458

experiences

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€690

Per person

4.7

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

Italy: Tuscany

6 days - 6 nights

3 departures available

August - September

Starting from

€1,041

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

August

€1,100

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

11 departures available

August - October

Starting from

€570

Per person

5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€1,150

€1,035

Per person

4.7

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

Italy: Tuscany

6 days - 7 nights

2 departures available

July - August

Starting from

€1,052

€999

Per person

5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

3 departures available

August - September

Starting from

€950

Per person

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

8 departures available

July - September

Starting from

€730

€657

Per person

4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 departures available

September - October

Starting from

€230

Per person

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

18090 reviews

Wind, sea and freedom: a week between Corsica and the Tuscan archipelago

07/16/2026

Carlotta P.

Wonderful experience! Joshua is an attentive, cautious, discreet and very kind skipper. We visited the north of Corsica and loved it. Joshua took us to different beaches and all really beautiful. Good winds!!

The North Dodecanese from Samos on a magnificent 15-meter boat

07/16/2026

Francesca T.

What a great experience! Fabio and Irene welcome you in their beautiful boat, making you feel immediately at ease. Expert guides of the Greek islands, take you to the most fascinating bays and places. Fabio, a captain with long experience, always makes you feel safe; Irene is an ideal travel companion. A holiday suitable for everyone, even those less used to sailing.

Magnificent weekend of approach to sailing on the island of Elba

07/16/2026

Alfredo M.

Nice experience, too bad the little wind for navigation but the important thing is to have been well in excellent company. Thank you Sandro for always indulging us and making us safe! Fair winds!

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

07/16/2026

Vincenzo T.

Weekend spent relaxing and having fun, we found a beautiful sea and thanks to Fabrizio's advice we fully enjoyed the boat and discovered beautiful places to swim safely with my family. It was definitely a wonderful experience.

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