Santorini Shines in Fall at the Canaves Collection Hotels

On the cliffs of Santorini’s caldera, or volcanic crater, perches the picturesque village of Oia, a maze of narrow streets lined with whitewashed buildings, blue-domed churches and breathtaking views of the caldera and the Aegean Sea. Located on the island’s northern tip, Oia offers a quintessential Greek island experience that puts it at the top of bucket lists worldwide.

It’s here that Santorini’s cave houses, known as canaves, first were carved into the volcanic rock of the cliffs in the 17th century. Originally used as storage spaces (particularly for wine) due to the rock’s natural insulation that kept interiors cool during the hot summer months and warm during the winter, canaves were transformed into homes with distinctive architecture. These unique dwellings are at the heart of the Canaves Collection of boutique hotels — five posh properties that each capture the essence of Santorini in their own special way.

Following the summertime heat and crushing crowds, fall is an ideal time for a Santorini getaway. During this idyllic period, a stay at a Canaves Collection property captures the essence of an endless summer.

Where to Stay in Santorini: Canaves Collection Highlights

From Cave Houses to Luxe Hotels

In the 1980s, a couple named Yiannis and Anna Chaidemenos saw greater potential in the old caves of Oia. Deciding to transform them into luxury accommodations, they laid the foundation for what would become today’s Canaves Collection and became one of the first families to introduce hospitality to the fishing village. Their sons, Marcos and Alexandros, inherited their passion and expanded the family’s vision. Today, their legacy is carried forward with modern touches and sustainable practices. From the original Canaves Ena, originally called Canaves Oia Traditional Houses, to the family-friendly Canaves Sunday Suites, there is a property to provide the perfect backdrop for a stay on this enchanting island for every type of traveler. 

TIP: Our Ciao Bambino Family Travel Advisor team can book the perfect Canaves Collection accommodations for your needs, often with exclusive perks and amenities. These accommodations are in high demand and fill up fast — reach out to us to book!

An Indulgent Escape for All Ages

The Chaidemenos family’s foray into hospitality began with the romantic Canaves Ena, ideally situated at the beginning of Oia within walking distance of restaurants, cafes and shopping areas. Opened in 1985, the property is newly furnished as of 2024 and sits 100 meters from Canaves Oia Suites, which was introduced in 1995. Accommodations are designed with large windows and private terraces that offer spectacular views of the caldera, while the interiors are a seamless blend of traditional Cycladic architecture and modern design.

What makes these properties truly amazing is that while many upscale hotels on Santorini shun children, the Chaidemenos family welcomes kids age 13 and up, so parents can experience the epitome of the island’s sophistication in a family-friendly environment. However, the intimate setting of Canaves Ena and Canaves Oia Suites is magical and best suited for babymooners enjoying one last getaway as the family grows, or empty nesters relaxing after the hustle and bustle of getting kids settled into college.

A concierge at every Canaves property can organize excursions on speedboats, motor yachts, catamarans and even helicopters, and guests will find relaxing on-property pools with the stunning views that lure visitors to Santorini. Onsite dining offers an unparalleled ambiance thanks to views of the Aegean Sea and the caldera, paired with refined Mediterranean fare made from ingredients sourced on the island. Guests can savor meals in the elegant restaurants or opt for an intimate dining experience on their private terrace, all while enjoying selections from the extensive wine list.

Fall into Family Luxury

If ever there was a reason to delay the start of school or take a fall break, Canaves Sunday Suites and Canaves Elefas Villas are it. As summer wanes and the tourist season comes to an end, the island feels like a private family escape. Combining astonishing beauty with the warmth and comfort of a family home, Canaves Sunday Suites is a sanctuary of just eight suites where families can immerse themselves in opulence while feeling completely at ease. 

Meanwhile, Canaves Elefas Villas provides a similar setting farther removed from the busy atmosphere of Oia. Conveniently located for exploring elsewhere in Santorini yet completely private, it welcomes children age 6 and up with just five villas, the largest a seven-bedroom dwelling that can accommodate 16 guests.

Both properties provide spacious, beautifully appointed accommodations designed to cater to the needs of families. Each suite features separate living and sleeping areas, allowing parents and children to have their own spaces. Some suites even come equipped with kitchenettes, giving you the convenience of preparing snacks and meals on demand. As with the entire Canaves portfolio, many units offer private plunge pools.

For larger families or groups, both Canaves Sunday Suites and Canaves Elefas Villas can be rented in full, housing up to 20 family members and friends for the ultimate multigenerational vacation or family reunion. The staff will even stock your villa with groceries and can provide a private butler and private chef at your request.

The Epitome of Family Vacations

Meanwhile, Canaves Epitome provides a more traditional resort setting for families traveling with younger kids. It boasts a selection of 53 opulent suites and villas designed to provide the utmost comfort and privacy, each with its own infinity pool, spacious living areas and large terraces offering breathtaking views not only of the sea, but also of Santorini’s stunning sunsets. The location above the fishing village of Ammoudi affords a front-row seat to the unbelievable color show as the sky transforms from day to night.

Canaves Epitome also offers a variety of exclusive experiences that allow guests to explore Santorini at their own pace. Visitors can enjoy a private sailing tour around the island to see hidden coves and marvel at the volcanic landscape, or a romantic sunset cruise complete with champagne and gourmet hors d’oeuvres. 

On-property, take in the views from the main infinity pool or sample from a range of activities that will keep kids entertained, from arts and crafts sessions to guided tours of the island’s highlights. Babysitting services allow parents to enjoy some one-on-one time and linger over a sunset dinner or the tranquil on-site spa. Amenities for children also are available, developed by Worldwide Kids.

Canaves Epitome truly immerses kids in island life, surrounding by a rich landscape filled with fragrant herbs, majestic olive trees, colorful citrus trees and flowering plants like bougainvillea and hibiscus.

As the autumn sun sets over the Aegean, casting a golden glow on the whitewashed buildings of Oia, the Canaves Collection creates lasting memories worthy of an off-season getaway. With each of the properties open through November, embrace the timeless beauty and unparalleled hospitality provided by the Chaidemenos family and let your next getaway be an unforgettable experience.

Relevant Links:

Browse all accommodations and activities in Greece on Ciao Bambino

Top Greek islands for families: How to choose the best match

A week in the realm of Greek gods: Visiting Crete with kids

72 hours in Athens, Greece with kids

Acropolis views at St. George Lycabettus Lifestyle Hotel

Photos courtesy of the Canaves Collection.

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.