greek odyssey

13 nights/14 days: September 27-October 10, 2025

Detour with Randy

Greece is central to understanding our world. Greece gave birth to democracy, philosophy, and the sciences. The ancient Greek city-states laid the foundation for modern political systems, emphasizing citizen participation and the rule of law. Greece's contributions to literature, through epic poems like the Iliad and the Odyssey, and theater, with playwrights like Sophocles and Euripides, continue to resonate in modern storytelling. Moreover, Greek mythology has left an indelible mark on art, literature, and popular culture worldwide. From its architectural marvels like the Parthenon to its enduring legacy in Olympic Games, Greece's impact endures, making it a fundamental cornerstone in comprehending humanity. Unpack the origins of Western civilization with me on this Greek odyssey!

highlights include

  • Enjoy mythological happy hours with a classics expert and master storyteller!

  • Consult the oracle at mystical Delphi

  • Heal what ails you in Epidaurus

  • Explore the “Minoan Pompeii” at Akrotiri

  • Walk in the footsteps of Agamemnon in Mycenae

  • Discover the birthplace of Apollo on Delos

Greek Theater Epidaurus Greece

itinerary

Join us on an odyssey through the cradle of Western civilization! From the proudly perched Parthenon to the mystical ruins of Delphi, we’ll muse in the stories of a civilization at the heart of our own. We’ll discover the birthplace of democracy and philosophy in Athens, the origins of the modern Olympics at Olympia, and the epicenter of medicine at Epidaurus. We’ll savor the flavors of the Mediterranean and toast to our adventures high above the sea-filled crater of Santorini at sunset. We’ll enjoy the added benefit of a classics expert and master story teller who will enrich our journey with tales of the mythology and history of this essential country.

When you set out for Ithaca, then pray that the road is long, full of adventure, full of knowledge.”
— C.P. Cavafy

day 1: arrival in athens

Bouganvilla on Narrow Street in Athens Plaka Greece

Saturday, September 27, 2025

Our odyssey begins in Athens’ colorful Plaka district at the base of the Acropolis. We'll gather in our hotel around 6 p.m. for a welcome reception with splendid views of the Parthenon. Afterward, we’ll dive into the meandering streets of Plaka, delighting in its vibrant shops, lively bars, and delectable tavernas.

Athens is a 30-minute taxi ride from the Eleftherios Venizelos international airport.

Hotel: Central Hotel | Meals: HH (Happy Hour) | Activity Level: Moderate

day 2: All things acropolis

Sunday, September 28, 2025

The morning is yours to explore Athens’ delightful shops, museums, and sites. We’ll dedicate the afternoon to the Acropolis, the religious center of ancient Athens. With the expertise of a local guide, we’ll visit the Acropolis Museum, built to showcase the Acropolis’ incredible sculptures. Then we’ll scale the rocky outcrop where Athena’s gift of the olive tree made her the namesake of Athens. From the Parthenon’s iconic columns to the Erechtheion's graceful Caryatids, we’ll experience the zenith of Classical Greek civilization at the golden hour-perfect for photos! We’ll descend into Plaka where we’ll enjoy a sumptuous meal of Greek specialties together.

Hotel: Central Hotel | Meals: B, D | Activity Level: Strenuous

day 3: healing vibes in epidaurus

Monday, September 29, 2025

We start our morning with a visit the to the National Archaeological Museum where we’ll experience an unparalleled collection of ancient marvels before boarding our coach for Epidaurus. Dedicated to Asclepius, the god of healing, Epidaurus was home to a healing center where pilgrims sought remedies and solace through sacred rituals and sacrifices to Asclepius’ father, Apollo. Renowned for its spectacular theater-an architectural marvel famed for its near-perfect acoustics-Epidaurus is a symbol of artistic and engineering mastery. This afternoon we’ll settle into the charming seaside town of Nafplio, where we’ll enjoy a slower pace for the next two nights.

Hotel: Park Hotel | Meals: B, D | Activity Level: Strenuous

DAY 4: seaside bliss in nafplio

Tuesday, September 30, 2025

The day is yours to explore Nafplio. Stroll through the narrow streets of the old town where Venetian and Ottoman influences blend seamlessly into a vibrant mix of cultures. Explore Syntagma Square, graced by elegant buildings and charming cafes, or wander along the waterfront promenade for breathtaking views of Bourtzi, a small fortified island. If you're feeling sporty, climb the 1000 steps to the Venetian fortress (or take a taxi directly to the back entrance) and be rewarded with stunning views of the Aegean Sea. After your day of exploring (or relaxing), we'll gather for a mythical happy hour at our hotel.

Hotel: Park Hotel | Meals: B, HH | Activity Level: Your Choice

Day 5: mighty mycenae, nimble nemea

Wednesday, October 1, 2025

Well rested from our seaside slumber, we venture this morning to mighty Mycenae. Founded by the hero Perseus and made famous by King Agamemnon of Illiad infamy, it was believed this city was built by the Cyclopean giants. After lunch at the base of this powerhouse city, we’ll detour to the delightful archeological site of Nemea-home to the Nemean Oracle and the Nemean Games-where we’ll warm up for the main event in Olympia. The afternoon finds us in the pastoral hills of Olympia where we’ll settle in for two nights, training over a mythical happy hour.

Hotel: Hotel Pelops | Meals: B, L, HH | Activity Level: Moderate

day 6: olympic spirit

Thursday, October 2, 2025

Lace up your running shoes because today we’ll visit the site of the ancient Olympic games. Held in Olympia every four years, these games were a celebration of Greek culture and unity. The competitions included events such as running, wrestling, boxing, and chariot racing. Beyond athleticism, these games held religious significance, honoring the Greek gods, especially Zeus, and fostering a temporary truce among warring city-states. We’ll run in the tracks of the ancient Greeks and reflect on the legacy of Olympic spirit that is still alive today. The evening we’ll enjoy another mythical happy hour before a free evening.

Hotel: Hotel Pelops | Meals: B | Activity Level: Strenuous

day 7: mystical delphi

Friday, October 3, 2025

The scenic drive from Olympia to Delphi awaits us. We’ll cross the spectacular Rio-Antirro Bridge, pass the Venetian fortress in Nafpakto to the Gulf of Corinth where we’ll hug the shimmering shoreline, ascending into the pine-laden hills of Delphi. Nestled amidst the rugged slopes of Mount Parnassus, Delphi was an ancient sanctuary revered as the center of the world. This mystical site was home to the legendary Oracle of Delphi who imparted enigmatic prophecies, drawing seekers from far and wide to decipher their destiny. Upon arrival, we’ll visit this mystical site, musing over our own destinies. The evening is free to enjoy Delphi’s cozy tavernas.

Hotel: Kastalia Boutique Hotel | Meals: B | Activity Level: Strenuous

day 8: mykonos: island of the winds

Saturday, October 4, 2025

This morning we bid Delphi farewell and make our way to Athens’ airport to catch our flight to Mykonos. Nestled in the heart of the Cyclades, Mykonos is known as the "Island of the Winds," welcoming us with its sun-kissed beaches, wave-lapped buildings, and iconic windmills standing sentinel over the azure horizon. This evening we’ll stroll through the labyrinthine streets of Mykonos town, where sugar cube buildings with vibrant blue accents create a postcard-perfect backdrop. We’ll enjoy dinner together in one of our favorite restaurants.

Hotel: Porto Mykonos | Meals: B, D | Activity Level: Moderate

day 9: to beach or not to beach

Sunday, October 5, 2025

Today is a free day to choose your own adventure. Get lost in the town’s labyrinth, satisfy your souvenir list at the myriad boutiques, savor the day away in the open air cafes, or visit one of Mykonos’ stunning beaches. Whatever you choose to fill your cup, we’ll gather together to fill our collective cups over our mythical happy hour at our hotel, watching the crimson sun sink into the Aegean Sea.

Hotel: Porto Mykonos | Meals: B, HH | Activity Level: Moderate

day 10: delos: island of apollo

Monday, October 6, 2025

This morning we’ll travel by boat to “Apollo’s island." Delos was believed to be the birthplace of Apollo, the god of the sun, and his twin sister Artemis, the goddess of the hunt. As a result, it became a major religious center and a bustling hub of trade and commerce. Today, Delos stands as an open-air archaeological museum, showcasing the remnants of its rich past. We will explore well-preserved ruins of temples, sanctuaries, theaters, and intricate mosaics, offering a fascinating glimpse into the island's former grandeur. The evening is free for exploration, relaxation, or dancing the night away at one of the island's famous beach parties.

Hotel: Porto Mykonos | Meals: B | Activity Level: Your Choice

day 11: seductive santorini

Tuesday, October 7, 2025

This morning we bid Mykonos farewell and ferry to stunning Santorini. Shaped by one of the largest volcanic eruptions in history around 1600 BCE, Santorini’s steep, multicolored cliffs host blue-domed churches, whitewashed alleyways, and unforgettable sunsets that paint the sky in shades of pink and orange. We’ll tuck into our own cliff-clinging hotel perched on the rim of the caldera with picture-perfect views over the crater. Tonight we enjoy possibly the most scenic mythical happy hour yet, toasting our first night in Santorini over sunset before dinner together at our hotel.

Hotel: Volcano View Hotel | Meals: B, HH, D | Activity Level: Moderate

day 12: santorini’s ancient side

Wednesday, October 8, 2025

There’s good reason Santorini is the most famous island in the world. Apart from its breathtaking sunsets, iconic blue-domed churches, and unique volcanic beaches, Santorini was home to a thriving civilization whose remains at Akrotiri, often referred to as the “Minoan Pompeii,” offer a glimpse into the ancient life of the island. Today we’ll dive into Santorini’s explosive past with a guided visit to Akrotiri. We’ll savor lunch seaside at Kamari’s black sand beach, and cap off our dive into Santorini’s past in Fira’s fine archeological museum. The evening is yours to lose yourself in Fira’s vertical streets, trendy bars, irresistible shops, and stunning sunsets.

Hotel: Volcano View Hotel | Meals: B, L | Activity Level: Strenuous

day 13: savoring santorini

Thursday, October 9, 2025

Our last day together is yours to soak up Santorini however you like. Hike along the caldera’s rim to Fira or Oia, swim in the crater’s thermal waters, visit one of Santorini’s volcanic beaches, or just lounge at our stunning hotel’s view-laden swimming pools. We’ll wrap up our odyssey over a final mythical happy hour at our hotel, followed by dinner together where we’ll toast to our adventures and plan our next detours!

Hotel: Volcano View Hotel | Meals: B, HH, D | Activity Level: Your Choice

day 14: detour over

Friday, October 10, 2025

Our odyssey concludes after breakfast. Santorini is a quick, 45-minute flight to Athens, where you can catch your return flight home, or you may choose to continue your exploration of the Greek isles by ferry. Knowing this won’t be our last detour together, don't say goodbye; instead say tha se tho syntoma ("I'll see you soon")!

Stunning Blues of Santorini Views from Fira Seahorse
Bronze Statue of Apollo Ahtens National Archeological Museum
Beautiful Labrythine Street in Mykonos with Blue Doors Whitewashed Houses Bouganvilla
Temple Detail Mystical Sacred Delos
Windmills in beautoful Mykonos Cycladic Islands Greece
Santorini Street Fira Mediterranean Whitewashed Houses

$5,495 per person (double/triple occupancy)

$6,195 per person (single occupancy)

10% deposit

$300 early pay discount until January 27, 2025 with coupon: EARLYPAY

FAQs

  • 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 transportation required for group activities from the first hotel to the last hotel of the detour (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.

  • Detour prices do not include international airfare or ground transportation to/from the airport.

  • 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.

  • Our groups range from 10-20 participants with 1-2 trip leaders and local guides to connect us to local culture and experiences.

  • 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!

  • We will meet at 6 pm the Central Hotel in Athens’ colorful Plaka neighborhood where we will have a welcome reception to become acquainted follow by a group dinner together.

  • The Athens Eleftherios Venizelos international airport is a quick 30-minute taxi ride to our hotel.

    Our trip ends on Santorini from where you may book your return flight or ferry to Athens, or use it as a jumping off point for further Mediterranean travels.

  • We will meet at 6 pm on September 28. 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.

  • 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.

  • Deposits are refundable for 30 days from receipt. After 30 days they are nonrefundable.

  • Final payment is due 90 days prior to detour commencement but you may pay in full any time prior to this.

  • Cancellations are allowed without penalty (excepting deposit) until the final payment deadline. After the final payment deadline 100% of funds paid are nonrefundable.

  • 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.

  • Yes, all published prices are per person, based on double occupancy, or when available, single occupancy. Please contact us for triple occupancy pricing.

  • 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.

  • 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.

  • 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. 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.