header cover
sailsquare logo

Small Cyclades

Greece:

Cyclades

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

-

Suitable for travellers:

> 10 years

Boarding from:

Paros

What's included

Cancellation policy

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

French

English

Italian

This experience, in a nutshell

We'll start from the island of Paros, located in the Aegean Sea, an island famous among windserf and kiteserf enthusiasts.

Ours is a fast and comfortable Ocealic cruising boat and you will be able to see it at work with exciting sailings that will take you to land in the most beautiful islands of the Cyclades.




Skhinoussa (or Skinoussa), an island with a relaxed and authentic atmosphere with its Chora, a beautiful village with traditional white houses, narrow streets and a central square. Koufonisia (or Koufonisia) small island famous for its beautiful white sandy beaches and crystal clear waters, Keros sacred and uninhabited island our favorite of this itinerary. Amorgos is rugged and fascinating with the beautiful Chora and the impressive monastery of Hozoviotissa, built overlooking the sea.




On board, Lorenzo and Annalisa, expert sailors, in addition to taking care of the management of the boat, will prepare excellent lunches for you, to also offer you the pleasure of good food.


No Departures available

experience image 0experience image 1
experience image 2
experience image 3

14+

Show all

Boat & Classes of Service

43 - 2010

Type

Sailboat

Length

13 m.

Toilets

2

Cabins

3

boat image 0boat image 1
boat image 2
boat image 3

11+

Show all

Our itinerary

Our trip starts here:

Paros.

Check-in: 6:00 PM

Our trip ends here:

Paros.

Check-out: 9:00 AM

Leg 1

The experience begins.

Boarding in the late afternoon at Paroikia Paros, welcome toast and accommodation in the respective cabins. We move to a quiet bay and dinner on the boat prepared by your skippers.

Leg 2

Schinoussa

Leaving the Gulf of Paroikia you  pass the strait (and with very shallow waters) between Paros and Anti Paros. Then a long sail with the wind crosswind and wide upwind to reach Schinoussa.

Schinoussa is a small island, where agricultural activities are still predominant and where tourism is still underdeveloped. The roads are not yet paved and the Chora consists of a few dozen houses along the main road. We'll anchor in the bay of Livadi and after lunch we'll spend a relaxing afternoon.  In the late afternoon a wonderful walk to Chora, then dinner in a small tavern with outdoor tables, where you can enjoy a very special traditional Greek cuisine.

Leg 3

Amorgos

We leave Schinoussa to reach Amorgos; A navigation that can be quite intense and fun awaits us. Amorgos is an arid, wild island surrounded by a blue sea that contrasts with the surrounding landscape.  We will anchor in the large bay of Katakopula. Lunch in the bay and then in the afternoon a visit to the Hozoviotissa monastery is a must, which is nestled in the rock 300 meters above the sea, on the south coast of the island. To reach it, it is advisable to rent a scooter; Then it will be necessary to climb the almost 1000 steps, but the effort will be rewarded by a breathtaking view and the welcome of the monks who usually offer a glass of rakomelo and fruit and sugar sweets. 

Leg 4

AntiKeros

10 miles of intense wide upwind to reach AntiKeros, two uninhabited islets separated by a narrow channel that forms a beautiful anchorage ideal for swimming and dining. Another short sailing upwind to reach Schinoussa, we will spend the night in a large bay in the south of the island.

Leg 5

Koufounissi

Today little navigation and a lot of relaxation! A short upwind to reach Kato Koufonissi, a small island with a dozen houses and long white beaches. You are still a few tens of meters from the beach in the crystal clear water. Afternoon of swimming and relaxing;  in the late afternoon transfer to Koufounissiwhich is half an hour away by boat. Social evening in Kofounissi.

Leg 6

Naxos

Stop in the bay in the south of Kato Kofounissi, then after lunch sail to the south of Naxos.

Dinner on the boat


Leg 7

Antiparos

A beautiful and intense sail awaits us in one of the windiest areas of the Aegean, the channel between Naxos and Paros; The first part of the sailing will be with the wind downwind and then we will move upwind. We will reach a small island in the channel between Paros and Antiparos . Lunch in the bay and afternoon of relaxation and in the evening we will reach Paroikia in Paros.

Dinner in the tavern


Leg 8

Last day

It's the least beautiful moment of the holiday, after breakfast there is the disembarkation. We say goodbye with the promise to see each other again soon. A wealth of beautiful memories is what you will take with you.

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

What's included in the price

•

Boat equipment and facilities

    Final cleaning

    Tender and outboard

    Bedding kit

•

Meals and beverages

    Purchase and storage of the galley

    Preparation of meals and drinks

•

Onboard staff

    Skipper

    Chef

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€250 - €250 Per person

See notes below

    Galley

    Food for the skipper

    Food for the crew

    Alcoholic drinks

    Drinks

    Mooring fees

    Fuel (boat/tender)

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Towels kit

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

French

English

Italian

4.9/5

out of

45

reviews

Skipper

Boat

Destination

avatar image

Fast cruising Cicladi Occidentali

09/8/2025

Beatrice D.

-

Netherlands

Annalisa and Lorenzo welcomed me on their boat and made me feel at home from day one. They made me discover the beauty of the Cyclades with its crystal clear waters and magical sunsets. They filled the days with their stories and delicious food! It was an unforgettable holiday and I will definitely come back for another trip with them!
avatar image

Fast cruising Cicladi Occidentali

08/26/2025

Sergio B.

-

Italy

Annalisa and Lorenzo are first and foremost two wonderful people. Then they are two very experienced sailors: they have sailed around the world; they know the waters of the Aegean by heart. Finally, they are also great as cooks: where do you find the barbecue on the boat and the freshly hand-pulled egg pasta below deck? Only from them! The bays where they took us were breathtaking.
avatar image

Small Cyclades

08/18/2025

Franesco B.

-

Italy

An exceptional holiday! Challenging sea conditions but two professionals proceeded impeccably. Together we sailed sublimely, overcoming adversity, finding ourselves immersed in a true and uncontaminated reality. Undoubtedly a recommendable holiday but I always suggest doing it with the mentality of those who want to help a companion (not a skipper), of those who want to savor intense and sincere realities forgetting some secondary comforts. Finally, special mention to the culinary skills of Lorenzo and Annalisa. Super
avatar image

Fast sailing holiday in the Aegean with gourmet cuisine

07/20/2025

Mercedes S.

-

Spain

It has been a real top 10 experience! Both skippers are incredibly professional and incredible hosts You feel at home as of minute one Awesome and balanced food and very comfortable cabins Postcard and magic spots visited away from crowds Annalisa and Lorenzo are A little treasure just discovered THANK YOU in capital letters! ❤️

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964