150

experiences

4.9

Super!

May Day between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€280

Per person

5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

5 departures available

August - September

€695

€626

Per person

4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

4 days - 4 nights

3 departures available

June

€400

Per person

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!

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

Greece: Ionian Islands

7 days - 7 nights

31 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

5.0

Super!

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

Greece: Sporades

6 days - 7 nights

18 departures available

May - September

Starting from

€650

Per person

5.0

Super!

Spring on Lake Garda

Italy: Lake Garda

1 day - 0 nights

One departure available

May

€99

Per person

Why book a holiday with Sailsquare?

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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.

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