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

4.8

Super!

Week in the north of Corsica, via Capraia - in company

Italy: Tuscany

7 days - 6 nights

One departure available

August

€890

Per person

cover image
avatar image

4.7

Kornati: the pearl of Croatia

Croatia: Kornati Islands

6 days - 7 nights

2 departures available

August

Starting from

€800

Per person

cover image
avatar image

4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

4 departures available

August - October

€650

Per person

cover image
avatar image

4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

5 departures available

August - September

Starting from

€700

Per person

cover image
avatar image

5.0

Super!

Sailing Holiday with a Hostess Among the Wonders of Northern Sardinia

Italy: Northern Sardinia

6 days - 6 nights

4 departures available

August - September

Starting from

€1,450

Per person

cover image
avatar image

5.0

Super!

Vento di Sicilia: from the Aeolian Islands to Trapani

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€920

Per person

cover image
avatar image

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€750

€675

Per person

cover image
avatar image

4.9

Super!

Quattro giorni all'Elba - Hostess a bordo

Italy: Tuscany

4 days - 5 nights

One departure available

August

€800

Per person

cover image
avatar image

4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

One departure available

September

€609

€579

Per person

cover image
avatar image

4.5

Ibiza & Formentera: an exclusive journey between sky and sea

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

August - September

Starting from

€1,010

Per person

cover image
avatar image

4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

One departure available

August

€1,290

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

18249 reviews

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

07/29/2026

Marta P.

-

IT

The skippers were very good, professional, fun and company. Egadi is a paradise on earth, an ideal destination to make peace with the world. Super comfortable and spotless boat... If the wind decides to participate, it sails which is a fairy tale. thanks Jo! thanks Andre!

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/29/2026

Maria Z.

Very nice experience, skipper super helpful to make us appreciate wonderful bays and beaches of the Pontine islands,
avatar image

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

07/29/2026

Claudio A.

-

IT

A sailing holiday simply fantastic! An unforgettable experience, between sea, relaxation and adventure. The skippers were very good: professional, prepared, helpful and always attentive to everyone's needs. (Very comfortable boat). They gave us beautiful moments, showing great attention to us, creating a very special atmosphere on board. Highly recommended, I can't wait to leave!
avatar image

Island of Elba and South Corsica fantastic week

07/29/2026

Alessandra G.

-

IT

Francesco was an excellent "host"! We had to revise the itinerary due to the weather conditions (little wind) but he was able to identify beautiful places without making us absolutely regret the tour that was planned! It was a fantastic experience to repeat

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