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.

99

experiences

cover image
avatar image
Mystic Shores: Exploring the Canaries

Duration:

7 days - 7 nights

Atlantic islands:

Canary Islands

Give this experience a try!

€448

€640

Per person

cover image
avatar image

4.3

Easter sailing on the Côte d'Azur

Duration:

3 days - 3 nights

France:

French Riviera and Porquerolles

avatar image
avatar image
avatar image

4 travellers

€324

€360

Per person

cover image
avatar image

5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

cover image
avatar image

5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

cover image
avatar image

4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€891

€990

Per person

cover image
avatar image

4.9

Super!

From Santorini to Milos: the fantastic Cyclades of the South

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€810

€900

Per person

cover image
avatar image

5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

cover image
avatar image

5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

avatar image
avatar image
avatar image

44 travellers

Starting from

€765

€850

Per person

cover image
avatar image

5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

avatar image
avatar image
avatar image

56 travellers

Starting from

€675

€750

Per person

cover image
avatar image
Spring in the Cinque Terre

Duration:

3 days - 2 nights

Italy:

Liguria

Give this experience a try!

€189

€210

Per person

cover image
avatar image

4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€711

€790

Per person

cover image
avatar image

4.5

Isole Egadi, Riserva dello Zingaro, San Vito Lo Capo - Hostess a bordo

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

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

15774 reviews

avatar placeholder

The Canary Islands seen from the boat and beyond

11/20/2024

Fabrizio d.

Bella esperienza e Cristian skipper preparato per ogni situazione che può verificarsi la barca e molto marina
avatar placeholder

European Mile Builder Sao Jorge Leg 4 Gibraltar to Las Palmas

11/19/2024

Jan C.

-

Poland

The trip was excellent. Very nice crew and Will was an excellent skipper. The boat was safe but a little tired.
avatar placeholder

Sailing adventure in Norway: chasing the Northern Lights

11/16/2024

Susan B.

-

Ireland

I was delighted to have the opportunity to experience sailing in this part of the world. The location and scenery was stunning. Marco and his wife Britta were excellent hosts. They take extra measures to ensure their guests are looked after. Marco was a very knowledgeable and experienced sailor and I would hope to have the opportunity to visit this area and sail with them again. Grazie Mille
avatar image

European Mile Builder Sao Jorge Leg 4 Gibraltar to Las Palmas

11/13/2024

Alessandro L.

-

Italy

Ottimo gruppo, bravo skipper. La rotta è stata completamente con il vento in poppa. La barca avrebbe bisogno di una piccola sistemata, ma in generale una ottima esperienza se si vuole incrementare la propria preparazione soprattutto nella navigazione notturna di altura.

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