activity Level: Moderate | Meals: B, D
day 6: pottery & home cooking
Friday, September 18, 2026
We start the morning at a local pottery workshop, discovering the island’s most ancient and renowned craft. From there, we dive into a hands-on culinary experience, exploring another of Naxos’s treasures—its food. At a local farm and cooking school, we’ll see authentic food production in action and gather fresh ingredients for our meal. Then, just like the locals, we’ll come together around a wooden table beside a wood-burning oven, savoring the flavors of the island in the most authentic way possible.
Hotel: Petali Village Hotel | Activity Level: Moderate | Meals: B, L
day 7: Kastro & Artemonas
Saturday, September 19, 2026
Today we storm the Kastro-one of the most mysterious places on Sifnos. The white-washed village sits upon a domed rock that towers above the sea; built to protect the town from pirates and other attacks. After exploring the labyrinthine streets and archeological museum, we’ll continue to the nearby village of Artemonas, the gem of Sifnos. This beautiful settlement displays some of the most elegant traditional old mansions of Sifnos with verdant gardens. You’ll have time to stroll the photogenic village with its unique Venetian and neoclassical architecture. The afternoon and evening are yours to enjoy the serenity of Sifnos.
Hotel: Petali Village Hotel | Activity Level: Strenuous | Meals: B
day 8: Savoring Sifnos
Sunday, September 20, 2026
Today is yours to experience Sifnos at your own pace. Lace up your hiking boots and explore one of the island’s 19 scenic trails, winding through terraced hills, olive groves, and whitewashed villages. Prefer a slower rhythm? Stretch out on a sun-drenched beach, whether it’s the golden sands of Vathi or the tranquil shores of Faros. For photography lovers, Sifnos is a dream—wander through charming alleys lined with sugar-cube houses, blue-domed churches, and vibrant bougainvillea. Savor a long taverna lunch, sample local cheeses and chickpea stew, or simply soak in the island’s laid-back elegance. The day is yours!
Hotel: Petali Village Hotel | Activity Level: Your Choice | Meals: B
day 9: Moonscaped Milos
Monday, September 21, 2026
Today we ferry south to Milos, a volcanic masterpiece where nature has painted the land in fiery reds, stark whites, and deep ochres. This island boasts over 40 distinctive beaches, each with its own character—Sarakiniko’s moon-like white rock formations, Kleftiko’s hidden sea caves, and Tsigrado’s tucked-away sands. Beyond its dramatic coastline, Milos is home to charming fishing villages like Klima and Mandrakia, where colorful boathouses line the shore. As the birthplace of the Venus de Milo, the island blends rich history with raw natural beauty. We’ll settle into our seaside retreat and gather for a delicious dinner, savoring Milos’ island flavors.
Hotel: Milos Breeze Hotel | Activity Level: Moderate | Meals: B, D
day 10: milos Island Tour
Tuesday, September 22, 2026
We'll kick off the day in Plaka, stepping back into Milos' ancient history at the Archaeological Museum. From there, we’ll head to the early Christian Catacombs and the ancient Theater, where we can take in sweeping views of the Aegean. Next, we’ll head to the colorful fishing villages of Klima and Mandrakia, soaking in their charm. In the afternoon, we’ll head to Sarakiniko, Milos' iconic moonscape beach, where we can snap stunning photos of its unique white volcanic rock formations and enjoy a refreshing swim in the crystal-clear waters.
Hotel: Milos Breeze Hotel | Activity Level: Strenuous | Meals: B
day 11: Kleftiko by Catamaran
Wednesday, September 23, 2026
Known for its pirate history, Kleftiko’s dramatic coastline features stunning rock formations and hidden sea caves accessible only by boat. Today we’ll explore Kleftiko by catamaran. As we cruise through turquoise waters with plenty of swim stops in the crystal-clear coves, we’ll marvel at underwater arches and vibrant marine life. We'll also have the chance to explore the caves by boat or even swim inside, experiencing the serene beauty and mystique of this unique Milos landmark. Lunch will be served aboard our boat. The afternoon and evening are free to enjoy Milos as you like.
Hotel: Milos Breeze Hotel | Activity Level: Moderate | Meals: B, L
day 12: Choose your own Adventure
Thursday, September 24, 2026
This final day on Milos is yours to enjoy at your own pace. Take a short ferry ride to the neighboring island of Kimolos, a hidden gem with whitewashed alleyways, quiet beaches, and a laid-back charm. Prefer to stay put? Unwind on one of Milos’ stunning beaches, lounge by our hotel’s pool, or take a leisurely swim in the turquoise waters. As the sun dips low, we’ll come together for a wine tasting at the Kostantakis Cave Winery, savoring local flavors as we toast to new friendships and unforgettable adventures before sitting down for one last dinner together.
Hotel: Milos Breeze Hotel | Activity Level: Your Choice | Meals: B, HH, D
day 13: Detour over
Friday, September 25, 2026
Our detour ends after breakfast, but that doesn’t mean your Cycladic exploration needs to. If you have time, consider venturing on to wild Folegandros or stunning Santorini, or dive into Athens’ layered history. If you’re homeward bound, it’s a 45-minute flight back to Athens where you can catch your international flight home.
$6,795 per person double occupancy
+$1,200 single supplement
10% deposit
Save $300 with EARLYPAY coupon until Jan 12
FAQs
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Each detour includes the price of all admissions to sights seen as a group; tours by local guides, meals as listed in the trip itinerary; accommodations each night of the detour including breakfasts; all domestic flights; all transportation required for group activities from the first hotel to the last hotel of the detour including in er-country flights (transportation for optional group activities and independent travel during the detour is not included), travel consultations and advice from our staff, guides, and vendors including suggestions, tips, and directions, and all trip leader, local guide, driver, and hotel tips. Prices do not include airfare to and from the detour, nor ground transportation to/from airports.
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Detour prices do not include international airfare or ground transportation to/from the airport.
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Each detour includes all breakfasts and about half of your lunches and dinners as indicated in the meal guide included in each itinerary: B=breakfast, L=lunch, D=dinner.
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Yes! Our detours are the perfect way for children (and adults) to learn in action. We welcome and celebrate multi-generational travel. History class was never so fun!
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Our detour begins in Naxos at our first hotel, where we will meet for a welcome reception around 6 pm. Our trip ends on Milos, where you can catch a short 40-minute flight back to Athens, or enjoy a scenic ferry.
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While this varies by detour, we generally plan to meet between 5-6 pm at our hotel on Day 1. If you plan to arrive a day early and want to stay in our trip hotel, please make arrangements with the hotel directly, indicating that you are part of our group.
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You can book a connecting flight to Naxos from your international flight to Athens. Likewise, you can book a flight from Milos to Athens for your connecting international flight home.
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Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.
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Deposits are refundable for 30 days from receipt. After 30 days they are nonrefundable.
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Final payment is due 90 days prior to detour commencement but you may pau in full any time prior to this.
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Cancellations are allowed without penalty (excepting deposit) until the final payment deadline. After the final payment deadline 100% of funds paid are nonrefundable.
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Each trip page has a “book now” button that links to our online registration and payment system. There you can pay the 10% per person deposit and choose to pay in installments or to pay the full amount.
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Yes, all published prices are per person, based on double occupancy, or when available, single occupancy. Please contact us for triple occupancy pricing.
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During the registration process you will have the opportunity to request single occupancy, if it is offered. Due to the boutique nature of our hotels, we are not always able to offer single accommodations, but are happy to pair you with another single traveler.
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Yes. You must be able to carry your own luggage up at least three flights of stairs and on uneven ground for up to a quarter mile.
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Dressler Detours are physically demanding. To enjoy the experience, you must be in good walking shape. The most active days may average 5 miles of walking (often over uneven surfaces and including lots of climbing/steps), lots of standing while listening to your guide during group sightseeing, and possibly stair-climbing while carrying your own bag up to your hotel room. This detour includes boat travel as well. We’ve included an activity guide for each day of our itinerary: light=mostly sedentary, moderate=walking 1-3 miles on mostly even ground, strenuous=walking 3+ miles on hills/uneven ground.