129

experiences

4.9

Super!

Weekend of relaxation and fun to discover the Island of Elba

Italy: Tuscany

3 days - 2 nights

4 departures available

June

€360

€288

Per person

4.8

Super!

The sea and sailing in winter, 2 days on the island of Elba

Italy: Tuscany

2 days - 1 night

6 departures available

January - December

€190

Per person

4.8

Super!

Capri Light Blue, thermal Ischia and colorful Procida

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

April - May

€373

€317

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€800

€720

Per person

5.0

Super!

Sailing weekend to the Columbretes Islands

Spain: The Balearic Islands

2 days - 2 nights

One departure available

December

€250

€238

Per person

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€460

Per person

4.8

Super!

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

Per person

4.9

Super!

A weekend of sailing in Capraia

Italy: Tuscany

2 days - 2 nights

6 departures available

February - April

€220

Per person

4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

November - December

€190

Per person

5.0

Super!

Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

4.9

Super!

2 June long weekend - Capraia and Cap Corse

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€380

Per person

4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

April - July

Starting from

€275

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!