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!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

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!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

cover image
avatar image

4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€280

Per person

cover image
avatar image

4.9

Super!

Holidays on the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€716

Per person

cover image
avatar image

4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

cover image
avatar image

5.0

Super!

Pula and the enchanting Kvarner islands: special price private cruise

Croatia: Kornati Islands

6 days - 6 nights

One departure available

August

€950

Per person

cover image
avatar image

4.3

La Dolce Vita on a sailboat: discovering the Côte d'Azur

France: French Riviera and Porquerolles

7 days - 6 nights

One departure available

August

€649

Per person

cover image
avatar image

4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

One departure available

September

€400

Per person

cover image
avatar image

4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

Per person

cover image
avatar image

4.0

New

Lampedusa, Lampione and Linosa among magical colors

Italy: Pantelleria and Lampedusa

7 days - 7 nights

2 departures available

October - November

€500

€348

Per person

cover image
avatar image

4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 nights

One departure available

September

€400

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

18488 reviews

Unforgettable adventure in the Aeolian Islands

08/15/2026

Marianna G.

-

IT

Overall it was a beautiful holiday, the Aeolian Islands are a magical place. It was a "rustic" and naturalistic holiday, an experience of sharing and the art of getting by. It was very hot so even at night it was difficult to sleep and during the navigation there was no wind to sail. Gaetano is a good person with stories to tell.
avatar image

Whale watching cruise with WWF guide in the Corfu archipelago

08/15/2026

Ilka B.

-

CH

We sailed from Santa Maria di Leuca to the Greek islands around Corfu – a fantastically beautiful trip that I will never forget! Roco was our captain and just great! He navigated us safely and confidently, was always friendly and warm and immediately made us feel welcome on board. Donatello was our whale watching guide – and he really is the best! With his great knowledge, his humor and his incredible enthusiasm for whales and dolphins, he not only imparted a lot of knowledge to us, but also shared his own fascination with us. He tirelessly looked out for animals and chose the best routes for us. And with success: We were able to observe sperm whales, beaked whales and dolphins. These encounters were beautiful and incredibly touching! The group on board was also great. From the very beginning, Donatello has made sure that everyone feels comfortable and gets along well with each other. So we had a wonderful time with exciting conversations, lots of laughter, fine food, games together and of course many fascinating moments on the water. The whole trip was just fantastically beautiful – a perfect mix of sailing, nature, adventure and wonderful people. Many thanks again to Roco, Donatello and the whole team for this unforgettable time! 💙🐋⛵
avatar image

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/15/2026

Michele A.

-

NL

With Luca and Tommy fantastic holiday guaranteed!
avatar image

Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/15/2026

Vittorio C.

-

IT

Saving Marco and Filippo, good skippers and nice guys, bad organization, and I would avoid going into details because there were many ambiguous things, as shared among the 80 participants. I do not recommend

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