header cover
logo

Log in

7 giorni a vela alle Cicladi con gran finale a Santorini

Greece:

Cyclades

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

August - September

Suitable for travellers:

18 - 70 years

Boarding from:

Paros

What's included

Cancellation policy

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

This experience, in a nutshell

Un viaggio straordinario tra le acque cristalline dell’Egeo, dalle coste di Paros fino alla magia vulcanica di Santorini. Questa crociera a vela nelle Cicladi vi condurrà attraverso le Piccole Cicladi, gioielli ancora autentici e poco frequentati, per poi spingersi verso Ios e raggiungere il suo traguardo scenografico tra i caldari e le scogliere a picco sul mare di Santorini.


Navigazioni a tratti impegnative su una barca veloce e divertente si alternano a giornate di totale relax in baie remote, bagni in acque turchesi e serate in taverne greche senza tempo. Ogni alba porta una nuova isola, ogni tramonto racconta una storia diversa.

€1,025

6 days - 7 nights

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

25+

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

Paros

The trip begins in the late afternoon in Paroikia, the main port of Paros, with its characteristic open bay and lively promenade. After boarding our fast cruiser boat 43, a welcome toast breaks the ice: we introduce ourselves, place our luggage in the cabins.


As soon as the last lights of sunset tinge the hills of Paros with orange, we cast off for a short sail to Antiparos. It's time to dive for the first swim of the holiday in the clear waters of the strait between two islets. It is the welcome that the Aegean Sea reserves for those who know how to wait for it.


The evening ends at anchor, with dinner prepared on board by the skippers. Table set in the cockpit, stars overhead, the silence of the sea around: a perfect start to the cruise

Leg 2

Schinoussa

We leave Antiparos early in the morning with a route to Schinoussa, one of the lesser-known pearls of the Small Cyclades. Sailing, with the wind typically crosswind or upwind wide, promises to be fast and engaging: excellent for those who want to take the helm or learn how to use the sails.


Schinoussa is an island that mass tourism has not yet reached. The roads are still partly unpaved, the rhythms of life sleepy and quiet. The Chora, a handful of white houses along the main road, transports those who arrive there to another era.


We anchor in the beautiful bay of Livadi for lunch on board and a relaxing afternoon of swimming and reading. In the late afternoon, a panoramic walk takes us to Chora for an aperitif in one of the outdoor cafes, where the colors of the island and the evening breeze make everything more beautiful.

Dinner on board, cooked by the skippers with fresh local products, lulled by the quiet of the bay.

Leg 3

Koufonissi

Short and pleasant sail to Koufonissi (or Kato Koufonissi), the smallest and liveliest island of the Small Cyclades. Here the sea reaches shades of turquoise and emerald that are difficult to forget.


The day is dedicated to pure relaxation: we drop anchor a few meters from a beach of fine white sand, in very shallow and transparent waters. The afternoon is spent swimming, snorkeling and siestas in the shade of the sail.


In the late afternoon we move to Koufonisia for a more mundane evening. The island has a double character: quiet and genuine during the day, lively and welcoming in the evening. Dinner in a typical tavern on the port, between grilled fresh fish and local wine, in the company of fishermen and the lucky few who have discovered this corner of Greece.

Leg 4

Secret desert island

Today one of the most exciting stops of the entire cruise awaits us: Keros. An uninhabited and remote islet, Keros is one of the most important archaeological sites in the Aegean: thousands of Cycladic marble idols have been found here, now exhibited in the major museums of the world.


The navigation from Koufonissi is short but often intense, with the Meltemi blowing decisively between the islands. We anchor in deep blue waters, surrounded only by rock and silence. Lunch on board and long swims in this corner of wild and unspoiled sea.


In the evening, the sky far from any light pollution turns into a spectacle: shooting stars, the Milky Way, the constellations that Greek sailors learned to read millennia ago. Dinner on board, under this same sky.

Leg 5

Amorgos

Today's stage depends on weather conditions. If the wind and the sea allow it, we go as far as Amorgos, the wild and fascinating island of the Cyclades; alternatively, we stay in the archipelago of the Small Cyclades and head for Iraklia.

Amorgos: Arid and rocky island, where the intense blue of the sea contrasts with the barren landscapes and the austere beauty of the area. We anchor in the large bay of Katapola and in the afternoon we venture towards the famous monastery of Hozoviotissa, set in the rock 300 meters above the sea.


The almost 400 steps leading to the entrance are rewarded with a breathtaking view and the warm welcome of the monks, who offer guests a glass of Rakomelo and fruit sweets. One of the most unforgettable experiences in the entire Aegean.

Leg 6

Bay deserted to Ios

Today I sail to Ios, an island with a dual character: wild and mountainous in the south, where remote bays can only be reached from the sea, worldly and lively in Chora in the north, famous throughout the Mediterranean for its nightlife.


We anchor in one of the magnificent bays of the south of the island, accessible only by boat: lunch in the cockpit with our eyes wide open on a panorama that seems painted. The afternoon is all ours between swimming and relaxing.

Leg 7

Grand finale in Santorini

The final sail takes us to Santorini, one of the most iconic and scenic places in the Mediterranean. As we get closer, the black cliffs overlooking the sea begin to loom on the horizon: the thrill of getting there by boat, slowly, without haste, is something unrepeatable.


We sail in the caldera of Santorini from north to south, passing under the imposing volcanic walls and admiring the white villages of Oia and Fira clinging to the overhangs. A spectacle that no photograph can really reproduce.


We anchor in front of the beach of Akrotiri, in the south of the island. From here, those who want can visit the famous archaeological site of Akrotiri, the "Pompeii of the Aegean", or simply enjoy the red sandy beach not far away.

The evening is our last together: farewell dinner on land, in a Greek tavern, between toasts and memories of a week spent between wind, sea and unforgettable islands.

Leg 8

See you in the Cyclades

Breakfast on board and disembarkation in Santorini. The holiday ends here, but the Cyclades stay 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

250€ a persona a settimana includono : Spese varie: spese portuali e marina, rifornimento acqua, rifornimento carburante per il motore ed il fuoribordo, gas cucina, pulizia finale. Servizio cucina + acquisto cambusa: 7 colazioni, 6 pranzi, 4 cene

    Galley

    Food for the skipper

    Food for the crew

    Alcoholic drinks

    Mooring fees

    Embarkation and disembarkation 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

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

Italian

English

French

4.9/5

out of

45

reviews

Skipper

Boat

Destination

avatar image

Fast cruising Cicladi Occidentali

09/8/2025

Beatrice D.

-

NL

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.

-

IT

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.

-

IT

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.

-

ES

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