With over half a century of arranging memorable trips to the Greek Islands and other handpicked destinations, Olympic Holidays is renowned for its insider knowledge and unrivalled expertise. Its in-house team is passionate about travel and regularly wins awards for incredible customer service and support. The company prides itself on its carefully curated collection, with its latest addition, the unspoiled island of Astypalaia, offering an enticing blend of authentic Greek charm and dazzling, crowd-free beaches.
A dreamy Dodecanese secret
Unlike Kos and Rhodes, its better-known neighbours in the Dodecanese archipelago, the butterfly-shaped island of Astypalaia remains blissfully off the tourist trail thanks to its remote location in the south-eastern Aegean. Reached by a two-hour ferry from Kos, or an hour-long hop by plane from Athens, it has a delightfully go-slow feel, with goats outnumbering residents and ruggedly beautiful hills sloping down to azure bays. Visitors come here to unwind, recharge and soak up the island’s laidback charm.
White-washed villages and hidden coves
Although it belongs to the Dodecanese island chain, Astypalaia’s architecture is more reminiscent of the Cyclades, with its sugar-cube houses and blue shutters. The most stunning example is clifftop Chora, the island’s main hub, where dazzling white buildings tumble photogenically towards the cobalt sea. The town is capped by the crumbling remains of a Venetian palace, lit up at night to spectacular effect. Exploring the slender lanes is a treat, with panoramic cafes, bars and seafood tavernas. For history-lovers, there is a small but excellent archaeological museum in Chora, along with ancient sites such as the infant cemetery at Kylindra and the imposing church of Panagia Portaitissa with its intricate frescoes. Beyond Chora, a wild landscape unfurls, dotted with traditional windmills, sleepy seaside villages and stunning beaches such as Kaminakia and Livadi, renowned for their astonishingly clear waters. Astypalaia is known for its commitment to sustainability and environment, with green initiatives such as the ‘Astybus’ making exploring the island both easy and eco-friendly. The app-based ride-sharing service offers on-demand electric minibus shuttles around the island in the summer.
Stylish Sleeps
Chrysalis Boutique Hotel is an elegant adult-only retreat moments from the centre of Chora, with mesmerising views of the iconic castle. Open-air terraces, homemade breakfasts and a range of wellbeing experiences (from massage to yoga) make it a serene base from which to explore this spectacular island.
Olympic Holidays offer 7 nights at the Chrysalis Boutique Hotel from £792pp (based on 2 adults sharing) staying on a B&B basis. Price includes flights from London Luton to Kos and onward ferry and ground transfers. Based on 24th September 2026 departure. For more information visit www.olympicholidays.com
Kallichoron offers a collection of beautifully restored traditional houses in Astypalaia, combining authentic island charm with contemporary comfort. From peaceful stone-built homes in the seaside village of Livadi to elegant residences tucked within the heart of Astypalaia Town beneath the Venetian Castle, each stay is designed to offer an authentic experience of island life. Blending local architecture, thoughtful modern touches and warm hospitality, Kallichoron provides a relaxed and stylish base for discovering the beauty of Astypalaia.
Olympic Holidays offer 7 nights at the Kallichoron Houses from £524pp (based on 2 adults sharing) staying on a room only basis. Price includes flights from London Stansted to Kos and onward ferry and ground transfers. Based on 30thSeptember 2026 departure. For more information visit www.olympicholidays.com
Perched above the whitewashed town of Astypalaia, Astypalaia Palace Hotel offers a peaceful island escape with sweeping views across the Aegean, the island’s iconic castle and the charming Cycladic settlement below. The hotel combines contemporary comfort with elegant Cycladic design, featuring a collection of stylish suites and studios designed for everything from romantic getaways to laid-back summer retreats. Private balconies come as standard, while many rooms also feature indoor or outdoor hot tubs, ideal for soaking up the sunset in complete privacy. With its calm atmosphere, warm hospitality and elevated position overlooking one of Greece’s most picturesque island towns, Astypalaia Palace Hotel is perfectly suited to travellers seeking a quieter, more authentic Greek island experience without compromising on comfort or style.
Olympic Holidays offer 7 nights at the the Astypalaia Palace Hotel from £682pp (based on 2 adults sharing) staying on a room only basis. Price includes flights from London Stansted to Kos and onward ferry and ground transfers. Based on 30th September 2026 departure. For more information visit www.olympicholidays.com
A perfect island-hopping break
Two Island Hop: For travellers wanting to combine the tranquillity and relaxed pace of Astypalaia with the lively appeal of bustling Kos, Olympic Holidays offers a perfect pairing. Starting with three nights in Kos, guests have ample time to explore its rich history and vibrant waterfront before making the easy, two-hour ferry ride to Astypalaia for a dose of relaxation and calm.
A 7-night Island Hopping experience with 3 nights on Kos and 4 nights on Astypalia starts from £1,037pp for departures from London Gatwick (other regional airports available). Island Hopping experiences are available from May – October. For more information visit www.olympicholidays.com
Multi Island hop: Aegean Butterfly is Olympic Holidays’ ultimate Dodecanese island-hopping adventure, showcasing four distinctly different Greek islands in one seamless itinerary. Beginning and ending on vibrant Kos, the 13-night journey explores the dramatic climbing paradise of Kalymnos, the laid-back charm and colourful harbours of Leros, and the unspoilt beauty of Astypalaia, known as the “Butterfly Island” for its distinctive shape. From hidden coves and crystal-clear waters to traditional whitewashed villages, authentic tavernas and scenic walking trails, each island reveals a different side of the Aegean. With flights, ferry crossings, transfers and accommodation all arranged, the itinerary offers an effortless way to experience the rich culture, landscapes and slower pace of Greece’s lesser-known islands.
The 13 night Aegean Butterfly Island Hopping experience starts from £1,371pp for departures from London Gatwick (other regional airports available). Island Hopping experiences are available from May – October. For more information visit www.olympicholidays.com
