Santorini 5‑Night Luxury Getaway – May

Day 1: Arrival & First Impressions

Morning: Arrive at Santorini (JTR) airport and transfer to your 4★+ hotel in Fira. Settle in, enjoy the panoramic view of the caldera from your balcony.

Afternoon: Stroll through the charming streets of Fira, explore local boutiques and sip a refreshing Greek coffee at a cliff‑side café.

Evening: Dine at a gourmet restaurant overlooking the sunset, such as Selene, and experience the iconic Oia sunset from a nearby viewpoint.

Day 2: Classic Santorini Highlights

Morning: Take a private guided tour of the ancient ruins of Akrotiri, the Minoan Bronze Age settlement preserved in volcanic ash.

Afternoon: Visit the famous white‑washed village of Oia, wander its narrow alleys, and browse art galleries.

Evening: Enjoy a sunset dinner cruise around the caldera, featuring fresh seafood and live Greek music.

Day 3: Beach Day & Local Flavors

Morning: Relax on the volcanic sands of Red Beach, swim in its crystal‑clear waters, and snorkel among the unique rock formations.

Afternoon: Head to Perissa Beach for a beachfront lunch of grilled octopus and a glass of chilled Assyrtiko wine.

Evening: Return to the hotel for a spa treatment, then explore the nightlife in Fira’s lively bars.

Day 4: Wine & Culinary Experience

Morning: Tour the renowned vineyards of Santo Wines and Venetsanos Winery, with tastings of premium local varieties.

Afternoon: Participate in a hands‑on cooking class learning to prepare traditional dishes like tomatokeftedes and fava.

Evening: Savor the dishes you created during a communal dinner, paired with additional wine selections.

Day 5: Scenic Walks & Sunset Views

Morning: Hike the famous Fira to Oia trail, enjoying breathtaking panoramas of the caldera and the Aegean Sea.

Afternoon: Stop at the picturesque village of Imerovigli for a light lunch at a cliff‑top café.

Evening: Conclude your stay with a private dinner at Canaves Oia Hotel’s terrace, watching the final Santorini sunset.

Day 6: Departure

Morning: Enjoy a leisurely breakfast with a view, then pack and check out of the hotel.

Afternoon: Transfer to the airport for your departure flight, carrying unforgettable memories of Santorini.

Evening: Arrival back home.

Time and Cost Estimates

• 4★+ Hotel (5 nights) – 5 nights – $250/night ≈ $1,250
• Airport transfers (round‑trip) – 2 hrs – $80
• Akrotiri archaeological site – 2 hrs – $12 entry
• Oia sunset viewpoint (no fee) – 1 hr – $0
• Sunset dinner cruise – 4 hrs – $150
• Red Beach & Red Beach lounge – 3 hrs – $20 (sunbed)
• Perissa Beach lunch & Assyrtiko tasting – 2 hrs – $40
• Spa treatment – 1.5 hrs – $100
• Santo Wines & Venetsanos Winery tour – 3 hrs – $70
• Greek cooking class – 3 hrs – $90
• Fira to Oia hike (incl. rest stops) – 4 hrs – $0
• Imerovigli café lunch – 1.5 hrs – $30
• Private dinner at Canaves Oia – 2 hrs – $180
• Miscellaneous meals & snacks – 5 days – $250
• Total Estimated Cost: $2,332

Tips

For a more relaxed pace, add an extra night and spend a full day exploring the lesser‑known villages of Megalochori and Pyrgos, or take a day‑trip to the nearby island of Thirassia. If you need to shorten the trip, combine the beach day with the wine tour by visiting the wineries after a morning swim at Perissa, and skip the private dinner in favor of a sunset meal in Oia’s public squares.