281

experiences

4.6

The Island of Elba, to make you live a special experience!

Italy: Tuscany

6 days - 5 nights

One departure available

August

€700

Per person

4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

4 departures available

August - September

Starting from

€490

Per person

4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

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

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

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

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

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

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

€690

Per person

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

4.9

Super!

Giglio Island - Festival of Grapes and Open Cellars

Italy: Tuscany

3 days - 3 nights

One departure available

September

€280

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

18613 reviews

Weekend Elba or Capraia

08/18/2026

valeria z.

Positive experience, both for the group with whom we shared the holiday, and for the skipper Sebastiano super helpful and affable. The only drawback is that in our opinion 10 people are too many for the size of the boat.

Sailing cruise in the Greek islands - The Saronic Islands

08/18/2026

Catherine B.

Very enjoyable cruise. Comfortable and well-equipped boat. The islands are all more beautiful than the others and what a joy to wake up alone in the world in a paradisiacal cove! Very good atmosphere thanks to Periklis who knows how to be as efficient as he is discreet and leaves a lot of room for those who want to take part in the navigation. I highly recommend this experience.

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/18/2026

Giulia M.

Having already had other experiences in the flotilla, in this one I found very little organization, too many things left to chance (starting, in my opinion, from skipper and coskipper not sufficiently prepared - indeed the coskipper seemed to be on vacation - for free) and then, apart from the sea conditions, the programs were not like those described (including packages). I definitely wouldn't stay here again, not to the Aeolian Islands at least.

Sailing week North Sardinia and South Corsica

08/18/2026

Nicole L.

Great experience. Me and 3 other friends reserved the boat for a week and had a great time. The skippers are two very kind and easy-going people. They gave us great advice, making us live a wonderful experience. The boat was comfortable and clean, equipped with accessories also for fun such as sup and tender. They also provided us with fins and masks. Relying on Marco and Giada was certainly an excellent choice that we will certainly consider again if we want to relive a week on a sailboat. For us the overall grade is 10/10 !!

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!