Spend your first morning on Santorini exploring some of the towns. While it’s certainly easy to get around the island on your own, there are plenty of tours for travelers with limited time.
Thera, or Fira, the main town, lies on the curve of the caldera, facing west. The ferries arrive into the port that lies south of the main town. Its picturesque white washed buildings cling to the sides of the cliffs.
The village of Emporio is famous for its century old churches and unique windmills. The nearby Perissa Beach is a great stopping place for lunch. Its black sand beaches make an excellent backdrop for photos, while the little tavernas serve mouthwateringly good, fresh fish.
Pyrgos is one of the least visited towns on the island. It lies inland, about seven kilometres from Thera, and is a classic example of defensive medieval architecture. The Venetian fortress above town affords great views of the surrounding countryside.
Hike from Fira to Oia
In the morning, lace up your walking shoes. From Fira, it is about a four hour hike to Oia, and vice versa. The walk follows the rim of the caldera and passes through Firostefani and Imerovigli as well as Fira and Oia. From the ridge, you’ll have spectacular views of both the inland plains and the Aegean Sea.
Don’t feel like the hike? Rental Scooters and ATVs are available. (Beware of the windy roads.) Start early in the summer, as it gets hot by late morning, and bring water. There are shops in which to buy water or snacks in the towns, as well as vendors on the street.
Watch the sunset in Oia
Before the sun sets, take a taxi or bus to Oia. This charming, bustling village has plenty of exciting places to dine. Watch the sun set over the caldera as the town literally lights up in epic shades of gold and rose. After the sun sets, stay for a traditional Greek dinner in a local taverna.
Oia is the most famous, for this is the town with the iconic blue domed roofs and whitewashed buildings. It is on the northern curve of the caldera, facing south toward the rest of the island. Oia is an ideal place from which to watch the sunset! While still a major tourist attraction, it is quieter than Fira. You will find many shops, cafes, and tavernas in Oia, as well as a lot of art galleries. There are remains of a Venetian fortress as well as old captain’s houses that are worth viewing.
Explore the Beaches
Spend the morning in town, or head for one of the popular beaches to soak up some sun. The beaches of Santorini are covered with volcanic pebbles in shades like red, rose, black, and white. Another option is to visit the famous hot mud baths for a unique bathing experience.
Visit a winery
In the afternoon, join a local guide on a half day wine tasting tour of the island. Wine production on Santorini dates back at least 5000 years. Greek wines are refreshing and delicious, thanks to the mild Mediterranean climate. However, the arid atmosphere posed some challenges to the early vintners. You’ll have the chance to speak with the vintners, who explain how the grapes adapted to a dry, volcanic environment.
Popular wines in Greece include Assyrtiko and Mandilaria. This tour stops at three different Greek wineries, where you can taste a wide variety of the wines available. You’ll also have the opportunity to taste local breads, cheese, olives, and meats.
Walk the 588 steps of the old Karavolades stairs
You can take the cable car down to avoid stepping on donkey droppings.
Walking upstairs is more advisable, because walking downstairs is slippery and afterwards you will feel your calf muscles for days.
If you consider riding a donkey, take a donkey up, but not down. They go faster downwards with the risk of slipping. Some say the donkeys get fed downstairs....
At the bottom of the stairs there is an amazing little seafood restaurant called Ammoudi Fish Tavern. Without a doubt it is the most perfect picturesque place that you imagine when you think of the old fishing village of Greece.
Sunset Catamaran Cruise
Cap off your spectacular Santorini itinerary with a five hour catamaran sunset cruise. The tour begins at the Ammoudi town port, which is on the shores below Oia, although they do offer hotel pick up for an extra price. The sailing allows you to view Santorini from a different angle, visit secluded beaches, and snorkel under the famous white cliffs. The return sailing occurs as the sun sets under the hills of Oia.
My personal favorite accommodations:
Canaves Oia Santorini (The Caves)
Built on the side of a cliff, Canaves is a polished all-suite hotel. Inviting, inspiring and elegantly classic suites and contemporary facilities, entice guest to experience luxury accommodation beyond comparison in the best luxury hotel in Oia Santorini. All hotel suites are freshly renovated and elegantly decorated in a dazzling white, minimal manner, featuring private verandas, al fresco dining areas and breathtaking views to the Caldera and the Aegean Sea.