Kythnos Bay, Greece. Photo: Customer/Charles Jenkins
4.7
| 46 reviews

Sail and Explore Greek Islands

4 nights
Easy

Set sail among the stunning, unspoilt islands of the Cyclades and discover its hidden hiking gems

What's Included?

Activities & Certified Guides

All itinerary activities with experienced, English-speaking captain and guides

Yacht

4 nights on a private yacht

Meals

All your breakfasts and lunches

Transfers

To and from the airport and everything in between

Equipment

SUP boards always at the ready

Small Like-minded Groups

Solo-friendly by design, join our small n’ sociable groups of up to 10 like-minded, active and outdoorsy people
From

excluding flights

What's it like?

4.7
| 46 reviews
Super!
May 2024
Laura W.
Super!
May 2024
Laura W.
Super!
May 2024
Laura W.
Super!
May 2024
Laura W.
Had an amazing time on this trip. The other...
November 2023
Phil
Had an amazing time on this trip. The other...
November 2023
Phil
Had an amazing time on this trip. The other...
November 2023
Phil
Fantastic experience. The boat was well equ...
October 2023
Alison
This trip was simply beautiful. The islands...
April 2023
Charles
This trip was simply beautiful. The islands...
April 2023
Charles
This trip was simply beautiful. The islands...
April 2023
Charles
This trip was simply beautiful. The islands...
April 2023
Charles
Great trip made even better by the awesome...
October 2022
Peter
Great trip made even better by the awesome...
October 2022
Peter
Great trip made even better by the awesome...
October 2022
Peter
Great trip made even better by the awesome...
October 2022
Peter
This is as my 1st MBA and it’s was awesome!...
October 2022
Jo
This is as my 1st MBA and it’s was awesome!...
October 2022
Jo
This is as my 1st MBA and it’s was awesome!...
October 2022
Jo
This is as my 1st MBA and it’s was awesome!...
October 2022
Jo
This sailing trip was a lot of fun. The hik...
October 2022
Nicki
This sailing trip was a lot of fun. The hik...
October 2022
Nicki
This sailing trip was a lot of fun. The hik...
October 2022
Nicki
This sailing trip was a lot of fun. The hik...
October 2022
Nicki
This sailing trip was a lot of fun. The hik...
October 2022
Nicki
My husband and I went on this trip for the...
October 2022
Blair
My husband and I went on this trip for the...
October 2022
Blair
My husband and I went on this trip for the...
October 2022
Blair
My husband and I went on this trip for the...
October 2022
Blair
This is a true Once in a Lifetime experianc...
October 2022
Duncan

Embark on an adventure around the idyllic Cyclades, renowned for their rich history, culture and traditional cuisine

Live aboard a private yacht, docking each night in a different bay and hiking to pristine beaches and ancient villages

Splash into turquoise waters and tuck into tasty Greek dishes as you sail between Kea, Kythnos and Serifos

Key Information

Day 1

Set sail

Lavrio Port, Greek Islands, Greece

Board your yacht in Lavrio Port and sail to the lush green island of Kea. Learn about life onboard from the skipper and arrive in time for a delicious local dinner in town.

Day 2

Kythnos

Kythnos, Greek Islands, Greece

Sail to a bay by the ancient Tetrapolis of Kea and see why its been attracting visitors since the 17th century. Take a dip in the sea, visit one of Kea’s most beautiful beaches and then set off for a relaxing afternoon’s sailing to the picturesque port of Loutra on Kythnos. The island is known for its natural warm springs, which you will have the chance to experience before heading out for dinner on the island.

Day 3

Serifos

Serifos, Greek Islands, Greece

Hike around the striking, arid countryside of Loutra, discover hidden castles and whitewashed churches and meet the farmers and shepherds who live off this dramatic landscape. Enjoy a swim and a light lunch before continuing on to Serifos island - an integral part of Greek mythology, associated with two of its most famous heroes: Ulysses and Perseus. If you're up for it, try a spot of paddle boarding off one of Serifos’ many secluded beaches.

Day 4

Kythnos

Apokrousi, Kythnos, Greek Islands, Greece

Explore Chora’s narrow, whitewashed alleys, overflowing with green, pink and purple bougainvillea. Hike the steep trail to the lovely Ag. Konstantinos chapel and enjoy the amazing views of the Aegean Sea and the islands of Kimolos, Milos, Sifnos and your next destination, Kythnos, this time the western side. Enjoy the gold-sanded beaches of Apokrousi and Kolona which connect the main island to the islet of Agios Loukas and once you've freshened up, head to a local taverna for a home-cooked Mediterranean meal.

Day 5

Lavrio Port and home

Lavrio Port, Greek Islands, Greece

Take a spectacular loop-hike to Vryokastro, ancient capital of Kythnos and spend your last day swimming or paddle boarding around this beautiful island. Set sail for Lavrio Port in the early afternoon, where a transfer will be waiting to take you back to Athens and home

Day 1

Boat · Twin share

Breakfast

Lunch

Dinner

Day 2 – Day 4

Boat · Twin share

Breakfast

Lunch

Dinner

Day 5

Departure day

Breakfast

Lunch

Dinner

What is the food like?

Both breakfast and lunch are provided on-board on a self-prepare basis. This means that your host will take care of providing the food, and you and your fellow travellers will plan and cook the meals together.

There will be as many local, organic and Mediterranean ingredients available as possible. For breakfast, you can expect yoghurt, fruit, cereals, juices, cheeses and bread and for lunch expect local salads, sandwiches, omelettes, and pasta.

Dinner will be taken on the islands, usually in small local tavernas with a range of seasonal dishes and fresh fish to try.

Vegetarian, vegan and most other dietary requirements can be provided for, just let your host know before the tour begins.

What is the accommodation like?

Sailing in the Cyclades, Greece
The Cyclades

You’ll typically stay on a 56-foot Ocean Star sailing yacht, equipped with five cabin/berth sections accommodating 10 guests, with five toilets. The boat has an indoor living room, kitchen and dining area, as well as an outdoor lounge and deck where you can relax when sailing. Cabins are double, twin-share, or triple share. All shared berths are allocated same gender.

Upgrades

For solo travellers looking for their own space, an optional private cabin can be booked for an extra charge, see Optional Extras for the price . Please request this at the time of booking (this is subject to availability)

This trip has been rated as Easy

You do not need to be particularly fit, but being in reasonable condition will certainly help you make the most of your trip. Sailing journeys are around 2-4 hours each day. On average the hike distances are approximately 8km. All hikes are optional and guests can relax on-board or at a nearby beach if they prefer. There are extended hiking routes possible for those who wish to go further and these are generally pretty straightforward.

No prior knowledge is required and your captain will brief you about life on board and the basics of sailing.The boat's interior is designed to achieve maximum space efficiency and you will soon become accustomed to the few steep stairs to your cabin.

The Cyclades has mild and moderately rainy winters and warm, sunny summers. Spring temperatures average 20°C. The wind blows frequently, cooling the heat of summer. July and August are the hottest months, with temperatures averaging 27°C. Autumn sees warm temperatures averaging 25°C.

Should adverse conditions prevail, your guide will have a back-up plan, such as alternative hikes or mooring in a different bay.

On very rare occasions, it is up to the judgement of the skipper to alter or cancel a sailing route and the hiking guide to do the same for a hike.

The Area

map

Logistics

Starts

Athens International Airport

14:45 on Day 1

Ends

Athens International Airport

14:30 on Day 5

Transfers

You’ll be picked up on arrival and dropped off in time for departure. Alternatively, you are free to arrive at any time and make your own way to Lavrio Marina. If you do so, please meet in Café Petrino at 15:15. Full directions will be provided before your trip departs.

Travel options

There are regular flights to Athens from airports across the UK and Europe.

Enjoy 12.5% Off Outdoor Gear

In need of a few more items? All bookings receive a 12.5% discount to use at Cotswold Outdoor, Snow + Rock and Runner's Need.

What do I need to bring?

Bags

  • A small rucksack
  • One soft-suitcase per person as baggage to be kept in the cabin

Clothes

  • Hiking shoes
  • Long walking socks
  • Sandals
  • Hiking trousers
  • Long sleeve shirts
  • Water-resistant jacket

Other

  • Sunglasses
  • Hat
  • Sun cream
  • A water bottle
  • Trekking poles
  • Bathing suit
  • Head-torch
  • Toiletries
  • Basic First Aid Kit
*Requests for optional extras can be made after booking on your “My Bookings” page

Single Cabin Upgrade

Payable Before Departure

Single Cabin Upgrade

Single cabin upgrade

Payable Before Departure

Single cabin upgrade

Laura W.(May 2024)
Super!
Super!
Super!
Super!
Super!

This was my first much better adventures trip and it was beyond what I had hoped for! George the skipper was amazing, we had a few changes due to unlucky winds but it made the trip even better! Everything he did was to make sure we were all safe and had a good time! Sailing boat life, the food, the bays, the hikes, the views… but it’s the people that you are with that really make it Panemorfi! Tears because it ended, but full of love because it happened…. Unforgettably perfect.

Callum Y.(May 2024)
An excellent trip which I

An excellent trip which I would thoroughly recommend. George, our skipper, was very friendly and was great at adapting the itinerary to our interests and the weather. I booked last minute and was glad I did. I will remember this trip for a while to come!

Phil(November 2023)
Had an amazing time on this trip. The other...
Had an amazing time on this trip. The other...
Had an amazing time on this trip. The other...

Had an amazing time on this trip. The other group members were interesting and great fun, and we had a wonderful time. The hikes were interesting too with our guide George telling us about the history of the island, and there was lots of time for swimming around in the sea! Lukas our host was fabulous too.

The food was unbelievable.

Alison(October 2023)
Fantastic experience. The boat was well equ...

Fantastic experience. The boat was well equipped and there was plenty of space for us all. Great facilities and local guides. Going at the end of the season meant we had the islands mostly to ourselves while still having the perfect boat weather. I want to take up sailing now!

John(October 2023)
Louise(May 2023)

The trip was very enjoyable. The sailing was great when the wind the allowed. The skipper had a good sense of humour, was very competent, and was aware of our comfort and safety. Seeing the Spring wildflowers was lovely on the hikes and the hike guide was well informed. We learnt a lot about the local herbs which went into our lunch! Swimming from the boat was a great moment and it was great to visit some of the islands off the beaten track.

Karen(May 2023)

Amazing experience! Lovely boat, beautiful islands, great hikes with spectacular views. Fotis (excellent skipper and great company) made sure we all had a great time!

Charles(April 2023)
This trip was simply beautiful. The islands...
This trip was simply beautiful. The islands...
This trip was simply beautiful. The islands...
This trip was simply beautiful. The islands...

This trip was simply beautiful. The islands we visited were truly lovely and unspoilt, and visiting in spring before the main summer tourist season kicked off was a good decision. The weather in April was warm, comfortable and (mostly) sunny, and we also got to see the islands as green and flowery as possible.

Living and travelling on the boat was a great experience. Skippers, Fotis and Lucas, did an awesome job looking after us, they kept us comfortable and safe and explained everything as we went along. We had almost no wind for actual sailing until the final day, but that's just the luck of the draw and we still had a good time pottering around by motor. It was brilliant fun when we could actually go by wind power, too. Fotis even hit the jackpot on the first day, and managed to pull a huge yellowfin tuna out of the sea, which a local restaurant cooked for us the same night. He made it clear that this is not a normal occurrence, though, so don't get your hopes up!

Walking guide George was extremely knowledgeable, and really got under the skin of Kythnos. We learned a huge amount about the island's history, flora, fauna, economics, and local lifestyle.

Overall there was a good balance between activity and relaxation, the food throughout was delicious, and the small Cyclades are certainly a recommended destination.

Peter(October 2022)
Great trip made even better by the awesome...
Great trip made even better by the awesome...
Great trip made even better by the awesome...
Great trip made even better by the awesome...

Great trip made even better by the awesome group of travellers we were lucky to spend time with. Favourite part was the remote beach at Kythnos where we stopped for the day.

Jo(October 2022)
This is as my 1st MBA and it’s was awesome!...
This is as my 1st MBA and it’s was awesome!...
This is as my 1st MBA and it’s was awesome!...
This is as my 1st MBA and it’s was awesome!...

This is as my 1st MBA and it’s was awesome! If you are hesitating to book, take the plunge and book!! Relaxing, exhilarating, fun and an amazing group of people. Don’t overpack as there is limited space on the yacht but saying that you have everything you need. You need to be happy to go with the flow as the winds and weather changes but that made the adventure more fun. Our skipper Foatis was amazing and we were kept safe and informed at all times. Great hiking with George as well! Amazing trip!!

Nicki(October 2022)