Big Fat Greek Holiday

Imagine whitewashed villages, volcanic beaches, turquoise waters, and spectacular sunsets.

Yes, it is quintessential Greece - and if planning a Greece island hopping trip, few routes are as magical as exploring the Cyclades. This itinerary focuses on three of the most stunning islands in Greece — Mykonos, Milos, and Santorini — over eight unforgettable days. Explore lively seaside towns, discover hidden beaches, sail to dramatic sea caves, and watch sunsets over the Aegean Sea.

Whether you’re planning a first trip to Greece, a honeymoon itinerary, or a bucket-list island adventure, this guide shows you exactly how to structure your trip. This route offers a perfect balance of lively beach towns, historic villages, natural beauty and wonders and the iconic Greek sunsets. Travel between islands is fairly easy using ferries (like FERRYHOPPER) connecting the Cyclades.

Proposed Greece Island Hopping Route

Day 1-3: Mykonos
Day 4-5: Milos
Day 6-9: Santorini

Day 10 : Departure from Santorini

Naxos and Paros are other favoured islands but these are the big 3 and most convenient by ferry route.

How to get around -

Start your journey with a direct flight to Mykonos - then ferry hop to Milos - then to Santorini from where you can take the flight out. (UK has direct flights to both mykonos and santorini.) Another option is to start with Athens which is a major aurpot hub and then ferry hop to all the island and finish back in Athens. That will ofcourse add another 3-4 days to your itinerary as you wouldn't want to not indulge in the beauty and history that Athens offers. If adding Athens to the trip i'd suggest doing it first since it is step heavy and then your islandic indulgences will feel justly earned. Steal my Athens itinerary.

White Churches

Courtyards

Platis Gialos Beach

Mykonos is the ideal place to start your island adventure. Known for its lively atmosphere, stunning beaches, and postcard-perfect streets, Mykonos has a lot to offer. It is also called the party island of Greece as every night the centre turns into a big bar with live music and people dancing away till 4 am in the morn.

The town is also famous for its:

narrow white alleyways
colorful bougainvillea decks
stylish boutiques and cafés

Platis Gialos Beach

Let’s begin with where to stay in Mykonos-

The Airport is 30 mins from the centre - we reached at 7 in the morn and got an early check-in. (Uber works. You can also catch a taxi or arrange a cab with your hotel) If coming via Athens, ferries depart from Piraeus Port, and the trip takes around 2–4 hours depending on the ferry type.

We chose Platis Gialos, since it offers the perfect balance between relaxation and accessibility. Located just a short drive from Mykonos Town, it’s one of the island’s most beautiful beaches with crystal-clear water, great restaurants, and easy access to beach clubs. It’s also well connected by water taxis to other famous beaches, making it an ideal base for exploring the island.

Nissaki Boutique Hotel

Infinity Pool

We stayed at Nissaki Boutique Hotel, a stylish luxury hotel perched between Platis Gialos Beach and Psarou Beach. The location was fantastic, the sea views were stunning, and the infinity pool overlooking the bay was a highlight. It’s a great choice if you want a relaxing stay while still being close to the island’s best beaches and nightlife. AND every corner of the hotel is a photo op.

We stayed in the VIP Suite with Sea View - a beautiful bedroom with a seating area, an expansive dressing table area, and an outdoor hot tub in the spacious terrace with Aegean Sea views. You wouldn't regret splurging on this balcony - we ended up taking so many photos here that it could be an album in itself.

Hotel's Infinity Pool

Hotel's Pool Area

Private Outdoor Hot Tub

Balcony in the VIP suite

Outdoor Bench

Hotel Spa

Next to the Hot Tub

More stay options in Platis Gialos

Luxury Spend – Petasos Beach Resort & Spa
A beautiful beachfront resort with elegant rooms, a large pool terrace, and a spa. The views over Platis Gialos Bay are spectacular.

Budget Friendly – Hotel Pelican Bay
A charming boutique-style hotel inspired by Cycladic architecture, located just a short walk from the beach with cozy rooms and a relaxing pool area.

Other great areas to stay in Mykonos

Mykonos Town (Chora)
Stay here if you want to be in the heart of the action. The area is famous for its whitewashed alleyways, boutique shops, restaurants, and vibrant nightlife. It’s perfect if you want to explore the island’s iconic windmills, Little Venice, and lively bars on foot.

Ornos
A quieter seaside area just 10 minutes from Mykonos Town. It’s great for families and travellers who prefer a relaxed atmosphere while still being close to the main attractions.

Psarou
One of the most exclusive beach areas in Mykonos, known for luxury beach clubs and upscale resorts. It’s ideal if you want a glamorous stay with stylish restaurants and beach parties.

Day 1:

We started our day in the stunning breakfast area of the hotel with gorgeous sea views. A string of glamourous yachts behind us, table by the bay where we could hear the waves, and see the island - we basked in this view while enjoying a morning cuppa and table service. The breakfast spread was excellent, and the service felt very warm and personalized.
MUST TRY - Ice Coffee in Greece.

After breakfast, we set out pre- noon to explore the Mykonos Town (Chora). Will let the pictures do the talking this time.

Evil eyes in every colour, at every shop

quirky seats for photo ops everywhere

little lanes you are meant to get lost in

The whole centre is extremely walkable. Just a short walk away are the Mykonos Windmills, historic landmarks overlooking the town and harbour. These are one of the most photographed spots in the Cyclades.

One of the most iconic areas to visit is Little Venice, a waterfront district where colourful buildings sit right on the edge of the sea. Waves crash against the balconies, creating one of the most romantic views on the island.

As evening approaches, enjoy sunset drinks in Little Venice before settling into a seaside restaurant for dinner. We chose Veranda which had these amazing seatings available at the edge of the water, for watching the sun dip into the Aegean while the windmills glow in golden light - a perfect introduction to our first evening in the Greek islands. TOP TIP - Get a seat atleast an hour before sunset time as these start to fill up really fast.

Veranda Restaurant

Windmill View

Golden Sunset

Iconic Windmill view

Watching the Sun set

Caught up in the moment

Seat Placements

Windmills in the night

By late evening, post dinner, the after effects of our super early flight started kicking in. So we headed back to our room, put our feet up and enjoyed the music coming from the yachts and a free light show from across the mountains. Then we took a swim in our hot tub and called it a night.

View from our balcony

Light Show (parties every night)

Music from Yacht Parties

Agios Ioannis, Ag. Ioannis Diakoftis PORT

Day 2:

One of the most memorable experiences in Mykonos is a sailing trip to the nearby islands of Delos and Rhenia as these islands offer a completely different perspective of the Cyclades. We took the Delos & Rhenia Islands Half-Day Trip by Boat and found it superb.

Delos is one of the most important archaeological sites in Greece and was once a major religious and trading centre of the ancient world. Walking through Delos feels like stepping back thousands of years. The island is uninhabited today, which makes the atmosphere even more surreal. It is part of UNESCO heritage.

According to Greek mythology, Delos is the sacred birthplace of the twin gods Apollo and Artemis. Legend says that their mother, Leto, found refuge on the floating island of Delos while fleeing the wrath of Hera. Because of this divine birth, Delos became one of the most important religious sanctuaries in the ancient Greek world.

Remnants of grand villas and markets

Terrace of the Lions

The courtyard of the House of Dionysus

Marble monuments presenting importance of Delos as a religious and commercial hub

Temple Of Isis perched on the hillside above the ruins of Delos

Theatre Quarter

Temple ruins overlooking the sea

Ancient stone reservoirs in the residential district of Delos, showcasing the sophisticated water systems

Mosaic floor and marble columns of the House of Dionysus

Ancient marble streets and benches in Theatre

The boat stops at Delos and then continues to Rhenia Island. Rhenia is known for its untouched beaches and turquoise waters and therefore becomes a perfect place to relax, swim, and snorkel in the Aegean Sea. The boat is docked for around 1-1.5 hrs and divers can take a cool plunge. We are not swimmers so we chose to roam about the island and wade our feets in the crystal clear waters (where we were bitten by tiny fish). Many boat tours also include a Greek lunch served onboard while anchored in a quiet bay.

TOP TIP is to not eat much since the return boat ride is extremely choppy and you'd not want to feel sick. Also keep your hair tied up as my flying locks went everywhere and became crisp in the sea breeze - the result was a Medusa look.

On our return to Mykonos in the late afternoon, we headed to the hotel for some rest, then a quick bath (and not so quick combing out the entangled hair) and a change of clothes. After that we set out to enjoy a relaxed evening wandering the town’s beautiful maze of streets. This time we started at the castle and the church - then made our way to the windmills and finally into the town.

Mykonos Castle ruins

Church of Panagia Paraportiani

Mykonos Castle area offers amazing sea views

Kastro's restaurant

Cafe seats hanging over sea

City in the backdrop

Windmills in the backdrop

Iconic Narrow Alleyways

Mikonu Locol Beer to try

Blue and White backdrops

Enjoy a bite and a drink in the narrow alleys - it is quite an experience.
As the sun sets, the shopping alleys come to life. This is a perfect time to do some shopping (or window shopping) from local boutique stores and enjoy the vibrant atmosphere. I bought a blue medusa face in clay, a light green glass evil eye and a greek face magnet - all three souveniours were beautiful and have fetched me compliments from house guests time and again.

Platis Gialos beach

Day 3:

We kept this day to enjoy the beaches in Mykonos. The island has dozens of beaches, each with its own vibe.

Ornos Beach

Located just a few minutes from Mykonos Town, Ornos Beach is a popular destination with calm waters and excellent seaside restaurants. It’s perfect for a relaxed beach day with swimming and lunch by the sea.

Platis Gialos Beach

Platis Gialos is one of the island’s most vibrant beaches. The long stretch of sand is lined with beach clubs and cafés, making it a great place to spend the afternoon.

Megali Ammos Beach

If you prefer something quieter, Megali Ammos is located close to town but offers a more peaceful atmosphere. In the evening, head back into Mykonos Town for sunset and dinner. The island becomes magical after dark as lanterns illuminate the narrow streets and restaurants fill with laughter and music.

Scorpio's table seating

Paraga Beach - private area

beach lounge seating

I'd highly recommend Scorpios Mykonos, a bohemian styled, beach club perched above Paraga Beach with sweeping views of the Aegean Sea. Being non-swimmers it was the perfect choice for us - in the afternoon we lounged on daybeds enjoying Mediterranean dishes and cocktails. And as the sun dipped, the terrace turned into an enviably iconic sunset spot with DJs and live musicians creating an unforgettable atmosphere. Reservations are highly recommended, especially in peak season.

Street markets come to life after 8

Tiny staircases

Upstairs seating in Veranda

Around 9pm we headed to our hotel and then post midnight we went back into Chora to enjoy the late night energy of the town on our last night here. We picked up some souvenirs for friends and ended up revisiting veranda for a 2am cocktail accompanied by the windmill view.

Next morning we had breakfast and lazed around in our hotel pool area till it was time to catch our ferry to Milos.

Where to Stay in Milos

We chose Adamas (also spelled Adamantas), the main harbour town of Milos, because it’s the most convenient base for exploring the island. Many boat tours depart from here, including the famous Kleftiko sailing trips, and you’ll also find plenty of restaurants, cafés, bakeries, and shops within walking distance. It’s a great choice if you want easy access to transport, dining, and sunset walks along the waterfront.

If you’re looking for a comfortable and stylish stay in Adamas, Captain Zeppos is a beautiful boutique option known for its elegant Cycladic design, personalized service, and peaceful atmosphere near the sea.

More stay options in Adamas-

Luxury Spend – White Pebble Suites
A stunning boutique hotel overlooking the sea with minimalist design, infinity pools, and beautiful sunset views.

Budget Friendly – Hotel Dionysis Studios
A charming and affordable stay located close to the harbor with clean, comfortable rooms and easy access to restaurants and ferry connections.

Other good areas to stay in -

Klima
One of the most picturesque villages on the island, famous for its colorful boat houses built right along the water. Staying here offers a unique and peaceful experience, especially for sunset lovers.

Pollonia
A charming seaside village on the northeastern coast known for its relaxed atmosphere and excellent seafood restaurants. It’s perfect for travelers looking for a quieter and more romantic stay.

Plaka
The island’s traditional hilltop village with narrow white streets, beautiful views, and some of the best sunset spots in Milos. Staying here gives you a more authentic Cycladic village experience.

Image by Monique Stokman

Photo by Edouard CHASSAIGNE

Photo by George Stathis

Day 4:

While Mykonos is lively and glamorous, Milos is known for its natural beauty and unique landscapes. This island was formed by volcanic activity, creating some of the most unusual beaches in Greece.

Our first stop was Sarakiniko Beach as it should be - because this was the reason we chose Milos over Paros. One of the most famous beaches in Greece, its smooth white rock formations resemble a lunar landscape, contrasting dramatically with the deep blue sea.

People love doing cliff jumping here its crystal waters are a swimmers delight. The view is surreal and no photographs we took did justice to it.

Next on our list was to visit Mandrakia, one of the most picturesque fishing villages on the island. This tiny harbor is famous for its traditional “syrmata”, colorful boat houses built directly into the rock along the shoreline. Fishermen once used these caves to store their boats during the winter, and today their bright blue, red, and yellow doors create one of the most photogenic scenes in Milos. The village is small but incredibly charming, with turquoise water, whitewashed houses, and fishing boats gently bobbing in the harbor. It’s the perfect place to slow down, take photos, and enjoy the peaceful atmosphere of the island.

If you’re visiting around lunchtime, stop at Medusa Restaurant, a beloved seaside taverna known for its fresh seafood and traditional Greek dishes. Their grilled octopus and seafood pasta are particularly popular, and the relaxed setting overlooking the water makes it one of the most memorable dining spots on the island.

Photo by Daciana Cristina Visan

Photo by Taty Gkiozos

Photo by Eleni Pechlivani

End the day in Klima, one of the most photogenic villages in the Cyclades. This tiny seaside settlement is built directly along the waterfront, each with brightly painted doors and balconies overlooking the sea. Originally used to store boats, these houses now create a postcard-perfect scene.

Klima is best visited in the evening when the atmosphere becomes especially magical. As the sun dips behind the horizon, the village glows in shades of pink and orange, making it one of the most beautiful sunset spots on the island. It’s the perfect place for a quiet stroll along the water and some incredible photos.

For dinner nearby, consider heading to Astakas Cafe Restaurant, a well-known waterfront restaurant just steps away from the colorful houses. The relaxed terrace overlooks the bay and is a wonderful spot to enjoy fresh seafood, traditional Greek dishes, and sunset views over the Aegean Sea.

Day 5:

One of the absolute highlights of visiting Milos was taking a boat tour around the island’s dramatic volcanic coastline. Many of Milos’ most spectacular landscapes are only accessible by sea, which is why sailing around the island is considered a must-do experience. Most boat tours depart from Adamas in the morning and last around 5–8 hours, depending on the route. We took this one from Get Your Guide (NO AD). As the boat cruises along the coastline, we passed towering cliffs, hidden beaches, and turquoise coves that felt completely untouched.

The main highlight of the tour is Kleftiko Sea Caves, one of the most breath-taking natural wonders in the Cyclades. This dramatic area is filled with towering white rock formations, sea arches, and caves carved into the cliffs by centuries of waves and wind. The water here is incredibly clear and glows in shades of turquoise and deep blue, making it perfect for swimming and snorkelling. Historically, Kleftiko was once used as a hiding spot by pirates who sailed through the Aegean Sea. The maze of caves and hidden coves made it the perfect place for ships to anchor discreetly, which adds an extra layer of intrigue to the landscape.

Another unforgettable stop on many boat tours is Sykia Cave. Unlike Kleftiko’s open sea caves, Sykia features a collapsed roof that forms a natural skylight above the water. Sunlight pours through the opening and reflects off the turquoise sea below, creating a surreal atmosphere that feels almost like a hidden lagoon.

Most boat tours, just like ours, include several swimming stops around the island, snorkelling gear, and bbq lunch served onboard. Between stops, you’ll cruise past dramatic coastal scenery, volcanic cliffs, and secluded beaches that are otherwise impossible to reach. The relaxed pace of the day makes this one of the most memorable experiences in Milos. (I'd recommend a sailboat over a speedboat)

After returning to Adamas in the late afternoon, it was the perfect time to unwind with a walk along harbour promenade replete with cafés and shops. After that we had early dinner at Aragosta – famous for its excellent seafood. You could also opt for Yankos Souvlaki – a casual Greek favorite or choose any one of the waterfront restaurants in town on your last night here.

The Next Day,

Leaving Milos behind, we headed for Santorini, the most famous island in Greece - formed by a massive volcanic eruption thousands of years ago, creating the dramatic caldera cliffs that define the island today. Santorini ferries usually start after noon so it is a good idea to plan a beach or small activity in the morning in Milos before your departure.

For our stay in Santorini, we were late for booking ahead as the prices hit the roof by then - Oia was out of the question so we divided our days in Pyrgos (2 nights) and Firostephani (2 nights). On a separate trip we have stayed in Fira and Finikia as well. So having stayed literally everywhere - I'd suggest choose a place based on whether you plan to drive, take a cab or a bus. It's as simple as that because no matter where we stayed - our experience was unique and wonderful. Choose Imerovigli for the views, Pyrgos for the history, Fira for bus transfers and and Finikia if on a budget as it offers walking proximity to Oia.

If you want the once-in-lifetime experience of Santorini then definitely choose Oia, the most iconic village on the island, famous for its most beautiful sunsets, whitewashed houses, blue-domed churches, and spectacular caldera views. It's perfect for honeymooners, people celebrating milestones, engagement proposals or everyday love. Perched high above the Aegean Sea, on the tip of the Caldera - the place is deeply romantic and every night the lights look legendary from here. Plan well in advance for relatively cheaper stays, because those get booked in a blink of the eye. However if budget is not a bar dont miss on staying here as it means you can wander the charming marble streets early in the morning or late in the evening after the crowds have thinned, which makes the experience even more magical. Adding a few pics of hotel entrances in Oia to give an idea of the vibe there.

Luxury Spend – Canaves Oia Suites - One of the most luxurious hotels in Santorini, known for its elegant cave-style suites, infinity pools overlooking the caldera, and exceptional service.

Budget Friendly – Fileria Suites - A charming boutique hotel located in the heart of Oia, offering comfortable rooms and easy access to the village’s restaurants, shops, and viewpoints.

Other great areas to stay in Santorini - based on my preference - (including the names of the hotels we stayed in - NO ADS)

Imerovigli - Often called the “Balcony of the Aegean,” Imerovigli offers some of the best caldera views on the island but with a much quieter and more romantic atmosphere than Oia. We stayed at Hotel Mylos - Situated in Firostephani, 10 mins walk to imerovigli, it offers a romantic setting with incredible caldera views at a budget price. Excellent property location, nice and hearty breakfast in the balcony, spacious rooms, and a peaceful terrace with amazing views.

Pyrgos - A charming hilltop village with narrow streets, traditional Cycladic architecture, and panoramic views of the island. It’s perfect for travellers looking for a more authentic and peaceful stay away from the crowds. We stayed at Chrisanthi Villa - a cozy and authentic home-like stay surrounded by narrow streets, local tavernas, and panoramic island views. The property provides comfortable accommodations in a peaceful setting while still being within easy driving distance of Santorini’s beaches and main attractions. We particularly loved the home-made breakfast, the jacuzzi, and the service here.

Fira - The lively capital of Santorini with dramatic caldera views, restaurants, nightlife, and easy access to buses that connect the entire island. It’s a great option if you want more dining, shopping and activity options. We stayed at M Residence Santorini Conelia Cave - A stylish cave-style residence in the heart of Fira, this property blends contemporary design with traditional Santorini architecture. With spacious suites, modern amenities, and easy access to restaurants, shops, and caldera viewpoints, it’s a great base.

Finikia – Elia 1968 Cave Houses - Located in the quiet village just outside Oia, this charming boutique stay features beautifully restored traditional cave houses carved into the volcanic rock. The suites combine Cycladic architecture with modern comforts, offering private terraces and a peaceful atmosphere away from the crowds while still being close to Oia which was a short and easy 12 mins walk to Oia. The area was very quaint with maze like lanes and small shops and cafes interspersed at every turn you make.

Hotel Mylos, Firostephani

Chrisanthi Villa, Pyrgos

M Residence Conelia Cave, Fira

Elia 1968 - Finikia

Day 6 -

We headed to our hotel from the ferry port. A charming hilltop village and once the island’s capital, Pyrgos still retains a wonderfully authentic atmosphere, with narrow cobblestone lanes, whitewashed houses, and historic churches scattered throughout the village. It was a bit of a walk and some stairs to our hotel and interestingly the hotel staff used donkeys to take up our luggage to the hotel, while we walked beside them along the narrow streets.

After checking in, we roamed around the maze of winding lanes, where there were cats and cafes in every corner and hilltop views available after every few stairs. The streets slowly climb toward the ruins of the old Castle of Pyrgos, a Venetian-era fortress built to protect the village from pirate attacks. As one walks up to the top, they pass small chapels and hidden viewpoints before reaching the castle ruins, where they are rewarded with a panoramic view of the island.

As the afternoon turned into evening, we dressed up and headed toward one of Santorini’s most famous wineries, Santo Wines, located just a short drive from Pyrgos. Perched high above the caldera, the winery features tiered terraces overlooking the volcanic cliffs and sea. Visitors can enjoy wine tastings featuring local varieties such as Assyrtiko while watching one of Santorini’s legendary sunsets. The golden light over the caldera combined with the island’s unique volcanic wines makes this moment unforgettable.

We chose to have late dinner close to our hotel later - at Cava Alta, another beautiful and casual spot - and finished the day with Vinsanto, the local desert wine (a must try)

Day 7 -

On this day we opted to explore the beaches and cover the southern Santorini and hired a car for the day.

The Itinerary included -

Red beach , Akrotiri
Castelli of Emporio
Perissa black sand beach
Megalochori village

We started our morning early with a visit to Red Beach, one of the most unique and dramatic beaches on the island. Located near the village of Akrotiri, this beach is famous for its towering red volcanic cliffs that contrast beautifully with the deep blue waters of the Aegean Sea. The striking landscape makes it one of the most photographed spots in Santorini. A short walk from the parking area leads you to the beach where you can relax, take photos, or even enjoy a swim if the weather allows. Just remember it has quite an uneven terrain so do wear sport shoes and carry flip-flops for the water.

TOP TIP - Because the beach is relatively small and popular with visitors, it’s best to arrive early in the morning before the crowds build.

Before noon, we reached The Good Heart Akrotiri, a beloved local taverna only a few minutes inland drive from the beach. Known for its warm hospitality and authentic Greek cuisine, this family-run restaurant is a favorite among both locals and travelers for its generous portions and home-style dishes. The menu features traditional Greek favorites like fresh salads, local vegetables, and homemade specialties prepared with ingredients grown in the surrounding countryside. The relaxed atmosphere and shaded terrace make it the perfect spot to enjoy a leisurely brunch before continuing your exploration of the island.

MUST DO!

While exploring the southern part of Santorini, do consider stopping at the Castelli of Emporio, a medieval fortress village built during the Venetian period to protect residents from pirate raids that once threatened the Cyclades. The fortified settlement is designed like a labyrinth, with tightly packed houses, stone archways, and hidden courtyards forming protective outer walls and narrow winding alleyways that were intentionally confusing to invaders. We had to keep asking people where to head even with our google maps!

Next, we drove across the island to Perissa Beach, one of Santorini’s most famous beaches. Unlike Red Beach’s dramatic cliffs, Perissa offers a long stretch of volcanic black sand framed by the towering Mesa Vouno mountain. The beachfront promenade is lined with cafés, beach bars, and restaurants, giving the area a lively but relaxed vibe. Spend some time strolling along the shoreline, enjoying a drink at one of the beach clubs, or simply relaxing by the sea. The calm waters here are ideal for swimming and cooling off during the warm Santorini afternoons.

Around 5 pm we headed towards the charming traditional village of Megalochori. Often overlooked by visitors rushing between the caldera towns, Megalochori offers a peaceful and authentic glimpse into traditional island life with beautiful tavernas, bell towers, and lots of photo ops. Here we had evening drinks and snacks at the local gem - Taverna Geromanolis - an outdoor area under shady trees, and spent some time exploring small artisan shops.

After an active and fruitful day, we returned to Pyrgos and chilled in our hotel courtyard for a while. Later we had dinner at a local cafe along with wine.

Day 8 -

For our last two days on the island - we moved towards the northern part of the island - checking into our hotel in Firostephani. We were very pleased with the amazing location of the hotel. We felt it was a very good move as we only had to rent the car for one day (previous day) and managed to see a lot of the island. From Firostephani - Imerovigli was a gorgeous 10 minute walk and Fira was extremely close-by as well.

One of the best things to do in Imerovigli is to simply wander the narrow cliffside paths that connect boutique hotels, small chapels, and scenic viewpoints. The village also sits along the famous caldera walking trail between Fira and Oia, so you’ll often see hikers. A short walk from the village leads to Skaros Rock, a dramatic rocky outcrop which is a beautiful spot for a short hike that offers incredible views of the caldera.

View from our balcony room in Hotel Mylos

Imerovigli photo ops

Imerovigli view points

For lunch we booked a table in Throubi, Imerovigli to celebrate an occasion - the place screams elegance and though expensive, the views from the restaurant and the food makes up for it. If you don't want to splurge, you could also go for drinks and titbits - just make a reservation beforehand. AND if you are looking for a LUXURY break you can stay here itself as Throubi is the in-house restaurant of Andronis Concept Wellness Resort. (Which offers free daily shuttle to Oia)

Entrance to Throubi

Terrace from the Restaurant

Loved these plates at Throubi

Thereafter, we headed to Oia as we had kept it for today. Starting around 2pm when the light begins to soften over the caldera, we wandered through Oia’s narrow marble streets lined with boutique shops, art galleries, and charming cafés, stopping at scenic viewpoints to admire the iconic blue-domed churches and sweeping views of the Aegean Sea. Jewellery shops in Oia are particularly in abundance and have really swoon-worthy pieces. Consider their gemstone and silver collections which are really unique and do not break the bank. As the evening approached, we headed towards the famous Oia Castle, one of the most popular sunset spots on the island, which gets extremely crowded. TOP TIP - Book your dinner at a restaurant with sunset view to avoid the crowds - we opted for an early dinner at Elinikon (reserve beforehand) and were very happy with our decision. After sunset the crowds start to thin in Oia as lot of people come via cruise excursions and bus tours so they leave post sunset. That is a great time to stroll around the square, and take in the night views and relax.

Elinikon Restaurant

Atlantis Bookstore

Terraces in Oia

Breathtaking views in Oia

Elinikon Restaurant

Oia - panoramic view

Oia as sun sets

crowds at castle point

3 bells church near castle point

Hidden viewpoints in Oia

Oia in moon light

An evening in Oia

Oia comes alive in the moonlight

hotel pools glistening in the night

Day 9 -

For our last day we planned -

Fira: 10 AM -2 PM
Travel Tip: Spend the morning in Fira, when the town is lively but not yet crowded with afternoon visitors and cruise passengers. Start with a leisurely stroll through pedestrian streets filled with boutique shops and local cafés, then make your way to the caldera viewpoints. Late morning is the perfect time to grab coffee or brunch at a terrace café overlooking the caldera - We chose Franco's Cafe. Also there is a cable car point in Fira for those who wish to enjoy that. We didn't have time for it as we had a cruise booked for the afternoon.

Sunset Catamaran Cruise 2:30 PM - 7:30 PM (pickup from fira included)

Explore Firostephani afterwards

9:30 PM Dinner at Osmo Restaurant (3 mins walk from our hotel)

Shopping in Fira

Bought this dress in Fira

Franco's Cafe

amazing cocktails + sea backdrop

A catamaran sunset cruise in is easily one of the most unforgettable experiences. Sailing along the dramatic caldera cliffs, you can stop to swim in crystal-clear waters near iconic spots like Red Beach and the volcanic hot springs. Enjoy drinks on board while watching Santorini’s famous golden sunset from the middle of the Aegean — a perspective you simply can’t get from land. It’s the perfect mix of relaxation, scenery, and romance.

Catamaran Cruise

Carry a light jacket as it gets a bit chilly around sunset

Pic doesn't do justice

Highly recommend dining at Osmo - the place is super pretty and the staff is very polite. The menu is vast - I ordered a Greek Salad with Santorini Tomatoes, he had the Seafood Orzo. Both were exceptionally nice and the portions were generous. They gave us a window table (we did a walk in) and the views were very pretty and similar to views from our hotel balcony. The restaurant has closed glass windows - so it is basically an outdoor feel with an indoor setting.

Osmo restaurant

cake cutting, courtesy of Staff

Bar seating

Caldera view from hotel balcony at night.

Day 10 - Catch ferry from the port to Athens or a flight back from the airport (in our case). Listing below some must try dishes while in Santorini.

Try Bagels with Koulouri bread

Ricotta-filled Cappellacci with Zucchini, Capers & Herbs

Stuffed Vine Leaves

Greek Salads

Interactive Map for This Itinerary

To help you visualize the journey and plan your own trip, here is an interactive map of all the locations mentioned in this itinerary. The map includes key stops across Mykonos, Milos, and Santorini — from beaches and villages to restaurants, sunset viewpoints, and historical sites.

You can zoom in to explore each island, click on individual pins to see the location names, and follow the route of the trip day by day. The map is also organized into layers, allowing you to toggle between different islands and categories of places.

Top Tip: Click the layers icon on the map to filter locations by island and easily plan your daily itinerary. You can also save the map to your own Google account so you can access it on your phone while traveling.

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