Luxury Santorini Escape – 14 Day Itinerary

Day 1: Arrival & Settling In

Morning: Arrive at Santorini Airport where a private luxury sedan awaits to whisk you to your ocean‑front villa in Imerovigli, offering breathtaking caldera views. The villa’s concierge will prepare a welcome basket of local delicacies.

Afternoon: Unwind by the infinity pool, sip chilled Assyrtiko, and explore the villa’s private terrace while the staff arranges your bespoke itinerary.

Evening: Enjoy a candlelit dinner on the villa’s rooftop, featuring a curated tasting menu of gourmet Greek cuisine paired with premium wines.

Day 2: Fira Exploration & Fine Dining

Morning: A private driver transports you to Fira, where you stroll the cliff‑side promenade, visit the Archaeological Museum, and admire the iconic whitewashed architecture.

Afternoon: Indulge in a luxury shopping experience at boutique ateliers, followed by a private guided tour of the historic Cathedral of Saint John the Baptist.

Evening: Dine at the Michelin‑starred Selene, savoring contemporary Cycladic dishes crafted by Chef M.-H. Koutoulas.

Day 3: Oia Sunset & Photography

Morning: Relax with a late breakfast on the villa’s terrace, then take a leisurely walk to the picturesque village of Oia, exploring its narrow lanes and iconic blue domes.

Afternoon: Participate in a private photography session with a professional photographer who captures the stunning vistas and your moments against the caldera.

Evening: Witness the legendary Oia sunset from a secluded spot, followed by a champagne toast on a private balcony.

Day 4: Private Yacht Sunset Cruise

Morning: Enjoy a spa morning at the villa, including a signature treatment at the Canaves Oia Spa.

Afternoon: Board a luxury yacht for a private cruise around the caldera, swimming in crystal‑clear waters and exploring hidden coves.

Evening: The yacht anchors for a sunset dinner with fresh seafood, accompanied by live violin music.

Day 5: Volcanic Adventure & Hot Springs

Morning: Set sail on a private boat to the active Nea Kameni Volcano, where a guided hike reveals volcanic landscapes and panoramic views.

Afternoon: Dip into the therapeutic waters of the nearby Palea Kameni Hot Springs, enjoying a relaxing soak amid steam.

Evening: Return to the villa for a private chef‑prepared Greek mezze dinner on the terrace.

Day 6: Wine Tasting & Gourmet Dinner

Morning: Leisurely breakfast followed by a stroll through the vineyards of Santo Wines, with panoramic views of the caldera.

Afternoon: A private sommelier guides you through a tasting of premium volcanic wines, paired with artisanal cheeses and olives.

Evening: Savor a gourmet dinner at Metaxi Mas, a hidden gem known for its creative Mediterranean cuisine.

Day 7: Akrotiri Archaeology & Red Beach

Morning: Explore the ancient Minoan settlement of Akrotiri on a private guided tour, uncovering frescoes and ruins preserved under volcanic ash.

Afternoon: Relax on the striking Red Beach, with a personal beach attendant providing refreshments and sun loungers.

Evening: Return to the villa for a relaxed dinner featuring locally sourced seafood, prepared by your private chef.

Day 8: Scuba Diving & Sunset Cruise

Morning: Dive into the Aegean with a certified instructor for two dives exploring vibrant marine life and underwater arches near Cape Columbo.

Afternoon: After surfacing, unwind with a light lunch at the beach club and enjoy a brief nap on the villa’s sun deck.

Evening: Board a luxury sunset cruise with champagne, gliding past the caldera while enjoying live acoustic music.

Day 9: Day Trip to Mykonos

Morning: Depart on a private chartered yacht for an exclusive day on Mykonos, arriving at the iconic Little Venice district.

Afternoon: Explore the island’s boutique shops, enjoy a beachfront lunch at Scorpios, and relax on the pristine sands of Psarou Beach.

Evening: Return to Santorini for a late dinner at the villa, followed by stargazing on the terrace.

Day 10: Greek Cooking Class & Leisure

Morning: Participate in an intimate cooking class with a renowned local chef, learning to craft traditional dishes such as moussaka and baklava.

Afternoon: Sample your creations for lunch, then spend the afternoon at leisure—perhaps a dip in the pool or a walk through the village of Imerovigli.

Evening: Enjoy the fruits of your labor with a sunset dinner on the villa’s terrace, paired with fine Greek wines.

Day 11: Private Charter to Naxos

Morning: Set sail on a private yacht to Naxos, arriving at the historic port of Chora.

Afternoon: Explore the marble streets, visit the ancient Portara gate, and enjoy a seaside lunch at a boutique taverna.

Evening: Return to Santorini for a relaxed evening with a private in‑villa movie screening and gourmet popcorn.

Day 12: Luxury Spa & Relaxation

Morning: Indulge in a full‑day spa experience at the villa’s private spa, featuring a signature volcanic stone massage and aromatherapy.

Afternoon: Take advantage of the villa’s private yoga instructor for a calming session overlooking the caldera.

Evening: Dine at Ambrosia Restaurant in Oia, renowned for its innovative tasting menu and panoramic sunset views.

Day 13: Leisure Day & Sunset Dinner

Morning: Enjoy a leisurely breakfast followed by optional activities such as a private horseback ride along the cliffs.

Afternoon: Spend time shopping for high‑end souvenirs in the boutique stores of Fira and Oia, with a personal stylist on hand.

Evening: Conclude the trip with a spectacular sunset dinner on a private terrace, featuring a multi‑course degustation prepared by a guest chef.

Day 14: Departure

Morning: Relish a final gourmet breakfast with a view of the Aegean, followed by a private checkout service.

Afternoon: Your luxury sedan transports you to the airport, where a VIP lounge awaits for a comfortable wait before your flight.

Evening: Fly home with unforgettable memories of an opulent Santorini adventure.

Time and Cost Estimates

• Luxury Villa (14 nights) – 14 nights – $11,200
• Private Yacht Sunset Cruise – 4 hrs – $2,500
• Wine Tasting at Santo Wines – 2 hrs – $1,200
• Helicopter Tour over Caldera – 30 min – $3,500
• Volcano & Hot Springs Private Boat – 5 hrs – $2,000
• Scuba Diving (2 dives) – 4 hrs – $1,000
• Greek Cooking Class – 3 hrs – $500
• Spa Treatment at Canaves – 3 hrs – $1,200
• Private Charter to Mykonos – 1 day – $6,000
• Private Charter to Naxos – 1 day – $4,000
• Private Island Car & Driver – 7 days – $3,000
• Fine Dining at Michelin Restaurants – 3 evenings – $4,500
• Shopping & Souvenirs – throughout – $2,000
• Luxury Airport Transfers – round trip – $1,500
• Private Photography Session – 2 hrs – $1,500
• Sunset Cruise with Champagne – 3 hrs – $2,000
• Guided Akrotiri Archaeological Tour – 2 hrs – $1,400
• Total Estimated Cost: $49,000

Tips

To extend the experience, add an extra night on the private yacht to explore nearby islands like Ios or a second day of exclusive spa treatments. If you wish to shorten the trip, combine the Mykonos and Naxos excursions into a single day‑trip cruise, or replace one fine‑dining evening with a casual beachfront dinner, keeping the overall budget comfortably under $75,000.