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!

Sailing weekend in Istria

Croatia: Istrian peninsula

3 days - 2 nights

4 departures available

September - October

€260

Per person

cover image
avatar image

4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

cover image
avatar image

4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

2 departures available

September - October

Starting from

€860

Per person

cover image
avatar image

4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€750

Per person

cover image
avatar image

5.0

Super!

Corsica as you've never seen it before!

France: Corsica

7 days - 7 nights

One departure available

August

€1,050

Per person

cover image
avatar image

4.9

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

4 departures available

August - September

Starting from

€790

Per person

cover image
avatar image

4.2

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

Per person

cover image
avatar image

5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

cover image
avatar image

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

€690

Per person

cover image
avatar image

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

cover image
avatar image

4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

5 departures available

September - October

Starting from

€230

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

18633 reviews

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/19/2026

Emanuele Z.

-

IT

Nice experience
avatar image

Mid-August on the Côte d'Azur!

08/19/2026

Melania Cinzia Z.

-

IT

The cruise was pleasant, without any particular inconvenience. Andrea is very focused on ensuring safety both during travel and during maneuvers for stops. The discordant note that I would like to highlight is that the title of the cruise indicates the Porquerolles which, in fact, are not included in the itinerary, so I would like more aligned information for the user who has to choose.

Pula and the enchanting Kvarner islands: special price private cruise

08/19/2026

Michele R.

Top experience! A week on the boat with my sailor girlfriend, in which everyone did what they felt, and I didn't want to do anything and I didn't do anything. Ilaria and Maurizio were good at respecting my wishes, but I recognize that they behaved very well: we went sailing a lot, they taught those who wanted to learn and managed the stages and movements with the right times. Very spacious boat, we were in the forward cabin which is very nice. For those who want to spend a week on a sailing boat, highly recommended!
avatar image

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

08/19/2026

Gloria D.

-

IT

A trip just right to completely take your head off. My husband had a lot of fun being at the helm with Gennaro. All very nice certainly with something to fix. Holiday suitable for those looking for adventure. 😍

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