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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.4

The unspoiled paradise of the BVI

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October

€607

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

One departure available

October

€325

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

One departure available

October

€1,100

Per person

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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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New

Gulf of Noli, bay of the Saracens, cave of the Falsari up to Varigotti

Italy: Liguria

1 day - 0 nights

2 departures available

September

€99

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

October - November

Starting from

€723

€650

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

September - November

Starting from

€700

€665

Per person

Why book a holiday with Sailsquare?

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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

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

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 - Sailboat holidays & skippered tours

19233 reviews

Let's discover Portofino, Santa Margherita and Sestri Levante together

09/28/2026

Cristina A.

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IT

Beautiful ride, professionalism and friendliness at the top
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A week sailing in the most beautiful places in the world

09/28/2026

sara s.

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IT

A wonderful experience!! We stayed a week with Piero and Giuseppina booking the whole boat. Despite the adverse weather forecast, the weather was always good. But we have always relied on the wise course decisions of Piero, who in addition to always being attentive and scrupulous, is a very good skipper in all aspects: his daily lessons will not be forgotten! A special mention goes to Giuseppina, with whom I immediately found myself in tune even with just a smile. His cuisine is spatial, better than that of many restaurants in the area! But Piero in the kitchen is not bad either, his spaghetti are excellent! Thank you for this trip and for the company!

Cyclades from Milos to Milos

09/28/2026

Alessio P.

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IT

Fabio is a very precise and professional skipper, thanks to the weather we were able to respect all the descriptions and the boat was really beautiful and comfortable. Although it was not within his competence, we tried some really good Roman dishes. Very skilled with the scientific 😎🤣 scopone It is a thank you to the legendary Irene. Highly recommend the experience

Fast Sailing Experience between Authentic Islands and Good Food

09/28/2026

Jaouen B.

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FR

Amazing trip! Analisa and Lorenzo were born to host: good vibes, quite communication, marvelous cooks, expeirenced adventurers (know plenty of secret places) and great skippers. I highly recommend them both. If you love snorkling, maybe the Cyclades are not the best location to pick.

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