Experience Greece beyond the postcard on this thoughtfully curated journey through Athens and the enchanting Cycladic Islands. Combining ancient history, authentic local culture, exceptional cuisine, and breathtaking island scenery, this nine-day adventure reveals the Greece travelers dream about—but few truly discover.
Begin in Athens, where timeless monuments and vibrant neighborhoods tell the story of one of the world's oldest cities. Explore the legendary Acropolis with a private guide, stroll through the charming streets of Plaka, and immerse yourself in local life as you sample traditional Greek specialties, wander bustling markets, and experience the city's dynamic culinary scene.
From Athens, fly to the island of Naxos, often considered the Cyclades' best-kept secret. Here you'll discover a slower, more authentic side of Greece. Stay along the stunning shores of Plaka Beach, where turquoise waters and golden sands create the perfect backdrop for relaxation. Venture into picturesque mountain villages, explore centuries-old olive presses, and join local hosts in preparing traditional Naxian dishes using ingredients gathered directly from family farms. Scenic hikes reveal hidden monasteries, Byzantine churches, lush river valleys, waterfalls, and ancient pathways that have connected island communities for generations.
Your journey culminates in iconic Santorini, where whitewashed villages cling dramatically to volcanic cliffs overlooking the sparkling Aegean Sea. Settle into an intimate luxury retreat in Oia, famous for its unforgettable sunsets and spectacular caldera views. Spend your days wandering charming cobblestone lanes, discovering hidden corners of the island, and sailing along Santorini's dramatic coastline. A sunset cruise aboard a small sailing vessel offers front-row views of the island's famous volcanic landscapes, secluded swimming coves, and the legendary sunset that transforms the caldera into shades of gold, orange, and crimson.
Throughout the journey, you'll enjoy hand-selected boutique accommodations that capture the unique character of each destination. Wake up to views of the Acropolis in Athens, unwind in a beachfront suite on Naxos, and soak in a private outdoor hot tub overlooking Santorini's caldera. Private transfers, expert local guides, and carefully curated experiences ensure a seamless and immersive travel experience from beginning to end.
This is Greece at its finest—a journey that blends iconic landmarks with authentic local experiences, celebrated cuisine, spectacular scenery, and luxurious accommodations. From ancient temples and charming island villages to vineyard-covered hillsides and unforgettable sunsets over the Aegean, every day offers new opportunities to connect with the culture, beauty, and spirit of Greece.
• Explore the Acropolis and historic Athens with a private guide
• Taste your way through Athens' vibrant food markets and local neighborhoods
• Discover authentic island life on beautiful Naxos
• Participate in a hands-on farm-to-table cooking experience with local hosts
• Hike through hidden villages, olive groves, waterfalls, and Byzantine sites
• Stay at luxury boutique properties in Athens, Naxos, and Santorini
• Enjoy spectacular caldera views from your suite in Oia
• Sail Santorini's coastline on a sunset cruise with dinner and local wine
• Experience the perfect balance of culture, cuisine, relaxation, and adventure
This itinerary was carefully selected by Alexis to showcase the best of Greece beyond the typical tourist route. By combining Athens' ancient wonders with the authentic charm of Naxos and the iconic beauty of Santorini, this journey offers a deeper connection to Greek culture, cuisine, history, and island life while enjoying exceptional accommodations and seamless service throughout.
Only 1 offer available for one couple/two persons. The last rooms have been secured for this trip.
Athens • Naxos • Santorini
Arrival & Get Settled
Airport Transfer with Meet & Greet - Private
Greece Arrival Welcome Package
Self-Guided: A Taste of Athens
Evening at Leisure
Upon arrival to Athens airport, an English-speaking Meet & Greet Assistant will welcome you and escort you to your waiting driver. They will travel with you to your accommodations to ensure a smooth check-in and be on hand to answer any questions you may have about your itinerary or the destination.
A curated Kensington Welcome Package is prepared for your arrival in Greece, including a printed copy of your itinerary and any admissions relevant to your journey.
With so many options to choose from, deciding on a restaurant to try during your stay in a foreign city can prove difficult. To assist, you’ll receive a supplemental composition within your final trip documents, showcasing our restaurant suggestions for Athens, as selected by Kensington Tours Destination Experts.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
See the Signature Sights in Style
City Tour with Acropolis & Plaka Stroll (4 hrs) - Private
Independent Exploration of Athens Beyond the Beaten Path
Evening at Leisure
With stunning monuments dating back to Antiquity, Athens is one of the world’s oldest cities and a fascinating place to discover. With your private guide, embark on a half-day orientation tour of the city, taking in the sites and neighborhoods that have shaped the unique character of Athens over several millennia. Start with a private, one-way transfer to the iconic Acropolis, an ancient citadel located on a rocky outcrop overlooking the city. Enroute, you’ll see the Temple of Olympian Zeus, the Panathenaic Stadium, where the first Olympic Games of the modern era were held in 1896 and pass by Hadrian’s Arch. Once you've arrived at the UNESCO World Heritage Site of the Acropolis, spend some time exploring this ancient fortress while your guide regales you with tales of its historical significance and architectural marvels. Pass through the Propylea, the stately entrance to the magnificent structures inside, and enjoy the spectacular panoramic view of the city and the entire basin of Attica before you. Explore the Parthenon, the best known and most awe-inspiring of structures of the Acropolis citadel. Visit the Erechtheion, whose temple is graced with the porch of the Caryatid. Revel in this immersive experience as you uncover the spirit of Athens through its celebrated landmarks and fascinating stories and conclude with a leisurely stroll through the beautiful Plaka neighborhood back to your hotel.
Venture beyond Athens’ historic core on an independent exploration that reveals the city through its lived-in neighborhoods, where working-class roots, neoclassical streets, creative energy, and local dining scenes shape daily life. Areas such as Psyrri, Thissio, Gazi, and Ano Petralona offer a more local view of Athens, from historic streets and hillside paths to relaxed tavernas and evening wine spots. Your Destination Expert provides tailored suggestions on where to pause, dine, and linger, and can advise on the best way to move between areas should transportation be helpful.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
City Streets and Tasty Treats
Flavors of Athens Walking Tour (with Tastings, 4 hrs) - Private
Syntagma Square Changing of the Guard at Your Own Pace
Evening at Leisure
Savor Athens on foot with your private guide, tracing the city’s culinary heritage through the everyday rituals of the Mediterranean diet. Follow the scent of warm bread, Greek coffee, and market spices into family-run shops and artisan stops for tastes such as cheese pies, honeyed loukoumades, and seasonal bites. The walk culminates at Varvakios Central Market, where stalls of produce, cheeses, herbs, and meats reveal the rhythm of Athenian food life.
Pause at Syntagma Square to watch the changing of the guard at the Tomb of the Unknown Soldier, set before the Parliament building. On the hour, the Evzones step into position in traditional dress, moving with a precise, ceremonial rhythm that’s quietly mesmerizing to see up close.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
A Change of Scenery
Private Airport Transfer
Air - Athens - Naxos [1 hr] - Economy
Private Airport Transfer
Naxos Town & Sunset at Portara at Your Own Pace
Evening at Leisure
Meet your driver for a private airport transfer.
Board a flight in Athens with direct service to Naxos. Approximate flight duration is 45 minutes.
Meet your professional driver for an airport transfer by private vehicle.
Explore Naxos Town in the golden light of early evening, when the stone lanes of the Venetian Castle and medieval Bourgos quarter soften and the harbor begins to glow. Wander past whitewashed homes and small shops before making your way to the Portara, the monumental marble gateway of an unfinished temple dedicated to Apollo, standing alone on the islet of Palatia as the sun settles over the Aegean. Afterward, linger in the Old Town over dinner at a traditional taverna or rooftop terrace. Your Destination Expert can share timing tips and favorite local spots to help shape the evening your way.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
Tastes and Traditions
Culinary Naxos (with Lunch, 4 hrs) - Private Tour
Evening at Leisure
Set out on a culinary journey starting from your hotel, accompanied by a private driver and a local English-speaking escort, to the picturesque village of Eggares. Situated on a fertile plain intersected by two rivers, Eggares stands as the primary supplier of produce on the island, radiating a truly blessed atmosphere. The agricultural tapestry of Greece is intricately woven with the cultivation of olive trees and the production of olive oil. Immerse yourself in this cultural richness with a visit to the village's olive press museum, a relic dating back to 1884, with claims from locals suggesting an even earlier origin in the early 19th century. This traditional olive press provides a window into the tools and techniques employed in manual olive oil extraction — a practice spanning millennia that now resides in the archives of history. Continue your expedition to the nearby village of Galini, meaning "serenity," where you'll embark on a gastronomic adventure guided by a local culinary expert ready to share traditional cooking insights. Select the finest ingredients from your host's organic farm, where home-grown fruits, vegetables, and herbs flourish. Witness the cultivation process firsthand, immersing yourself in the authenticity of organic produce. With ingredients prepared, engage in crafting a traditional Naxian dish from start to finish. After savoring the flavors of your culinary creations, return to your hotel with your private driver, bringing a delightful conclusion to this immersive and flavorful experience.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
Explore with an Expert
Naxos Mountain Villages & River Hike (with Lunch, 6 hrs) - Private
Evening at Leisure
Step back in time on a private guided hike through the breathtaking landscapes of Naxos, where history and nature intertwine along riverbanks, ancient mills, and timeless villages. Meet your private driver and hiking escort at your hotel and transfer to Kinidaros, the starting point of your seven-mile journey. Stroll through its terraced streets before heading northeast along a rural path that gradually descends into a stone-paved trail. As the trail opens to sweeping views of the Chalantron region, you’ll reach a serene riverbank lined with six historic watermills, including the 18th-century Mill of Hadji. A short detour unveils the grand basilica of Agios Artemios and the Byzantine Agios Demetrios complex, each bearing centuries of history. Continuing west, follow a shaded river trail through dense vegetation, passing waterfalls, hidden springs, and wildlife such as crabs, turtles, and butterflies. Arriving at a dramatic ravine, marvel at the imposing four-arched aqueduct before ascending to a hidden monastery and the tower of the Pradouna notables. The final stretch leads past traditional homes and the ruined Byzantine monument of Panagia Monastiriotissa before reaching Eggares. Here, visit a beautifully restored olive mill and admire the Byzantine monument of Taxiarchis before unwinding with a local lunch, wine, and Greek coffee. Concludes with a private transfer to your accommodation.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
The Journey Continues…
Private Port Transfer
Ferry - Naxos - Santorini [2 hrs] - Business Class
Private Port Transfer
Self-Guided: A Taste of Santorini
Evening at Leisure
Meet your driver for a private port transfer.
Board a high-speed ferry for a transfer from Naxos to Santorini. Approximate transfer time is 2 hours.
Meet your driver for a private port transfer. For your comfort, a private assistant will be on hand to help you navigate the busy Santorini port and make your onward connection.
With so many options across the island to choose from, deciding on a restaurant to try out in Santorini can prove challenging. To assist, you’ll receive a supplemental composition within your final trip documents, showcasing our top restaurant suggestions for Santorini, as selected by Kensington Tours Destination Experts.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
SANTORINI
Sail the Seas
Independent Discovery of Oia
Santorini Sunset Sailing (with Dinner, 6 hrs) - Small Group Tour with Private Transfers
Evening at Leisure
Known for its stunning, otherworldly views and sunsets, along with charming back streets, Santorini’s town of Oia is a great place to enjoy some time at leisure to explore on your own. Within your final trip documents, you’ll receive a supplemental composition outlining our suggestions for a self-guided stroll through Oia, as selected by Kensington Tours Destination Experts.
Santorini is especially captivating at sunset, and this intimate small group sailing experience offers an unhurried way to take it all in from the water. With no more than 14 guests on board, enjoy a relaxed evening cruise lasting up to six hours, depending on the season. Transfer by private vehicle to the port and set sail around the island’s dramatic coastline. Begin at the iconic Red Beach, a striking volcanic landscape known for its crystal-clear waters and excellent swimming and snorkeling. Continue to White Beach, accessible primarily by boat, where towering white cliffs rise above dark volcanic sand scattered with pumice stone. Enjoy about 30 minutes at leisure to swim and snorkel in the sheltered cove. Back on board, unwind as a barbecue dinner is prepared and served on deck, paired with crisp Santorinian wine. As you sail back toward the port, pause below the village of Oia to watch the sun set over the caldera, casting the sea and cliffs in shades of red, orange, and purple. After sunset, return to the port and enjoy a private transfer back to your hotel.
Enjoy a free evening to follow your interests, whether you step out to explore or unwind at your hotel.
Until Next Time…
Meet your driver for a private airport transfer.
Where you’re staying
Depart on your own flight arrangements
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