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All Inclusive Sailing Holidays & skippered cruises

Experience an all-inclusive sailing holiday, pay the initial fee and forget about galley costs and skipper's services. Services offered by the skipper. The ideal way to be carefree once on board and keep your daily expenses under control.

58

experiences

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4.8

Super!

Catamaran in the sea of Ulysses - All inclusive

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+19 travellers

have booked

Starting from

€1,250

Per person

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5.0

The perfect island-hopping in Greece! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

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+40 travellers

have booked

€1,590

Per person

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European Mile Builder Sao Jorge Leg 4 Gibraltar to Las Palmas

Duration:

6 days - 6 nights

Atlantic islands:

Canary Islands

Give this experience a try!

€475

Per person

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European Mile Builder Leg 7 Gibraltar to Las Palmas

Duration:

6 days - 6 nights

Atlantic islands:

Canary Islands

Give this experience a try!

€475

Per person

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4.8

Super!

A day on a boat in the Gulf of Alassio - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Liguria

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+8 travellers

have booked

Starting from

€160

Per person

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4.8

Let's sail in relaxation on Lake Garda - All Inclusive

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+33 travellers

have booked

Starting from

€150

Per person

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Eolie a vela con skipper ed hostess, all inclusive con cucina vegana

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+29 travellers

have booked

€1,750

Per person

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5.0

A splendid day .... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+91 travellers

have booked

Starting from

€99

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+122 travellers

have booked

Starting from

€129

Per person

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Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

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+2 travellers

have booked

€130

Per person

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Tour of Portovenere and Cinque Terre

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€95

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

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+17 travellers

have booked

Starting from

€125

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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.

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

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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - All Inclusive Sailing Holidays & skippered cruises

648 reviews

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All inclusive day trip sailing around the Golfo Paradiso - flex dates

07/23/2024

massimiliano r.

-

Italy

Bella esperienza. Kit e la moglie molto disponibili.
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An all-inclusive day on a sailing boat

07/22/2024

Giulia D.

-

Italy

Bellissima giornata. Luigi e Federica con la loro professionalità, accoglienza e simpatia hanno contribuito a rendere questa esperienza ancora più bella e divertente. Mio nipote di 10 anni si è divertito molto. Consiglio a tutti questa gita in barca, anche perché via mare si vedono panorami e acque meravigliosi e unici.
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All Inclusive Cruise to the Egadi Islands

07/22/2024

paola z.

Ho trascorso una settimana nella quale ho vissuto emozioni speciali: gli skipper hanno creato un’atmosfera di pura energia. La barca molto comoda e pulita; la loro organizzazione ci ha permesso di ammirare luoghi magici. Il cibo è stato: memorabile. La natura e il vento hanno fatto il resto. Grazie di cuore Agata e grazie Leonardo!!! Spero di ripetere la crociera
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Gulf of Tigullio on a Sailboat - All inclusive!

07/22/2024

Alberti B.

-

Italy

Bellissima esperienza

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6 reasons for an all-inclusive sailing holiday:

  • If you're the kind of person who doesn't like organising trips, looking for restaurants and planning your next plans, this type of holiday is for you. Booking an all-inclusive sailing holiday will make you feel more relaxed and you won't have to worry about anything.
  • Whether family, with friends, couple or alone, you will find the skippered sailing holiday that best suits your tastes and needs.
  • You'll discover a multitude of secret corners that are difficult to reach by land, so you can explore incredible places without the presence of tourists.
  • You will have a unique experience on board a sailing boat or catamaran, discovering dream places from a different perspective
  • You will have no time for boredom, you can enjoy activities all day long, from excursions by sea and land, sailing courses to learn how to sail, leisure or sports activities such as surfing, diving, etc. and, of course, time to relax by sunbathing on the deck of your boat.
  • You'll be travelling in the company of a local skipper, who knows every corner of the region, to help you discover the secret gems of each place you visit - a sailing holiday that won't leave you indifferent!

The best destinations for sailing trips in the Mediterranean:

All-inclusive sailing holidays in the Balearic Islands

The leading sailing destination in Spain. On each of its islands you can breathe a different air, because they all have something different to offer. However, they are all beautiful islands with turquoise, almost paradise-like waters. Enjoy the Mediterranean landscape and its dream islands close to home.

All-inclusive trip to the Greek islands

Trace the history of this magnificent country on board a sailing boat or catamaran, discovering its past through its fascinating and almost endless islands, as there are some 3,054 islands of which only 80 are inhabited, so you won't be bored for a minute! Try their delicious traditional food: tzatziki, tarama, moussaka and their famous Gyros.

All-inclusive travel to Sardinia

Have you ever seen such crystal-clear waters as those of Sardinia? Its coasts have absolutely nothing to envy to those of the Caribbean. You will discover its most heavenly beaches so that you can take a swim and enjoy the sun at the same time. Don't forget to visit some beaches such as Playa Rosa, Playa del Cavaliere or the beaches of Cala Coticcio, famous for their enormous rocks of different shapes.

All-inclusive trip to the Maldives

One of the most desirable tropical countries in the world, located in the Indian Ocean. This idyllic destination will leave you speechless with its breathtaking wild landscapes and totally unspoilt turquoise waters. You won't want to wait a second to dive in. You can also enjoy extraordinary moments under the sea during a snorkelling or scuba diving session to explore the underwater flora and fauna.

Why go on an all-inclusive sailing holiday?

Goodbye worries

Accommodation, transport, skipper, hostess, meals... all this and more will be included in your trip, so you won't have to worry about a thing. You'll have a trip with all the comforts and your holiday skipper will organise everything exclusively for you, so you can relax and let go.

Ideal for families

Travelling with children can often be stressful when it comes to organising holidays because you have to plan activities, food etc. and look after the children at the same time. However, if you book an all-inclusive holiday, you can be sure that peace and quiet and relaxation are also included.

Price without surprises

We generally think that all-inclusive plans are expensive, but nothing could be further from the truth, we spend much more when we improvise and often have surprises when we check our bank account when we get home. On an all-inclusive holiday you'll have everything under control, you won't spend more than you set out to spend at the start of the experience.

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