Santorini, Koufonisia, Naxos, Paros & Mykonos

There are few holidays in Europe that combine beautiful beaches, charming villages, incredible food and iconic scenery quite like island hopping through the Cyclades.

On my latest Greek island-hopping adventure, I travelled through Santorini, Koufonisia, Naxos, Paros, Antiparos and Mykonos, experiencing six completely different islands in one trip. From dramatic cliff-top views and tiny islands to endless sandy beaches and glamorous beach clubs, each destination offered something completely unique.

This itinerary starts in Santorini and finishes in Mykonos, making use of direct UK flights at both ends while following one of the most efficient ferry routes through the Cyclades.

If you’re planning your own Greek island-hopping adventure, here’s everything I learned along the way.

Planning a Cyclades Island Hopping Trip

One thing that’s important to understand when planning a Greek island-hopping holiday is that you can’t simply pick islands and join them together on a map. Your itinerary needs to work with the ferry schedules.

While ferry services are frequent during the summer months, not every island has direct connections to every other island, and departure times can vary depending on the day of the week and the season. Sometimes the most logical route geographically isn’t actually the easiest route by ferry.

That’s why I always recommend building your itinerary around ferry timings first and then deciding how many nights to spend on each island.

For this trip, the ferry journey times worked brilliantly:

• Santorini to Koufonisia – approximately 1 hour 45 minutes
• Koufonisia to Naxos – approximately 40 minutes
• Naxos to Paros – approximately 30-45 minutes
• Paros to Mykonos – approximately 45 minutes

None of the journeys felt overly long and most travel days only took up a small part of the day, leaving plenty of time to enjoy each destination.

Essential Cyclades Ferry Tips

The ferries are all part of the experience, but there are definitely a few things I wish I’d known before travelling.

Book the Fast Ferries

Where possible, choose the smaller high-speed ferries rather than the larger ferries that transport vehicles. The boarding process is usually less chaotic and the journey is much quicker.

Don’t Arrive Too Early

Unlike many ferry ports around Europe, there isn’t much happening around the ports in either Naxos or Paros. Arriving around 20-30 minutes before departure is normally plenty.

Expect Delays

Not one of our ferries departed exactly on time. Don’t stress if departure times slip a little – it seems to be perfectly normal. Keep your travel days free from any commitments and don’t book a ferry the same day as your flights.

Take a Hard-Shell Suitcase

Your luggage may be exposed to sea spray during loading and unloading. A hard case provides far better protection than a soft suitcase.

Keep Valuables With You

Suitcases are normally stacked at the rear of the ferry or stored below deck. Keep passports, wallets, electronics and valuables in a separate bag with you.

Ignore the Seat Numbers

Officially, your ticket has an allocated seat. In reality, very few people seemed to pay any attention to them.

Separate Luggage Queues

Many ferries split passengers into two queues: Small luggage and carry-on bags & Large suitcases. If you’re travelling light, you can often keep your luggage with you throughout the journey.

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Stop 1: Santorini

Best For: Iconic Views & Bucket List Moments

Santorini is one of the easiest Cyclades islands to reach from the UK and makes the perfect starting point for an island-hopping adventure.

It’s probably the island everyone pictures when they think of Greece. Whitewashed buildings clinging to dramatic cliffs, blue-domed churches and sunsets that attract crowds every evening.

Yes, it’s busy and it’s expensive, but it’s also absolutely worth seeing.

Spend your time wandering through Oia, taking in the incredible caldera views and enjoying long lunches overlooking the Aegean.

Accommodation, dining and drinks are noticeably more expensive here than on the other islands, but that’s one of the reasons I like visiting Santorini on an island hopping trip combining with some of the more affordable islands.

Base yourself in either Oia for the best views and typical experience, or Imerovigli for a more relaxed and less busy stay. If you’re feeling active, do the Fira to Oia hike – take lots of water as there’s not much but views along the way.

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Stop 2: Koufonisia

Best For: Crystal-Clear Water, Relaxation & Slow Island Living

This was my favourite stop along the way. Tiny, relaxed and incredibly beautiful, it feels like Greece from decades ago. There are very few cars, almost everything is walkable and the water is some of the clearest you’ll find anywhere in Europe.

Where To Stay

Stay just outside the main town rather than directly in the centre. You’ll still be within walking distance of everything but enjoy a quieter atmosphere.

What To Do

The must-do day on Koufonisia is a hike to Pori Beach (wear sensible shoes!), then relax with a a drink at Waves and enjoy lunch at Kalofego. When you’re done take the boat taxi back.

Also make time to:

• Explore the Chora
• Visit the windmill area and Windmill Hotel
• Walk around the opposite side of the harbour for sunset
• Discover the hidden coves and swimming spots dotted around the coastline

Where To Eat & Drink

Bars

• Mylos Bar – overlooking the harbour from the windmill
• To Kyma – beachfront drinks by the sea

Restaurants

• Stou Lo Lou – Greek music, dancing and a fantastic atmosphere
• Finikas Taverna – right on the beach
• Kalofego – the perfect lunch stop at Pori Beach
• Remezzo – great option in the centre of town

Why Visit?

If your ideal holiday involves swimming in crystal-clear water, long lunches, beach hopping and slowing the pace of life right down, you’ll absolutely love Koufonisia.

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Stop 3: Naxos

Best For: Beaches, Food & Exploring

Naxos is the largest island in the Cyclades and offers a completely different experience to Koufonisia. For me, this is the island with the best beaches. Think miles of golden sand, shallow turquoise water and a fantastic collection of beach bars and restaurants.

Where To Stay

I’d strongly recommend staying around Plaka Beach or Agia Anna, rather than Naxos Town itself. The beaches here are exceptional and provide the perfect base for a relaxing stay. The further north you travel along the beach, the busier it becomes. Personally, I preferred the quieter Plaka end.

What To Do

Explore the Beaches

Many visitors could happily spend an entire week moving between the beach clubs, tavernas and swimming spots along this coastline.

Hire a Buggy

A buggy is a great way to move between beaches and restaurants.

Hire a Car

If you’re staying longer, hire a car and explore some of the inland villages and mountain scenery.

Visit Saint Anna Winery

A lovely afternoon away from the beach and a chance to sample local wines.

Visit Naxos Town

Although it wasn’t my favourite area to stay, it’s definitely worth visiting. The Temple of Apollo attracts huge crowds at sunset, but the views are spectacular. For a slightly more relaxed sunset experience, head to Naxos Apothecary for drinks overlooking the harbour.

Where To Eat

• Paradiso – dining directly on the sand
• Nikos & Maria – fantastic traditional food
• Apostolis – our favourite restaurant in Naxos Town (book ahead)

Why Visit?

Naxos combines incredible beaches, excellent food and enough variety to keep both beach lovers and explorers happy.

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Stop 4: Paros

Best For: Restaurants, Evening Atmosphere & Variety

Paros sits perfectly between laid-back Naxos and glamorous Mykonos. It has beautiful beaches, excellent restaurants, boutique shopping and a lively atmosphere without feeling overwhelming.

Where To Stay

Without a Car

Stay in Naoussa. Everything is on your doorstep and the harbour comes alive every evening.

With a Car

Stay at Seesoo boutique hotel. The hospitality is exceptional and the sunset views are among the best we experienced anywhere in Greece. Seesoo is perfectly located to visit Antiparos.

What To Do

Explore Naoussa

The harbour is at its best during the early evening. Wander through the narrow streets, browse the boutiques and enjoy dinner overlooking the water. Pre-book restaurants in peak season as it gets extremely busy.

Visit Antiparos

This is an absolute must. From Pounda, the crossing takes just seven minutes and costs approximately €1.50 per person.

While there:

• Explore the town
• Walk to Sunset Bar
• Enjoy dinner at Epostrofe

There’s also a longer ferry service available from Naoussa.

Explore Aliki

The south coast generally offers quieter beaches and a more relaxed atmosphere.

Where To Eat

• Marema overlooking Kolymbithres Beach
• Porfira by the Pounda ferry terminal (the best fish we ate all trip)
• Thalassamou in Aliki
• Epostrofe in Antiparos

Why Visit?

Paros offers a fantastic balance of beaches, restaurants, shopping and nightlife, making it one of the most versatile islands in the Cyclades.

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Stop 5: Mykonos

Best For: Luxury, Beach Clubs & Glamour

Mykonos makes the perfect final stop on this itinerary.

By this stage you’ve experienced dramatic caldera views, tiny island life, endless beaches and charming harbour towns, so ending with luxury hotels, stylish restaurants and glamorous beach clubs feels like a celebration of the trip.

While it’s famous for its party scene, there is also a much more relaxed side to the island. Beyond the beach clubs, you’ll find beautiful boutique hotels, excellent restaurants, charming whitewashed streets and some of the most picturesque sunsets in the Cyclades.

What To Do

The highlight of any visit to Mykonos is spending an evening in Mykonos Town. Arrive in the late afternoon (after the cruise ships have gone) and wander through the maze of narrow streets lined with boutiques, bars, churches and restaurants before the crowds reach their peak.

As sunset approaches, make your way to either:

• Little Venice for waterfront cocktails overlooking the sea
• The famous windmills for one of the best sunset viewpoints on the island

Both offer spectacular views as the sun sinks into the Aegean.

After sunset, head back into the heart of Mykonos Town for dinner. One of my favourite spots is Kastro’s, perched above the water with one of the most iconic dining settings on the island.

Why Visit?

Mykonos offers a completely different experience to the rest of the islands on this itinerary.

It’s stylish, energetic and glamorous, yet still retains plenty of traditional Cycladic charm away from the beach clubs.

Whether you’re looking for luxury hotels, fantastic restaurants, lively beach clubs or simply one unforgettable final stop before heading home, Mykonos delivers it all.

To find out more about Mykonos – read my guide here.

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How Long Should You Stay?

For me, three nights on each island was the sweet spot. It’s enough time to explore properly, relax on the beach, enjoy local restaurants and avoid feeling like you’re constantly moving. Anything shorter starts to feel rushed, while much longer can reduce the appeal of island hopping.

Tempted…?

If you’re looking for a holiday that combines incredible beaches, fantastic food, beautiful scenery and genuine variety, this itinerary is hard to beat.

And if you’d like help planning your own Greek island-hopping adventure, I’d love to help create the perfect itinerary. Get in touch today!