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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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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

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4.9

Super!

A day of sailing in the Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

May

€99

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

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4.9

Super!

VelaTrek weekend on the Island of Elba All-inclusive - 2 boats

Italy: Tuscany

3 days - 2 nights

2 departures available

May - September

€390

€351

Per person

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4.9

Super!

Long weekend sailing in Istria between nature and history

Croatia: Istrian peninsula

3 days - 3 nights

One departure available

April - May

€360

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Malé to Kulhudhuffushi

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February

€2,650

Per person

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5.0

Super!

Chioggia to Corfu

Greece: Ionian Islands

8 days - 7 nights

One departure available

May

€550

Per person

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5.0

Super!

Aeolian Islands and Egadi Islands in a week with chef on board

Italy: Aegadian islands

7 days - 7 nights

One departure available

July - August

€950

Per person

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5.0

Super!

Dreamy Maldives by sailboat - From Kulhudhuffushi to Malé

Indian Ocean: The Maldives

11 days - 11 nights

One departure available

February - March

€2,650

Per person

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5.0

Super!

Sail around Menorca! - Cook on board

Spain: The Balearic Islands

5 days - 5 nights

4 departures available

June - August

Starting from

€900

€765

Per person

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

2 departures available

September

€900

Per person

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5.0

Super!

Sailing from Menorca to Sardinia

Spain: The Balearic Islands

5 days - 5 nights

One departure available

June

€700

€595

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.

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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.

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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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