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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.

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4.9

Super!

7 giorni a vela alle Cicladi con gran finale a Santorini

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€790

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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5.0

Super!

Pula - Monfalcone

Croatia: Istrian peninsula

6 days - 6 nights

One departure available

August - September

€950

Per person

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4.8

Super!

From Tavolara to Ogliastra, the great emotions of Eastern Sardinia

Italy: Southern Sardinia

5 days - 4 nights

One departure available

September

€1,200

Per person

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4.9

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August - September

€790

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€940

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Italy: Tuscany

2 days - 2 nights

One departure available

September

€250

€238

Per person

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5.0

Super!

Santa Candida between Ventotene and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

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4.8

Super!

Following the North Star: From Kefalonia to Corfu

Greece: Ionian Islands

6 days - 7 nights

One departure available

August - September

€650

€585

Per person

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4.3

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

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.7

Palma de Mallorca All Inclusive on 18m Ketch

Spain: The Balearic Islands

6 days - 7 nights

3 departures available

August - September

Starting from

€1,290

€1,117

Per person

Why book a holiday with Sailsquare?

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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.

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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

18801 reviews

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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/24/2026

Francesco P.

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IT

Week conditioned by the uncertain weather that prevented us from reaching Corsica (the organizers were clear about this from the beginning... nothing to complain about, only bad luck), Elba and Capraia are still wonderful and we enjoyed them to the fullest. What was missing at the organizational level was a clear and decisive leadership: there were no flotilla activities (packages, group dinners, launches, mini-regattas, etc.) but we were a group of 6 boats that simply moored nearby. The activities on land were left completely to chance and even after returning to port, a day early, no alternatives were proposed to keep the participants engaged, who in fact left over 24 hours earlier. For the rest, I am satisfied to have found an exceptional skipper (Federico) and a well-matched, helpful and fun crew! Last note on the boat: a few defects here and there between sails, tender engine, broken portholes and a clogged bathroom, but I imagine that in the week of August you can't expect an impeccable state of the rental boats.
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Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/24/2026

Walter B.

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IT

Relaxation, fun, laughter and beautiful people. Dani, a prepared skipper who is always on point, and Alice, impeccable in coordinating the group: a perfect match. Thanks also to the special correspondents of Marmaglia TV!
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The Wild Flotilla: dive into the wilderness of Tuscany & Corsica

08/24/2026

Carolina B.

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IT

Fantastic companions and skippers! Too bad for the weather and some logistical details. It was a holiday made unforgettable by people: I found some really great travel companions with whom a beautiful feeling was created, and our skipper was exceptional, professional and helpful at all times. Unfortunately, the weather was not on our side and did not allow us to see the entire planned itinerary, including Corsica. The staff did their best to handle the situation, although the flotilla organization turned out to be a bit weak. It would have been nice to visit more places, more beaches and have more structured activities with more moments of sharing between the various boats to make more of a group. A small flaw concerns the maintenance of the catamaran, which at the end of the trip showed a few too many wear problems due to those who manage the rental, but nothing that ruined the overall experience. Overall a beautiful human experience that I would do again immediately for the quality of the group and the crew!
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Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

Gennaro P.

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IT

Safety, professionalism and big laughs. Bringing together people who don't know each other on a boat is never trivial, but Roberto and Antonio were exceptional. They were able to steer the boat with great skill and at the same time create a relaxed, fun (we laughed a lot) and inclusive atmosphere. Roberto manages every situation at sea with exemplary calm and competence, flanked by an impeccable Antonio who is always on point. A wonderful week that I will carry inside me for a long time. Thank you both very much!

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