Two weeks island hopping in the Greek Cyclades
Greece itinerary
Created by:
itinerary-hub
Published on:
Oct. 15, 2020
14 days
688 km
7 steps
This is a two week itinerary in the Greek island group of the Cyclades in the Aegean Sea. Visit some of Greece's most beautiful and picturesque islands with stunning landscapes and authentic towns.
Step 1: Naxos
2 days recommended
Naxos
Naxos is the largest island in the Cyclades, offering a perfect mix of beautiful beaches, historic sites, and traditional villages without the tourist crowds of its neighbors. The island's main town, also called Naxos or Chora, welcomes visitors with its iconic ancient marble doorway - the Portara - standing tall since 522 BC, framing gorgeous sunset views.
The island has an impressive history dating back thousands of years. Once an important center for Cycladic civilization, Naxos later became known for its marble quarries, which provided materials for many ancient Greek sculptures and buildings. Today, you can still see impressive marble statues called 'kouros' left unfinished and abandoned in ancient quarries.
Naxian cuisine is worth noting - the island is famous for its exceptional local produce. The fertile land yields fantastic potatoes, cheese (especially the local graviera), and citrus fruits. Naxos also produces its own distinctive spirits, including kitron, a liqueur made from citron leaves.
The mountainous interior hides charming villages like Apeiranthos, known for its marble streets and preserved architecture. These inland communities maintain authentic Greek traditions and offer a glimpse into local life that coastal resorts often lack. With crystal clear waters along its shores and rugged mountains dominating its interior, Naxos provides a more diverse landscape than most Greek islands.
Best hotels in Naxos:
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Panormos Hotel and Studios (budget hotel)
Panormos Hotel and Studios sits just steps from Agios Georgios Beach, making it an excellent choice for those who love being by the sea. The sandy shore is only a minute or two away, and many rooms feature balconies with lovely views of the Aegean. Inside, the studios are designed with soft purple accents and come equipped with kitchenettes, perfect for guests who prefer to prepare their own meals. The front desk staff are always ready to assist, whether it’s arranging bike rentals or offering recommendations for water sports in the area.
The location is ideal, providing a peaceful stay while still being close to the action. A short 10-minute walk takes you to the center of Naxos Town, where you’ll find charming restaurants and shops. The port is also within easy reach, just a 15-minute stroll away. Whether exploring the island or unwinding by the shore, this hotel offers a convenient and comfortable stay.
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Liana Beach Hotel & Spa (medium range hotel)
Liana Beach Hotel & Spa in Agios Prokopios, Naxos, offers a stunning seaside escape where traditional Cycladic charm meets modern luxury. This beachfront hotel provides direct access to golden sands and crystal-clear waters, while its elegant design blends effortlessly with the island’s natural beauty. Guests can lounge by the outdoor pool or enjoy a pampering session at the spa, which features soothing massages, beauty treatments, and a relaxing sauna. The on-site restaurant serves flavorful Greek and Mediterranean dishes, all with breathtaking sea views.
Accommodations range from stylish rooms to spacious suites, many boasting private balconies overlooking the shimmering Aegean. For an added touch of indulgence, select rooms include private hot tubs. The combination of top-tier amenities, an unbeatable location, and a welcoming staff ensures a truly memorable stay. Whether soaking up the sun on the beach or unwinding in the comfort of a well-appointed suite, this hotel offers an ideal setting for a rejuvenating getaway in Naxos.
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Best hostels in Naxos:
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Step 2: Ios
2 days recommended
Ios
Ios is a small but vibrant island in the Cyclades group in Greece, famous for its beautiful beaches and lively nightlife. The main town, Chora, sits on a hilltop with its characteristic white-washed buildings and blue-domed churches creating that classic Greek island look that you always see in photos.
During summer, Ios transforms into a party hotspot, attracting younger travelers looking for fun. However, there's much more to this island than just partying. The island has over 30 beaches, with Mylopotas being one of the most popular thanks to its golden sand and clear blue waters.
Ios also has an interesting history dating back thousands of years. It's said to be the final resting place of the famous poet Homer. The island was named after the ancient Greek word for violets, which supposedly once covered its hills.
Beyond the beaches and bars, Ios offers authentic Greek culture in its more remote villages. Local tavernas serve traditional Greek cuisine using fresh ingredients from the island.
The island strikes a nice balance between developed tourist areas and untouched natural beauty. It's possible to find secluded spots even during the busy season if you're willing to explore beyond the main areas.
Best hotels in Ios:
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Skala Sunset Hotel and spa (budget hotel)
Skala Sunset Hotel and Spa is a true gem in Ios, offering breathtaking panoramic views of the town, the sea, and some of the most stunning sunsets you’ll ever see. The rooms are spacious, impeccably clean, and designed for comfort, with private balconies that let guests take in the incredible scenery. The pool area is a fantastic spot to unwind, whether you’re lounging in the sun or simply enjoying the peaceful surroundings. Guests can also start their day with a delicious breakfast featuring a variety of fresh, flavorful options.
What truly sets this hotel apart is the warm and attentive service. The staff go above and beyond to ensure every guest has a fantastic experience, always ready with helpful recommendations and a welcoming attitude. Located just a short walk from the town center, it offers easy access to Ios’ vibrant energy while still maintaining a tranquil atmosphere. For those seeking relaxation paired with breathtaking views, Skala Sunset Hotel and Spa is an outstanding choice.
Best hostels in Ios:
Step 3: Santorini
2 days recommended
Santorini
Santorini is nothing short of spectacular. This Greek island in the Aegean Sea stands out with its iconic white-washed buildings topped with bright blue domes perched on dramatic cliffs. The island is actually what remains of a massive volcanic eruption that occurred around 3,600 years ago, which created the stunning caldera views that leave visitors in awe.
The sunsets in Oia are famous worldwide, painting the sky in vibrant oranges and pinks as the sun dips below the horizon. But Santorini offers more than just pretty views. The island boasts unique black, red, and white sand beaches due to its volcanic nature. The ancient site of Akrotiri provides a fascinating glimpse into Minoan civilization preserved under volcanic ash, sometimes called the 'Greek Pompeii.'
Food lovers will appreciate Santorini's culinary scene, featuring local specialties made with ingredients grown in the volcanic soil. The island produces exceptional wine from grapes cultivated in some of the oldest vineyards in the world, where vines are trained into unique basket shapes to protect them from strong winds.
While summer brings crowds, Santorini holds its charm year-round. The island balances its tourism fame with authentic Greek culture that persists in villages away from the main tourist spots, where locals continue traditions that have existed for generations.
Best hotels in Santorini:
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The Best (budget hotel)
Nikolas Hotel in Karterados, Santorini, is a cozy and welcoming place that captures the charm of a traditional Greek island stay. With its signature blue and white design, it blends beautifully with Santorini’s classic aesthetic. The rooms are spacious and comfortable, featuring thoughtful extras like electric kettles and mini-fridges to keep drinks cool.
The outdoor pool area is a highlight, offering a great spot to unwind under the Mediterranean sun. The staff go out of their way to make guests feel at home, whether it’s helping with transportation or sharing recommendations for local dining. While it’s not right in the middle of Fira, the town is only a short 5-10 minute drive away, making it a convenient base for exploring the island. With its relaxing atmosphere and excellent service, this hotel is a solid choice for those looking to experience Santorini without the crowds of the main tourist hubs.
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Cavo Tagoo Santorini (luxury hotel)
Cavo Tagoo Santorini is a breathtaking luxury hotel in Imerovigli, offering panoramic views of the Aegean Sea and the island’s iconic caldera. The rooms and suites have a sleek, modern design, with many featuring private pools or hot tubs, allowing guests to unwind while watching the famous Santorini sunset. Every detail is designed for comfort and style, creating an unforgettable stay.
The infinity pool is a standout feature, appearing to merge seamlessly with the sea, making it an ideal spot to relax with a cocktail in hand. Guests can enjoy Mediterranean cuisine at the on-site restaurant, dining outdoors with stunning views. What truly makes this hotel special is the exceptional service—the staff goes the extra mile to ensure a personalized and memorable experience. Whether you’re planning a romantic escape or simply want to indulge in pure luxury, this hotel offers an incredible setting to soak in Santorini’s beauty.
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The Philoxenia Project (medium range hotel)
The Philoxenia Project in Santorini is an elegant getaway perched on the cliffs of Akrotiri, offering breathtaking views of the Aegean Sea and caldera. Its infinity pools and private terraces create the perfect setting for relaxation, while the luxurious suites and villas combine classic Cycladic design with modern comforts, giving each space a stylish yet peaceful feel.
The staff provides exceptional service, handling everything from organizing excursions to serving delicious Greek dishes at the on-site restaurant. Though the location is tucked away from the busiest areas, it remains conveniently close to Santorini’s top attractions. Whether unwinding by a private pool, enjoying a spa treatment, or sipping cocktails while watching the sunset, this spot offers a tranquil escape with a truly spectacular backdrop. It’s an excellent choice for couples or anyone looking for a quiet, luxurious experience on the island.
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Veggera Beach Hotel (resort)
Veggera Beach Hotel sits right across from Perissa Beach, giving guests direct access to Santorini’s famous black sand shoreline. The laid-back atmosphere, combined with two inviting pools and a bar area, makes it a great place to unwind. The rooms are clean and comfortable, with balconies that overlook the lush garden, providing a peaceful spot to relax after a day in the sun.
The staff are welcoming and always ready with helpful recommendations, especially Alex at the front desk, who knows all the best local spots. Mornings start with a delicious Greek-style breakfast, perfect for fueling up before a beach day. When the sun sets, guests can take a short stroll to the many restaurants and bars along the beachfront. With everything within easy reach, including the sea, pool, and dining options, Veggera Beach Hotel is a fantastic choice for those looking to enjoy a stress-free vacation by the water.
Best hostels in Santorini:
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Bedspot Hostel (boutique hostel)
Bedspot Hostel is a fantastic choice for travelers wanting to stay right in the center of Fira, Santorini. It's just a short walk from the bus station, shops, and top attractions, making it easy to explore the island. The rooms are modern, well-maintained, and feature comfortable beds with privacy curtains for a bit of personal space.
The staff are welcoming and always happy to share recommendations on things to do around Santorini. Guests can use the shared kitchen and lounge area to connect with fellow travelers, while the rooftop terrace offers a relaxing spot to enjoy the sunset over the caldera. The hostel is kept spotless with daily cleaning, ensuring a fresh and tidy environment. For its location and amenities, it’s a great option for those looking for a social yet comfortable place to stay in Fira.
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Central Hostel Oia (hostel)
Central Hostel Oia is a welcoming spot located right in the center of Oia, Santorini. Its prime location puts you just steps away from charming shops, great restaurants, and the famous sunset views the town is known for. With only eight beds, the hostel offers an intimate and relaxed atmosphere, making it a great place to meet fellow travelers.
The shared areas are bright and inviting, featuring a cozy lounge and a small but well-equipped kitchen. There's also a lovely terrace where guests can unwind and take in the surroundings. The beds are comfortable, and the bathrooms are kept clean and well-maintained. While the hostel is simple, it has all the essentials for a pleasant stay. The friendly staff go out of their way to make guests feel welcome and are always happy to share local recommendations. For travelers looking for an affordable and central place to stay in Oia, this hostel is a great choice.
Step 4: Milos
2 days recommended
Milos
Milos is a volcanic island in the Aegean Sea, part of the Cyclades group in Greece. It's famous for its incredible moon-like landscapes and more than 70 beaches with crystal clear waters in all kinds of colors - white, pink, and red sands surrounded by turquoise waters.
The island is where the famous Venus de Milo statue was discovered in 1820, which now sits in the Louvre Museum in Paris. This gives you an idea of the rich history that runs through Milos - with ancient catacombs dating back to the 1st century and remnants of mining operations that have been active since prehistoric times.
The main town, Plaka, sits on a hill with narrow streets perfect for exploring. Nearby, Klima is a traditional fishing village with colorful boat houses (syrmata) built into the rocks right at the water's edge. These unique structures serve as homes on the top floor and boat storage below.
The local cuisine focuses on fresh seafood and traditional Greek dishes, often with a twist unique to the island. And unlike some of its more famous neighbors like Santorini or Mykonos, Milos offers an authentic Greek experience without massive crowds, making it a perfect spot for travelers looking to experience the beauty of the Cyclades in a more relaxed atmosphere.
Best hotels in Milos:
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Christina Rooms (budget hotel)
Christina Rooms is a charming and affordable accommodation just a short walk from Papikinou Beach in Adamantas, Milos. The rooms are clean and comfortable, featuring air conditioning and free Wi-Fi. Many of them also have balconies where guests can relax and take in the views of the surrounding area.
The location is fantastic, with a quick 10-minute walk to the port, where you'll find plenty of restaurants and shops. The staff is very welcoming and helpful, with Viktoria, who runs the place, offering great advice on local attractions. Though simple, Christina Rooms provides excellent value in a prime location. The lovely garden and small terrace, perfect for enjoying your morning coffee, make it an ideal budget-friendly option for those looking for a comfortable base to explore Milos.
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Arco Solium Suites (medium range hotel)
Arco Solium Suites is a chic hotel located in the vibrant town of Adamantas, Milos. Just a short stroll from Lagada Beach, it offers an excellent base for exploring the island. The rooms are spacious and modern, with comfortable beds and private balconies that provide either city or garden views, making it easy to unwind after a day of sightseeing.
The staff at Arco Solium Suites are exceptionally helpful, always ready to assist with car rentals or recommend local attractions. A highlight of the stay is the impressive breakfast spread, which caters to a wide range of tastes, including options for those with dietary restrictions. Although the hotel doesn’t have a pool, it compensates with amenities like free Wi-Fi, room service, and a shared lounge area. The thoughtful attention to detail makes this a great spot for a relaxed stay while exploring Milos.
Best hostels in Milos:
Step 5: Serifos
2 days recommended
Serifos
Serifos is a stunning Cycladic island in Greece that sits a bit off the radar compared to its famous neighbors like Santorini or Mykonos. That's exactly what makes it special - fewer crowds but all the Greek island beauty you could want.
The island is known for its pristine beaches with crystal clear waters. Livadakia, Agios Sostis, and Psili Ammos are some of the most beautiful spots to enjoy the Mediterranean sun. The main town, Chora, perched on a hill overlooking the harbor, looks like a perfect postcard with its white houses climbing up the rocky slope.
Serifos has a rich mining history dating back to ancient times. The abandoned mines near Megalo Livadi tell stories of the island's industrial past, which peaked in the early 20th century before declining. These rusty remnants create an interesting contrast against the natural beauty of the landscape.
The local cuisine focuses on fresh seafood and traditional Greek dishes, often with a unique Serifos twist. Marathopites (fennel pies) are a local specialty worth trying, along with the island's goat cheese and thyme honey.
With only about 1,400 permanent residents, Serifos maintains an authentic Greek island atmosphere that's increasingly hard to find. The locals are known for their hospitality and maintaining traditions that have nearly disappeared on more developed islands.
Best hotels in Serifos:
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Marietta (budget hotel)
Marietta is a lovely place to stay in Livadakia, Serifos, offering a convenient location just a short walk from the beach and close to the port. This makes it easy to explore the island while having a relaxing spot to return to. The rooms are comfortable and well-equipped, featuring balconies where you can unwind and enjoy the fresh sea air. Standard amenities include air conditioning, free WiFi, and flat-screen TVs, while some rooms offer terraces with scenic sea views for an extra touch of luxury.
What sets Marietta apart is its welcoming atmosphere and friendly hospitality. The staff go out of their way to make sure guests feel at home, offering helpful recommendations and making every stay special. Whether you're spending the day soaking up the sun on nearby beaches or wandering through Livadakia's charming streets, this is a great spot to enjoy all that Serifos has to offer.
Best hostels in Serifos:
Step 6: Paros
2 days recommended
Paros
Paros, a stunning island in the Cyclades, is often celebrated for its enchanting combination of traditional Greek charm and beautiful beaches. It's a place where whitewashed villages with blue-domed churches sit beautifully against the backdrop of the Aegean Sea.
This Greek paradise offers a perfect balance of relaxation and adventure. The island is famous for its fine white marble, known as Parian marble, which was used to create masterpieces like the Venus de Milo. The main town of Parikia and the fishing village of Naoussa are filled with narrow cobblestone streets, blooming bougainvillea, and tavernas serving fresh seafood.
Paros has a rich historical past, with traces of Minoan, Mycenaean, and Byzantine civilizations. The Church of Ekatontapiliani (Church of 100 Doors) in Parikia dates back to the 4th century and is one of the oldest and most important Byzantine monuments in Greece. Beyond history, the island is also a water sports hub, particularly for windsurfing at Golden Beach.
The local food scene is vibrant with restaurants serving traditional Greek dishes using locally sourced ingredients. Paros offers a delightful mix of cosmopolitan vibes and authentic Greek island life, making it an appealing destination for all types of travelers.
Best hotels in Paros:
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Apollon Boutique Hotel (budget hotel)
Apollon Boutique Hotel in Parikia is a delightful place to stay, just a short stroll from the beach. The rooms are both cozy and stylish, featuring modern comforts like flat-screen TVs and free Wi-Fi. Guests can unwind in the charming garden, a perfect spot to enjoy the sunshine and relax in a peaceful setting.
The location is ideal, offering a quiet atmosphere while still being within walking distance of restaurants, shops, and the port. The welcoming staff go out of their way to provide helpful recommendations on the best spots to explore around Paros. A standout feature is the breakfast buffet, which is a favorite among visitors. With its combination of comfort, convenience, and warm hospitality, Apollon Boutique Hotel makes for an excellent home base to experience the island.
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Parocks Luxury Hotel & Spa (luxury hotel)
Parocks Luxury Hotel & Spa offers a breathtaking seaside escape on the island of Paros. With its prime beachfront setting and panoramic sea views, it’s an ideal destination for a relaxing Mediterranean getaway. The rooms and suites are elegantly designed, with many featuring private pools or jacuzzis on the terrace for an added touch of indulgence. Guests can unwind in style while soaking in the beauty of the Aegean.
The hotel boasts excellent facilities, including two swimming pools, a spa, a fitness center, and a private beach area. The on-site restaurant serves flavorful Greek and Mediterranean dishes made with fresh, local ingredients. For those eager to explore, bike rentals and activities like cooking classes and boat tours can be arranged. What truly makes this place special is the exceptional hospitality, with staff dedicated to ensuring a memorable stay. Whether lounging by the infinity pool or watching the sunset from a private balcony, guests are sure to enjoy a luxurious island experience.
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Kanale's Rooms & Suites (medium range hotel)
Kanale's Rooms & Suites in Paros offers a wonderful stay just a short stroll from the lively center of Naoussa. With its prime location near Piperi Beach, guests can enjoy stunning views of the Aegean Sea while staying in stylishly decorated rooms. Each accommodation is designed with bright, modern touches and includes conveniences like free Wi-Fi, air conditioning, and satellite TV, ensuring a comfortable experience.
A standout feature is the rooftop restaurant, where guests can savor delicious Mediterranean dishes while admiring breathtaking sea views. The hotel also boasts a relaxing pool area and hot tub, perfect for unwinding after a day of exploring. The friendly staff go the extra mile, offering helpful local tips and assisting with things like ferry tickets. Blending traditional Cycladic architecture with contemporary design, Kanale’s provides an inviting atmosphere, ideal for those who want to be close to Naoussa’s dining and nightlife while still enjoying a peaceful escape.
Best hostels in Paros:
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Frangiscos (hostel)
Frangiscos in Parikia, Paros, is a great choice for travelers eager to experience the charm of the Greek islands. Its location is incredibly convenient, just a short walk from both the port and the main beach, making it easy to explore the town or enjoy a day by the sea. The rooms are simple yet comfortable, featuring air conditioning and private bathrooms, with many offering balconies where guests can sip coffee while taking in the surroundings. If you prefer to relax without heading to the shore, the hotel has a refreshing pool area lined with lounge chairs.
What sets this place apart is its welcoming and laid-back atmosphere. The staff go out of their way to assist guests and even organize group dinners, creating a great opportunity to meet fellow travelers. With a prime location and a social vibe, it’s a fantastic base for soaking in the beauty and culture of Paros.
Step 7: Mykonos
2 days recommended
Mykonos
Mykonos is a stunning island in Greece's Cyclades group, known for its bright white buildings with blue doors that look amazing against the backdrop of the clear blue Aegean Sea. This island has a perfect mix of relaxing beaches and exciting nightlife that keeps tourists coming back year after year.
The island has a rich history dating back to ancient Greek mythology, supposedly named after the grandson of Apollo. In the 1960s, it became popular among celebrities and the international jet set, helping transform it from a simple fishing village to a world-class destination. Today, the island keeps its traditional Cycladic architecture while offering modern luxury experiences.
Mykonos Town (Chora) is the heart of the island with its famous Little Venice area and the iconic windmills that have become the island's trademark. The maze-like streets were originally designed to confuse pirates but now create a charming atmosphere for exploring the many boutiques, restaurants, and galleries.
Beyond the beautiful beaches and party scene, Mykonos has archaeological sites worth visiting, including the nearby island of Delos, the mythical birthplace of Apollo. The local food scene offers incredible Greek dishes, fresh seafood, and excellent local wines that complete the Mykonos experience.
Best hotels in Mykonos:
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Matogianni Hotel (budget hotel)
Matogianni Hotel is ideally located right in the middle of Mykonos Town, so you're just steps away from the vibrant atmosphere of the island. The rooms are cozy and comfortable, with a blend of traditional and modern Cycladic design. Some rooms even feature private balconies, perfect for enjoying the lively surroundings or a sunset view.
What really makes this hotel stand out is its unbeatable location, surrounded by Mykonos’ famous narrow streets, charming boutiques, and bustling restaurants and bars. Despite the central location, the rooms offer a surprising level of peace and quiet. The friendly staff are always available to share local recommendations or assist with anything you need. Although there’s no pool, the beach is just a short walk away, and the garden provides a peaceful spot to unwind after a busy day exploring the island.
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Nomad Mykonos (luxury hotel)
Nomad Mykonos is a luxurious getaway located near Kalo Livadi Beach on the Greek island of Mykonos. Offering stunning views of the sea, the hotel provides a serene atmosphere with spacious rooms and suites, many of which come with private pools and terraces for an added touch of relaxation.
The on-site restaurant serves fresh Greek and Mediterranean dishes, prepared with locally sourced ingredients. Guests can unwind by the outdoor pool, enjoy drinks at the bar, or treat themselves to spa services. The attentive staff goes out of their way to ensure a memorable experience. With its stylish boho-chic design and tranquil setting, Nomad Mykonos is perfect for couples or groups of friends seeking a luxurious escape. Though a bit further from Mykonos Town, its secluded location only adds to the peaceful ambiance, making it a great spot to relax and take in the stunning Aegean views.
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Amyth of Mykonos Agios Stefanos (medium range hotel)
Amyth of Mykonos Agios Stefanos offers a spectacular stay along the coast of Mykonos, with stunning Aegean Sea views from its prime location just a short stroll from Agios Stefanos Beach. The modern, elegant rooms and suites are designed with style and comfort in mind, featuring private terraces, many with their own pools or hot tubs, perfect for enjoying the scenic surroundings. Inside, you'll find luxurious amenities, including coffee machines, flat-screen TVs, and marble bathrooms equipped with plush robes and high-end toiletries.
Beyond the rooms, Amyth offers plenty to enjoy, including a beautiful infinity pool with a bar, a fitness center, and indulgent spa services. The on-site Mediterranean restaurant serves exquisite local dishes, making it easy to enjoy the flavors of Mykonos. The staff is dedicated to providing exceptional service, ensuring a truly pampered stay. With its luxurious amenities and peaceful ambiance, it's the ideal destination for a romantic getaway or upscale escape.
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Royal Myconian (resort)
Royal Myconian is a gorgeous beachfront resort on Elia Beach in Mykonos, offering breathtaking views of the Aegean Sea from nearly every part of the hotel. The rooms are elegant and cozy, featuring private balconies perfect for enjoying the stunning ocean vistas.
The pool area is a highlight, with plenty of loungers for relaxing and a pool bar serving refreshing cocktails. The beach is just a short walk away, equipped with umbrellas and chairs for guests to enjoy.
The food here is exceptional, with a breakfast buffet packed with a variety of options. For dinner, Ambrosia restaurant delivers mouthwatering Mediterranean cuisine paired with amazing sunset views. The staff is friendly and attentive, ensuring a fantastic stay. Although it’s on the more expensive side, the luxurious amenities and excellent service make it a great choice for a memorable Mykonos getaway.