6-Days Sailing and Hiking the Small Cyclades

Sail between remote islands in the Cyclades group and explore unique landscapes on guided hikes across the islands.

REF: 08576

6-Days Sailing and Hiking the Small Cyclades

Sail between remote islands in the Cyclades group and explore unique landscapes on guided hikes across the islands.

The Cyclades Islands are famous the world over for their crystal blue waters, whitewashed villages, and endless beaches. Visit remote islands in the group on a private sailing tour. Each day you’ll hike along ancient paths to hidden coves, picturesque villages, and solitary bays, then return to your yacht to sail to the next destination. Your hassle-free trip includes:

  • 6 days sailing and hiking among the Cyclades islands, with an additional day on either end for arrival/departure
  • 7 nights aboard a private sailing yacht
  • Experienced skipper to sail the boat
  • Professional, English-speaking local guide
  • Breakfasts aboard the yacht
  • Drinking water
  • Taxes and port fees

Perfect for:
This tour is perfect for active travelers who want to break away from the typical Greek island tourist experience to explore the more remote and unspoiled islands in the group by land and sea.

Contact the host

Service & Itinerary back to top

Saturday: Arrive on Paros

Arrive at the fishing port of Piso Livadi at 17:00 to drop your luggage off in your cabin and meet your crew. You’ll eat a traditional dinner at a taverna in Piso Livadi before returning to your yacht for the night.

Sunday: Iraklia

After a morning swim you’ll sail to the island of Iraklia and drop anchor in Agio Georgios fishing port. There you’ll spend the day relaxing, swimming, and exploring on your own. In the early evening your guide will lead you to Saint John’s Cave, the largest cave in the Cyclades, famous for its impressive stalactites. You’ll hike from there to the main village of Panayia for a delicious dinner at a local taverna before returning to the boat.

Monday: Antikeri and Amorgos

Set sail for the tiny deserted island of Antikeri for a lunchtime swim, then continue on to the island of Amorgos. There you’ll anchor in Aegiali Bay, and in the evening you’ll take a walk through the picturesque villages of Tholaria, Stroumbos and Langada. In Langada you’ll stop for dinner and music at a taverna, then return to your yacht for another peaceful night on the water.

Tuesday: Amorgos hiking

Today will be devoted to exploring the northeast corner of Amorgos, an area protected under Natura 2000 designation. The walk will first take you to the quaint village of Langrada, and then to the Monastery of Saint Theologos for a rest and snack, then onward to Stavros Church on the highest hill on the island. From there you’ll enjoy incredible views of the Aegean Sea and beautiful rock formations offshore. Hike back to Aegiali for dinner.

Wednesday: Donousa

You’ll continue on your sailing adventure to the tiny island of Donousa, one of the smallest islands in the Cyclades. You’ll drop anchor in the bay of Kedros and enjoy a swim. In the evening you’ll walk along a coastal trail to the town of Messaria for dinner, then return to your yacht for the night.

Thursday: Koufonisia Islands

In the morning you’ll set sail for the Koufonisia Islands, known for their perfect turquoise waters, pristine beaches, and Natura 2000 designation. You’ll spend the day in Kato Koufonisi Bay, then walk around the island in the evening for dinner with the only family on the island! Their taverna serves food they produce themselves, and there are no words for how good it is! Return to your yacht for your last night on board.

Friday: Paros

On your last full day of the tour you’ll sail back to Piso Livadi port on Paros. You’ll arrive in the afternoon and hike along the Byzantine Path to the old village of Lefkes and onward to the town of Prodromos where you’ll enjoy a delicious local dinner—and hopefully some live music!—with your friends and guides. Head back to the marina for your last night aboard the yacht.

Saturday: Departure

Have your final on-board breakfast and perhaps a morning swim, then check out of your yacht by 10:00.

Please note that the itinerary is subject to change based on weather conditions. The starting and ending island will remain the same.

Accommodation back to top

You will stay on board a Jeanneau Sun Kiss 45 sailing yacht. The yacht features 4 double cabins, 2 bathrooms, a beautiful teak interior, and a large sundeck. There is ample room inside to socialize in comfort as you sail from island to island. This trip is limited to 6 people, striking the perfect balance between comfort and cost.

Dates & Prices back to top

Sat, May 12th 2018, for 7 nights
Per Person
Sat, Jun 16th 2018, for 7 nights
Per Person
Sat, Aug 25th 2018, for 7 nights
Per Person
Sat, Sep 1st 2018, for 7 nights
Per Person
Sat, Sep 22nd 2018, for 7 nights
Per Person
Sat, Sep 29th 2018, for 7 nights
Per Person
Sat, Oct 6th 2018, for 7 nights
Per Person

Prices include

  • Accommodation
  • Meals As Described
  • Skipper
  •  Airport Transfers 

Custom & Private Trips back to top

Organising a private group? We make it super easy.

  • Customised itineraries for private groups, stags/hens or team trips
  • Receive a shareable private itinerary to send your group
  • Each member can reserve and pay individually
  • No more group organising faff

This trip can run for private groups - min 2 people max 6 - from April until October.

Get a quote now!

Trip Photos

Location back to top

View map

The Cyclades are a group of islands southeast of mainland Greece. There are 220 islands in the group, including popular and highly touristed islands like Santorini and Mykonos, as well as myriad tiny and lesser known islands. The name “Cyclades” refers to the circular arrangement of the islands around Delos, a sacred island at the center of the group. Greek mythology tells that each of the islands was a nymph frozen by the god Poseidon in a fit of anger.

The islands are visited by travelers from around the world who come to swim in the crystal blue waters and explore the bright beaches. Inland from the sea, each island has its own unique landscape to explore, from volcanic landforms to whitewashed villages to thermal springs. The interiors of the islands are less visited than the coasts, providing endless opportunities for exploration and adventure.

Start point?
You will meet your host at the Piso Livadi fishing port on Paros. Your host will be in touch before the trip to finalise details.

Finish point?
Your trip will end at the Piso Livadi fishing port on Paros. Your host will be in touch before the trip to finalise details.

Getting there and away?
There are frequent flights from Europe to Athens, Mykonos or Santorini. From those destinations take a ferry to Paros. One-way ferry times are 4 hours from Athens, 50 minutes from Mykonos, or 2.5 hours from Santorini. Once on Paros take a taxi or bus to the Piso Livadi fishing port from either the main town or from the Paroiki port where the ferries arrive.

Frequently Asked Questions back to top

What extra costs are there?

The following are not included in the tour price:

  • Flights to and from Greece
  • Ferry to and from Paros
  • Accommodation before and after the tour
  • Lunches and dinners
  • Skipper’s meals, fuel costs, marina fees and a yacht cleaning at end of tour (total approximately €60 per person)
  • Travel insurance

Can I book on my own?

Sure can! A lot of people do, it’s a great way to meet like-minded people.

How big will the group be?

This trip will run with a minimum of 2 people, and a maximum of 6. Please note, if there are not 2 people booked the trip may be rearranged or cancelled.

How fit do I need to be?

This tour is suitable for anyone with a basic level of fitness. No previous hiking or sailing experience is required.

What’s the weather like?

The climate in the Cyclades Islands is Mediterranean. From May to September the air temperature ranges from 20 – 25 °C, with the sea temperature lagging one degree behind. Days can often be breezy, especially on the water, but they’re also clear and sunny with practically no chance of rain.

What’s the food like?

Greek food is delicious! You’ll enjoy a variety of foods served at island tavernas. Menu items include Greek salad, fresh seafood, moussaka (kind of like lasagna), souvlaki (meat skewers served on a platter or in a wrap), and dolmades (stuffed grape leaves). Most tavernas serve food they produce themselves, so it’s fresh, delicious, and a great value. Breakfasts served on the yacht are typically light, with fresh fruit, olives, and yogurt providing the staples.

Can my dietary restrictions be accommodated?

Absolutely! Just let us know at booking.

What should I pack?

You will need to provide your own hiking gear, including hiking shoes, breathable clothing, a water bottle, and a small backpack. You’ll want a jacket for cooler evenings. Bring plenty of sun protection (hat, sunglasses, sunblock). Don’t forget a swimsuit!

Rated 5.0 out of 5 by 1 adventurer

By Serena on 16/09/2017 who travelled in August, 2017

It was an amazing experience! The itinerary changed due to weather conditions but we made the most of our time anyway thanks to Annie's experience. I discovered a new way of exploring the Greek Islands and I'll definitely go back there for more sail and more hicking!

MBA Verified Review

Book Now

Continue to secure payment
Visa Mastercard Amex

Prices include

  • Accommodation
  • Meals As Described
  • Skipper

Why Use Us?

We’re inspiring people to make more of their time off. Here’s how:

Oh, and we're highly rated on Trustpilot because of all that.

 Loading map...
Photos Details Map Share Book

Loading similar products...