Outdoor adventures meet ultimate luxury on this two-week trip around Greece. Explore Athens by bike and kayak to the Temple of Poseidon, then you're off to Crete and the ancient city of Chania. Walk the streets of the Old Town, venture into the Samaria River Gorge, and relax on the pink sands of Balos Beach before transferring to Heraklion for visits to the Cave of Zeus and Knossos Palace. End in Santorini, cruising around the island via catamaran and savoring a decadent picnic at a local organic farm.


  • See Athens' hidden corners with a guided cycling tour
  • Visit the historic ruins of Delphi and stroll through ancient olive groves
  • Discover idyllic lagoons and islands off Crete by private speedboat
  • Wind your way through Europe's longest river gorge in Samaria National Park
  • Hike to Santorini's volcanic caldera, then treat yourself to a farm-fresh picnic 

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner with Acropolis View Athens
Day 2 Guided Bike Tour Around the City, Acropolis at Sunset Athens
Day 3 Day Trip to Delphi: Hiking, Ancient Olive Groves & the Oracle Athens
Day 4 Sea Kayaking Tour of Sounio & Poseidon Temple, Athenian Riviera Dinner Athens
Day 5 Fly to Chania, Cultural Walking Tour, Food & Wine Tastings Chania
Day 6 Motorboat Cruise to Balos Beach & Gramvousa Islands Chania
Day 7 Hiking Fun in Samaria River Gorge, Authentic Cretan Dinner Chania
Day 8 Transfer to Heraklion, Explore the City, Farm-to-Table Dining Experience Heraklion
Day 9 Guided Excursion to Lassithi Plateau: Cave of Zeus & Knossos Palace  Heraklion
Day 10 Ferry to Santorini, Evening of Dinner & Wine Santorini
Day 11 Free Morning to Explore, Sunset Catamaran Cruise & Barbecue  Santorini
Day 12 Driving Tour Around Santorini, Megalochori Village & Wine Tasting Santorini
Day 13 Guided Hike of Santorini's Caldera, Farm Picnic in Oia Santorini
Day 14 Depart Santorini  

Detailed Itinerary

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

Experience terrace dining with views of the Acropolis (Photo courtesy of AthensWas Hotel) 

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: Guided Bike Tour Around the City, Acropolis at Sunset

See Athens via bike on a privately guided tour

Get active today as you set out on a privately guided bike tour around the city. Meet your local guide in the morning, and after a quick safety and equipment briefing, you'll visit some of Athen's most popular spots, all via a safe, traffic-free route. Ride around the historic center, getting to know this phenomenal city from a different perspective as your guide shares insight into daily life and the historic landmarks you'll pass by. There will be plenty of time to stop and rest, grab a snack, or take advantage of photo ops. 

Later, take a private walking tour of the Acropolis. You'll be accompanied by an expert archaeologist/guide, taking you to the mighty Acropolis just in time for sunset. Ascend from the south slope, taking in the city views below as you climb. Visit the Theatre of Dionysus, Asclepius Sanctuary, and the Concert Hall of Herodes Atticus, summiting at the foot of the Acropolis. Your guide will provide detailed explanations of each site, its history, and its meaning. Stand in the greatness of the Erechtheion, Propylaea, Nike Temple, Beule Gate, and the Philopappos as the sun slowly drops. 

From here, make your way back downhill and into Athen's oldest neighborhood, Plaka. With your guide, make your way up a hill to Anafiotika, a small district with twisting alleys and whitewashed houses built in the Cycladic style. Walk through the cobblestone streets and deep into Plaka, as your guide unveils lesser-known details and history of the historical buildings, chapels, and monuments. Return to your hotel in time to rest up for tomorrow's adventures! 

Day 3: Day Trip to Delphi: Hiking, Ancient Olive Groves & the Oracle

Walk the ancient ruins where the Oracle of Delphi once sat

Step away from the busy city this morning with a private day trip to Delphi, the ancient religious sanctuary dedicated to the god Apollo. Meet your guides after breakfast and make the scenic drive, heading toward Mount Parnassos. Arrive at a hiking path where you'll continue on foot, making your way through the ancient olive grove that sits between the Oracle of Delphi, a shrine once occupied by the future-predicting priestess Pythia, and the sea. The grove is protected as a UNESCO-listed landscape and is composed of more than 1.5 million olive trees.

After your hike, indulge in a traditional lunch at an olive oil farm. Meet a family who has produced olive oil for generations, as you try freshly pressed oil, olives, and tapenade, all derived from the local olive trees here. Relax for a bit after your meal, then continue on a two-hour private tour of the Delphi site. See the Oracle, the ruins of the theater and stadium, ending with a visit to the Delphi Museum. Here, you'll find treasures such as the bronze statue of the Charioteer of Delphi, the Sphinx of Naxos, and what is thought to be the first-ever recorded notation of a melody.

Day 4: Sea Kayaking Tour of Sounio & Poseidon Temple, Athenian Riviera Dinner

Paddle along the Athenian Riviera and see the Temple of Poseidon

Get active today with a private kayaking tour, meeting your guide in the morning and heading toward Cape Sounio (Sounion), which is 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 paddle 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. Bask in 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, to include 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 for your final night in the city. 

Plan your trip to Greece
Chat with a local specialist who can help organize your trip.

Day 5: Fly to Chania, Cultural Walking Tour, Food & Wine Tastings

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

After breakfast, 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 striking 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 over Chania. Rooms here offer private pools and Jacuzzis and a lovely 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 that is considered Crete's national drink. 

Day 6: Motorboat Cruise to Balos Beach & Gramvousa Island

Take a private motorboat cruise around Balos Lagoon

Visit Balos Beach today, nestled in a protected tropical lagoon that's one of Crete's most popular destinations for locals and visitors alike. In the morning, you'll head to the port and board your private motorboat, as the captain and crew introduce themselves and give you an overview of what the day will bring. Set out across the turquoise waters of the Aegean Sea, watching Chania disappear in the distance as you zip across the waves to Balos. 

Upon arrival, you'll have plenty of time to relax, taking in the stretch of white and pink sands and swimming in the clear, shallow waters of the lagoon. Have lunch at the beach or onboard the boat, then stop by Gramvousa, a small, uninhabited island that once served as a hideout for pirates. Get some sun and fun on the peaceful beach and snorkeling area, and if you like, you can visit the remains of a Venetian castle located at the top of the island. Return to Chania in time for dinner at a local restaurant and an evening stroll around town. 

Day 7: Hiking Fun in Samaria River Gorge, Authentic Cretan Dinner

Trek through the dramatic natural beauty of Samaria River Gorge

Experience the great outdoors of Crete today on a full-day 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 note this is a somewhat strenuous hike, with proper shoe wear and attire 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 comfortable, 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 8: Transfer to Heraklion, Explore the City, Farm-to-Table Dining Experience

Relish the quiet luxury of Heraklion's Manili Villas (photo courtesy of Manili Boutique Suites & Villas)

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, where you can stroll around the village or have lunch. Upon your arrival in Heraklion, check in at the Manili Boutique Suites & 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 hearkens to the island's Venetian past. Highlights include the elegant Loggia, now used 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 ensure the menu accommodates any specific dietary requirements or allergies. 

Day 9: Guided Excursion to Lassithi Plateau: Cave of Zeus & Knossos Palace 

Tour the colossal ruins of Knossos Palace, whose origins stretch back to the Neolithic period

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. 

Day 10: Ferry to Santorini, Evening of Dinner & Wine

Take in views of the Aegean Sea from your private terrace (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 top destination for visitors from across the globe, yet it still 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 property 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 experience optimum relaxation amid endless panoramas of the surrounding sea. Don't linger too long in your rooms, however, as you'll be heading out shortly for 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 11: Free Morning to Explore, Sunset Catamaran Cruise & Barbecue 

Set sail for a luxury sunset cruise around Santorini 

Make it a leisurely morning at your hotel, relaxing at the pool or spending some time at one of the island's pristine beaches. If you're interested in Greece's wine production, you can also take a guided tour of the island's private wineries. Your local 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 12: Driving Tour Around Santorini, Megalochori Village & Wine Tasting

See the whitewashed buildings and Cycladic architecture of Megalochori 

Learn more about the history of Santorini today on a private driving tour. You'll meet your driver in the morning and embark on a scenic drive around the countryside, taking in the island's most iconic sights. Stop by archaeological highlights, such as Akrotiri, a Bronze Age settlement that was buried by volcanic ash during an eruption, then stroll through the whitewashed houses and winding streets of Oia

See the island's black-sand beach and stop for lunch at an authentic restaurant, getting a taste of fresh produce and cheeses. Afterward, stop at a local winery to learn more about Santorini's winemaking history through the centuries, trying three different varietals of the island's wines. 

This afternoon, you'll visit the village of Megalochori, where you'll explore its ages-old mansions and Cycladic architecture. Learn about canaves, the typical cave-shaped constructions of Santorini made by their self-taught architects, then stop for a wine tasting and sample some local delicacies. End with a sunset visit to Prophet Elias Mountain, the highest point of Santorini, with views of the entire island.

Day 13: Guided Hike of Santorini's Caldera, Farm Picnic in Oia

Sample Greek olive oil and picnic at an organic farm in Oia 

One of the best ways to experience the famous views of Santorini is to hike along its Caldera, created thousands of years ago by a huge volcanic eruption. This morning, meet up with your private guide to see more of this impressive landscape, starting along the popular route out of Fira, and then 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 of the caldera and Aegean Sea, then return to your hotel for your final night in Greece.

Day 14: Depart Santorini

Until next time, Greece! 

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 - 14 Days
Map of Luxury & Adventure in Greece: Athens, Crete & Santorini - 14 Days