Oia Santorini 5 Day Itinerary

5-Day Itinerary for Oia, Santorini

Things to Know:

  • Best Time to Visit: Shoulder seasons (April-May & September-October) offer pleasant weather and fewer crowds.
  • Currency: Euro (€)
  • Language: Greek

Transportation:

  • Airport Transfers: Pre-book a taxi or shuttle from Santorini Airport (JTR) to Oia (~30 minutes).
  • Local Buses: Frequent and affordable, connecting Oia with other villages on the island.
  • Taxis: Readily available but can be expensive.

Accommodation:

  • Budget: Airbnb rentals, pensions in the village outskirts.
  • Mid-Range: Boutique hotels with caldera views, charming cave houses.
  • Luxury: Five-star resorts with infinity pools and spa facilities.

Day 1: Arrival & Oia Exploration

  • Morning: Arrive at Santorini Airport (JTR) and transfer to your accommodation in Oia. Settle in and enjoy the breathtaking caldera views.
  • Afternoon: Stroll through the winding streets of Oia, admire the whitewashed houses with blue accents, and explore charming boutiques.
  • Evening: Witness the iconic sunset over the Aegean Sea from a vantage point like Oia Castle or a rooftop bar.

Dinner Recommendation: Ammoudi Fish Tavern for fresh seafood by the water.

Day 2: Ancient Thera & Wine Tasting

  • Morning: Hike up to the ruins of Ancient Thera, an archaeological site offering panoramic views of the island and caldera.
  • Afternoon: Visit a local winery like Santo Wines or Boutari Winery for a wine tasting experience and learn about Santorini’s unique volcanic wines.
  • Evening: Enjoy dinner at a traditional taverna in Oia, savoring Greek delicacies like moussaka, souvlaki, or fresh grilled fish.

Dinner Recommendation: Roka Restaurant for modern Greek cuisine with caldera views.

Day 3: Santorini Sunset Cruise & Red Beach

  • Morning: Relax on the black sand beaches of Perissa or Kamari.
  • Afternoon: Embark on a romantic sunset cruise, sailing along the coastline and witnessing the breathtaking sunset from the Aegean Sea. Some cruises include dinner and swimming stops.
  • Evening: Visit the unique Red Beach with its striking red cliffs and volcanic sand.

Dinner Recommendation: Sunset Taverna for delicious seafood while enjoying the sunset views.

Day 4: Imerovigli & Skaros Rock

  • Morning: Hike from Oia to Imerovigli, a neighboring village with stunning caldera vistas. Stop by Skaros Rock, an ancient fortress offering panoramic views.
  • Afternoon: Explore the charming alleys of Imerovigli and enjoy lunch at a local café or taverna.
  • Evening: Relax back in Oia and indulge in a massage or spa treatment for ultimate relaxation.

Dinner Recommendation: La Maison for fine dining with an exquisite atmosphere.

Day 5: Departure

  • Morning: Enjoy one last breakfast overlooking the caldera. Soak up the magical atmosphere of Oia before heading to Santorini Airport (JTR) for your departure.

Tips:

  • Book accommodation and tours in advance, especially during peak season.
  • Wear comfortable shoes for exploring the hilly streets.
  • Carry sunscreen, a hat, and sunglasses as the sun can be strong.
  • Be prepared to walk uphill, especially in Oia.
  • Learn some basic Greek phrases – locals appreciate the effort.

Enjoy your unforgettable trip to Oia, Santorini!