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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!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

June

€360

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

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4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

8 departures available

June - August

Starting from

€450

€360

Per person

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4.9

Super!

Week among the queens of the archipelago - Elba, Capraia and Corsica

Italy: Tuscany

7 days - 6 nights

One departure available

August

€1,090

€872

Per person

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5.0

Super!

Seyschelles Islands... Welcome to paradise!

Indian Ocean: Seychelles

11 days - 11 nights

3 departures available

April - June

Starting from

€2,400

€2,040

Per person

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4.9

Super!

Traveling and Dreaming in the Gulf of Poets - All inclusive

Italy: Liguria

2 days - 2 nights

One departure available

May

€360

Per person

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4.8

Super!

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

11 departures available

May - October

Starting from

€272

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

26 departures available

April - October

Starting from

€500

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

Per person

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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

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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

8 departures available

May - September

Starting from

€220

Per person

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5.0

Super!

June 2nd long weekend in the Tuscan Archipelago with PROFESSIONAL CHEF SKIPPER

Italy: Tuscany

4 days - 4 nights

One departure available

May - June

€500

€475

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17623 reviews

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Wellness Adventure Retreat

01/14/2026

Donna S.

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Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!
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Come and discover Guadeloupe and its archipelago: a paradise on the water

01/14/2026

Sophie P.

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Canada

An unforgettable sailing trip in Guadeloupe and the islands 🌴 We discovered Les Saintes, Marie-Galante and had a huge crush on Petite-Terre 💙 Sabrina and Patrick are incredibly welcoming and friendly. We spent a week on their sailboat, in a friendly and soothing atmosphere between tarot games and chili lovers and underwater excursions. 🌶️🃏 🐠 Patrick and Sabine are excellent skippers, very professional and reassuring. . This trip allowed us to really rest and recharge. An experience that I recommend without hesitation ✨ Sophie and Louis
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Experience the Befana as you have never seen it before... by boat!

01/14/2026

federico b.

-

Italy

Beautiful 4 relaxing days despite the adverse weather, the legendary Francesco solved with trips to beautiful and really interesting places, excellent crew immediately close-knit.
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Dream New Year's Eve sailing in Thailand

01/14/2026

Marina G.

-

Italy

Gianluca is a delightful person attentive to the well-being of customers. Clean boat with everything you need. Very centered galley. Let's wait for another itinerary to do with Gianluca!

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