The stunning Greek Island of Santorini, set on an ancient volcanic caldera in the Aegean Sea, offers a myriad of seductive charms. Whether you’re seeking a romantic bolthole or fun in the sun with friends, you’ll find beaches with sailing and watersports, excellent local cuisine, pretty villages, amazing museums, and enchanting spots for sundowners. TLTB founder, Susie Marquis, shares expert tips from her travels around the island for the most memorable experiences and the best luxury villas to rent in Santorini.
Sunsets on Santorini
In addition to gloriously long sunny days, you’ll also witness some of the world's most beautiful sunsets on this gorgeous Greek island. My favourite sunset viewing point on Santorini is the picture-postcard village of Oia. Situated at the end of the caldera, the village features narrow streets, pretty cube-shaped houses and blue-domed churches, and wonderful caldera views – all beautiful by day and absolutely stunning by night. Understandably, many artists have fallen in love with Oia, which accounts for the many interesting little art galleries. Wandering through the labyrinth of streets, you’ll also discover a great selection of jewellery and clothes boutiques, as well as many atmospheric cafés, bars and restaurants.
At the bottom of the village (down 300 steps to the sea!), is Ammoudi Bay, a lovely old fishing port, where you’ll discover a cluster of traditional tavernas, including one of our favourites, Sunset Fish Tavern. If you prefer to admire the sunset from a quieter location, head to the lighthouse at Akrotiri, situated at the other end of the caldera. Akrotiri dates to the Minoan Bronze Age and is arguably the most important archaeological site in the Aegean. The town was destroyed by the volcanic eruption around 1600 BC, and you can take a tour of the excavations of streets and squares, and discover more about this seismic event at the Museum of Prehistoric Thera and the Archaeological Museum.
If you want to explore more history and mythology, we highly recommend a visit to the fascinating Lost Atlantis Experience Museum. Over 3000 years ago, a catastrophic volcanic eruption consumed Santorini, causing the middle of the island to disappear into the ocean below. The island has long been assumed to be the home of the legend of Atlantis.
In the middle of the rim of the caldera, between Oia and Akrotiri, is the island’s picturesque capital, Fira, with a larger choice of restaurants and shops, and also the centre of Santorini’s nightlife. Like the beautiful villages of Oia, Imerovigli, and Firostefani, Fira also offers magnificent caldera and sea views. There are some great bars and restaurants here including Archipelagos Restaurant, located in one of the oldest captains' houses on the caldera cliffs of Fira. Built in 1860, and restored with respect to the traditional architecture, the restaurant’s beautiful terraces literally hang over the caldera, making it an ideal spot to enjoy the views by day or by night. We also recommend Argo restaurant, located on the main footpath in Fira overlooking the caldera, and also with wonderful sea and sunset views from the upstairs dining area. For the energetic, a great daytime Santorini experience is the long walk along the cliffs of the caldera, from Fira to Oia. It’s around 10 km, but some of the trail is paved, and the views are absolutely sensational.
Around 9 km inland from Fira, is the very pretty traditional village of Megalochori, with its beautiful architecture, narrow streets and picturesque squares. It's also known for its rich wine tradition, with the vineyards just outside the village producing some of the most famous wines on Santorini. Many of the wineries offer organised tours, as well as wine tastings. We recommend the Boutari Winery, close to Megalochori, on the way to Akrotiri, and also Santo Winery, situated in the old village of Pyrgos. In a wonderful location high on the caldera, Pyrgos is the best-preserved medieval settlement on the island. Santo Winery hosts popular wine tastings and wedding ceremonies and is ideal for special events. Estate Argyros is also worth checking out for tastings. It’s the largest private owner of vineyards in Santorini and situated inland between Fira and Megalochori.
One of the best things to do during your stay on Santorini is to take a sailing cruise, and we highly recommend our friend, Theo, owner of Santosails. Theo offers some wonderful sailing experiences including a 5-hour Private Day Sailing Cruise into the famous caldera, visiting the Red and White beaches with their hidden caves, and allowing for optional snorkeling and swimming time. The cruise also sails towards the volcanoes, Nea and Palea Kameni, and to the old ports of Fira and Oia (Ammoudi). Another particularly tempting cruise is the 5-hour Private Sunset Cruise, which leaves from Oia, and takes in Thirassia island, the caldera and Fira. Food and drinks are included on all the cruises.
Top luxury villas to rent in Santorini
Set in Imerovigli village, on the highest point of the caldera, offering breath-taking panoramic views across the Aegean, 2-5 bedroom Villa Eros will steal your heart. This stunning Greek villa is perfect for honeymooners and romantic escapes, as well as families and groups of friends. It’s also an amazing venue for small weddings. The large sun terrace is equipped with sunbeds, a swimming pool, an outdoor Jacuzzi, and a pergola shaded sitting and dining area. The villa offers concierge services from arranging private yachts, speed boats and helicopters, to winery and sightseeing tours. Private yoga and massage sessions can also be arranged on the large terrace.
The village of Firostefani is characterised by its beautiful white architecture, with churches, cave-like houses and narrow streets. Another stunning villa on the edge of the caldera, and with incredible views, Villa Firostefani is also conveniently located just 1½ km away from Fira village. Built almost entirely inside the rocks, this exceptionally beautiful 'cave-house' features arches and curves, both very typical of the traditional architecture of Santorini. The large main terrace has an outdoor living area and swimming pool, also with a heated Jacuzzi. At a lower level, another outdoor living area also offers stunning views of the caldera, the volcano and the sunset. This 3-bedroom property is also the perfect choice for hosting a wedding or other special occasion.
An exceptional small villa in Imerovigli, 2-bedroom Villa Skaros is owned by an exclusive boutique hotel. It’s set in a stunning location above the caldera, with amazing sunset views and the famous historic Skaros Rock. A huge black peak at the edge of the village, Skaros Rock was formed by ancient volcanic activity, and there are also some ruins of an old castle. The villa offers beautiful interiors and has its own secluded sun terraces and a private pool. Guests here can also benefit from the hotel amenities, including a wonderful Champagne Lounge with sunset views, an award-winning restaurant, and a new yoga and pilates studio.
Villa Chapel is another gorgeous 2-bedroom property. Set in a stunning location in Oia with a spacious terrace and wonderful views, it’s perfect for a romantic holiday. Guests can enjoy panoramic vistas of the caldera, the windmills, the castle of Oia, and the village’s colourful houses nestled against the steep volcanic cliff. As its name suggests, the villa even has a charming 18th-century chapel on its terrace, as well as an outdoor chromatherapy Jacuzzi tub. Guests here also benefit from a range of exclusive services, which include a choice of enticing breakfasts each morning, served in a local café, or delivered to the property for a small surcharge.
Akrotiri Estate is a stunning 5-bedroom villa on the caldera in the village of Akrotiri, only 12 km away from Fira, and just 3 km from the famous Red Beach. The views of the caldera from the large terrace are wonderful. The swimming pool here is designed to give the feeling of being part of the natural landscape, creating the illusion that you are swimming into the blue waters of the Aegean Sea. The terrace is furnished for relaxing outdoors, and there are also two outdoor dining areas. With the backdrop of the blue waters of the pool and sea, the location adds a special atmosphere to your breakfast, lunch, or dinner under the stars. There is a villa manager available to assist during your stay. This exceptional villa rental is perfect for weddings and other special events on Santorini.
We also offer more beautiful villas to rent in Santorini and many more in our other Greek Island locations:
Mykonos, Corfu, Paxos, Zakynthos, Paros, Naxos, Crete, Hydra