522

experiences

4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€540

€513

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€650

Per person

New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

July

Starting from

€300

€270

Per person

4.6

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

2 departures available

July - August

Starting from

€800

€600

Per person

5.0

Egadi Sail & Relax: the archipelago to experience

Italy: Aegadian islands

7 days - 7 nights

10 departures available

July - September

Starting from

€550

€495

Per person

4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

6 departures available

July - October

Starting from

€420

€399

Per person

4.8

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

4 departures available

July - August

Starting from

€410

€369

Per person

5.0

Super!

Stintino, Asinara and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

September

€620

Per person

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

9 departures available

July - November

Starting from

€500

€425

Per person

4.7

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

July - November

Starting from

€600

€540

Per person

4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

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

17915 reviews

Leave everything for the Island of Elba

06/29/2026

Marco D.

Really crazy experience! We were a group of 6 friends and had a blast. Impeccable organization, Joshua q super helpful and great atmosphere. It was a different experience than usual, perfect to share with friends and to remember. We absolutely recommend it to anyone who wants to spend a weekend full of fun and the sea. Definitely to be redone!

Week end Liguria Costa Azzurra

06/29/2026

salvatore r.

It was a great experience... Olaf TOP👍

Weekend of sea and colors between Ischia, Procida and Vivara

06/29/2026

Manuela M.

Very nice experience, comfortable and clean boat, Gennaro the skipper a person always available and kind. Highly recommended!

An exclusive weekend on Elba between aperitifs and sailing

06/29/2026

Alessandra R.

Very positive experience, Elba always enchanting. The Skipper Luca L. very kind and professional, a great connoisseur and lover of the Tuscan archipelago, with the timing and talent necessary to transform what is in the galley into very pleasant moments at the table in the cockpit, after a perfect swim and in the middle of a fabulous sunset.

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 20 3514 4220

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!