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

4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

40 departures available

January - December

Starting from

€300

€270

Per person

cover image
avatar image

5.0

Super!

Weekend between Ponza and Palmarola Comfortable - max 4 people

Italy: Pontine Islands

3 days - 2 nights

2 departures available

June - July

Starting from

€440

Per person

cover image
avatar image

5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

10 departures available

June - August

Starting from

€390

€351

Per person

cover image
avatar image

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

6 departures available

July - August

Starting from

€850

€765

Per person

cover image
avatar image

4.8

Super!

Summer is made for the Aeolian Islands! Weekly cruise

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

May - September

Starting from

€700

€630

Per person

cover image
avatar image

4.8

Super!

A sailing trip through history and food and wine to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

cover image
avatar image

4.9

Super!

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

4 departures available

May - July

Starting from

€320

Per person

cover image
avatar image

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

cover image
avatar image

5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

cover image
avatar image

4.9

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

11 departures available

June - September

Starting from

€980

€882

Per person

cover image
avatar image

5.0

Super!

Ibiza & Formentera: one week with cook on board

Spain: The Balearic Islands

6 days - 6 nights

2 departures available

September

€750

€675

Per person

cover image
avatar image

5.0

Super!

Long weekend in Sardinia

Italy: Northern Sardinia

4 days - 3 nights

One departure available

June

€450

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

17665 reviews

Weekend among the most beautiful coves of Elba

05/17/2026

Giulia L.

-

Italy

New experience for me and my partner, excellent company, beautiful places, well organized trip, Carmen and Marco nice and easy-going, they were able to put us all at ease, we will remain a beautiful memory!

Let's discover the Aeolian Islands together by sailing

05/17/2026

Tim D.

-

Germany

Mario is an excellent skipper. Through him we were able to see the most beautiful corners of the Aeolian Islands. His local knowledge and contacts on all the islands gave us an unforgettable trip. We were also lucky enough to have his incredibly lovely wife on board. Even though communication was not easy (we didn't speak Italian and she didn't speak English), she made the trip even more beautiful. We thank them very much for this wonderful sailing holiday.
avatar image

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

05/12/2026

Paola A.

-

Italy

We immediately felt comfortable with everything and everyone. We left as strangers and came back as a group of friends. The treatment was higher than expected. WELL DONE WELL DONE !

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

05/11/2026

Lucia K.

-

Switzerland

Our sailing holidays around Corfu were simply exceptional. The combination of crystal-clear waters, stunning islands, and peaceful hidden bays made every single day unforgettable. The crew Andrea, Marta & Mattias was incredibly friendly, professional, and always made us feel welcome and relaxed on board. The itinerary was perfectly balanced between discovering beautiful Greek islands, enjoying time at sea, and experiencing authentic local culture. The food was another highlight — fresh, delicious, and healthy, with plenty of local specialties prepared with care. It was truly a unique and unforgettable experience that we would highly recommend to anyone looking for the perfect mix of adventure, relaxation, and comfort.

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