Combine outdoor fun with 5-star luxury on this 10-day adventure through Greece. Start on the mainland with a kayaking trip along the Athenian Riviera; then, you're off to Crete, where you'll balance a rugged hike through the Samaria River Gorge with food and wine tasting around the Old Town of Chania. Stop in Heraklion for farm-to-table dining and a descent into the mythical Cave of Zeus, and end on Santorini for a private sunset sailing cruise and a trek through the island's volcanic landscapes.


  • Relax at the 5-star AthensWas Hotel and take in panoramic views of the Acropolis 
  • Kayak beneath the clifftop Temple of Poseidon on the Athenian Riviera
  • Hike the rocky mountain peaks and rushing waters of Samaria River Gorge
  • Tour the ruins of Knossos Palace, once thought to house the mythical Minotaur
  • Learn about wine production and picnic at an organic farm on Santorini

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner with Acropolis View Athens
Day 2 Sea Kayaking Tour of Sounio & Poseidon Temple, Athenian Riviera Dinner Athens
Day 3 Fly to Chania, Old Town Cultural Walking Tour, Food & Wine Tastings Chania
Day 4 Hiking Fun in Samaria River Gorge, Authentic Cretan Dinner Chania
Day 5 Transfer to Heraklion, Explore the City, Farm-to-Table Dining Experience Heraklion
Day 6 Guided Excursion to Lassithi Plateau: Cave of Zeus & Knossos Palace  Heraklion
Day 7 Ferry to Santorini, Evening of Dinner & Wine Santorini
Day 8 Free Morning to Explore, Sunset Catamaran Cruise & Barbecue  Santorini
Day 9 Guided Hike of Santorini's Caldera, Farm Picnic in Oia Santorini
Day 10 Depart Santorini  

Detailed Itinerary

Day 1: Arrive in Athens, Welcome Dinner with Acropolis View

Enjoy incredible views from your hotel's Michelin-starred restaurant (photo courtesy of AthensWas)

Welcome to Greece! Your flight lands in the capital city of Athens, a bustling metropolis that combines ancient landmarks and architecture with a modern, upscale vibe. Your driver will meet you at the airport and transport you to your accommodations at the AthensWas, a 5-star boutique hotel located just steps from Greece's famed Acropolis. Offering tastefully appointed rooms with a 70s retro theme, you'll enjoy luxurious amenities, proximity to major sightseeing spots, and an on-site Michelin-starred restaurant with panoramic rooftop views. 

Once you've had a chance to rest and regroup, head out on a self-guided exploration of the city, starting with a walk around the Acropolis. This ancient citadel sits above the city and is considered the cornerstone of Greek history and culture. In addition to being the home of the Parthenon, you'll find the ruins of several historically significant buildings here, not to mention stunning city views. Stroll down Dionysiou Areopagitou Street, making your way along the narrow pathways of Plaka and Anafiotika, and stop in at the Monastiraki neighborhood's lively flea market for souvenirs. 

This evening, discover the culinary wonders of Athens with dinner at a recommended restaurant. Options include everything from traditional Mediterranean meals to high-end fusion and quaint seaside cafés. You'll be able to choose based on your own preferences, and a private driver can be arranged if you desire. 

Day 2: Sea Kayaking Tour of Sounio & Poseidon Temple, Athenian Riviera Dinner

Explore Cape Sounio and the Temple of Poseidon via a privately guided kayak tour 

Discover more of Greece today via a private kayaking tour, meeting your guide in the morning and heading toward Cape Sounio (Sounion), located on the southern tip of the Attica peninsula. This scenic drive takes you along the Athenian Rivera, a beautiful coastline with hidden bays and white-sand beaches. Arrive at your launch site, and after a safety and equipment briefing, begin your paddling adventure along the turquoise waters of the coast.

Cruise along the sparkling sea, stopping on the island of Archi if the weather permits or on one of the many beaches for a swim and snack. Then, continue to Cape Sounio and the Temple of Poseidon, a gorgeous marble ruin that was originally built in the fifth century to honor the god of the sea. Enjoy sea-level views of the temple, then come ashore to tour the temple grounds on foot, taking in the immense columns and ancient remains. 

The day ends with an indulgent gourmet dinner at one of the Riviera's premiere restaurants. Choose from dishes that include fresh fish and other seafood (including a "catch of the day" prepared two ways), traditional Greek appetizers, and delicious local desserts, all paired with various wines. Afterward, your driver will return you to your hotel in Athens, where you can rest up after your excursion.

Day 3: Fly to Chania, Old Town Cultural Walking Tour, Food & Wine Tastings

Stroll the colorful streets and harbor of Chania's Old Town 

This morning, check out of your hotel and head to your next destination, Chania. This picturesque port town is located on the island of Crete and is known for its beautiful Venetian harbor, winding streets, and delicious cuisine. Your driver will transfer you to the airport for the one-hour flight, and another driver will meet you to take you to your hotel, the Domes Zeen Resort. This 5-star accommodation sits nestled within a lush, tropical garden, with easy beach access and views of Chania town. Rooms here offer private pools and Jacuzzis, city views, and a chic bohemian aesthetic. 

Relax at your hotel for a bit, then step out on a privately guided walking tour of Chania's Old Town, which takes you through the layers of this ancient city's history, culture, and gastronomy. Your guide will introduce you to local artisans to learn about their crafts and work, and you'll have a chance to explore the town's centuries-old market, home to assorted Cretan products and groceries.

Watch a pastry maker prepare handmade phyllo dough, stroll around the old Ottoman and Jewish Quarters, and see the Street of the Knives, where traditional Cretan knives are crafted. End the tour at a local restaurant, enjoying a traditional repast of meze (small plates), wine, and raki, a grape-based pomace brandy considered Greece's national drink. 

Day 4: Hiking Fun in Samaria River Gorge, Authentic Cretan Dinner 

Get out in the great outdoors of the Samaria River Gorge

Experience the great outdoors of Crete today on a privately guided hike through what is considered Europe's longest river gorge, Samaria. Part of Samaria National Park, a UNESCO Biosphere Reserve in Crete's White Mountains, the 10-mile (16 km) trek takes you along rocky mountain peaks and scenic countryside, all accompanied by the sights and sounds of the rushing river. Travelers should take note that this is a somewhat strenuous hike, and proper footwear and attire are highly recommended. 

You'll meet your guide in the town of Omalos, setting out from the Omalos Plateau and following the riverbed. Take in the steep mountain views and hills, hiking along the well-maintained route as your guide explains more about the history of the region. Pass through the narrow walls of the Iron Gates, then cross the river via bridges and continue along the bottom of the gorge. End on the shores of the Libyan Sea at Agia Roumeli, where you can have lunch or relax with a swim before taking the ferry to Sougia or Sfakia for your private transfer back to Chania. 

Tonight, enjoy an authentic Cretan dinner at one of Chania's top-notch restaurants. Try dishes such as kalitsounia (small pies of spinach and herbs), handcrafted cheeses, dakos (soaked barley rusk with tomatoes and feta), or kreatotourta (meat pie), all while sipping organic Cretan wine. 

Day 5: Transfer to Heraklion, Explore the City, Farm-to-Table Dining Experience

Experience farm-to-table Cretan fare in Heraklion

Depart Chania this morning for Heraklion, Crete's capital city. Your private driver will collect you from your hotel, and you'll make the scenic coastal drive, stopping along the way at the seaside town of Rethymno. Here, you'll have a chance to stroll around the village or have a leisurely lunch. Upon your arrival in Heraklion, check in at the Manili Boutique Suites and Villas, a 5-star retreat with custom wood furnishings, stone accents, and pool and barbecue areas. Room options here include private suites with their own hot tub, expansive three-bedroom villas, and tranquil sea-view terraces.

Drop off your luggage, then take an afternoon walk along the city streets, exploring age-old architecture that hints at the island's Venetian past. Highlights include the elegant Loggia, now in use as the town hall, and the Koules Venetian fortress along the harbor walls. Visit the Archaeological Museum, home to one of the largest collections of Minoan artifacts in the world, and Lion's Square. If you're hungry, be sure to grab a snack at the popular Anchorage Traditional Mezedopolio.

This evening, experience an authentic farm-to-table dinner at a top-rated restaurant. Sample dishes based on traditional Cretan recipes and fresh ingredients, all sourced from a local farm and cultivated with sustainable agriculture practices. Your travel specialist will also make sure the menu accommodates any specific dietary requirements or allergies. 

Day 6: Guided Excursion to Lassithi Plateau: Cave of Zeus & Knossos Palace 

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Chat with a local specialist who can help organize your trip.
Walk the paths of the ancients at Knossos Palace

After breakfast, hop in your luxury chauffeured vehicle for a private tour of eastern Crete's Lassithi Plateau. Located approximately 43 mi (70 km) from Heraklion, the plateau stretches across 50 square miles (13,000 ha) and features colorful villages with rich traditions, historic sites, and incredible cuisine, all set against the backdrop of expansive, fertile plains. 

Cruise along tranquil roadways, taking in the lush forests and farmlands, many of which are dotted with iconic windmills. Stop at the village of Krasi to see its monumental plane tree, with a trunk that spans nearly 80 feet (24 m) and is thought to be more than 2,000 years old. Visit Byzantine monasteries and see ancient Cretan art, as well as a family-owned ceramic shop. Have lunch at a village café, then head to the Cave of Zeus, a phenomenal limestone cavern that was once worshipped as the birthplace of the thunder god. 

Finish your tour with a visit to Knossos Palace, whose origins date back to the Neolithic era. Legend has it that the palace was the residence of King Minos, who is rumored to have kept the Minotaur within a labyrinth here. Meander through the remains of the palace as your guide shares insight into its history and role in Greek culture. Return to Heraklion in time for dinner and a sunset walk around town. 

Day 7: Ferry to Santorini, Evening of Dinner & Wine

Hop over to Santorini and spend the afternoon poolside (photo courtesy of Andronis Concept-Wellness Resort)

You're off to Santorini, known for its cliffside white and blue houses (built on the side of a once-active volcano), exquisite sunset views, and endless beaches. The island is a popular destination for visitors from across the globe, yet retains an authentic, old-world feel. Check out of your hotel in the morning and take a private transfer to the port, where you'll catch a high-speed ferry over to the island.

A driver will meet you and take you to your hotel, the Andronis Concept-Wellness Resort, a 5-star haven located in the village of Imerovigli. With suites and villas that offer private infinity pools, cave pools, and terraces with private hot tubs, you'll enjoy peaceful relaxation amid breathtaking panoramas of the surrounding sea. Don't linger too long in your rooms, however, as you'll be heading out shortly to enjoy dinner at a local restaurant.

Santorini's restaurant scene is legendary, and whether you're in the mood for fine dining or something more casual, you'll have your pick of top restaurants tonight. Try Santorini's signature fava (split pea purée), tomatokeftedes (tomato fritters), or apochti (salted pork loin) alongside flavorful local wines. Your travel specialist will provide you with options based on your taste and will book a reservation for you.

Day 8: Free Morning to Explore, Sunset Catamaran Cruise & Barbecue 

Take a luxurious sunset cruise around Santorini

Enjoy a leisurely morning at your hotel, relaxing at the pool, or spending some time at one of the island's gorgeous beaches. If you're interested in Greece's wine production, you can also take a guided tour of the island's private wineries. Your private guide will collect you from your hotel and you can visit local vineyards, learning how the grapes are grown and the methods used to keep the vines healthy—some of which date back more than 3,500 years. Try different varietals, and stop in at the Underground Wine Museum to see the evolution of winemaking over the centuries.

Later, see more of Santorini via a private sunset cruise. Your driver will take you to Vlychada port, where you'll be welcomed onboard a luxury catamaran by your captain and crew. Your first stop is Red Beach, a volcanic beach with—you guessed it—red-hued sand. This is a great spot for swimming, snorkeling, and Instagram-worthy photos. Next up is White Beach, where you can swim while the crew sets out a sumptuous Greek barbecue. Feast on shrimp saganaki, grilled chicken, vegetables, pasta, and more before ending the day with a sunset dip in Santorini's hot springs. 

Day 9: Guided Hike of Santorini's Caldera, Farm Picnic in Oia

Hike along Santorini's Caldera for panoramic views 

One of the best ways to experience the famous views of Santorini is to hike along the Caldera, created thousands of years ago by a huge volcanic eruption. This morning, meet up with your private guide to see more of this incredible landscape, starting along the popular route out of Fira and making your way to some of the hidden and more authentic sides of the island. Hike along the well-kept trails as your guide shares information about the history and lore of the area, then finish with a picnic at an organic farm in the village of Oia

Walk along cobblestone paths to the first organic blackcurrant vineyard on Santorini, where you'll see local varieties of herbs such as capers and thyme. Learn about the production and harvest of the produce, visit the property's on-site cave, and try a tasting of infused olive oil curated on the farm, all followed by a picnic meal. Take in the sunset views over the Aegean Sea, then return to your hotel to enjoy your last evening in Greece. 

Day 10: Depart Santorini 

Say goodbye to Santorini this morning

After 10 days of luxury and adventure, it's time to say farewell to Greece. Your driver will collect you from your hotel this morning and transport you to the airport for your flight home. Safe travels!

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Map of Luxury & Adventure in Greece: Athens, Crete & Santorini - 10 Days
Map of Luxury & Adventure in Greece: Athens, Crete & Santorini - 10 Days