Santorini and the Cyclades by Private Yacht and Villa
Travel Destinations: Greece
13 Day Itinerary | Athens, Kea, Syros, Mykonos, Naxos, Paros, Sifnos, Santorini
Island hop Greece’s stunning isles aboard a private yacht and enjoy a sumptuous luxury villa stay on Santorini.
• Take to Greece’s iconic islands in style: aboard your private yacht.
• Savor fine wines and Greek delicacies on Mykonos and Naxos.
• Marvel at beautiful Venetian and Neoclassical architecture on Syros.
• Surrender to the splendor of Paros’ rich history and ancient relics.
• Ease into the finest sunsets of the world from your private villa in Santorini.
Independent Travel
Independent trips are either entire trips you take privately or solo extensions to a group tour.
Sailing
Small-ship adventures on the world’s great seas, rivers, and other places only accessible by boat.
Ultra Luxe
Embark on an unparalleled journey of extravagance and exclusivity, where every detail is meticulously crafted to provide the utmost in opulence and personalized service.
Flexible
With no pre-set departure dates, choose when you want to go and for how long.
At A Glance
Day 1 – Athens to Kea
• Port (Piraeus) Transfer
• Yacht All-Inclusive Package – Luxe Plan
• Yacht Crew Meet & Greet
• Cruising: Athens- Kea (Tzia Island)
Day 2 – Kea to Syros
• Cruising: Kea – Syros
Day 3 – Syros to Mykonos
• Cruising: Syros- Mykonos
• Exploring Mykonos Island with Wine Tasting & Mezes
Day 4 – Mykonos to Naxos
• Cruising: Mykonos – Naxos
• Naxos Culinary Tour
Day 5 – Naxos to Paros
• Cruising: Naxos – Paros
Day 6 – Paros to Sifnos
• Cruising: Paros- Sifnos
Day 7 – Sifnos to Santorini
• Cruising: Sifnos – Santorini
Day 8 – Santorini
• Yacht Disembarkation & Villa Arrival
• Private Port Transfer
• Villa Assistant Meet & Greet
• Villa Staffing & Provisioning
Day 9 – Santorini
• Exclusive Island Tour with Wine Tasting & Lunch
Day 10 – Santorini
• Southern Santorini Cycling Tour
Day 11 – Santorini
• Day at Leisure
• Afternoon Santorini Villages & Oia Sunset
Day 12 – Santorini
• Villa Features & Amenities
• Dining Suggestion – Petra Restaurant & Bar
Day 13 – Santorini
• Private Airport Transfer
Itinerary
Day 1 – Athens to Kea
Your incredible Luxe Yacht All-Inclusive Package includes a crewed charter rate, Advanced Provision Allowance including fuel, all onboard food and beverages, dockage as described in your itinerary, taxes & fees, crew gratuity, 24/7 concierge service, customized itinerary planning, and yacht
provisioning. Yacht toys, amenities, and activities will be organized by your dedicated yacht crew. Each day features up to five hour of cruising time.
Welcome aboard! Enjoy a welcome glass of champagne as you meet your dedicated crew who will be at your service for the duration of your charter. These knowledgeable crew members will ensure you have an experience of a lifetime while attending to your needs and and creating the trip of your dreams.
Due to its proximity to Attica, Kéa (also called “Tzia”) is an easily accessible paradise boasting a variety of stunning scenes. Steep mountains, small fields, olive groves, vineyards, valleys, picturesque coves, exciting hiking trails and off-the-beaten-track beaches all call Kea home. For those fascinated by geology, Kea offers a number of small caves to explore. On the south side of Nikolaos Bay, once a pirate stronghold in the 13th century, lies the historic port of Korissia. Korissia invites you to visit the remains of its ancient town walls as well as the Sanctuary of Apollo.
Day 2 – Kea to Syros
Boasting plenty of beauty and finesse, Syros is ready to seduce and lure you to its unique rhythm. Home to a historic harbor, Syros brims with splendor due to its superb capital. Discover the island’s abundance of Venetian and Neoclassical buildings, and its many small villages representing the Cycladic settlements. Enjoy a privately guided walking tour of the old town, gaining insight into its history, culture and architecture
Day 3 – Syros to Mykonos
Incredible Mykonos is a wonderful Cycladic island, and a must-visit at any time of the year. Surrounded by Tinos, Syros, Paros and Naxos, Mykonos enchants with stretches of golden beaches and inviting, crystal waters. Discover a paradise of white stone juxtaposed against a backdrop of dramatic mountains. Mykonos is made for memories.
Mykonos is world-famous for being a beautiful Greek island, home to white-washed houses, narrow winding paths, great sandy beaches, and a distinct cosmopolitan flair. Meet your private guide and driver and spend a half-day learning about the local Mykonians, their culture and way of life. You’ll then visit the village of Ano Mera, well-known for its wine production and a quaint town square filled with Greek taverns. Visit a traditional farm in Ano Mera for a wine tasting of 3 types of traditional Greek wine, and sample the local white and red wines. For a unique treat, try the dessert wine Liasto, a naturally sweet wine originating in Greece. Pair your wines with a selection of meze, including a dip made with traditional kopanisti cheese and yogurt, a snack of aged gruyere cheese from Naxos served with honey, Mykonian prosciutto louza, bread, and salad. Return to your hotel by private vehicle after the tasting.
Day 4 – Mykonos to Naxos
The journey continues to picturesque Naxos, famous for its beaches, hiking, and unique shops and galleries. Explore the island’s scenic small villages, surrounded by ethereal ancient monuments, Byzantine Churches, Venetian castles, and classical Greek ruins. All of these stunning wonders complement Naxos’ dramatic coastline.
Set out with a private driver-guide on a half-day culinary discovery which combines cuisine, history, culture, and agriculture. Your first stop is a visit to a family-owned olive oil mill in the village of Kaloxylos, where you can sample their delectable olive oil products after learning how this ”liquid gold” was once painstakingly prepared. Your next stop is a local farm where you’ll meet the owner and be taken on a visit of the grounds, learning about Naxian agriculture as you gather seasonal vegetables from the farm’s yield. You’ll then be invited into the farmhouse where you’ll join the owner in her kitchen for an informative cooking class where you’ll use the vegetables you’ve picked as you learn how to prepare a traditional Naxian meal. Dine on your own creation for lunch, before concluding with a return transfer to your hotel.
Meals included: Lunch
Day 5 – Naxos to Paros
Surrender to the splendor of Paros, home to charming white-washed homes and enticing nightlife. Situated in the center of the Cyclades islands, Paros is the very picture of a traditional Greek island. Explore a world brimming with beautiful, authentic villages, sun-soaked beaches, and breathtaking relics from a rich history. Paros offers plenty of delights for everyone – especially for wine lovers.
Day 6 – Paros to Sifnos
Set sail for spectacular Sifnos, known as the “Island of Flavors.” Home to a collection of traditional villages and churches, Sifnos boasts plenty of wonders waiting to be discovered. Historic monasteries and charming chapels are spread throughout the island, inspiring those who visit with remarkable architecture and beautiful frescoes. When visiting Sifnos, be sure to indulge in local culinary specialties, including mastelo – lamb cooked in red wine and spices.
Day 7 – Sifnos to Santorini
Your final sailing destination is beautiful Santorini, Queen of the Cyclades. Santorini was once the site of the world’s largest volcanic eruptions, now transformed into a submerged volcano and caldera. Amazing villages have been constructed on the edge of the caldera, boasting Cycladic architecture and breathtaking views of the sea. Apart from its fabulous caldera villages, Santorini is also beloved for its romantic sunsets, the volcano and hot springs, and a number of luxurious hotels featuring dramatic views.
Day 8 – Santorini
It’s time to say goodbye to your crew and transfer to your private villa for the next leg of your journey.
Meet your driver for a private port transfer. For your comfort, a private assistant will be on hand to help you navigate the crowded Santorini port, and make your onward connection.
On arrival, a villa representative will greet you and provide an orientation of your spectacular private retreat.
During your stay, villa staff will ensure a convenient and seamless time. Experienced personnel are here to make your stay exceptional and unforgettable.
Accommodation: Private Villa
Day 9 – Santorini
On the outskirts of the village of Imerovigli, a village to the north of Santorini, sits Santorini IV – a stunning architectural marvel, offering stunning views of the Aegean sea with the island of Thirasia nearby in the distance. Featured by the likes of Conde Nast, Santorini IV blends timeless ‘Greek Isle’ aesthetics like intricate stone work and iconic limestone structures with all-modern comforts creating a calming and idyllic, rustic landscape. Cobblestone paths and olive trees lead you to the tiered villa, nestled into the islands hills where upon entering, massive windows and retractable walls open up to the blue expanses of the Aegean Sea. Stepping outside the structure on the main level is the beautiful infinity pool area with elegant sunbeds and a cozy, shaded lounge and barbeque areas with panoramic views. Descending to the next level you will find a second pool with more sunbeds, a seating an area and an outdoor bathroom for swimmers’ convenience. The main structure is three stories tall and holds eight bedrooms all with their own washroom, ensuite or otherwise, as well as a full equipped kitchen, living room, gym and powder rooms.
Villa Highlights
• Two turquoise infinity pools
• Fully-equipped Gym with multiple guest, powder rooms
• Private gardens with olive trees and sculpted flowering plants
• Room for wedding services or events up to 300 people
Accommodation: Private Villa
Meals included: Lunch
Day 10 – Santorini
Picturesque villages line the dramatic seaside cliffs of Santorini, surrounded by rolling vineyards edging out a unique terroir in the middle of the volcanic setting in the Aegean. Meet with your private escort and driver to explore quaint villages such as Mesa Gonia and Exo Gonia and accentuate your visits with some wine touring. Start with a visit to Mesa Gonia, a village of rolling vineyards and a major wine producing region. The village is home to the majestic 12th century Byzantine church of Panagia Episkopi, one of the oldest and most interesting on the island.
Continue to a quaint winery surrounded by vineyards, a beauty quietly hidden into the volcanic rock. This historic winery was used by local families, making their own wine for centuries. Now, tradition and history meet the next generation of wine making. A tour of the grounds is a memorable experience, starting from the outer space with the layers of the black volcanic stone, pass through the canava’s old functional spaces – where now “Pure” wine ages silently – and end in the impressive cellar. After this short but impressive “travel in time”, the wine tasting of the Pure Santorini Assyrtiko will stimulate your senses. Crème de la crème of Santorini in your glass. The most significant examples of the indigenous grape variety to Santorini, the Assyrtiko will be chosen for you and you will be able to taste Assyrtiko wines from different producers of the island, showing different vivification techniques. The tasting offers a great opportunity to explore Santorini’s volcanic terroir and discover Assyrtiko’s diversity.
After your wine tasting you’ll visit Megalochori village, a traditional cobblestone-lined village with Neo-classical houses, for a stroll through the village. From here, head to Perivolos beach for a relaxing afternoon. Enjoy a gourmet lunch with a bottle of wine in a local restaurant, then spend the afternoon enjoying the sparkling azure waters on the southern end of the island. Make sure to bring your swimsuit with you for this afternoon leisure time on the beach. At the end of the afternoon, return to your hotel by private vehicle.
Accommodation: Private Villa
Day 11 – Santorini
Stretch your legs and head to southern Santorini for a private cycling tour through the hidden treasures of Santorini. A private vehicle will transfer you to the starting point of your private cycling tour, equipped with full suspension electric AMT mountain bikes. Begin your adventure at the black sand beach of Perivolos, and cycle through ancient paths and trails with your professional guide, visiting traditional villages that see far fewer tourists than other parts of the island. Stop for refreshments and a tour of Emporio village, a village with a distinctly medieval character, then cycle to Megalochori village for a short stop at Veggera Restaurant. Enjoy a wine tasting break and snack at the restaurant. Cycle back to the black sand beach at Perivolos where a rejuvenating smoothie awaits, and enjoy relaxing on the beach with your private sunbed and umbrella. At the end of the visit, transfer back to your hotel by private vehicle.
Accommodation: Private Villa
Day 12 – Santorini
Enjoy a full day at leisure on the beautiful island of Santorini. Enjoy time on the beach relaxing by the sea or explore the local streets and cafes.
Santorini’s picturesque countryside is best experienced in the late afternoon and early evening, as the waning daylight gives way to the “golden hour” and offers a striking visual contrast against the iconic whitewashed backdrop of Oia. Meet with your private guide and driver and head into the Santorini countryside to discover the island’s picturesque villages. Start with a visit to Mesa Gonia, a village of rolling vineyards and a major wine producing region. The village is home to some majestic Byzantine churches. Continue to Pyrgos, a hilltop town that served as the island’s capital until the early 19th century. The village offers panoramic views of the island in every direction and has charming medieval architecture. Continue your evening with a visit to the village of Oia, set upon the caldera’s cliffs. Oia marks the dramatic backdrop to a world-famous sunset. Its narrow passageways throng with people each evening to catch a glimpse of the sun going down. The most popular spot to watch the sunset is by the Kastro walls. At the end of your visit, return to your hotel by private vehicle.
Accommodation: Private Villa
Day 13 – Santorini
In addition to ultimate privacy and exclusivity, indulge in a wealth of amenities offered by your luxury villa. Enjoy access to a private pool, state-of-the art fitness center, sauna, media room, tennis court, and/or a unique add-on that only a first-class villa retreat could provide.
Petra offers a creative menu of Greek cuisine, with a twist! Tasting everything from squid to wagyu, Petra offers an incredible menu, signature cocktails and wine tasting, all with a fantastic view of the caldera. Each week, Petra offers exclusive special event nights, including cocktail nights, live music and degustation. Custom menus, vegetarian and gluten free options are all available on request. For an extra special evening, enjoy a wine or cheese tasting session at the White Cave or upgrade to a romantic dinner at the Panorama Balcony.
Accommodation: Private Villa
Day 14 – Santorini
Meet your driver for a private airport transfer.
Captivating Moments
Get captivated by a stunning collection of sample images from this trip.
Additional Information
This sample itinerary is meant to inspire your next trip. It is ready to be customized to suit your interests, tastes and budget so you can connect with local cultures and experience authentic travel on your own terms and departing whenever you choose. Itinerary details and availability are subject to change, please inquire for up-to-date information and pricing.
What’s Included
• A fully customized itinerary based on your interests and schedule
• 24/7 in-destination support from our local office
• All accommodation stays, tours and transfers for scheduled activities are covered, unless otherwise listed in the itinerary
• A private driver for tours and transfers (in some countries our local private guides also act as your driver – your Destination Expert will discuss with you if applicable)
• Local private guides or shared tours that take you through your itinerary highlights and experiences, your final itinerary will confirm the type of tour
• A greeting at the airport or at your accommodation from one of our representatives – your expert will confirm your meet and greet location with you
• One suitcase and one carry-on per person for trip transfers
What’s Not Included
• Your international airfare – please do let your expert know if you’d like to receive pricing from our Air Team
• Travel insurance, which we offer and can be purchased after you’ve booked your tour
• Visas (unless noted)
• Excess baggage charges, and where applicable, baggage not included in your fare
• Early check-in or late check-out from hotels (unless otherwise specified)
• Optional enhancements like room or flight upgrades, optional tours, or local camera or video fees
• Passport fees, immunization costs, and local departure taxes (when applicable)
Book This Trip
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