Cyclades Island Hopping: Yacht Getaways Review (2024 Guide)

written by local expert Anna Faustino

Anna is a co-founder of Adventure in You and has been traveling the world for the last 9 years. She has spent time living in Thailand, Mexico, Indonesia, and Spain and is our local expert in these areas. Her expertise on travel, gear, and building businesses have been featured on Foundr, Business Insider, Yahoo Travel, and more.

Thinking about planning a Cyclades island hopping trip? I’ve got you covered.

You see, my husband Tom and I decided to get married on the beautiful island of Paros in Greece. To celebrate, we went on a sailing trip, island hopping around the Cyclades.

In case you don’t know, the Cyclades is a cluster of islands in the heart of the Aegean Sea. It is one of our favorite places on Earth. Renowned for its postcard-perfect white-washed buildings, crystal-clear waters, and delicious seafood, the Cyclades are a must-visit while in Greece.

While some islands like Mykonos and Santorini attract travelers with their vibrant nightlife and iconic sunsets, we much prefer islands such as Paros and Naxos which offer tranquil villages and untouched landscapes.

In this article, I am going to share our in-depth experience sailing around the Cyclades with Yacht Getaways, the boat sailing company we used.

Sailing with Yacht Getaways in Greece
Sailing with Yacht Getaways

Yacht Getaway Paros Explorer Route

We decided to hop onboard the Paros Explorer trip which is essentially a 7-day sailing trip around smaller islands in the Cyclades. It also gives you the opportunity to discover some of the best places to visit in Greece. A few of the popular stops on this route are:

  • Paros & Naoussa Bay
  • Naxos
  • Koufonisia
  • Schouinoussa
  • Ios
  • Antiparos

What I loved about this particular trip was that it brought you to a few smaller islands. Most people when they island hop around the Cyclades usually head to popular places like Mykonos and Santorini.

Personally, we LOVE the smaller islands better as we think this is where the laid-back Greek charm and allure really come to life. It is worth noting that although there is a set sailing route, the skipper takes into account the wind and the weather which can cause changes in your itinerary.

In our case, we were experiencing strong winds which caused us to hang around Paros and Antiparos for longer than expected which means we ended up cutting out Ios Island.

This was absolutely fine for us as safety is paramount when going on a sailing trip. Below I will briefly talk about each island and fill you in on the highlights.

tom and anna having fun with island hopping
Tom and Anna island hopping in Greece

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Cyclades Island Itinerary

Paros Island

This is where we started our trip and is one of our favorite Greek Islands. Nestled in the heart of the Cyclades, it stands out with its charming blend of traditional architecture, serene beaches, and vibrant local life.

Whether you’re wandering the narrow streets of Parikia, watching the sunset in Naoussa, or exploring their many cute shops, Paros offers a unique mix of authentic Greek culture and laid-back island vibes.

For our sailing trip, instead of docking on Naoussa Bay, we sailed a little bit further and anchored in a bay. Our Skipper arranged for a local Greek taxi to drop us back into town so we could eat a meal in one of the many restaurants in Naoussa.

views from a catamaran in greece
Views from a catamaran in Greece

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Since the wind wasn’t on our side for the first few days, we ended up only sailing a few hours towards Antiparos.

Just a stone’s throw away from Paros, Antiparos is the laid-back sibling in the Cyclades family.

Less frequented by the tourist crowds, Antiparos exudes an understated elegance, making it perfect for travelers seeking a more tranquil Greek island experience.

You can wander down its narrow alleys, savor fresh seafood by the harbor, or explore its hidden caves; Antiparos offers a taste of unspoiled island life. Our day in Antiparos was actually one of our favorites as we rented an ATV to explore the island.

10 years ago, I spent two glorious weeks hanging out in Antiparos so it was nice to return again after so many years away. If you can, I highly recommend visiting the caves as well as driving all the way to the South where you can see tons of incredible beaches and coves.

beautiful ocean of Antiparos for sailing
Beautiful ocean views of Antiparos

Koufonisia & Schouinoussa

These two neighboring islands are located near each other so I decided to talk about them both at the same time. If you’re looking for smaller islands within the Cyclades to explore, these two are perfect for you.

We LOVED Koufonisia and spent around 1.5 hours hiking along the coast. There is a beautiful trail that takes you to the other side of the island which is rough and rugged. Along the way, there are multiple beaches that you can stop and swim at.

Schouinoussa on the other hand is a SMALL island with about 206 residents. While there is nothing much going on here, there is a cute strip of restaurants and bars. There is also a really nice spot by the windmills which offer fantastic sunset views.

Schouinoussa at sunset
Schouinoussa at sunset


Our next big stop was Naxos Island which is the largest of all the Cyclades. As the island is so big, you will need to be strategic about what you want to see and map out your day. Luckily, we had some friends who happened to be on the island so we jumped in their car and drove to a few ruins.

We decided to hike up to Zeus’ childhood cave. Although the cave itself was slightly underwhelming, the hike and the views along the way made it for us. Just make sure to bring proper shoes as there are a lot of loose rocks.

As mentioned, due to the wind, we had to give Ios a miss and instead, spent more time in Paros.

Tom and Anna with views in Naxos
Tom and Anna with views in Naxos

Yacht Getaways Review: A Detailed Overview

So as mentioned, we used a company called Yacht Getaways to explore the best of the Cyclades Islands. We traveled around on a luxurious catamaran that could accommodate 8 people + 2 crew members.

How it Works

As soon as you get onboard, you get assigned cabins then the captain gives you a brief on what to expect for the week, plus a few other safety tips.

In a nutshell, you will spend your days sailing between the different islands, while making pit stops to hidden beaches and coves.

Breakfast and lunch are served on board then by mid-afternoon, you dock on land which means you are free to explore and dine before heading back to the boat.

We particularly loved the fact that we got to spend ample amounts of time on each island, allowing us to see and explore, even if it was just for a couple of hours.

During our stops, we rented dune buggies or cars and went exploring before heading back to the main area for a meal in one of the many Greek restaurants.

exploring greek islands
Beautiful architecture on the Greek islands

The Cabins

There’s a total of 4 rooms on the catamaran, each equipped with an ensuite bathroom, and shower (complete with hot water!).

We were actually pleasantly surprised at how spacious the cabins were. We left our main luggage in our hotel in Paros Island and brought a hand carry-sized luggage which was perfect. This left us with a ton of space in our cabin which meant our 6 nights on board were a lot more comfortable.

the cabins of Cyclades Island
Cabins of Cyclades Island

The Food Onboard

When you go on a Yacht Getaway trip, apart from your captain, you also get a hostess who prepares amazing breakfasts and lunches for you.

The meals were always freshly made using local ingredients. For example, for breakfasts, we would usually have a fruit platter along with some Greek yogurt and honey accompanied with some eggs or pancakes.

For lunch, we would always have big salads, a protein of some sort, and a bottle of white wine or rose. We were pleansantñy surprised with the food and enjoyed all our meals!

If we were to comment, the only thing I would say was that we wish it was more protein-heavy as we had a few vegetarian-only meals.

Throughout the day, there was always a supply of water, coffee, tea, and snacks.

breakfasts with yacht getaway
Fresh fruit platter & eggs for breakfast with Yatch Getaway

Cost of Yacht Getaway in Greece

Overall, the cost of a sailing holiday in Greece is fairly reasonable, considering it includes both transportation (sailing around the Cyclades can get pricey), plus accommodation and meals.

Depending on which route you choose, prices vary from €1500-1800 per person for the entire week.

As mentioned, this included 6 nights onboard, 2 meals a day, access to paddleboards, snorkels, etc. plus drinks. We found this to be great value plus a once-in-a-lifetime experience.

yacht getaway greece
We spent a lot of time reading onboard!

Sailing around the Cyclades Islands

As mentioned, once you dock, you get the chance to explore the islands. In Antiparos, we rented a dune buggy. In Naxos, we rented a car with a few friends so we could hike to Zeus’ cave.

A worry for us was that we wouldn’t have enough time on each island but we actually had a couple of hours each day which was more than enough time.

Before leaving the boat, our skipper Daan and hostess Rom would send over restaurant recommendations on each island. For foodies like us, this was great as they have literally been on these islands multiple times.

Apart from the time spent docking on the islands, our personal favorites were sailing to hidden coves and beaches. This for us was the highlight of our trip as we got to visit places that we wouldn’t have been able to if we were island hopping around the Cyclades ourselves.

Our skipper Daan would take us to secluded beaches and coves where we could swim, paddleboard, and sunbathe to our heart’s content.

Yacht Getaways Crew
Yacht Getaways Crew

Best Time to Island Hop in the Cyclades

There are two main periods to travel around the Cyclades and each one has its own pros and cons. If you’re looking for the best time to visit Greece, take these into consideration.

Peak Season (July to August)

Pros: The weather is at its sunniest and warmest, perfect for beach lounging and water activities. The island is buzzing with energy, events, and nightlife.

Cons: These are the busiest months, so expect crowded beaches, longer queues at attractions, and higher accommodation prices.

Shoulder Season (September-October):

Pros: The weather is pleasant and warm, but not scorchingly hot. The sea remains inviting for swimmers. You’ll get the vibrant island life minus the massive crowds of peak season. Prices can be moderately cheaper, and availability is generally better.

Cons: Some days, especially in late October, can be a tad unpredictable weather-wise. However, these brief spells rarely dampen the overall experience.

Personally, we love visiting Greece in September as it isn’t as busy anymore. Peak season can be a bit chaotic. Our skipper also said that since there are a lot more boats at sea, docking up on hidden bays can get busy.

Tom sailing on a boat in Greece
Tom sailing on a boat in Greece

Overall Yacht Getaway Review

In a nutshell, we absolutely loved our time aboard Yacht Getaways. It’s 100% a trip we would do again and we now consider it the best way to see and explore the Greek Islands.

The trip was a great balance of relaxation, exploration, and adventure which was exactly what we wanted. We spent a lot of time reading, sunbathing, day drinking, and swimming in the crystal blue waters.

It was honestly just perfect! If you’re thinking about booking a similar trip around the Cyclades, check out Yacht Getaways – we highly recommend them!

Aside from their sailing trips around Greece, they also run trips in Croatia, Montenegro, Italy, and Turkey!

yacht sailing at sunset
Yacht sailing at sunset in Greece

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