Luxury Highlights of Greece: Athens, Mykonos, Naxos, Santorini & Crete - 14 Days

Day 1: Arrive in Athens, Tour the Acropolis & Museum

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 Athens Capital Center Hotel, a 5-star accommodation in the exclusive Kolonaki district. Here, you'll find tastefully appointed rooms, carefully curated artwork, and a rooftop pool that offers expansive views of the Acropolis and city lights. 

Once you've had time to rest and regroup, meet your guide for a private tour of the historic Acropolis and Acropolis Museum. 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. Stroll the same paths that legends such as Socrates and Plato once walked and learn more about how notions like democracy were created and evolved to become a crucial part of modern Greece. 

Pass by the hill known as the Areopagus, or Hill of Ares, which served as the site for the judicial court in ancient times, then continue to the Acropolis Museum, which houses all the findings of this archaeological site. See artifacts found at the Acropolis and its surrounding slopes, with items dating back to the Greek Bronze Age, as well as the Roman and Byzantine periods. End the day at your hotel, where you can relax by the pool and feast on contemporary Mediterranean dishes at the on-site restaurant. 

Day 2: Explore the Athenian Riviera: Temple of Poseidon & Fine Dining

Strike out into Greece's spectacular countryside today with a private driving tour along the Athenian Riviera. Head out with your guide in the early afternoon, traveling along the 30-mile (48 km) coastline, which stretches from Athens all the way to Cape Sounio (Sounion).

Here, you'll find everything from glitzy city suburbs to hidden lagoons, not to mention one of ancient Greece's most famous monuments, the Temple of Poseidon. This fifth-century archaeological site overlooks the Saronic Gulf and its islands, dominating the southernmost tip of Attica. Walk the grounds, taking in the immense columns and ancient remains as your guide shares stories and legends about the people who built a temple to honor the god of the sea. 

The day ends with an indulgent gourmet dinner at Ithaki, one of the Riviera's premier restaurants. Dine on fresh fish and other seafood, traditional Greek appetizers, and delicious desserts, all set against a backdrop of Riviera views and gentle sea breezes. 

Day 3: Ferry to Mykonos, Oysters & Bubbles Experience

You're off to the island of Mykonos today, otherwise known as the "island of the winds." While the island is renowned for its cosmopolitan vibe, Mykonos is also home to stone-paved alleys, quintessential blue and white cottages, and a host of archaeological history. Your driver will collect you from your hotel after check out and take you to Athens port for a high-speed ferry ride to the island. 

Upon arrival, take a private transfer to the 5-star Cavo Tagoo Mykonos. This luxury retreat is built into a natural cliffside, with rooms and villas that include private pools, hot tubs, and terraces overlooking the blue waters of the Aegean Sea. The aesthetic here says "barefoot chic," with distinct architecture that pays homage to the island's natural beauty. 

Later this afternoon, you'll have the opportunity to taste some delectable seafood fresh from the sea. Your private guide will collect you from your hotel and take you for a sampling of local oysters and clams, all washed down with delicious bubbly. The head guide is a local fisherman who knows all the secrets of proper oyster and clam harvesting, and he will not only offer up a lovely picnic but also teach you about the different textures and flavors of the shellfish as you try them. Return to your hotel afterward to relax or take a sunset stroll around the island.

Day 4: Luxury Catamaran Cruise, Evening Walking Tour

After a leisurely morning, see the island from a different view as you head out for a half-day private catamaran adventure. Meet your driver at your hotel and transfer to the Ornos Bay port, where you'll be welcomed onboard your luxury vessel. Get introduced to your captain and crew, and after a safety briefing, it's time to hoist the sails and head out into the Aegean. 

Cruise to the south end of Delos and make your first stop at Rhenia, a small, undeveloped island where you can swim and snorkel in its quiet coves. Then, sail to another secluded cove and enjoy the water while your crew prepares a sumptuous seven-course meal. Dine on salads, grilled meats and fish, calamari, and local vegetables, all accompanied by wines or soft drinks. End this perfect day with one last swim, then set sail again, stopping by Delos once more to catch a glimpse of the archaeological site and enjoy the sunset as you return to port. 

This evening, get better acquainted with Mykonos on a private sunset walking tour. Together with your expert local guide, you'll stroll through the labyrinth of Mykonos Old Town district, visiting the small port and picturesque churches around the area. See the famed windmills, once used to grind barley, wheat, and other grains by harnessing the power of the meltemi, or northern wind, and end at the Little Venice neighborhood, where you'll find elegant homes sitting right on the water and lovely views of the sea. Have drinks at one of the seaside cafés, or continue your walk around town at your own pace. 

Day 5: Ferry to Naxos, Guided City Highlights Tour 

Your next destination is the island of Naxos, the largest of the Cyclades islands and home to charming villages, medieval mansions, and endless stretches of white sand beach. After checkout from your Mykonos hotel, your driver will transport you to the port for a quick ferry ride across the sea. During your approach, you'll see the iconic landmark Portara, a giant door once a temple to Apollo. Upon arrival, a transfer will take you to your 5-star hotel, 18 Grapes. Featuring 18 signature rooms and suites, this peaceful oasis offers in-room pools, sea-view rooms, and a spa with a sauna and hammam. 

After hotel check-in, head out for a privately guided tour of the island, starting with a visit to Damalas Village, where you'll visit a pottery shop and see live demonstrations of pottery-making. Then, move to the southwest side of the village to learn about another practice that is a deep part of Greek culture and identity: the production of olive oil. See the village's restored olive oil press as your guide explains the workings of it and why these practices are still so important to the Greek way of life. 

Next is the village of Halki, where you'll visit the island's oldest citron distillery. Sample some of this unusual drink, then make your way to the Paleochristian church of Panagia Drosiani, which has what is considered one of the oldest naves in the Balkans. See the marble village of Apeiranthos, with architecture that has remained relatively untouched since the Venetian Empire, walking the narrow, marble-paved mule tracks. Finish the day at Melanes village and the Kouros or Apollo statue, left "sleeping" in a garden for centuries until its dramatic discovery.

Day 6: Full-Day Boat Tour of South Naxos & the Cycladic Islands 

Get out on the water today, exploring the southeast coast of Naxos and taking advantage of some of the incredible beaches around the island. In the morning, meet your guide and head to the port, where you'll board a high-speed motorboat. Meet your captain and get a quick safety briefing, then head out along the coastline. Your first stop will be Kalantos, the island's southernmost natural port, where you can swim, snorkel, and see Rina Cave, which has a freshwater spring and an abundance of birdlife. 

Visit the secluded coves of Panormos Beach, which has a lovely pebbled shoreline and shady palm trees, then head to the tiny island of Kato Koufonissi, an uninhabited paradise with sandy beaches and crystal-clear waters. Just next door to Kato, you'll find Ano Koufonini, a much livelier spot with restaurants, shops, and bars. You'll have time to walk around town and grab a bite to eat, or rent bikes to see more of the island before returning to Naxos for the evening.

Day 7: Ferry to Santorini, Sea View Dinner at Lycabettus Restaurant

Check out of your hotel this morning and depart for your next island escape, Santorini. Known for its cliffside blue and white houses (built on the side of a once-active volcano), sunset views, and endless beaches, the island is a popular destination for visitors from across the globe.

A private transfer will take you to the port, where you'll hop on a ferry to the island. Upon arrival, another driver will meet you and transport you to your hotel, the Canaves Oia Suites. This 5-star boutique hotel features gorgeous accommodations that blend traditional and modern design. The suites and villas offer private plunge pools, hot tubs, and open views of the sea at every turn, making for an incredibly relaxing stay. 

Rest up at the hotel for a bit or take a stroll through the island's quaint neighborhoods, then meet your private driver and head to what is considered one of the island's top restaurants, Lycabettus. Enjoy a dining experience like no other as you sit out on their cliffside terrace with the sea at your feet and partake of fresh local seafood, steaks, and, of course, top-notch wine from Santorini's own vineyards. Finish the day watching the sun drop below the sea as you linger over that last glass of wine and dessert.

Day 8: Santorini Island Tour with Beaches, Wine Tasting & Historic Sites 

Step back in time with a private tour of the historical and cultural sites around Santorini. After breakfast, meet your guides and start with a visit to the ruins of ancient Akrotiri, destroyed during a volcanic eruption in the 16th century BCE and buried in ash. Visit the nearby Lost Atlantis Museum to see artifacts and learn more about the history of the eruption, then head to Red Beach, whose red-hued sand gives it an otherworldly glow. 

Stop in at one of Santorini's local wineries for a vineyard tour and tasting as your guides share information about how the island's grape varietals are nationally safeguarded. Try several different wines alongside a four-course lunch, then take a stroll on the island's famous black sand beach. 

Continue to Pyrgos, Santorini's oldest village, built on a hill and offering panoramic views of the whole island. Make a stop at Prophet Elias, Santorini's highest point, and see the islands' Caldera stretched before you, then end the tour with a stop at a local restaurant for sunset cocktails. Relax at your hotel this evening and rest up for tomorrow's travels.

Day 9: Ferry to Crete, Explore the Capital City of Heraklion

After breakfast, hop back on the ferry for a ride to the island of Crete, landing in its capital city, Heraklion. This picturesque port town is known for its vibrant Old Town district, peaceful shorelines, and extensive archaeological history. Upon arrival, your driver will transfer you to the Phaea Blue Palace, a 5-star, family-run boutique hotel. Nestled between the tiny fishing village of Plaka and the port of Elounda, the rooms and bungalows here offer beautiful views of the sea with clean, natural decor and options for private pools and terraces.

Check in and drop off your bags, then stroll through the city streets, exploring age-old architecture that harkens to the island's Venetian past. Highlights include the elegant arches of the Loggia, now in use as the town hall, and the Koules Venetian fortress along the harbor walls. 

In the afternoon, don't miss the Archaeological Museum, home to one of the largest collections of Minoan artifacts in the world. Finish with a walk through Lion's Square, and if you're hungry, stop at a café to taste traditional bougatsa (custard pie) or have a glass of raki, a grape-based pomace brandy considered Crete's national drink. 

Day 10: Tour Knossos Palace & Heraklion Archaeological Museum

Hop in your chauffeured vehicle today for a private tour around Crete. You'll start 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.

After Knossos, visit the Heraklion Archaeological Museum, one of Greece's largest and considered to have one of the most important collections of Minoan art. Artifacts include bone and ivory objects, clay pottery, coins, jewelry, and more. Learn about the history of these ancient items and how they represent each period. Finish the tour at Heraklion Central Market, once the site of a revolution between Crete and the Turks and now a popular spot for souvenir shopping or getting a bite to eat. 

For dinner tonight, check out the many fine dining options Crete has on offer, trying some of the delectable local fare that the island is known for. Sample dishes like dakos salad (barley rusks soaked in olive oil and topped with tomato and cheese), or taste some of Crete's own cheese varietals, such as graviera or mizithra. Have a slice of kalitsounia (cheese pie) and finish with some lihnarakia (star-shaped cookies)—all accompanied by flavorful Greek wine, of course! 

Day 11: Transfer to Chania, Walking Tour of Old Town, Food & Wine Tastings

Depart for Chania today, a picturesque port town known for its striking Venetian harbor, winding streets, and delicious cuisine. Your driver will collect you from your hotel for the scenic two-hour drive and drop you off at your accommodations at the Domes Zeen Resort. This 5-star property sits nestled within a lush, tropical garden, with easy beach access and views of Chania town. Rooms offer private pools and Jacuzzis, city views, 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 with a traditional repast of meze (small plates), wine, and raki.

Day 12: Secrets of Eastern Crete: Monasteries, Mountains & Villages 

Get a local's point of view today as you take an off-the-beaten-path driving tour of eastern Crete. This private tour, curated to your specific interests, takes you along the island's winding roads, passing endless olive groves, ancient Byzantine monasteries, and timeless villages. 

Visit the hanging Byzantine monastery of Kremasta, built on a hill at an altitude of 1,300 feet (397 m) so that it appears to be "hanging" from the slope. Then, head to the villages of Kritsa and Kroustas, where time has slowed to a standstill and history prevails. Soak up the scent of honey and dough that drift from the local kafenio (cafés), and stop for a delicious snack while you're there! 

Drive along the forested mountains, stopping along the seaside cliffs for eye-catching panoramas of both the Libyan and Cretan Seas, and if you like, you can take a hike through Sarakinas Gorge, where sheer rock walls rise above rivers and small streams. End the day in the town of Ierapetra, enjoying a refreshing dip in the warm waters of the Libyan Sea.

Day 13: Sailing Cruise to Balos & Gramvousa Island

Visit Balos Beach today, a protected tropical lagoon that is 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 fly across the waves and 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 Island, a small, uninhabited island that once served as a hideout for pirates! Enjoy some sun and fun on the peaceful beach and snorkeling area, and if you like, visit the remains of a Venetian castle at the top of the island.

Return to Chania and make the most of your last afternoon in Greece by exploring more of the city on your own. Lose yourself in the winding streets, have dinner at one of the restaurants overlooking the Venetian harbor, or get in a bit more swim time at one of the city's local beaches. 

Day 14: Depart Chania

Sadly, it's time to say farewell to Greece. At the appointed time, your driver will collect you from your hotel and transport you to the airport for your flight home. Safe travels!

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