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

4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

cover image
avatar image

5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

4 departures available

October - November

Starting from

€220

€198

Per person

cover image
avatar image

4.7

Squid Festival- Capraia Island

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€250

Per person

cover image
avatar image

New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€400

Per person

cover image
avatar image

4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

cover image
avatar image

4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

2 departures available

October

€690

Per person

cover image
avatar image

4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

One departure available

April - May

€300

Per person

cover image
avatar image

5.0

New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

October

€275

Per person

cover image
avatar image

4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

12 departures available

October - December

€1,400

Per person

cover image
avatar image

4.4

The British Virgin Islands, an enchanted paradise

Caribbean: BVI - British Virgin Islands

10 days - 10 nights

One departure available

March

€1,350

€1,147

Per person

cover image
avatar image

5.0

Raja Ampat: beyond the known routes

Indian Ocean: Indonesia

10 days - 10 nights

2 departures available

January - February

€1,570

Per person

cover image
avatar image
Sailing week of yesteryear in the clear waters of Sardinia

Italy: Southern Sardinia

6 days - 6 nights

3 departures available

October

€750

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

19234 reviews

All-Inclusive Sailing: Capri, Positano, Amalfi

09/28/2026

Nathalie P.

-

FR

Very nice cruise with our skipper Alessandro who was very knowledgeable and very attentive. Highly recommend.

Let's discover Portofino, Santa Margherita and Sestri Levante together

09/28/2026

Cristina A.

-

IT

Beautiful ride, professionalism and friendliness at the top
avatar image

A week sailing in the most beautiful places in the world

09/28/2026

sara s.

-

IT

A wonderful experience!! We stayed a week with Piero and Giuseppina booking the whole boat. Despite the adverse weather forecast, the weather was always good. But we have always relied on the wise course decisions of Piero, who in addition to always being attentive and scrupulous, is a very good skipper in all aspects: his daily lessons will not be forgotten! A special mention goes to Giuseppina, with whom I immediately found myself in tune even with just a smile. His cuisine is spatial, better than that of many restaurants in the area! But Piero in the kitchen is not bad either, his spaghetti are excellent! Thank you for this trip and for the company!

Cyclades from Milos to Milos

09/28/2026

Alessio P.

-

IT

Fabio is a very precise and professional skipper, thanks to the weather we were able to respect all the descriptions and the boat was really beautiful and comfortable. Although it was not within his competence, we tried some really good Roman dishes. Very skilled with the scientific 😎🤣 scopone It is a thank you to the legendary Irene. Highly recommend the experience

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