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

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

Italy: Sicily

2 days - 1 night

2 departures available

October

€215

Per person

cover image
avatar image

4.4

From Martinique to Guadeloupe riding the trade winds

Caribbean: Guadeloupe

10 days - 10 nights

One departure available

February

€1,250

€1,125

Per person

cover image
avatar image

4.7

Island of Elba and South Corsica fantastic week

Italy: Tuscany

7 days - 6 nights

11 departures available

June - August

Starting from

€660

Per person

cover image
avatar image

4.9

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

4 departures available

July - August

Starting from

€1,037

Per person

cover image
avatar image

5.0

Unspoilt Balearic Islands for max 4 guests: Mallorca and/or Menorca

Spain: The Balearic Islands

6 days - 6 nights

14 departures available

June - September

Starting from

€1,132

€906

Per person

cover image
avatar image

4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

cover image
avatar image

4.8

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€962

€866

Per person

cover image
avatar image

5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

cover image
avatar image

5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

June - October

Starting from

€690

Per person

cover image
avatar image

4.1

Totano's cup 2027 weekend of sailing and party on the island

Italy: Tuscany

3 days - 2 nights

One departure available

October

€350

Per person

cover image
avatar image

New

Sailing Week Sardinia and Corsica

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

October

€600

Per person

cover image
avatar image

4.4

L'Île de Beauté: sailing in Corsica with night return

France: Corsica

6 days - 7 nights

5 departures available

July - August

Starting from

€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

19274 reviews

A taste of the magnificent Island of Elba

10/14/2026

Annachiara P.

-

IT

It was a beautiful weekend!! Alberto is an experienced and prepared skipper who is totally dedicated to what he is passionate about. We really appreciated his willingness to meet us and, compatibly with weather conditions and times, to adapt the weekend to our needs: although we were licensed, we needed to regain confidence with going to sea (sailing!), without giving up relaxation. Alberto was a great teacher and we learned so much! He took us to beautiful places and we really enjoyed our time together (and the classical guitar under the stars added that extra touch :D). A special thanks to Claudia for her company and for the super aperitifs she prepared for us! The boat is beautiful, maintained with great care, order and cleanliness. They were two wonderful days. Thank you very much Alberto and Claudia!! We hope to repeat it soon!
avatar image

The Saronic Islands sailing, skippered and on-board kitchen

10/14/2026

Kaija H.

-

FI

Annalisa and Emanuel hosted a very nice and safe sailing trip in their boat involving everyone. Despite the changed route plans due to bad weather the previous week, they were able to replan us a nice trip in the Cyclades Islands. We visited beautiful natural bays, enjoyed sailing, swimming, snorkling, sun bathing, fishing, ancient historical places and delicious fresh home-cooked food. Annalisa and Emanuel are the best and most patient hosts I have ever had!
avatar image

Sailing and Trekking in the Aeolian Islands

10/14/2026

Massimo G.

-

IT

A week in full relaxation in the Aeolian Islands.Mario is a professional and helpful skipper with his customers, putting them immediately at ease, For your holiday in this archipelago I highly recommend to contact him .... MARIO

Barcolana Weekend: experience the largest regatta in the world

10/13/2026

Francesco S.

-

IT

Ilaria in a nutshell Great skipper Great cook Super nice

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