The Greek islands have become synonymous with honeyed beaches, show-stopping sunsets, ancient ruins, electric nightlife, and a Mediterranean sea that shimmers a million shades of blue. But while their soaring popularity has brought an increase in inter-island exploration, finding the perfect Greek island-hopping itinerary can be a tricky task.
Indeed, there are hundreds of postcard-pretty inhabited islands to choose from – from the rip-roaringly popular big hitters to the lesser-known, still-hidden gems – with each offering something unique and unforgettable.
For this trip, I spent a week hopping between three of the Cycladic islands; the cluster of Greek islands located in the central part of the Aegean. If you’re spending time in the Cyclades, it’s pretty impossible to skip Santorini, arguably Greece’s most popular island. If you haven’t already been, you’ve undoubtedly seen the bright blue dome of the caldera nestled between clusters of white houses popping up on your Instagram feed in the summer. Thanks to its popularity, Santorini has invested in luxury accommodation and welcomed a host of new boutique hotels that make your time on the island all the more special.
After Santorini, I decided to head to two of Greece’s lesser-known islands to escape the crowds, and experience the best of both worlds. And it was a trip I’ll never forget.
Here’s how to spend the perfect week hopping between the Greek islands this year…
Santorini
DAY 1: Check into the new Nobu Hotel Santorini, around 20 minutes from the airport and perched high on Imerovigli’s volcanic cliffs, offering sprawling views over the bright-blue Aegean all the way to the jumble of white-washed Oia homes in the distance. Nobu Santorini is positioned along the epic Fira to Oia walking trail – around 10.5km long – and you’ll often see hikers passing by. If the entire trail doesn’t take your fancy (I wouldn’t blame you, it can take all day in the Mediterranean heat), there’s a short, circular route just past the hotel reception which takes about an hour along a dirt path, past the pine tree-surrounded Prophet Elias Church, with beautiful views over the sea and villages below.
Back at the hotel, relax on the sun-drenched, plush sofas or take a dip in the tiered pools; an infinity pool at the front and a larger swimming pool behind. Or head to your room – one of just 25 – via stone paths lined with palm trees, olive bushes and potted aloe plants. The rooms are typical multi-story caves, decorated almost entirely in pristine white, with touches of black and dark wood; a fusion of Japanese minimalist chic with classic Cycladic architecture. Most have private terraces with a hot tub or pool; perfect for swooning over those fiery Santorini sunsets.
Head down to dinner where Nobu’s internationally-adored dishes take centre stage – yellowtail sashimi, black cod miso – alongside a selection of creative, delicious cocktails and Hokusetsu sake. This is undoubtedly the best Japanese food you’ll find on Santorini.
DAY 2: Head down early for breakfast – as soon as you’re able to prise yourself from the impossibly soft, cloud-like beds – which is served on the terrace above reception. Take in the views over the sparkling sea while tucking into the likes of the ‘Santorini breakfast’ (cold cuts, smoked salmon, local Greek yoghurt with thyme honey and a fresh salad with cucumber and feta); the ‘Matsuhisa Benedict’ with tofu and snow crab; or lighter options like chia pudding with mango and coconut or bircher muesli.
As soon as you’ve sipped the last of your freshly-squeezed juice or matcha latte, head back downstairs to reception and ask for a taxi into Oia town centre (about 20 minutes). If you’ve been on Instagram in the last five years, you’ll know that this is a very busy and popular area. Get there as early as possible – ideally before 9am – to avoid the heaving crowds queueing to take photos of the famed caldera, a sea of white-washed buildings and deep-blue domes against the glittering water. It’s easy to spend hours meandering through Oia’s bustling, bougainvillea-lined streets, popping into the shops selling handmade jewellery and art, or stopping to snack on gelato or koftas.
Spend your afternoon at leisure – visiting a winery, a monastery, or heading back to your hotel for a dip in the pool – just make sure you catch the sunset (preferably with a cocktail in hand).
Milos
DAY 3: Take the ferry to Milos island, just over 2 hours away. A far cry from Santorini’s tourist-heavy streets, Milos is remote and impossibly beautiful with a rugged, volcanic landscape that makes you feel as though you could be stepping foot on Mars. The first thing you’ll want to do on arrival is rent a car; the island is remote and taxis are expensive. You’ll likely arrive late in the afternoon, so head straight to check in at Milos Cove, a five-star resort whose impressive design is so futuristic against the otherworldly landscape you may question whether, actually, this is Mars after all. The hotel has 42 superb suites and villas with private pools and terraces, surrounded by pink volcanic rocks with stunning views over the Aegean.
Spend some time exploring the hotel, booking in for a massage at the blissful Obsidian Spa, chilling by the impressive infinity pool, or swimming in the sea via the hotel’s private Agkali beach, before heading to dinner at Pathos Restaurant. Here, you’ll find fine-dining Mediterranean cuisine with Italian flair (I still dream about the succulent lobster cannelloni in a rich tomato cream) and an impressive drinks list boasting delicious cocktails and local wines.
DAY 4: Head to breakfast and choose between the American buffet breakfast or a la carte brunch options before hopping in your rental car and heading to one of Milos’s main attractions, Sarakiniko Beach (or ‘moon beach’), on the northeastern shore of the island. The white, lunar-like volcanic rocks shaped unusually by the waves – and contrasted beautifully against the turquoise waters – make this a beach unlike any other. Again, the earlier you arrive, the better – crowds pick up towards late morning and are at their heaviest in the early afternoon. On one end of the beach, you’ll find the brave jumping from rocks which have risen to form cliffs over the sea.
Afterwards, drive around 10 minutes to Medusa restaurant, a traditional café perched right on the water’s edge serving delicious, fresh seafood (it doesn’t get much fresher than the fisherman ferrying just-caught octopus from the shore to the restaurant’s kitchen).
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Spend the rest of your day exploring Milos island, from strolling around Plaka village (the capital of Milos), visiting picturesque fishing villages like Klima and Fourkovouni, or taking a boat tour of Milos’s famous sea caves in Kleftiko, Papafrangas or Sykia.
Paros
DAY 5: Leave plenty of time for check-out and returning your rental car before catching the ferry from Milos to nearby hidden gem Paros, a traditional Cycladic island with a laidback, sleepy atmosphere during the day, and a buzzy, lively energy in the evening. Here, you’ll find the ideal marriage of chic restaurants and bars, with unspoilt stretches of sandy beaches and authentic inland villages.
Check in to Cosme Paros, the third and newest Kanava hotels property (the others being popular Parilio and Acron Villas), which opened its doors in 2022. Situated in the trendy Naousa neighbourhood, Cosme is a tranquil haven of white stone, traditional textures and local art, connected by walkways and passages designed to mirror Greek villages. With 40 pristine suites and a calm, intimate atmosphere, it feels like a luxury boutique hotel but with the facilities of a grand beach resort – an incredible spa with Korres treatments, a half-moon infinity pool with cabanas perfect for relaxing with a good book (and snacking on a fresh poke bowl or crispy calamari from the poolside bar), and a beach club with private sun-loungers just steps away from the hotel’s restaurant.
Head for sunset drinks at Circe Bar, then on to dinner at beachfront Parostia Restaurant. Here, chef Yiannis Kioroglou dishes up ‘Medite-Grecian’ cuisine using fresh, local ingredients, and plates are made for sharing – whether from the starters (don’t miss the artichokes with smoked eel, yuzu mayonnaise and bottarga), or garden-grown salads, to melt-in-the-mouth ceviche, meats and fish grilled on a charcoal oven and lip-smackingly-good bowls of buttery pasta, washed down with crisp, local white wine.
DAY 6: If you can tear yourself away from Cosme, spend your last day (sob) exploring Paros island. Unlike Milos, Paros is easily explored on foot, so grab your sunhat and sunscreen and head out after a breakfast of Greek kagianas eggs or a fruit-laden breakfast bowl at sunny Volta restaurant. Spend time getting lost in the labyrinthine, sun-dappled streets of Nassoua and Parikia, where you can’t help but dive in and out of artisan stalls and vintage shops (I picked up a beautiful gold ring at Greg Jewels). Grab lunch at one of the many family-run traditional tavernas along the harbour.
In the afternoon, pop in to Moraitis Winery for a tour, a tasting session or to pick up a bottle of local wine to take home with you, to be saved for a special occasion. If wine isn’t your thing, soak up the afternoon sun on Kolymbithres or Golden Beach or wander around Panagia Katapoliani, a Byzantine church dating back to 326 AC with stunning interiors.
DAY 7: From Paros, you can catch a ferry back to Santorini – which takes between 1 hour 40 minutes to 3 hours, depending on the boat and how many stops it makes – to fly home, suitcase brimming with souvenirs, skin sun-kissed, and heart full.
