Following a delicious breakfast, start the circumnavigation of Santorini! You’ll begin at the beautiful Caldera Beach on the southwest coast and then paddle west towards the point of Faros. Enjoy a breathtaking caldera view with the cliffs of Santorini on your left and the smaller islands of Thisaria and Nea Kameni on your right. Spot colorful doors of traditional Greek boat houses carved right into the seaside cliff walls.
Turn back east along the coast to your cappuccino stop at Pigadia Beach. Your lunch stop is at the historic Akrotiri Beach, where you’ll take some time to visit the ruins of Akrotiri. The destination for the night is near the southernmost tip of the island of Fira, where your friendly hosts await you in their beautiful villas. After a swim and a shower, visit a fine Santorini winery, beautifully perched atop cliffs, for some wine tasting and one of many caldera sunset. Head back to a seaside taverna for dinner.
Meals: Breakfast and dinner
Accommodation: Family-owned inn or hotel
You did a wonderful job of rolling with the “windy punches”. Without hesitation, I’d recommend you to those who trust me. Warmest regards”