header cover

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.

594

experiences

cover image
avatar image

5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€180

Per person

cover image
avatar image
Discovering the wonderful Hvar - Vis - Korcula

Duration:

6 days - 7 nights

Croatia:

Split Archipelago

Give this experience a try!

Starting from

€518

€575

Per person

cover image
avatar image

5.0

Autour de Lanzarote, Isla de lobos and La Graciosa!

Duration:

6 days - 7 nights

Atlantic islands:

Canary Islands

Give this experience a try!

€725

Per person

cover image
avatar image

4.8

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

6 days - 7 nights

Italy:

Aegadian islands

avatar placeholder
avatar placeholder
avatar placeholder

+8 travellers

have booked

Starting from

€523

€550

Per person

cover image
avatar image

5.0

San Blas: the paradise of the Caribbean

Duration:

6 days - 7 nights

Caribbean:

San Blas Islands - Panama

avatar placeholder
avatar placeholder
avatar placeholder

+14 travellers

have booked

€900

Per person

cover image
avatar image

4.9

Day on Lake Maggiore

Duration:

1 day - 0 nights

Italy:

Lake Maggiore

Give this experience a try!

€130

Per person

cover image
avatar image

5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar placeholder
avatar placeholder
avatar placeholder

+14 travellers

have booked

€99

Per person

cover image
avatar image

5.0

Daily trip on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

Starting from

€100

Per person

cover image
avatar image
Easter Monday in Sailing

Duration:

1 day - 1 night

Italy:

Liguria

Give this experience a try!

€120

Per person

cover image
avatar image
Easter Monday on a sailing boat

Duration:

1 day - 0 nights

Italy:

Lazio

Give this experience a try!

€90

Per person

cover image
avatar image
The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€500

Per person

cover image
avatar image

5.0

5-day sailing course: discovery and learning

Duration:

5 days - 4 nights

France:

French Riviera and Porquerolles

Starting from

€626

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

14253 reviews

avatar image

A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

-

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..
avatar placeholder

Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

-

Italy

At first, from my son Guglielmo , a special thanks to J.B. for his prompt interest and kind concern when we had problems to get in touch because of my smartphone (next time better an e sim). Than, even if i'm not exactly the best guest to have on bord, i received any kind of support to make me feel confortable and enjoy my stay.. You'll find someone who loves his job and who knows how to do it at best. Really good experience thanks also to Adriana, LuLu e Franco. See you soon!
avatar placeholder

Guadeloupe and its islands in ten days

02/9/2024

Franck P.

-

France

J’ai passé un super séjour sur le Mango qui est un voilier de voyage hyper abouti. Des vrais sensations de Voile…..! Merci à Jean Baptiste pour son accueil authentique qui aime partager ces connaissances et qui m a fait les beaux sites traversés…. À très bientôt. Franck
avatar placeholder

Guadeloupe and its islands in ten days

02/8/2024

Lucie C.

-

France

Super accueil. Jean Baptiste est très agréable très professionnel et surtout très securisant en.mer. il connaît son bateau dans tous les détails. Très bon séjour avec une bonne ambiance. Jean Baptiste nous a fait decouvrir de très beaux endroits. . nous le recommandons vivement. Adriana Lucie et Franck

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

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964