header cover
logo

Log in

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.

cover image
avatar image

5.0

New

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

€590

Per person

cover image
avatar image
Odysseus trip to Zakynthos - Kefalonia-Ithaka

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€890

Per person

cover image
avatar image

4.8

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

Italy: Lake Garda

1 day - 0 nights

9 departures available

September - October

€150

Per person

cover image
avatar image

New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

One departure available

September - October

Starting from

€1,645

Per person

cover image
avatar image

5.0

Capraia and Elba Island - Sun, Sea and Fun!

Italy: Tuscany

4 days - 3 nights

2 departures available

September - October

€400

Per person

cover image
avatar image

5.0

Mindfulness, the here and now... on the sea!

Italy: Liguria

2 days - 1 night

One departure available

October

€340

Per person

cover image
avatar image

5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September - October

€607

Per person

cover image
avatar image

4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€312

Per person

cover image
avatar image

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

cover image
avatar image

4.4

Premium

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€845

€676

Per person - min 2 pax

cover image
avatar image

4.8

Weekend of emotions in the Blu Pontino

Italy: Pontine Islands

3 days - 2 nights

One departure available

November

€225

Per person

cover image
avatar image

4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€325

€309

Per person

Why book a holiday with Sailsquare?

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

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

19162 reviews

North Corsica & Tuscan Archipelago: we love to travel a lot

09/19/2026

francesca vera p.

-

IT

Beautiful holiday, lovely places. Thanks to Marco and his travel companions!
avatar image

Five days barefoot between Tuscany and Corsica

09/19/2026

Mariella D.

-

IT

The holiday went well. Matteo was helpful. For 4 nights, arriving in Corsica becomes very long the navigation and inevitably the possibilities of swimming are reduced. Then the cost of fuel can affect a lot
avatar image

A sailing story between Favignana, Levanzo and Marettimo

09/19/2026

Alessandro P.

-

IT

First experience of a week on a sailing boat: I can only be enthusiastic! To the itinerary with a "right" navigation for a baptism was added a skipper who was not only technically capable, but also attentive to everything (even to my being a vegetarian) and to everyone's well-being, through a valid program, taking time in the first person also to go and buy the necessary on land and pamper ourselves with the right music playlist. To be added then the reassuring assistance from his team, both before departure and during navigation. The group was varied but in each one there was respect and desire to feel good alone and with others, so much so that no one ever backed down in the daily routine of preparing meals and tidying up the necessary. The boat, [hidden], also proved to be a friend: adequate spaces, functional bathrooms, practical kitchen: a great boat kept to perfection and with care. Finally, the sea of the Egadi Islands is magnificent and even the islands have treasures made up of people to chat with, but also paths to explore. To conclude: the organizational part was excellent but we must not forget that the favor of temperatures, sea and wind - which are an exclusive matter of Jupiter, Neptune and Aeolus - made everything more beautiful and enjoyable.

Five days barefoot between Tuscany and Corsica

09/18/2026

daniela s.

-

IT

It was an unforgettable experience, the travel companions were delightful, efficient and fun. Lorenzo, the captain was splendid in managing the crew lightly and equally splendid in managing the storm while sailing

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964