header cover
sailsquare 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

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€1,020

€918

Per person

cover image
avatar image

5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

8 departures available

April - July

Starting from

€360

Per person

cover image
avatar image

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

cover image
avatar image

4.8

Super!

From Milos to Athens: the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

cover image
avatar image

5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

5 departures available

May - July

Starting from

€350

Per person

cover image
avatar image

4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€600

€540

Per person

cover image
avatar image

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€680

Per person

cover image
avatar image

4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

cover image
avatar image

4.8

Super!

Discovering the wild Peloponnese

Greece: Peloponnese

7 days - 7 nights

One departure available

July

€880

Per person

cover image
avatar image

4.8

Super!

Route to the South: The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€850

€765

Per person

cover image
avatar image

4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

cover image
avatar image

5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17626 reviews

avatar image

Easter on the Island of Elba

04/9/2026

Miriam C.

-

Italy

Very pleasant sailing experience. The boat was in good condition. Everything went according to expectations and the navigation was safe and relaxing. The only negative note concerns the owner, Enrico. During communications he was often grumpy, with a rather rigid attitude and not inclined to confrontation. This made the interaction less pleasant, especially at times when more availability and friendliness would have been useful. Overall, I recommend the experience for the quality of the boat and the service at sea, but I suggest the owner to improve the approach with customers to make everything really impeccable.
avatar placeholder

Easter in Capraia and Corsica

04/9/2026

Monica L.

-

Italy

Weekend absolutely up to expectations. Marco is a trained skipper, with great experience, very helpful, kind and caring towards his crew. His boat is hospitable and excellently cared for by him. All positive!!
avatar image

Easter: Whale Watching Expedition in Pelagos Sanctuary with WWF Guide

04/8/2026

Agnese F.

-

Italy

Unique experience, with excellent chances of whale sighting. In 3 days we made 3 close sightings of dolphins and bottlenose dolphins
avatar image

Easter in Capraia and Corsica

04/8/2026

Giovanni G.

-

Italy

Unique and beautiful experience, from start to finish. Starting with the skipper: exceptional, inclusive and very experienced of the sea and the places visited, always constructive and aimed at making us live a positive experience; the places visited were beautiful, with exceptional views, small villages in the middle of nature, with trekking, walks and stops for local shopping; The company of the whole crew (and friendly boats) was fun and collaborative, aimed at creating an enjoyable group experience; The perfect boat, equipped with every comfort, including USB recharges for almost every bed just to give an example. An experience certainly to be repeated and that I recommend

Customer Support

nightLifeGeneralInfo

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!

search

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