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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.

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4.7

Ibiza All Inclusive on an 18m ketch with skipper and skipper

Spain: The Balearic Islands

6 days - 7 nights

7 departures available

June - August

Starting from

€1,200

€960

Per person

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5.0

Super!

All inclusive week in Croatia - Embarking and disembarking in Rimini

Croatia: Split Archipelago

7 days - 7 nights

2 departures available

July - September

Starting from

€936

Per person

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4.9

Super!

Sailing dreams in the Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

5 departures available

July - August

Starting from

€350

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

June - August

Starting from

€1,115

€1,059

Per person

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5.0

Super!

Day trip on a sailing boat

Italy: Tuscany

1 day - 0 nights

20 departures available

June - July

Starting from

€150

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

Per person

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4.9

Super!

Traveling and dreaming in the Gulf of Poets - All Inclusive

Italy: Liguria

2 days - 1 night

3 departures available

July - September

Starting from

€250

Per person

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5.0

Super!

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

24 departures available

June - September

Starting from

€79

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi and Sorrento Coast

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

June - July

€865

Per person

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5.0

Super!

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

Italy: Tuscany

1 day - 0 nights

34 departures available

June - August

Starting from

€125

Per person

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5.0

Super!

The awakening of the lake

Italy: Lake Garda

1 day - 0 nights

2 departures available

July

€69

Per person

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5.0

Super!

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

July

€99

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

738 reviews

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Sailing, swimming and aperitif at sunset ... What else?

06/21/2025

Aaron C.

-

Italy

Magnifica giornata in relax. Anche se non abbiamo trovato vento, Emanuele è riuscito a farci partecipare alla navigazione e a metterci a nostro pieno agio. Da rifare!
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Capri Dream Premium - Catamaran cruise full board

06/21/2025

Matteo B.

Super vacanza con uno skipper (Gianmarco) bravissimo, disponibile per qualsiasi richiesta. La cuoca (Grazia) superlativa, ogni giorno ci ha preparato dalla colazione alla cena dei menù super buoni!! Grazie ad entrambi per averci fatto passare una settimana indimenticabile! A presto.
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A fantastic day on a boat in the blue sea of Tuscany

06/17/2025

Giulia L.

-

Italy

Giornata stupenda, skipper gentilissimo e super disponibile.
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Dalmatian Dream - week on catamaran ALL INCLUSIVE with hostess/cook

06/12/2025

Altamir T.

-

Brazil

The experience of the Dalmatian Dream cruise, from May 24th to 31st, was not entirely satisfactory. Despite all the efforts of Captain Marino and the cook Mila, the program was interrupted several times for repairs to the boat. As a result of these problems, comfort and well-being were also impaired. Despite these problems, it is worth noting that the food was excellent and that the general conditions of the cabin were good. Additionally, the reception service at the office was kind and attentive, providing support and guidance in my specific case for a health problem

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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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