150

experiences

4.8

Long weekend on Elba: 4 days of sun and sailing

Italy: Tuscany

3 days - 3 nights

7 departures available

July - September

Starting from

€410

€369

Per person

New Year's Eve in the Egadi Islands on a sailing boat - Comfort & All Inclusive

Italy: Aegadian islands

2 days - 2 nights

One departure available

December - January

€510

Per person

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

12 departures available

June - September

Starting from

€430

€409

Per person

5.0

Superlative Corsica: East Coast in stages

France: Corsica

8 days - 7 nights

One departure available

June - July

€1,450

Per person

4.4

Journey to the most beautiful islands of the Aegean: Leros, Lipsi, Samos and Chios

Greece: North Egean Islands

6 days - 7 nights

One departure available

June

€660

Per person

4.3

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

9 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

5.0

Superlative Corsica: East Coast in stages

France: Corsica

8 days - 7 nights

One departure available

July

€1,450

Per person

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

5.0

Three days to discover the Pink Granite Coast

France: Brittany and Normandy

3 days - 2 nights

One departure available

May

€345

Per person

5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

10 departures available

April - June

Starting from

€300

Per person

4.4

Sailing from the magnificent Peloponnese to beautiful Zakynthos and Kefalonia

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€660

Per person

4.8

New Year's Eve on Elba on two boats: sequins in the dinette!

Italy: Tuscany

3 days - 2 nights

One departure available

December - January

€250

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

17616 reviews

Weekend on Elba "Only for four" for maximum comfort

11/25/2025

D. D.

Italy

Great weekend! Impeccable welcome on Friday evening, really much appreciated. Very professional and prepared skipper (also the other crew members) - experienced hands-on in the challenging (but fun) crossing. I learned a lot (main objective - achieved). I hope to have the chance of another experience together soon.

A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.

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!

Call us at

+44 2035144220

Read our

Contact & Support

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!