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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.

13

experiences

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4.5

9 days of ocean sailing catamaran Lagoon 42 - Palma de Mallorca - Gibraltar

Duration:

8 days - 8 nights

Spain:

Andalusia

Give this experience a try!

€1,002

Per person

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4.5

1 week ocean sailing catamaran Lagoon 42 - Gibraltar to Madeira

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

Give this experience a try!

€949

Per person

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4.5

1 week ocean sailing catamaran Lagoon 42 - Madeira to Tenerife

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

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2 travellers

have left

€896

Per person

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European Mile Builder Leg 6 Malta to Gibraltar

Duration:

9 days - 9 nights

Spain:

Andalusia

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Alessandro P.

has left

€475

Per person

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5.0

Navigation in stages from Tahiti to Manila (Philippines) - First stop

Duration:

15 days - 15 nights

Pacific Ocean:

French Polynesia

Give this experience a try!

€2,200

Per person

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5.0

Navigation in stages from Tahiti to Manila (Philippines) - Second stage

Duration:

9 days - 9 nights

Pacific Ocean:

Fiji Islands

Give this experience a try!

€1,300

Per person

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5.0

Navigation in stages from Tahiti to Manila (Philippines) - Third stage

Duration:

16 days - 16 nights

Pacific Ocean:

Fiji Islands

Give this experience a try!

€2,000

Per person

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5.0

Navigation in stages from Tahiti to Manila (Philippines) - Fourth stage

Duration:

21 days - 21 nights

Pacific Ocean:

Fiji Islands

Give this experience a try!

€2,600

Per person

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4.5

7 days Jochseesailing Catamaran Lagoon 42 - Cagliari Sardinia to Mallorca

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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Pierre V.

has left

€949

Per person

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5.0

Tahiti to Tonga sailing

Duration:

20 days - 20 nights

Pacific Ocean:

French Polynesia

Give this experience a try!

€3,074

Per person

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5.0

Sail to the Fiji Islands: Tonga to Viti Levu

Duration:

13 days - 13 nights

Pacific Ocean:

French Polynesia

Give this experience a try!

€1,569

Per person

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5.0

From the Fiji Islands to New Zealand: a unique adventure

Duration:

10 days - 10 nights

Pacific Ocean:

Fiji Islands

Give this experience a try!

€1,590

Per person

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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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Find out before you book who's waiting for you on board

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Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Offshore sailing adventures & skippered holidays

590 reviews

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From the Saronic Islands through in the Corinth Canal by catamaran

09/23/2024

Ernest FABBRI F.

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Switzerland

Super semaine ! Le groupe était international et très sympathique. L'ambiance était calme et reposante. Fulvio prend grand soin de son bateau, qui est un des plus joli et authentique sur lequel nous avons navigué. Il nous a fait découvrir plein de criques pour les baignades et de petits ports typiques pour les promenades
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Lots of sea and lots of sailing - from Corsica to Tuscany

09/12/2024

fabrizia b.

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Italy

Esperienza bellissima per i luoghi visitati e la grande professionalità dello skipper. Ivo trasmette un tale amore per il mare e per la vela che non puoi non rimanerne coinvolto. Incuriosita da una nostra conversazione in barca, una volta rientrata ho riletto Moby Dick e c'è un passo che più di ogni altro rappresenta lo spirito e le emozioni che questa vacanza mi ha regalato: " Chiamatemi Ismaele. Alcuni anni fa - non importa quanti esattamente - avendo pochi o punti denari in tasca e nulla di particolare che m'interessasse a terra, pensai di darmi alla navigazione e vedere la parte acquea del mondo. E' un modo che ho io di cacciare la malinconia e di regolare la circolazione" Grazie f
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Catamaran immersed in the nature of Sardinia in search of well-being, from Carloforte to Cagliari

09/6/2024

Barbara T.

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Italy

Esperienza molto piacevole, apprezzati l' itinerario, il comfort del catamarano, la disponibilità dello skipper e della cuoca volontaria.
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Enjoy: in the blue painted blue of the Aeolian Islands

08/20/2024

Paola T.

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Italy

Bellissima la destinazione e l'itinerario di massima (sebbene diverso da programma iniziale nonostante meteo favorevole). Il feedback, solo parzialmente sufficiente, non può essere rivolto a Giovanni e Matteo in quanto non erano loro i nostri skipper come abbiamo scoperto solo alla partenza. I punti maggiormente dolenti sono stati la capienza della barca (troppo piccola per 10) e la distribuzione delle cabine e dei bagni (non allocate equamente). Ma soprattutto, la partenza ritardata di un giorno per via di un guasto al frigo (non imputabile ovviamente agli skipper) che ha comportato una spiacevole notte in porto persa rispetto al programma iniziale. Consigliamo di definire in autonomia e in anticipo questi aspetti oltre che l'organizzazione delle attività sulle isole, in quanto l'organizzazione degli skipper è parziale e spesso orientata a soluzioni troppo turistiche. Da un punto di vista umano, è un'esperienza che consigliamo assolutamente, abbiamo trovato persone splendide e il clima in barca era bellissimo.

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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 .

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