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

4.9

Super!

Midweek getaway between Elba and Capraia

Italy: Tuscany

3 days - 3 nights

3 departures available

July - August

Starting from

€410

€369

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

cover image
avatar image

5.0

Super!

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

11 departures available

June - October

Starting from

€1,200

Per person

cover image
avatar image

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August

€650

Per person

cover image
avatar image

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

June - September

€280

Per person

cover image
avatar image

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

July

Starting from

€390

Per person

cover image
avatar image

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

2 departures available

August

€510

€459

Per person

cover image
avatar image

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

3 departures available

June - July

Starting from

€285

Per person

cover image
avatar image

4.9

Super!

Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

3 departures available

July - August

€800

Per person

cover image
avatar image

4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

cover image
avatar image

5.0

Super!

Four days in Ponza and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

July

€490

Per person

cover image
avatar image

4.8

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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

17727 reviews

avatar image

4-day cruise course

06/6/2026

Alexis D.

-

GB

Superb first experience on a sailboat for my father and I. Fabienne was very pedagogical with us, which allowed us to progress quickly. The boat is very well equipped and sailing around the islands was a very nice experience.

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

06/6/2026

Annina P.

-

CH

We had an unforgettable time in the Cyclades! Our skipper Dimitris introduced us to sailing, which was totally new for us but totally exciting and a very nice experience on the sea. It was a great mix of sailing and time on land to explore new places. We enjoyed it very much & highly recommend it:)
avatar image

June 2nd long weekend between Procida, Ischia and Ventotene

06/6/2026

Valentina G.

-

IT

Really nice long weekend of the second of June, well-kept and comfortable boat and group with which we immediately created harmony, also thanks to Umberto, a nice, prepared skipper and a great connoisseur of the places, who organized everything with care, always making us feel at home
avatar image

2 June long weekend - discovering the Gulf of Poets and Portofino

06/5/2026

Annalisa P.

-

IT

Skipper very kind and responsive even pre departure, boat a bit spartan. Destination with very beautiful landscapes, but necessarily a bit "uncomfortable", as there are not many shelters/ports for stops

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