528

experiences

4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

Per person

New

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

2 departures available

July

€300

€270

Per person

5.0

Super!

La Maddalena Archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

July - August

€750

Per person

4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

5 departures available

July - September

Starting from

€400

€360

Per person

5.0

Super!

Tuscany and North Corsica on a sailing boat

Italy: Tuscany

7 days - 7 nights

One departure available

August

€1,060

Per person

5.0

Super!

A sailing holiday: discovering the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

3 departures available

August

€650

Per person

4.8

Super!

Weekend on Elba, sea, colors and scents.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€200

Per person

4.8

Super!

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

Italy: Pontine Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€900

Per person

5.0

Super!

Luxury routes among the wonders of Northern Sardinia with hostess

Italy: Northern Sardinia

6 days - 6 nights

8 departures available

July - September

€1,600

Per person

5.0

Summer 2026 - Catamaran week in the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

€1,020

Per person

5.0

Super!

Weekend in the Pontine Islands between Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

One departure available

July

€350

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.

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

17883 reviews

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

06/27/2026

Viviana M.

Super week!! Fantastic sea, wonderful beaches with crystal clear waters and delicious cuisine. Alessandro, skipper and Carlo, were very kind and company! My sister and I spent a relaxing and fun week together with the group who traveled with us and we made friends with. Recommended for people who love the sea, the wind in their hair and need lightness, simplicity and freedom! Thank you for this great week!

Trip with photographer to the Pontine - Life changing experiences

06/27/2026

elena b.

It was a wonderful experience, a continuous surprise, nature, the boat, the company! Thank you captain Francesco, we hope that our paths cross again, in the sea or in the desert, who knows...

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

06/27/2026

Michele O.

Unique experience for those who love sailing. The competent Skipper Riccardo has values that show true love for the sea, and there is no shortage of good food.

A romantic and luxurious vacation in the Aeolian Islands

06/27/2026

Anna D.

Unforgettable days on board Zadar. The owners Ram and Ronit, in addition to being experienced sailors, are attentive and pleasant hosts. They welcomed us with great sympathy and made us feel at home immediately. The boat is very beautiful, comfortable and impeccably maintained. We built the itinerary together and they met all our desires. Top also the freedom to cook fresh fish bought directly from local fishermen: an authentic experience! We will gladly come back!

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