Astypalaia Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

Things to do in Astypalaia

Astypalaia offers a delightful mix of beach relaxation, cultural exploration, and outdoor activities. Visitors can indulge in sailing, enjoying the stunning coastal views and crystal-clear waters. The island's charm lies in its picturesque villages, rich history, and inviting beaches, making it an ideal destination for those seeking both adventure and tranquility. Embrace the local culture and savour traditional cuisine as you immerse yourself in this beautiful Aegean paradise.

Shopping

In Astypalaia, you can wander through charming local shops in Chora, offering unique handcrafted souvenirs. If you're up for a drive, head to the nearby town of Kylindri for a larger selection of boutiques and traditional markets, showcasing local crafts and delicious delicacies.

Recreation

In Astypalaia, the Astypalaia Wellness Retreat offers holistic treatments amidst serene landscapes, perfect for rejuvenation. Explore yoga sessions by the beach, or indulge in a detox programme featuring local organic ingredients, ensuring a revitalising escape tailored to both body and mind.

Adventure

Explore Astypalaia's rugged terrain by hiking to the Venetian Castle for stunning views. Discover hidden coves by kayaking along the coastline, or go snorkelling in crystal-clear waters teeming with marine life. For a thrilling experience, try windsurfing on the island's breezy shores.

Nightlife

Astypalaia offers a charming nightlife with laid-back bars and vibrant tavernas. Head to Chora for lively spots like the popular Astropalati and the enchanting Platanos, where you can enjoy cocktails and local music while soaking up the island's warm atmosphere under the stars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Astypalaia

Astypalaia offers a delightful blend of beach and cultural experiences, perfect for outdoor enthusiasts. Key attractions include the beautiful Astipaleas Beach, the historic Astypalaia Castle, the charming Astypalea Windmills, and the picturesque town of Astypalea. Whether you seek romance or adventure, this enchanting island caters to all types of travellers, ensuring a memorable getaway in the South Aegean.

  • Astypalea Windmills: These historic windmills, perched on a hill, offer a glimpse into the island's rich cultural heritage. Their iconic white structures against the blue sky create a picturesque scene, perfect for photography enthusiasts and history buffs alike.
  • Astypalaia Castle: Dominating the landscape, this charming castle combines culture and romance. As you explore its ancient walls, enjoy breathtaking views of the Aegean Sea and the charming town below, making it ideal for a romantic stroll.
  • Central Square: A vibrant hub of local life, Central Square is perfect for relaxing and people-watching. Surrounded by cafes and shops, it’s an excellent spot to savour local delicacies and unwind after a day of excursions.

Best time to go to Astypalaia

The best time to visit Astypalaia is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are moderately high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January56.1°F (13.4°C)Light RainMostly SunnyAverageLow
February56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
March57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
April61.7°F (16.5°C)No RainSunnyAverageAverage
May67.5°F (19.7°C)No RainSunnyAverageAverage
June73.8°F (23.2°C)No RainSunnyModerately HighHigh
July78.1°F (25.6°C)No RainSunnyModerately HighHigh
August78.8°F (26.0°C)No RainSunnyModerately HighHigh
September75.4°F (24.1°C)No RainSunnyAverageAverage
October70.2°F (21.2°C)No RainSunnyModerately LowAverage
November65.1°F (18.4°C)Light RainMostly SunnyModerately Low
December59.5°F (15.3°C)Light RainMostly SunnyModerately Low

Tips to save on your trip to Astypalaia

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Astypalaia.
  • Consider traveling to Astypalaia during the low season (January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Astypalaia Beach Holiday

Get ready to live out those beachy daydreams on your upcoming Astypalaia holiday. Enjoy a relaxing stroll, savour the spectacular coastal views and collect unique seashells on your trip to Astypalaia. Located just 0.97 kilometres from the town centre, Livadi Beach is the place to be for many sun-seeking visitors. Have a look through our Astypalaia packages and watch your travel budget go further!

Things You Should Know About Astypalaia

  • If waking to the sounds of the ocean is your idea of getaway bliss, see what's available among our Astypalaia beach hotels. You're sure to find something that has everything you need for an ideal beachside stay.
  • A holiday in Astypalaia means staying in apartments for many visitors. Astypalea Villas and Viva Mare Studios are a few of the top options here.
  • The population of Astypalaia is roughly 1,150. If you'd like a few great travel tips, there are lots of locals who'll be happy to give you advice. Our Astypalaia things to do page is also a wealth of useful information.
  • One sight to put on your itinerary is Astypalaia Castle. But there are many other fantastic things to discover around this area. Tick off more of them with our bargain Astypalaia holiday deals.

Top hotels in Astypalaia

Pylaia Boutique Hotel & Spa

Pylaia Boutique Hotel & Spa

3 out of 5
Chora Astypalaia Astypalaia Island
8.8/10 Excellent! (23 reviews)
Excellent boutique hotel
Room are modern updated and chic Bed was fine Food was excellent. They make omelets on request and specialty coffees without charge Baked good are from a nearby bakery and were excellent. We even went to the bakery to buy items

Reviewed on 1 Aug, 2025

Pylaia Boutique Hotel & Spa
Ihthioessa Boutique Hotel

Ihthioessa Boutique Hotel

2 out of 5
A Punta Astypalaia Astypalaia Island
9.6/10 Exceptional! (13 reviews)
Nice & polite staff. Good breakfast and clean rooms

Reviewed on 29 Dec, 2025

Ihthioessa Boutique Hotel
Tholaria Boutique Hotel

Tholaria Boutique Hotel

2 out of 5
Chora Astypalea Astypalaia Astypalaia Island
9.2/10 Wonderful! (10 reviews)
The hotel has 'local colour ' features and is perfectly located in the Chora. Our room had a fantastic sea view overlooking a small cove. Breakfast had new additions daily using local products as much as possible. Above all Maria is the most pleasant and accommodating host ever!!!! Always there to ...

Reviewed on 25 Aug, 2025

Tholaria Boutique Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.