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

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

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

7 departures available

August - November

Starting from

€500

€348

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!

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!

Cruise for Singles from Sanremo to Saint-Tropez

France: French Riviera and Porquerolles

8 days - 7 nights

One departure available

August

€650

Per person

cover image
avatar image

5.0

Super!

Wandering between Tigullio and Cinque Terre

Italy: Liguria

7 days - 7 nights

One departure available

September

€700

Per person

cover image
avatar image

4.6

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

7 departures available

July - September

Starting from

€700

Per person

cover image
avatar image

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

7 departures available

July - September

Starting from

€1,450

Per person

cover image
avatar image

4.8

New

Egadi mon amour: seven days to fall in love, be amazed and relax.

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

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

5 departures available

July - August

Starting from

€390

Per person

cover image
avatar image

4.5

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

August

Starting from

€850

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

4 departures available

August - September

€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

18089 reviews

avatar image

The North Dodecanese from Samos on a magnificent 15-meter boat

07/16/2026

Francesca T.

-

IT

What a great experience! Fabio and Irene welcome you in their beautiful boat, making you feel immediately at ease. Expert guides of the Greek islands, take you to the most fascinating bays and places. Fabio, a captain with long experience, always makes you feel safe; Irene is an ideal travel companion. A holiday suitable for everyone, even those less used to sailing.
avatar image

Magnificent weekend of approach to sailing on the island of Elba

07/16/2026

Alfredo M.

-

IT

Nice experience, too bad the little wind for navigation but the important thing is to have been well in excellent company. Thank you Sandro for always indulging us and making us safe! Fair winds!
avatar image

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

-

IT

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

Long weekend among the queens of the archipelago - Elba and Capraia

07/15/2026

Giovanni P.

-

IT

Great experience!! Edoardo top, beautiful boat, scary sea!!

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