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!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

€1,150

€1,035

Per person

cover image
avatar image

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€690

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August - September

Starting from

€1,041

Per person

cover image
avatar image

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

14 departures available

July - October

Starting from

€570

Per person

cover image
avatar image

4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

6 departures available

July - September

Starting from

€900

Per person

cover image
avatar image

4.7

Whale watching cruise with WWF guide between Northern Corsica and the Tuscan Archipelago

Italy: Tuscany

6 days - 7 nights

One departure available

July

€1,052

Per person

cover image
avatar image

4.1

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

33 departures available

January - December

Starting from

€300

€270

Per person

cover image
avatar image

4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€650

€585

Per person

cover image
avatar image

4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

3 departures available

August - September

Starting from

€280

Per person

cover image
avatar image

4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

July - October

Starting from

€700

Per person

cover image
avatar image

4.4

Sailing holiday on the Côte d'Azur: experience the charm of the French Riviera

France: French Riviera and Porquerolles

6 days - 7 nights

10 departures available

July - September

Starting from

€730

€657

Per person

cover image
avatar image

5.0

Super!

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€790

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

17929 reviews

Long live Elba and Capraia

07/1/2026

Marina M.

Beautiful experience. Filippo is a professional and experienced skipper. We sailed both under sail and by motor in complete safety, the skipper was available to explain the maneuvers, involving the crew members who wanted to do it in the management of the boat. Clean, comfortable, efficient, well-equipped boat. Very beautiful island of Capraia perfect for a three-day weekend.
avatar image

Four days in the Pontine Islands, just a stone's throw from Rome

07/1/2026

Gea O.

-

IT

The experience with Antonio was beautiful. he took us to discover the Pontine Islands, between stories and making us explore the caves with the tenderino. In addition.... He is an excellent cook!! I hope to get back on his boat soon. Thank you Antonio!
avatar image

Weekend of emotions in Ponza and Palmarola!

07/1/2026

Francesca B.

-

IT

Valter in addition to being a professional strike was super hospitable and company! The boat is very well maintained and has satisfied us in every request. I'll consider it for another adventure
avatar image

Weekend Elba or Capraia

07/1/2026

Chiara P.

My friend and I booked a sailing holiday taking advantage of the last two places available. Unfortunately, at the start we discovered that the number of participants was higher than what had been communicated to us, with a consequent reduction in the spaces on board, which on a sailboat are already quite limited. Also, no one had informed us that it was a bachelor party with a group of 9 men (more than those who were reported on the site and more than the number of people allowed to board) If we had known in advance, we would have definitely chosen another date or requested a refund, as it was not the kind of experience we were looking for. Nicola's willingness must be recognized, who tried in some way to manage the situation. However, throughout the holiday we had to adapt to the needs and schedule of the rest of the group, partially giving up on the experience we expected. Too bad, because with a more transparent communication from the organizing agency it would have gone differently. For the experience I still leave 4 stars, with the hope that in the future more attention will be paid to this type of situation.

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