• Sign up
  • Log in
Sailsquare
      • All Greece
      • Ionian Islands
      • Cyclades
      • Dodecanese
      • Saronic Islands and Athens area
      • All Italy
      • Northern Sardinia
      • Aeolian Islands
      • Aegadian islands
      • Tuscany
      • Liguria
      • Pontine Islands
      • Amalfi Coast
      • All Spain
      • The Balearic Islands
      • Andalusia
      • Catalunya
      • Galicia
      • Valencia
      • All Caribbean
      • BVI - British Virgin Islands
      • Antigua and Barbuda
      • Cuba
      • Grenadines & Martinique
      • Guadeloupe
      • Bahamas
      • Belize
      • All Indian Ocean
      • Bali
      • The Maldives
      • Mauritius
      • Seychelles
      • Corsica
      • French Riviera and Porquerolles
      • Brittany and Normandy
      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
      • Day trips
      • Flotilla
      • Offshore
      • Sport & wellness
      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
      • Catamaran
      • Gulet and sailing ship
      • Monohull
      • Mediterranean
      • Families
      • Couples
      • Solo Travellers
      • Exotic
      • Whale watching
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • You have 0 messages!
  • 0 new alerts for you!
  • Message area
  • Holiday wishlist
  • My profile
  • Edit account
  • Log out
      • All Greece
      • Ionian Islands
      • Cyclades
      • Dodecanese
      • Saronic Islands and Athens area
      • All Italy
      • Northern Sardinia
      • Aeolian Islands
      • Aegadian islands
      • Tuscany
      • Liguria
      • Pontine Islands
      • Amalfi Coast
      • All Spain
      • The Balearic Islands
      • Andalusia
      • Catalunya
      • Galicia
      • Valencia
      • All Caribbean
      • BVI - British Virgin Islands
      • Antigua and Barbuda
      • Cuba
      • Grenadines & Martinique
      • Guadeloupe
      • Bahamas
      • Belize
      • All Indian Ocean
      • Bali
      • The Maldives
      • Mauritius
      • Seychelles
      • Corsica
      • French Riviera and Porquerolles
      • Brittany and Normandy
      • Split Archipelago
      • Kornati Islands
      • Turkey
      • French Polynesia
      • Norway
      • Adventure
      • Courses & regatta
      • Day trips
      • Flotilla
      • Offshore
      • Sport & wellness
      • WWF Sailing Cruises
      • Whole boat with skipper
      • All inclusive
      • Crewed
      • Catamaran
      • Gulet and sailing ship
      • Monohull
      • Mediterranean
      • Families
      • Couples
      • Solo Travellers
      • Exotic
      • Whale watching
  • Rent a boat
  • Call us
    +44 20351 44220
    • ITA
    • FRA
    • DEU
    • ESP
  • ITA
  • FRA
  • DEU
  • ESP
Offshore sailing adventures & skippered holidays

Offshore sailing adventures & skippered holidays

If what you're looking for is the adrenaline rush of sailing long miles on a sailing boat, then deep-sea sailing and crossings, even oceanic ones, are what you need. oceanic crossings, are what you need. Crossing the Atlantic Atlantic Ocean or simply sailing the Mediterranean is a unique experience for those who love the sea.

  • Sailing Holidays
  • Offshore

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 33 reviews
    confirmed

    One way Santorini Paros cruise via Small Cyclades (Ios, Koufonissi, Amorgos, Schinoussa)

    from 2 July - 7 nights
    Cyclades Greece
    5 people
    are onboard
    838€ Per person
  • 34 reviews
    confirmed

    June from Naples to the Aeolian Islands on a sailing boat, desire for freedom and lightheartedness

    from 2 July - 7 nights
    Aeolian Islands Italy
    4 people
    are onboard
    689€ Per person
  • 4 reviews
    confirmed

    From Greece to Malta, flights are still cheap, don't wait

    from 2 July - 6 nights
    Malta Malta
    1 person
    is on board
    732€ Per person
  • 99+ reviews
    confirmed

    ONE WAY - JOURNEY AND MAGIC - among the most coveted and seductive islands of the planet: ELBA - SOUTH CORSICA - MADDALENA - TAVOLARA up to VILLASIMIUS

    from 3 July - 6 nights
    Northern Sardinia Italy
    2 people
    are onboard
    630€ Per person
  • 4 reviews
    confirmed

    From La Spezia to Naples, sailing among the most beautiful islands of the Tyrrhenian Sea

    from 8 July - 9 nights
    Tuscany Italy
    2 people
    are onboard
    299€ Per person
  • 1 review
    confirmed

    South Sardinia sailing

    from 9 July - 7 nights
    Southern Sardinia Italy
    5 people
    are onboard
    742€ Per person
  • 28 reviews
    2 discounted
    spots

    History, science, art and eco-sustainable nautical tourism: live your adventure in the Mediterranean Sea!

    from 9 July - 6 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    636 583€ Per person
  • 23 reviews
    confirmed

    From the Kornati to the pearls of Puglia: Vieste and the Gargano

    from 9 July - 7 nights
    Kornati Islands Croatia
    5 people
    are onboard
    626€ Per person
  • 4 reviews
    confirmed

    Crossing from Malta to the Egadi islands, flights still cost a little 150NM

    from 9 July - 6 nights
    Aegadian islands Italy
    7 people
    are onboard
    732€ Per person
  • 13 reviews
    confirmed

    EARLY BOOKING - Sardinia of emotions, from Ogliastra to Tavolara: last cabin!

    from 11 July - 4 nights
    Northern Sardinia Italy
    2 people
    are onboard
    1.123€ Per person
  • 1 review
    almost
    confirmed

    Corfu-Kefalonia aboard an exceptional 47-foot sailboat for 2 privileged people

    from 11 July - 7 nights
    Ionian Islands Greece
    1 person interested
    in this holiday
    1.283€ Per person
  • 16 reviews
    confirmed

    Sailing in offshore CATAMARAN with the experience of Captain Marco

    from 11 July - One day
    Tuscany Italy
    Join in on this experience!
    159€ Per person
  • 1
  • 2
  • 3
  • 4
  • 5

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Offshore sailing adventures & skippered holidays

440 reviews
20 / 10
Giulia E.

Giulia E.

review about Sailing and catamaran trekking between Pantelleria, Linosa and Lampedusa June 2022

10 / 10
I couldn't find better! Beautiful experience! In addition to the landscapes and trekking done and the bays of Pantelleria, Linosa and Lampedusa, postcard places, the experience was perfect Thanks to the company of the people with whom I was traveling and in particular to Fulvio, skipper and owner of Magdalena 43 and his sailor. An exquisite person, full of stories to tell, very good cook, sunny and with a big heart. We visited the islands on land, snorkelled, taught me how to do freediving and many other things about sailing at sea. For those who are open to know new things, to experience a new way of traveling in harmony with nature and its times ... I really recommend Fulvio and his Magdalena :)
Emanuele C.

Emanuele C.

review about Offshore navigation 370 nm. Sicily / Sardinia Nautical Education Vacation May 2022

10 / 10
Unique experience and amazing people! A trip full of emotions and that I will never forget, Marco and Valentina welcomed me on the boat, and immediately made me feel at home. During the three days of travel I had the pleasure of getting to know them better. Marco is a calm and kind person, a super competent and professional skipper. Always willing to teach his crew how to fix the course and sails, regardless of the level of experience. Master of sailing and unique life. Valentina, also very kind, is a bomb of energy and happiness, always ready to entertain and spoil the crew with aperitifs and delicious dishes. I will never forget the crossing of the Tyrrhenian Sea. Between naps tickled by the waves of the sea, aperitifs with traditional food and white wine, and shifts at the command during which to learn to manage the boat. And finally, three days of pure relaxation and fun in Sardinia immersed in unique coves with emerald water.
Francy M.

Francy M.

review about One way offshore sailing course from Neptune to Sardinia May 2022

8 / 10
The idea of the Tyrrhenian crossing was fascinating: not seeing lands emerged for a long journey and witnessing the changing colors of sky and sea will remain dear to me! Skipper Alberto was helpful and attentive to the needs of his crew and other travel companions. really a discovery! Fantastic experience!!
Andrea M.

Andrea M.

review about 10 days from Athens to Santorini via Milos and Folegandros October 2021

10 / 10
THE BEST SKIPPER IN THE WORLD. We had a wonderful 10 days. Super professional and prudent but above all he knows the sea very well. We will come back to visit you!
Rafael G.

Rafael G.

review about Sardinia, from Barcelona: high altitude crossing and well-deserved relaxation September 2021

10 / 10
Alfons and Gonzalo on the boat and Inma on land form a great and compact team, the trip has been an experience, the crossing from Bcn to Alguero is a mini challenge for those who are thinking about being on the high seas without having to cross the Atlantic.... ;) Sardinia keeps multiple secrets, the visits we did very well but the island gives of itself to return again Thanks for the expedition
Sébastien R.

Sébastien R.

review about One way Cyclades with experienced captain and amazing food :) September 2021

10 / 10
A week spent aborad the ZORBA with Captain Greg & Aga... and what a week ! :-) A warm welcome, a cruise oriented customer satisfaction while being responsive to the weather forecast while ensuring safety, a professionalism to explain the conditions of navigation, guides to discover the best spots of the Cyclades and typical local restaurants. But especially two people TOP! Two apathic people, playful, plaisant, patient and who take the time for each one. A week with 10 polish people who have all made the effort to speak english to integrate me in their discussions and create a real exchange on board. I can only recommend Greg & Aga! :-)
Yugho Y.

Yugho Y.

review about Zadar, Kornati islands, Split: fairytale sailing in the Dalmatian sea September 2021

10 / 10
Highly recommended! Great memories with Riccardo, Giada and the team! Hope to come back soon!
Federica V.

Federica V.

review about Cruise from the Aeolian Islands to Nettuno passing the Calabrian coast, Cilento and Ischia August 2021

10 / 10
Unique holiday that I recommend to anyone! Bruno was great at making us feel at home, trying to satisfy our requests. In addition, he turned out to be a very good cook. The boat is very well kept. Super recommended!
Manuela L.

Manuela L.

review about The best holiday is on a sailing boat in the Ionian islands August 2021

10 / 10
Wonderful holiday, we would repeat it immediately, and again with Manuele. Beautiful bays, excellent company and rating 10 to the boat, spacious and equipped. Manuele made us feel at home, he is professional, competent, helpful as well as being a great cook. Praise to his homemade cutters! He knows how to listen and please the crew.
Pietro S.

Pietro S.

review about 3 boats from Genoa to Rome: Cinque Terre, Porto Venere, Capraia, Elba, Giglio, Argentario July 2021

10 / 10
Young, fun and helpful. Wonderful holiday
Magali P.

Magali P.

review about From 9 to 15 August: sea and sea only! August 2021

10 / 10
A wonderful week ! Alessandro is an exceptional skipper who will make your cruise unforgettable ! He will share his pleasure in sailing with the whole crew. Teenagers will learn a lot from him ! With kindness, sympathy and humour, he will bring you to paradises :-) Well done Captain and thank you again !
Andrea T.

Andrea T.

review about Traveling internship - The North coast of Sicily August 2021

10 / 10
Unforgettable course, beautiful places and beautiful boat! Emmanuelle very good follows you step by step and teaches you the secrets for safe navigation with also maneuvers moorings, knots and so on and so forth! Absolutely recommended!
Marta P.

Marta P.

review about Aeolian between history, culture and traditions July 2021

10 / 10
It was my first sailing trip, and it was gorgeous. Salvatore is super experienced, an excellent cook, and always available, for advice on what to see and / or do. I hope to be able to come back soon to hear him scream "Engineer, the top blè!"
Desirèe T.

Desirèe T.

review about Cruise from Mallorca to Ibiza passing through Formentera, one of the most beautiful places in the Mediterranean July 2021

10 / 10
For me it was the first sailing experience, and I must say it was fantastic! Maurizio very good skipper very nice and always available, also very prepared and a feeling of total security! Great experience! I would do it again
Adriana V.

Adriana V.

review about From La Spezia to Olbia, across Elba and the Costa Smeralda July 2021

10 / 10
Skipper, crew and boat to say the least perfect. In addition, the owner's friendliness and competence made the experience on board pleasant and created an atmosphere of extreme harmony among the participants. Absolutely recommended!
Elisabeth M.

Elisabeth M.

review about From Egadi to Palermo in caique with cook on board! July 2021

10 / 10
We had a very good time. Congratulations to Lisa and Mauro, but also to Ege, who in addition to being an excellent cook, was also an excellent Skipper, always present and attentive. Thanks again to all.
STEFANO M.

STEFANO M.

review about Transfer from Lefkas (Ionian) to Skiathos (Sporades) via Corinth Canal June 2021

10 / 10
Davide is a great skipper! We did together a week of transfer around the Peloponnese with a night sailing, so not the typical sailing holiday. Davide is safe and prudent in planning the routes and bringing the boat to make the holiday pleasant and relaxing. Choosing when to stop and when to start again with challenging itineraries makes the difference. Nice and good company both on the boat and in the evenings going out to visit the various attractions where we stopped. Great food and very relaxed in handling boat and passengers sailing! Excellent company also of fellow travelers, Enzo and Daniele! Definitely recommended!!
Enrico B.

Enrico B.

review about Crossing from Cesenatico to Lefkada - An unmissable adventure! - Hostess on board May 2021

10 / 10
Omar and Enrica are two wonderful people nice, hospitable and pleasant. Omar is a very experienced skipper and Enrica is very good at managing the boat. The Bavaria 46 is a comfortable hull and jealously and lovingly and with care and taste by both. Experience to be repeated
Claudio V.

Claudio V.

review about Offshorse Salining course towards Elba Island or Capraia December 2020

10 / 10
very well everything
Enrico B.

Enrico B.

review about Océano atlántico, from Málaga to Madeira, adventure and unforgettable emotions. November 2020

10 / 10
Filippo is a great skipper !!!!! The navigation was interesting and of a good standard. It is a holiday that requires a bit of sailing experience given the period. The boat comfortable . Week for many but not for all !!! The only real problem that Filippo is a "pippa" fishing !!! So you only eat Flemish stew !!!
ANTONELLA D.

ANTONELLA D.

review about magical week in full comfort on the Aeolian Islands August 2020

10 / 10
Francesco excellent skipper.helpful and attentive to every guest whoever is .beautiful experience
Gabriel P.

Gabriel P.

review about Morbihan Islands Tour August 2020

10 / 10
Cruise more than perfect with Jean-Baptiste! Trusted person and pedagogue, He involved us in navigation. I rediscovered Brittany in a different way. We get comfortable in the boat, even better when the whole crew is at the top ;) ATM
Luca D.

Luca D.

review about From Genoa on 1.08: routes to Capraia-Elba and then La Maddalena and Stintino to Alghero August 2020

10 / 10
the greatest sea wolf I have ever known :)
Giacomo G.

Giacomo G.

review about Navigation from Carloforte to Alghero, along the whole Sardinian west coast of Sardinia August 2020

10 / 10
Our first experience on a sailboat was memorable, we discovered a new way of vacationing and learned to appreciate aspects that until a week ago we took for granted. Giovanni is an experienced skipper, freediving instructor, excellent chef, skilled speaker and who knows what else: the ideal person to lead this type of adventure. A big thank you then to Giovanni and we hope to repeat in the future a trip like this, maybe back on board the boat!
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

6 reasons to take part in a sea crossing or deep-sea sailing

  • Learn to sail in the company of professional skippers who will pass on their passion for the open sea.
  • Experience the magic of night sailing: sailing accompanied by silence and the stars is an unparalleled experience.
  • Experience the magic of real sailing: discover routes that are less common and far from mass tourism to experience a unique adventure!
Be aware of the magic of real sailing: discover routes that are less common and far from mass tourism to experience a unique adventure!
  • Test yourself sailing long distances in the open sea.
  • Sail in the company of dolphins and whales: starting from Liguria and from South of France, cross the Cetacean Sanctuary to reach Corsica.
  • Experience the feeling of absolute freedom . The days will be free of any haste and the times will be marked by alternating between the sun and starry skies.

The best itineraries for sailing on the open sea

Are you interested in sailing away from the coast, surrounded only by the open sea? Embarking in the company of a passionate skipper for a crossing, including ocean, is the ideal experience for those who love long voyages and for those who want to experience a unique adventure by enriching their nautical knowledge.

From Liguria to Corsica: crossing the Mediterranean on a sailing boat

One of the most fascinating routes for offshore sailing is right behind the house: the Mediterranean triangle enclosed between the Liguria , the Côte d'Azur , the Tuscany and the Corsica is known as the Cetacean Sanctuary . It is a marine protected area where you can sail in the open sea in the company of dolphins and whales. The departure is generally from one of the ports of west of the Ligurian Riviera or from the French Riviera.

Some skippers choose to set sail in the evening, carry out a night navigation with shifts and land on the coasts of Corsica at dawn. Another possibility is to leave Liguria or the south of France at dawn to fully enjoy offshore sailing during the day. In this way your skipper can pass on his seafaring knowledge and you can test yourself at the helm or adjusting the sails. During the day someone will be able to practice trolling, to have lunch with fresh fish.

For those who are just starting out with offshore navigation, we suggest the route departing from Tuscany, which often sees an intermediate stop in Capraia, before reaching the mythical rock of Giraglia in Corsica. The Giraglia is famous for being one of the stops of sailing regattas in the Mediterranean, including the Giraglia Rolex Cup , departing from Saint Tropez, and the 151 Miles departing from Livorno.
Are you a group of friends? This route is perfect for you, whether you want to try your hand at sailing, or experience a long weekend on a sailing boat in company: rent a whole boat with skipper to live an exciting experience starting from the comfortable ports of Tuscan coast .

Atlantic crossing on a sailing boat

The crossing of the Atlantic Ocean to reach the turquoise Caribbean seas is the best known ocean route. This long experience on a sailing boat consists of two sections. The first route lasts a week, departing from Balearic Islands or from south of Spain to reach Tenerife or Gran Canaria < / a>, passing through Gibraltar. Once you have landed in the Canary Islands it is time to wait for the ideal weather window to head to the Caribbean . When the winds are favorable your unforgettable adventure in the blue of the Atlantic will begin!

Generally the crossing of the Atlantic Ocean by sailing boat lasts at least 20 days ; the stages and the navigation rhythms depend on the winds and the weather. On board a sailboat, everyone always has a specific role, but in this case it is even more important that each crew member respects the sailing shifts and is always vigilant. For this reason, most skippers require their travel companions to have a minimum of experience in offshore sailing.

After the long Atlantic voyage you wish to relax for a week in the crystal clear waters of the Caribbean Sea, soaking up the sun aboard a catamaran or of a sailing boat ? You are in the right place and you will be spoiled for choice: Martinique , Guadelupa , St. Vincent and the Grenadines and St. Lucia await you!

Offshore navigation in the North Sea

Cold? I'm not afraid of you! When we talk about offshore sailing, we must also think of routes less traveled by mass tourism . Starting from the coasts of the Basque Country in Spain, sailing in the Bay of Biscay, or Bay of Biscay, is the ideal experience for those who want to learn the fundamentals of offshore navigation and have a period of less than 2 weeks.

For the more adventurous, Iceland and the great north are certainly a essential destination ; we suggest the departure from the port of Reykjavik with a stop at the Faroe Islands, characterized by steep cliffs and home to sea birds. Once you have landed on the coast of Scotland, you can reward yourself with an excellent glass of scotch like a real sea dog!

If you are looking for breathtaking landscapes and unspoiled nature, you absolutely cannot miss the magic of the midnight sun , sailing through the waters of a Norwegian fjord . Stop among the fishing villages that populate the Lofoten islands in Norway is a unique adventure.
On the opposite side of the Atlantic ocean , in Canada , you will instead admire the green of the coniferous forests that is reflected on the blue of the sea. Along the canal that will take you to Québec-City you can take part in a sailing course with professional skippers.

Crossing the English Channel on a sailboat

The north fascinates you but you still don't feel ready for such a challenging navigation? Crossing the Manche is the perfect adventure to get closer to offshore sailing in small doses.
Setting sail from one of the ports of Brittany near Calais, in a few hours you will find yourself enjoying an excellent Fish & Chips in the Southern England . Do you think this is a less adventurous sailing experience? Far from it! The English Channel is known for the strongest tides and currents in Europe, which is why after this 3-day adventure you will be ready to tackle even the most demanding voyages.

Crossing the Pacific Ocean: from Panama to the Hawaiian Islands to Alaska

If your dream is to spend as much time as possible on board a sailboat sailing the Pacific Ocean, we suggest the longest route ever : from Panama Canal to Honolulu Your adventure will last at least 4 weeks and you will sail for almost 5000 miles : a long journey during which you will have the opportunity to deepen your seafaring knowledge and discover all the secrets of life on board during a ocean crossing.

Another less traveled route suitable for lovers of the sea and nature is certainly the one to the north: starting from Hawaiian Islands awaits you one of the most exciting crossings passing through different climates, until you reach the coasts of Alaska .

Everything you need to know to go deep-sea sailing or a crossing

When is the best time to sail across the Mediterranean?

In addition to being an excellent experience to enrich your seafaring knowledge, sailing in the sea triangle between Liguria , Corse and Côte d'Azur is the perfect opportunity to spot whales. The best time for sightings is between mid-April and late October . On the way back, always keep an eye on the bow: it will be easy to see a group of dolphins playing in the waves created by your sailing boat.

What is the best time to sail across the Atlantic?

Most skippers organize the crossing from east to west between October and November and sail back to the Mediterranean between April and May. If you want to escape from the cold of winter, we advise you to leave during the autumn to enjoy the best weather conditions while sailing and the tropical climate once you reach the Caribbean.

What experience do you need to participate in offshore sailing?

No nautical license is required to book an offshore sailing experience. Depending on the duration of the crossing and its difficulty, the skippers will be able to ask you a minimum of experience at sea in order to guarantee shifts during navigation. If you want to experience the adrenaline of sailing in the open sea for the first time, we recommend that you always ask the skipper for the level of difficulty of the chosen route.

How long does it take to have an offshore sailing experience?

It depends on the course you choose and the winds blowing on your sails. A long weekend is enough to sail from Liguria to Corsica, with return, or to cross the English Channel.
Generally the Atlantic crossing from east to west lasts a total of 3 weeks : a week to sail from the south of Spain to the Canary Islands, while the second leg from Gran Canaria to the French Antilles two weeks. The Pacific Ocean crossing will certainly be longer, lasting an average of 4 weeks.

How much does an offshore sailing cost?

The prices of a sailing trip vary according to the duration and the route of the trip. In general, prices start from € 500 per week for offshore navigation routes in the Mediterranean up to € 1,000 per week to cross the Atlantic or the Pacific. A offshore weekend in the English Channel offers very affordable prices, starting from € 200 per person .

Offshore: best destinations

  • Italy (52)
  • Greece (28)
  • France (8)
  • Atlantic islands (7)
  • Croatia (6)
  • Spain (6)
  • Malta (2)
  • Caribbean (1)
  • Montenegro (1)
  • Africa (1)

Other travel ideas

  • Monohull (2116)
  • Whole boat with skipper (1873)
  • Crewed (509)
  • All inclusive (424)
  • Catamaran (379)
  • Day trips (209)
  • Courses & regatta (179)
  • Gulet and sailing ship (116)
  • Offshore (112)
  • Flotilla (55)

Let's talk Sailsquare

Huffpost Sailing Today Yahoo!
Sailsquare press review

Sailsquare

  • Team
  • Careers
  • Press Room
  • Press Releases
  • Sustainable Tourism
  • General Terms & Conditions
  • Privacy

Travellers

  • Contact & Support
  • Blog
  • Customer Reviews
  • Sailsquare Concept
  • Ambassador Program
  • Traveller policy

Skippers & Businesses

  • List a holiday
  • Contact & Support
  • Provider Policy
  • Code of Conduct

Follow us on

Facebook Instagram Youtube Sailsquare blog

Secure online payments

Mastercard Visa America Express Apple Pay

Top Destinations

  • Italy
  • Greece
  • Aeolian Islands
  • Tuscany
  • Northern Sardinia
  • Pontine Islands
  • Ionian Islands
  • France
  • Aegadian islands
  • Croatia
  • Cyclades
  • Spain
  • The Balearic Islands
  • Gulf of Naples
  • Caribbean
  • Southern Sardinia
  • Dodecanese
  • Split Archipelago
  • Liguria
  • French Riviera and Porquerolles
  • Lake Garda
  • Corsica
  • Indian Ocean
  • Saronic Islands and Athens area
  • Amalfi Coast
  • Canary Islands
  • Grenadines & Martinique
  • Venice and the Gulf of Trieste
  • Sicily
  • Guadeloupe

Top Travel Ideas

  • Adventure
  • Catamaran
  • Courses & regatta
  • Day trips
  • Flotilla
  • Gulet and sailing ship
  • Monohull
  • Offshore
  • Sport & wellness
  • Whole boat with skipper
  • All inclusive
  • Crewed
  • WWF Sailing Cruises
© 2022 Sailsquare Srl - Società Benefit • All rights reserved - VAT 07860990964