340

experiences

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

5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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

4.9

Weekend in the Gulf of Alassio and Gallinara Island

Italy: Liguria

2 days - 2 nights

One departure available

August

€300

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

5.0

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

6 departures available

August - September

Starting from

€790

Per person

4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

Per person

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

4 departures available

August - September

Starting from

€700

Per person

4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September

€790

Per person

5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

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

18359 reviews

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

08/4/2026

Sarah L.

This trip was way above my expectations. Matteo is a terrific skipper, everything was perfectly planned, the itinerary was great and well balanced between different bays to enjoy the sea, and some places where we could visit small beautiful towns. We had a lovely time with the others as well, we all became friends quite quickly through Matteo’s sense of community, the week was a delight. Thank you again for this unexpected experience, I am very grateful.

Face to face with the Archipelago(s)

08/4/2026

Noemi V.

Overall very positive experience. The weather conditions also allowed us to unfurl the sails. The skipper accompanied us with great professionalism and unparalleled sympathy. Thank you Frankie! Hoping to replicate!

Sailing in Tigullio: Half-Day Experience from Rapallo

08/4/2026

LUCA ADRIANO B.

Well organized sailing excursion. We bathed, without haste, in two beautiful places.. Captain and crew treated us well with lots of focaccia and pizza for a snack!

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

08/4/2026

Silvia P.

Beautiful boat experience, attention to guests is above everything. Skipper friendly person, always attentive, from the first moment of meeting. His pastes are good, in particular the garlic, oil and chilli, to take your breath away... with a good glass of wine, then, everything tastier!! ... and a good master of knots ... Seriously, great holiday!

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!