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

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

6 departures available

July - October

Starting from

€650

€585

Per person

cover image
avatar image

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August - September

€1,020

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

2 departures available

July - September

€400

Per person

cover image
avatar image

4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€700

Per person

cover image
avatar image

4.9

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€650

Per person

cover image
avatar image

5.0

Super!

Educational cruise between Tuscany and Corsica

Italy: Tuscany

14 days - 14 nights

One departure available

August

€1,700

Per person

cover image
avatar image

5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

€950

Per person

cover image
avatar image

5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€600

Per person

cover image
avatar image

4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

€585

Per person

cover image
avatar image

5.0

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

3 departures available

July - August

Starting from

€390

Per person

cover image
avatar image

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

cover image
avatar image

5.0

Super!

EXPERIENCE THE MAGIC! Sailing and relaxing in a maritime wonderland!

Croatia: Istrian peninsula

7 days - 7 nights

2 departures available

August

€649

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

18139 reviews

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

07/21/2026

Elena P.

-

IT

Beautiful experience. Exciting marine biology lessons. Dolphin watching and some sea turtles. Swimming in the sea. Life on board a sailboat is a great learning and adaptation experience. Congratulations in particular to the marine biologist, Mar, for her welcome and availability, as well as the ability to involve the group.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

07/21/2026

Giulio M.

-

IT

My wife and I have just spent an unforgettable week in the Sporades islands on a beautiful, extremely comfortable and welcoming sailboat. Skipper Gianfranco proved to be an exemplary professional, very prepared and always attentive to everyone's safety. Thanks to his knowledge of the area, he took us to coves sheltered from the wind, making us discover real corners of paradise In addition to his technical skills, he was able to create, right from the start, a relaxed and fun atmosphere on board; He has always been very helpful in explaining sailing techniques, advising things to see on land, showing us the best places to taste local delicacies or simply having a chat in front of a sunset. A big thank you to Gianfranco.

Week end Liguria Costa Azzurra

07/20/2026

Serena B.

-

IT

First experience on a sailing boat, very positive for me! Olaf is a very experienced skipper and good company! The group was very pleasant!

Moments that last a lifetime - In Croatia from Rimini - All inclusive

07/20/2026

Patrizia G.

-

IT

Beautiful holiday with the skipper Gabriele very reliable and Samantha always attentive, caring and joyful with the guests! the crossing is long but it is an experience to try!

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